Category: 18436-73-2

Chen, Junli; Campbell, Adrian P.; Urmi, Kaniz F.; Wakelin, Laurence P. G.; Denny, William A.; Griffith, Renate; Finch, Angela M. published the article 《Human α1-adrenoceptor subtype selectivity of substituted homobivalent 4-aminoquinolines》. Keywords: human adrenoceptor selectivity homobivalent aminoquinoline; 4-Aminoquinolines; 5-HT(1A)-receptor; Affinity; Selectivity; α(1)-adrenoceptor.They researched the compound: 4-Chloro-8-methylquinoline( cas:18436-73-2 ).COA of Formula: C10H8ClN. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:18436-73-2) here.

A series of ring-substituted ethyl- and heptyl-linked 4-aminoquinoline dimers were synthesized and evaluated for their affinities at the 3 human α1-adrenoceptor (α1-AR) subtypes and the human serotonin 5-HT1A-receptor (5-HT1A-R). We find that the structure-specificity profiles are different for the two series at the α1-AR subtypes, which suggests that homobivalent 4-aminoquinolines can be developed with α1-AR subtype selectivity. The 8-Me ethyl-linked analog has the highest affinity for the α1A-AR, 7 nM, and the greatest capacity for discriminating between α1A-AR and α1B-AR (6-fold), α1D-AR (68-fold), and the 5-HT1A-R (168-fold). α1B-AR selectivity was observed with the 6-Me derivative of the ethyl- and heptyl-linked 4-aminoquinoline dimers and the 7-methoxy (7-OMe) derivative of the heptyl-linked analog. These substitutions result in 4- to 80-fold selectivity for α1B-AR over α1A-AR, α1D-AR, and 5-HT1A-R. In contrast, 4-aminoquinoline dimers with selectivity for α1D-AR are more elusive, since none studied to date has greater affinity for the α1D-AR over the other two α1-ARs. The selectivity of the 8-Me ethyl-linked 4-aminoquinoline dimer for the α1A-AR, and 6-Me ethyl-linked, and the 6-Me and 7-OMe heptyl-linked 4-aminoquinoline dimers for the α1B-AR, makes them promising leads for drug development of α1A-AR or α1B-AR subtype selective ligands with reduced 5-HT1A-R affinity.

There is still a lot of research devoted to this compound(SMILES：CC1=C2N=CC=C(Cl)C2=CC=C1)COA of Formula: C10H8ClN, and with the development of science, more effects of this compound(18436-73-2) can be discovered.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 18436-73-2, is researched, Molecular C10H8ClN, about Potent antiviral activity of novel multi-substituted 4-anilinoquin(az)olines, the main research direction is anilinoquinazoline anilinoquinoline preparation antiviral agent Dengue virus; 4-Anilinoquinazoline; 4-Anilinoquinoline; Antiviral; Dengue Virus; Flavivirus.Recommanded Product: 18436-73-2.

Screening a series of 4-anilinoquinolines and 4-anilinoquinazolines enabled identification of potent novel inhibitors of dengue virus (DENV). Preparation of focused 4-anilinoquinoline/quinazoline scaffold arrays led to the identification of a series of high potency 6-substituted bromine and iodine derivatives The most potent compound 6-iodo-4-((3,4,5-trimethoxyphenyl)amino)quinoline-3-carbonitrile inhibited DENV infection with an EC50 = 79 nM. Crucially, these compounds showed very limited toxicity with CC50 values >10μM in almost all cases. This new promising series provides an anchor point for further development to optimize compound properties.

There is still a lot of research devoted to this compound(SMILES：CC1=C2N=CC=C(Cl)C2=CC=C1)Recommanded Product: 18436-73-2, and with the development of science, more effects of this compound(18436-73-2) can be discovered.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Aminoalkylphenols as antimalarials. II. (Heterocyclic amino)-α-amino-ο-cresols. The synthesis of camoquin, published in 1948, which mentions a compound: 18436-73-2, Name is 4-Chloro-8-methylquinoline, Molecular C10H8ClN, SDS of cas: 18436-73-2.

In view of the high antimalarial activity of certain substituted α-amino-ο-cresols, earlier work (C.A. 41, 414d) has been extended to analogs containing heterocyclic nuclei. This reports the preparation of a group of 122 (heterocyclic amino)-α-amino-ο-cresols and a related group of 12 (heterocyclic amino)benzylamines, as well as the new intermediates used therein. This work has resulted in the preparation of a promising antimalarial (SN 10,751) named camoquin, as well as other compounds which are the most active 4-aminoquinoline derivatives heretofore reported in trophozoite-induced Plasmodium gallinaceum infection in the chick. Catalytic reduction of the appropriate nitrophenol in the presence of Ac2O gave these 4-acetamidophenols: 2-Cl, m. 144°, 55% yield; 2-Ph, m. 160°, 60%; and 2-acetamidophenols: 4-Cl, m. 186°, 52%; 4-Ph, m. 165°, 89%; and 4-tert-Bu, m. 170°, 79%. 2-Allyl-4-acetamidophenol, m. 93-4°, was obtained in 83% yield from the rearrangement of 4-CH2:CHCH2OC6H4NHAc. The Mannich reaction on the substituted acetamidophenols gave these 4-acetamido-α-substituted-ο-cresols: diethylamino (I), m. 135°, 82%; dibutylamino, m. 73°, 87% (picrate, m. 183-5°); dibenzylamino, m. 230°, 75%; (2-methyl-1-piperidyl) (HCl.H2O, m. 175°, 65%); 4-morpholinyl, m. 133°, 27%; [methyl(2-hydroxyethyl)amino] (HCl, m. 198°, 50%); (2-butylamino), m. 156°, 37%; (2-hydroxyethylamino) (HCl, m. 230°, 31%); the 6-allyl derivative of I, m. 86°, 58%: the 5-acetamido isomer of I (HCl, m. 210°, 33%); and these 6-acetamido-α-diethylamino-4-substituted-ο-cresols: Cl (HCl, m. 212°, 66%); tert-Bu (HCl, m. 158°, 53%); and Ph (HCl, m. 183°). Acid hydrolysis of the appropriate 4-acetamido compound gave these 4-amino-α-substituted-ο-cresols (di-HCl salts) (all m. with decomposition); diethylamino, SN 12,458, m. 218-20°, 96%; 1-piperidyl, m. 153-5°, 91%; and 4-morpholinyl, m. 259-60°, 45%. The Mannich reaction on 4-nitrophenol (A) and the reaction of the amine on 2-(chloromethyl)-4-nitrophenol (B) were used to prepare these α-substituted-4-nitro-ο-cresol HCl salts (all m. with decomposition): diethylamino, A, m. 224°, 40%; diisopropylamino, B, m. 193°, 19%; dibutylamino, B, m. 176°, 75%; diisobutylamino (free base), B, m. 113°, 43%; diisoamylamino, B, m. 132°, 32%; isopropylamino, B, m. 238°, 38%; isobutylamino, B, m. 247°, 29%; tertbutylamino, B, m. 275°, 20%; 1-piperidyl, A, m. 260°, 68%; and α-diethylamino-4-nitro-6-phenyl-ο-cresol, A, m. 125°, 21%; and 4-tert-butyl-α-diethylamino-6-nitro-ο-cresol, A, m. 103°, 50%. The method of Price and Roberts (C.A. 40, 5739.5) was used to prepare these substituted 4-chloroquinolines: 6-Me, m. 55°, 50%; 6-anilino, m. 148°, 6%; 7-EtO, m. 76°, 53%; 7-hexyloxy, a high-boiling liquid, 41%; 8-Me, m. 99°, 71%; 5,7-di-Me, m. 59°, 51%; 5,8-di-Me, m. 51°, 59%; 5-chloro-8-methoxy, m. 127°, 6%; 5-methyl-8-methoxy, m. 78°, 45%; 6,8-di-Me, m. 90°, 82%; and 6,7,8-trichloro, m. 156°, 39%. The (heterocyclic amino)-α-alkylamino-ο-cresols were prepared by minor variations of the general procedure of heating the chloroheterocycle with the amino-α-alkylamino-ο-cresols in aqueous or alc. solution on the steam bath. The latter were obtained either by acid hydrolysis of the acetamido derivatives or by catalytic reduction of the nitro derivatives and were usually condensed without isolation. The products are isolated either as the free bases or HCl salts. All the quinine equivalents (Q) reported here are based on the B4 test using P. gallinaceum in the chick. Nearly all the HCl salts m. with decomposition and are colored yellow to orange. 4-(4-Quinolylamino)-α-diethylamino-ο-cresol (II) di-HCl, SN 12,452, m. above 300°, was obtained in 48% yield and had a quinine equivalent of 3 (designated hereafter in the form Q 3). Analogs of II, substituted on the quinoline nucleus: 2-Cl (2HCl, SN 11,986, m. 248°, 30%, Q <0.07); 3-Ph, SN 11,631, m. 155°, 31%, Q 0.4; 6-MeO (2HCl, SN 10,274, m. 270°, 75%, Q 8); 6-Cl (HCl.0.5H2O, SN 11,597, m. 220°, 60%, Q 3.0); 6-Me, SN 11,559, m. 172° (2HCl, m. 238°, 56%, Q 4); 6-anilino (2HCl.H2O, SN 12,361, m. 196°, 63%, Q 0.2); 6-dimethylamino (3HCl.0.5H2O, SN 11,984, m. 235°, 73%, Q 2.5); 6-nitro (2HCl.1.5H2O, m. 210°, 63%, Q 0.8); 7-MeO (2HCl.0.5H2O, SN 11,554, m. 210°, 43%, Q 7); 7-EtO (2HCl.2H2O, SN 11,281, m. 136°, 44%, Q 7); (7-hexyloxy, SN 11,634, m. 153°, 35%, Q 0.5; Q 7); 7-Me (2HCl, SN 12,699, m. 245°, 93%, Q 9); 7-Cl (camoquin) SN 10,751, m. 208°, 86%, Q 25 (2HCl.0.5H2O, m. 243°); 2HCl.H2O, m. 183°; (2HCl.2H2O, m. 160°, 90%); 8-Cl, SN 11,551, m. 212° (2HCl.0.5H2O, m. 253°, 79%, Q 0.5); 8-MeO (2HCl.1.5H2O, SN 11,594, m. 241°, 50%, Q 0.8); 8-Me (2HCl.H2O, SN 11,601, m. 253°, 66%, Q 0.7); 5-chloro-3-Me (2HCl, SN 11,985, m. 258°, 48%, Q 0.3); 5,7-di-Cl (2HCl, SN 12,700, m. 200°, 65%, Q 3); 5,7-di-Me (2HCl, SN 11,561, m. 242°, 67%, Q 10); 5,8-di-Cl (2HCl.H2O, SN 11,596, m. 235°, 60%, Q 0.25); 5,8-di-Me (2HCl, SN 11,560, m. 249°, 80%, Q 0.6); 5-chloro-8-methoxy [2HCl, SN 12,162,(incorrectly given as 12,161 in original), m. 231°, 80%, Q 0.4]; 6-methoxy-2-Me (2HCl, SN 9223, m. 278°, 45%, Q 1.2); 6-methoxy-2-Ph (2HCl.1.75H2O, SN 11,592, m. 198°, 61%, Q 0.25); 6,7-di-Cl (2HCl, SN 12,161, m. 257°, 71.5%, Q 5); 6,7-di-MeO (2HCl, SN 13,395, m. 258°, 68%, Q 2.5); 6,7-di-Me, SN 11,990, m. 215°, 49%, Q 6; 6,8-di-Me (2HCl.H2O, SN 11,558, m. 264°, 54%, Q 0.6); 7-chloro-2-Ph (2HCl, SN 11,232, m. 260°, 41%, Q 0.3); 7-chloro-3-Ph, SN 12,228, m. 165°, Q 1; 7-chloro-3-Me (2HCl, SN 10,492, m. 260°, 64%, Q 6); 8-methoxy-5-Me (2HCl, SN 11,632, m. 210°, 90%, Q 0.6); 6,7,8-tri-Cl (2HCl, SN 11,633, m. 277°, 40%, Q <0.3); and 6-HO (2HCl, SN 11,563, m. 262°, 64%, Q 0.2) (prepared by HBr demethylation of the 6-MeO derivative). 4-(6-Methoxy-4-quinolylamino)-α-dibutylamino-ο-cresol (III) (2HCl.1.25H2O, m. 193°, 10%, Q 9); the (7-chloro-3-methyl-4-quinolylamino) analog of III (2HCl.1.5H2O, m. 177°, 43%, Q 10). 4-(6-Methoxy-4-quinolylamino)-α-1-piperidyl-ο-cresol (IV) (2HCl.0.5H2O, SN 12,038, m. 270°, 80%, Q 8); analogs of IV: (6,7-dimethoxy-4-quinolylamino) (2HCl, SN 13,413, m. 230°, 40%, Q 4); (7-chloro-3-methyl-4-quinolylamino) (2HCl, SN 12,360, m. 270°, 47%, Q 2); (6-methyl-4-quinolylamino) (2HCl, SN 12,456, m. 240°, 41%, Q 2.5). 4-(6-Methoxy-4-quinolylamino)-α-4-morpholinyl-ο-cresol (V) (2HCl, SN 11,989, m. 265°, 57%, Q 1); analogs of V: (7-chloro-3-methyl-4-quinolylamino) (2HCl, SN 12,362, m. 242°, 33%, Q 0.15); (6-methyl-4-quinolylamino), SN 12,457, m. 239°, 50%, Q 0.8. 5-(7-Chloro-4-quinolylamino)-α-diethylamino-ο-cresol, SN 13,730, m. 173°, Q 9; 6-(7-chloro-4-quinolylamino)-α-diethylamino-4-(diethylaminomethyl)-ο-cresol-1.5H2O, m. 145°, Q 5; 4-chloro-α-diethylamino-6-(6-methoxy-4-quinolylamino)-ο-cresol (2HCl, SN 12,885, m 205°, 50%, Q 0.5). 6-Chloro-4-(7-chloro-4-quinolylamino)-α-diethylamino-ο-cresol (VI), SN 13,729, m. 225°, Q 12; analogs of VI: 6-Ph (0.5H2O, m. 235°, 25%); 6-allyl, SN 11,991, m. 148°, 44%, Q 10; 6-allyl-α-1-piperidyl, SN 12,697, m. 190°, 32%, Q 4; 6-allyl-α-diallylamino, SN 13,394, m. 131°, 25%, Q 0.7. 6-Allyl-α-diethylamino-4-(6-methoxy-4-quinolylamino)-ο-cresol, SN 12,039, m. 161°, 33%, Q 7. Variations of the alkylamino group on the cresol portion of camoquin were studied: α-amino-4-(7-chloro-4-quinolylamino)-ο-cresol (VII) (2HCl.0.5H2O, SN 1603, m. 325°, 80%, Q 6); analogs of VII (substituents on the α-amino group): benzoyl (HCl, SN. 11,557, m. 289°, 80%, Q 0.15); Et (2HCl, m. 280°, Q 40, 4% conversion, prepared by the Mannich reaction of EtNH2, (HCHO)x, and 7-chloro-4-(4-hydroxyanilino)quinoline (HCl, m. above 320°, 94%)); Pr(2HCl.0.5H2O, m. 244°, 24%, Q 30); iso-Pr (2HCl, m. 287° 50%, Q 40); Bu (2HCl, m. 254°, 6%, Q 30); sec-Bu (2HCl.H2O, m. 252°, 3%, Q 50); iso-Bu (2HCl, m. 256°, 65%, Q 75); tert-Bu (2HCl, m. 285°, 36%, Q 40); Am (2HCl, m. 266°, 15%, Q 50); (1-methylbutyl 2HCl, m. 231°, 22%, Q 40); iso-Am (2HCl, m. 279°, 20%, Q 50); hexyl (2HCl, m. 280°, 56%, Q 25); (2-ethylbutyl (2HCl, m. 263°, 15%, Q 50)); heptyl (2HCl, m. 278°, 29%, Q 15); octyl, m. 150°, 15%, Q 2.5; allyl (2HCl, m. 257°, 3%, Q 20); 1-methylallyl (2HCl.1.75H2O, m. 95°); cyclohexyl (2HCl.0.25H2O, m. 252°, 30%, Q 30); 2-hydroxyethyl (2HCl.H2O, m. 182°, 15%, Q 3); 2-methoxyethyl (2HCl, m. 271°, Q 25); benzyl (2HCl, m. 270°, Q 16); (α-methylphenethyl) (2HCl.0.25H2O, m. 243°, 31%, Q 25); di-Me (2HCl, m. 290°, 85%, Q 6); N-ethyl-N-butyl(2HCl, m. 240°, 65%, Q 30); di-Pr, SN 13,835, m. 181°, 11%, Q 25; di-Bu, SN 14,105, m. 164°, 20%, Q 35; diiso-Bu (0.5H2O, m. 166°, 38%); diiso-Am (0.5H2O, m. 135°); dihexyl (2HCl, m. 220°, 40%, Q 0.5); diheptyl (2HCl, m. 203°, 52%, Q 1); dioctyl (2HCl, m. 192°, 46%, Q 0.2); bis(2-ethylhexyl) (2HCl.H2O, m. 154°, 1%, Q 3); methyl(2-hydroxyethyl) (2HCl, SN 12,363, m. 250°, 63%, Q 3); butyl(2-hydroxyethyl), SN 14,824, m. 149°, 22%, Q 12; bis(2-hydroxyethyl), m. 193°, 25%, Q 0.6; dibenzyl (2HCl, m. 235°, 74%, Q 2.5); N-methyl-N-Ph (H2O, m. 140°, 39%, Q 0.07); N-ethyl-N-Ph, m. 131°, 54%, Q <0.05. Further analogs of VII: α-1-piperidyl (2HCl.2.5H2O, SN 11,636, m. 302°, 77.5%, Q 25); α-(2-methyl-1-piperidyl) (2HCl, SN 12,357, m. 288°, 66%, Q 20); α-4-morpholinyl (2HCl, SN 11,987, m. 292°, 60-5%, Q 4). Compounds containing heterocyclic nuclei other than the 4-quinolyl include the following 4-(heterocyclic amino)-α-diethylamino-ο-cresols: 9-acridyl (2HCl, SN 12,356, m. 265°, 45%, Q 1.5); (3-chloro-9-acridyl) (2HCl, SN 12,355, m. 267°, 52%, Q 3); (4-methoxy-9-acridyl) (2HCl, SN 12,164, m. 245°, 50%, Q 0.15); (3-chloro-5-methyl-9-acridyl) (2HCl, SN 11,988, m. 275°, 40%, Q 0.25); 2-quinolyl (2HCl, SN 9559, m. 230°, 48%, Q 0.12); (6-methoxy-2-quinolyl) (2HCl, SN 11,537, m. 237°, 20.5%, Q 0.7); (5-nitro-2-quinolyl) (2HCl, SN 9307, m. 245°, 33%, Q <0.07); (2-amino-4-pyrimidyl) (2HCl, SN 9591, m. 258°, 41%, Q 1.1); [2-(1-piperidyl)-4-pyrimidyl], SN 10,177, m. 156°, 31%, Q 0.4; (2-amino-6-methyl-4-pyrimidyl) (2HCl, m. 245°, 55%); (4-methoxy-2-benzothiazolyl) (2HCl, SN 11,189, m. 163°, 47%, Q <0.07); (6-chloro-2-methoxy-9-acridyl) (VIII), SN 8617, m. 175°, 50% (H2O, m. 117°; 2HCl, m. 280°, 76%, Q 4; 2HCl.2H2O, m. 180°); analogs of VIII: α-(ethylbutylamino) (2HCl, m. 252°, 36%, Q 5); α-dibutylamino (2HCl, SN 11,599, m. 246°, 69%, Q 2.5); α-diallylamino, SN 13,163, m. 158°, 16%, Q 0.5; α-dihexylamino (2HCl, m. 254°, 23%, Q 0.4); α-dioctylamino (2HCl, m. 285°, 20%, Q <0.06); α-1-piperidylamino (2HCl, SN 11,536, m. 287°, Q 0.6); α-hexylamino (2HCl.H2O, m. 226°, 7%, Q 1); α-(2-hydroxyethylamino) (2HCl.H2O, SN 11,233, m. 284°, 90%, Q 0.2); α-benzamido (HCl.0.5H2O, SN 11,589, m. 294°, 95%, Q <0.04). 5-(6-Chloro-2-methoxy-9-acridylamino)-α-diethylamino-ο-cresol (2HCl.0.5H2O, SN 9614, m. 237°, 50%, Q 1); 4-tert-butyl-6-(6-chloro-2-methoxy-9-acridylamino)-α-diethylamino-ο-cresol (IX) (2HCl, SN 11,544, m. 271°, 98%, Q 0.6); 4-Ph analog of IX (2HCl, SN 11,553, m. 274°, 84%, Q 0.5); 4-diethylaminomethyl analog of IX (3HCl.H2O, SN 11,550, m. 257°, 73%, Q 2); 6-allyl-4-(6-chloro-2-methoxy-9-acridylamino)-α-diethylaminο-ο-cresol (X) (2HCl, SN 11,234, m. 233°, 65%, Q 3); α-diallylamino analog of X (2HCl.H2O, SN 13,399, m. 188°, 12%, Q 0.3); and α-1-piperidyl analog of X, SN 12,701, m. 164°, 44%, Q 2. A series of nitrobenzylamines was prepared by condensation of the nitrobenzyl chloride with the amine in absolute EtOH. During the course of this work, 2-(chloromethyl)-4-nitrophenetole,m. 72-5°, was obtained in 75% yield from the chloromethylation of 4-nitrophenetole. The nitrobenzylamines were reduced catalytically in absolute EtOH and the resulting aminobenzylamines without isolation were condensed with the chloroheterocycle. Thus were obtained: N,N-diethyl-3-nitrobenzylamine, b6 145-8°, 60%; 4-nitro isomer (XI) (HCl, m. 162°, 45%); analogs of XI: N,N-di-Pr (HCl, m. 138°, 68%); N-monoisopropyl (HCl, m. 232°, 82%); N-monoisobutyl (HCl, m. 214°, 64%). N,N-Diethyl-5-nitro-2-methoxybenzylamine (XII) (HCl, m. 178°, 72%); analogs of XII: N-monoisobutyl (HCl, m. 176°, 63%); N-monoamyl (HCl salt could not be separated from an impurity of AmNH2.HCl). N,N-Diethyl-5-nitro-2-ethoxybenzylamine (HCl, m. 182°, 56%). 3-(7-Chloro-4-quinolylamino)-N,N-diethylbenzylamine (2HCl.2H2O, SN 11,590, m. 128° (all these HCl salts m. with decomposition), 85%, Q 1); 4-(7-chloro-4-quinolylamino)-N,N-diethylbenzylamine (XIII) (2HCl, SN 12,455, m. 261°, Q 4); N,N-di-Pr analog of XIII (2HCl, m. 255°, 60%, Q 4); the N-monoisopropyl analog of XIII (2HCl salt, m. 303°, 23%, Q 10); N-monoisobutyl analog of XIII (2HCl.H2O, m. 288°, 76%); 5-(7-chloro-4-quinolylamino)-N,N-diethyl-2-methoxybenzylamine (XIV), m. 203°, 64%, Q 25; N-monoisobutyl analog of XIV (2HCl.0.25H2O, m. 194°, 76%, Q 17); N-monoamyl analog of XIV (2HCl, m. 288°, 42%, Q 15); 2-ethoxy analog of XIV (2HCl.2H2O, m. 247°, 73%, Q 8); 3-(6-chloro-2-methoxy-9-acridylamino)-N,N-diethylbenzylamine (XV) (2HCl.0.75H2O, SN 10,984, m. 278°, 55%, Q 0.5); the 4-substituted benzyl isomer of XV (2HCl.0.5H2O, SN 10,028, m. 260°, 92%, Q 0.4); and 5-(6-chloro-2-methoxy-9-acridylamino)-2-methoxy-N,N-diethylbenzylamine (2HCl.0.5H2O, m. 212°, 67%, Q 3). 6-Chloro-9-(4-hydroxyanilino)-2-methoxyacridine, m. 266° (decomposition) (HCl, orange, m. above 300°, prepared in 98% yield from p-NH2C6H4OH and 6,9-dichloro-2-methoxyacridine on the steam bath), failed to undergo the usual Mannich reaction. Failure of this reaction led to the development of the method of synthesis used for all of the heterocyclic derivatives reported in this paper. If you want to learn more about this compound(4-Chloro-8-methylquinoline)SDS of cas: 18436-73-2, you may wish to communicate with the author of the article,or consult the relevant literature related to this compound(18436-73-2).

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 4-Chloro-8-methylquinoline( cas:18436-73-2 ) is researched.Product Details of 18436-73-2.Calligaris, Mario; Illuminati, Gabriello; Marino, Gianlorenzo published the article 《Nucleophilic heteroaromatic substitution. XXVII. Piperidino dechlorination and methoxy dechlorination of 6- and 8-alkyl-4-chloroquinolines. Steric hindrance to specific solvation》 about this compound( cas:18436-73-2 ) in Journal of the American Chemical Society. Keywords: KINETICS PIPERIDINO DECHLORINATION; METHOXY DECHLORINATION; PIPERIDINO DECHLORINATION KINETICS; DECHLORINATION PIPERIDINO KINETICS; SOLVATION. Let’s learn more about this compound (cas:18436-73-2).

Kinetic data for the reaction of 6- and 8-alkyl-substituted 4-chloroquinolines with piperidine in four different solvents and with NaOMe in MeOH were obtained and compared. The tert-butyl group located at the position peri to the aza group is found to cause rate-depressing effects and significant increases in the energy and entropy of activation when the solvent is hydroxylic (methanol) whereas only minor changes are observed in aprotic or poor proton-donor solvents (toluene, HCONMe2, and piperidine). The results are interpreted in terms of steric inhibition of specific solvation (H bonding). 15 references.

If you want to learn more about this compound(4-Chloro-8-methylquinoline)Product Details of 18436-73-2, you may wish to communicate with the author of the article,or consult the relevant literature related to this compound(18436-73-2).

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Nucleophilic heteroaromatic substitution. XXVII. Piperidino dechlorination and methoxy dechlorination of 6- and 8-alkyl-4-chloroquinolines. Steric hindrance to specific solvation》. Authors are Calligaris, Mario; Illuminati, Gabriello; Marino, Gianlorenzo.The article about the compound:4-Chloro-8-methylquinolinecas:18436-73-2,SMILESS:CC1=C2N=CC=C(Cl)C2=CC=C1).Reference of 4-Chloro-8-methylquinoline. Through the article, more information about this compound (cas:18436-73-2) is conveyed.

Kinetic data for the reaction of 6- and 8-alkyl-substituted 4-chloroquinolines with piperidine in four different solvents and with NaOMe in MeOH were obtained and compared. The tert-butyl group located at the position peri to the aza group is found to cause rate-depressing effects and significant increases in the energy and entropy of activation when the solvent is hydroxylic (methanol) whereas only minor changes are observed in aprotic or poor proton-donor solvents (toluene, HCONMe2, and piperidine). The results are interpreted in terms of steric inhibition of specific solvation (H bonding). 15 references.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

COA of Formula: C10H8ClN. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 4-Chloro-8-methylquinoline, is researched, Molecular C10H8ClN, CAS is 18436-73-2, about Synthesis of bicyclic N-arylmethyl-substituted iminoribitol derivatives as selective nucleoside hydrolase inhibitors. Author is Berg, Maya; Bal, Gunther; Goeminne, Annelies; Van der Veken, Pieter; Versees, Wim; Steyaert, Jan; Haemers, Achiel; Augustyns, Koen.

The purine metabolism of Trypanosoma and Leishmania spp. provides a good target in the search for new selective drugs. Bicyclic N-arylmethyl-substituted iminoribitols were developed as inhibitors of T. vivax nucleoside hydrolase, a key enzyme of the purine salvage pathway. The obtained results and structure-activity data confirmed our model for inhibitor binding with a hydrogen bond between a nitrogen atom of the nucleobase mimetic and the protonated Asp40 from the enzyme. This interaction depends on an optimal pKa value, which can be influenced by the electronic properties of the substituents. These compounds are potent, selective inhibitors of nucleoside hydrolase and are inactive toward human nucleoside phosphorylase.

Here is a brief introduction to this compound(18436-73-2)COA of Formula: C10H8ClN, if you want to know about other compounds related to this compound(18436-73-2), you can read my other articles.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 18436-73-2. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 4-Chloro-8-methylquinoline, is researched, Molecular C10H8ClN, CAS is 18436-73-2, about A mild and efficient method for the preparation of 3-(2′-aminoaryl)pyrazoles from 4-chloroquinolines. Author is Borges, Julio C.; de Oliveira, Cesar D.; da Silva Pinheiro, Luiz C.; Marra, Roberta K. F.; Khan, Misbahul Ain; Wardell, James L.; Wardell, Solange M. S. V.; Bernardino, Alice M. R..

The authors described a mild and efficient method for the formation of 3-(2′-aminoaryl)pyrazoles in excellent yields from reactions of 4-chloroquinolines with hydrazine. These heterocyclic ring opening reactions occur under much milder conditions then previously described. The structures of the compounds were determined by spectral data and confirmed by x-ray diffraction anal. of 3-(2′-amino-3′-methylphenyl)pyrazole [monoclinic, C2, a 25.9750(3), b 9.5820(6), c 7.8299(7) Å, β 107.541(3)°, V 1858.2(2) Å3, Z 8].

Here is a brief introduction to this compound(18436-73-2)Related Products of 18436-73-2, if you want to know about other compounds related to this compound(18436-73-2), you can read my other articles.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Aminoalkylphenols as antimalarials. II. (Heterocyclic amino)-α-amino-ο-cresols. The synthesis of camoquin》. Authors are Burckhalter, J. H.; Tendick, F. H.; Jones, Eldon M.; Jones, Patricia A.; Holcomb, W. F.; Rawlins, A. L..The article about the compound:4-Chloro-8-methylquinolinecas:18436-73-2,SMILESS:CC1=C2N=CC=C(Cl)C2=CC=C1).Recommanded Product: 4-Chloro-8-methylquinoline. Through the article, more information about this compound (cas:18436-73-2) is conveyed.

In view of the high antimalarial activity of certain substituted α-amino-ο-cresols, earlier work (C.A. 41, 414d) has been extended to analogs containing heterocyclic nuclei. This reports the preparation of a group of 122 (heterocyclic amino)-α-amino-ο-cresols and a related group of 12 (heterocyclic amino)benzylamines, as well as the new intermediates used therein. This work has resulted in the preparation of a promising antimalarial (SN 10,751) named camoquin, as well as other compounds which are the most active 4-aminoquinoline derivatives heretofore reported in trophozoite-induced Plasmodium gallinaceum infection in the chick. Catalytic reduction of the appropriate nitrophenol in the presence of Ac2O gave these 4-acetamidophenols: 2-Cl, m. 144°, 55% yield; 2-Ph, m. 160°, 60%; and 2-acetamidophenols: 4-Cl, m. 186°, 52%; 4-Ph, m. 165°, 89%; and 4-tert-Bu, m. 170°, 79%. 2-Allyl-4-acetamidophenol, m. 93-4°, was obtained in 83% yield from the rearrangement of 4-CH2:CHCH2OC6H4NHAc. The Mannich reaction on the substituted acetamidophenols gave these 4-acetamido-α-substituted-ο-cresols: diethylamino (I), m. 135°, 82%; dibutylamino, m. 73°, 87% (picrate, m. 183-5°); dibenzylamino, m. 230°, 75%; (2-methyl-1-piperidyl) (HCl.H2O, m. 175°, 65%); 4-morpholinyl, m. 133°, 27%; [methyl(2-hydroxyethyl)amino] (HCl, m. 198°, 50%); (2-butylamino), m. 156°, 37%; (2-hydroxyethylamino) (HCl, m. 230°, 31%); the 6-allyl derivative of I, m. 86°, 58%: the 5-acetamido isomer of I (HCl, m. 210°, 33%); and these 6-acetamido-α-diethylamino-4-substituted-ο-cresols: Cl (HCl, m. 212°, 66%); tert-Bu (HCl, m. 158°, 53%); and Ph (HCl, m. 183°). Acid hydrolysis of the appropriate 4-acetamido compound gave these 4-amino-α-substituted-ο-cresols (di-HCl salts) (all m. with decomposition); diethylamino, SN 12,458, m. 218-20°, 96%; 1-piperidyl, m. 153-5°, 91%; and 4-morpholinyl, m. 259-60°, 45%. The Mannich reaction on 4-nitrophenol (A) and the reaction of the amine on 2-(chloromethyl)-4-nitrophenol (B) were used to prepare these α-substituted-4-nitro-ο-cresol HCl salts (all m. with decomposition): diethylamino, A, m. 224°, 40%; diisopropylamino, B, m. 193°, 19%; dibutylamino, B, m. 176°, 75%; diisobutylamino (free base), B, m. 113°, 43%; diisoamylamino, B, m. 132°, 32%; isopropylamino, B, m. 238°, 38%; isobutylamino, B, m. 247°, 29%; tertbutylamino, B, m. 275°, 20%; 1-piperidyl, A, m. 260°, 68%; and α-diethylamino-4-nitro-6-phenyl-ο-cresol, A, m. 125°, 21%; and 4-tert-butyl-α-diethylamino-6-nitro-ο-cresol, A, m. 103°, 50%. The method of Price and Roberts (C.A. 40, 5739.5) was used to prepare these substituted 4-chloroquinolines: 6-Me, m. 55°, 50%; 6-anilino, m. 148°, 6%; 7-EtO, m. 76°, 53%; 7-hexyloxy, a high-boiling liquid, 41%; 8-Me, m. 99°, 71%; 5,7-di-Me, m. 59°, 51%; 5,8-di-Me, m. 51°, 59%; 5-chloro-8-methoxy, m. 127°, 6%; 5-methyl-8-methoxy, m. 78°, 45%; 6,8-di-Me, m. 90°, 82%; and 6,7,8-trichloro, m. 156°, 39%. The (heterocyclic amino)-α-alkylamino-ο-cresols were prepared by minor variations of the general procedure of heating the chloroheterocycle with the amino-α-alkylamino-ο-cresols in aqueous or alc. solution on the steam bath. The latter were obtained either by acid hydrolysis of the acetamido derivatives or by catalytic reduction of the nitro derivatives and were usually condensed without isolation. The products are isolated either as the free bases or HCl salts. All the quinine equivalents (Q) reported here are based on the B4 test using P. gallinaceum in the chick. Nearly all the HCl salts m. with decomposition and are colored yellow to orange. 4-(4-Quinolylamino)-α-diethylamino-ο-cresol (II) di-HCl, SN 12,452, m. above 300°, was obtained in 48% yield and had a quinine equivalent of 3 (designated hereafter in the form Q 3). Analogs of II, substituted on the quinoline nucleus: 2-Cl (2HCl, SN 11,986, m. 248°, 30%, Q <0.07); 3-Ph, SN 11,631, m. 155°, 31%, Q 0.4; 6-MeO (2HCl, SN 10,274, m. 270°, 75%, Q 8); 6-Cl (HCl.0.5H2O, SN 11,597, m. 220°, 60%, Q 3.0); 6-Me, SN 11,559, m. 172° (2HCl, m. 238°, 56%, Q 4); 6-anilino (2HCl.H2O, SN 12,361, m. 196°, 63%, Q 0.2); 6-dimethylamino (3HCl.0.5H2O, SN 11,984, m. 235°, 73%, Q 2.5); 6-nitro (2HCl.1.5H2O, m. 210°, 63%, Q 0.8); 7-MeO (2HCl.0.5H2O, SN 11,554, m. 210°, 43%, Q 7); 7-EtO (2HCl.2H2O, SN 11,281, m. 136°, 44%, Q 7); (7-hexyloxy, SN 11,634, m. 153°, 35%, Q 0.5; Q 7); 7-Me (2HCl, SN 12,699, m. 245°, 93%, Q 9); 7-Cl (camoquin) SN 10,751, m. 208°, 86%, Q 25 (2HCl.0.5H2O, m. 243°); 2HCl.H2O, m. 183°; (2HCl.2H2O, m. 160°, 90%); 8-Cl, SN 11,551, m. 212° (2HCl.0.5H2O, m. 253°, 79%, Q 0.5); 8-MeO (2HCl.1.5H2O, SN 11,594, m. 241°, 50%, Q 0.8); 8-Me (2HCl.H2O, SN 11,601, m. 253°, 66%, Q 0.7); 5-chloro-3-Me (2HCl, SN 11,985, m. 258°, 48%, Q 0.3); 5,7-di-Cl (2HCl, SN 12,700, m. 200°, 65%, Q 3); 5,7-di-Me (2HCl, SN 11,561, m. 242°, 67%, Q 10); 5,8-di-Cl (2HCl.H2O, SN 11,596, m. 235°, 60%, Q 0.25); 5,8-di-Me (2HCl, SN 11,560, m. 249°, 80%, Q 0.6); 5-chloro-8-methoxy [2HCl, SN 12,162,(incorrectly given as 12,161 in original), m. 231°, 80%, Q 0.4]; 6-methoxy-2-Me (2HCl, SN 9223, m. 278°, 45%, Q 1.2); 6-methoxy-2-Ph (2HCl.1.75H2O, SN 11,592, m. 198°, 61%, Q 0.25); 6,7-di-Cl (2HCl, SN 12,161, m. 257°, 71.5%, Q 5); 6,7-di-MeO (2HCl, SN 13,395, m. 258°, 68%, Q 2.5); 6,7-di-Me, SN 11,990, m. 215°, 49%, Q 6; 6,8-di-Me (2HCl.H2O, SN 11,558, m. 264°, 54%, Q 0.6); 7-chloro-2-Ph (2HCl, SN 11,232, m. 260°, 41%, Q 0.3); 7-chloro-3-Ph, SN 12,228, m. 165°, Q 1; 7-chloro-3-Me (2HCl, SN 10,492, m. 260°, 64%, Q 6); 8-methoxy-5-Me (2HCl, SN 11,632, m. 210°, 90%, Q 0.6); 6,7,8-tri-Cl (2HCl, SN 11,633, m. 277°, 40%, Q <0.3); and 6-HO (2HCl, SN 11,563, m. 262°, 64%, Q 0.2) (prepared by HBr demethylation of the 6-MeO derivative). 4-(6-Methoxy-4-quinolylamino)-α-dibutylamino-ο-cresol (III) (2HCl.1.25H2O, m. 193°, 10%, Q 9); the (7-chloro-3-methyl-4-quinolylamino) analog of III (2HCl.1.5H2O, m. 177°, 43%, Q 10). 4-(6-Methoxy-4-quinolylamino)-α-1-piperidyl-ο-cresol (IV) (2HCl.0.5H2O, SN 12,038, m. 270°, 80%, Q 8); analogs of IV: (6,7-dimethoxy-4-quinolylamino) (2HCl, SN 13,413, m. 230°, 40%, Q 4); (7-chloro-3-methyl-4-quinolylamino) (2HCl, SN 12,360, m. 270°, 47%, Q 2); (6-methyl-4-quinolylamino) (2HCl, SN 12,456, m. 240°, 41%, Q 2.5). 4-(6-Methoxy-4-quinolylamino)-α-4-morpholinyl-ο-cresol (V) (2HCl, SN 11,989, m. 265°, 57%, Q 1); analogs of V: (7-chloro-3-methyl-4-quinolylamino) (2HCl, SN 12,362, m. 242°, 33%, Q 0.15); (6-methyl-4-quinolylamino), SN 12,457, m. 239°, 50%, Q 0.8. 5-(7-Chloro-4-quinolylamino)-α-diethylamino-ο-cresol, SN 13,730, m. 173°, Q 9; 6-(7-chloro-4-quinolylamino)-α-diethylamino-4-(diethylaminomethyl)-ο-cresol-1.5H2O, m. 145°, Q 5; 4-chloro-α-diethylamino-6-(6-methoxy-4-quinolylamino)-ο-cresol (2HCl, SN 12,885, m 205°, 50%, Q 0.5). 6-Chloro-4-(7-chloro-4-quinolylamino)-α-diethylamino-ο-cresol (VI), SN 13,729, m. 225°, Q 12; analogs of VI: 6-Ph (0.5H2O, m. 235°, 25%); 6-allyl, SN 11,991, m. 148°, 44%, Q 10; 6-allyl-α-1-piperidyl, SN 12,697, m. 190°, 32%, Q 4; 6-allyl-α-diallylamino, SN 13,394, m. 131°, 25%, Q 0.7. 6-Allyl-α-diethylamino-4-(6-methoxy-4-quinolylamino)-ο-cresol, SN 12,039, m. 161°, 33%, Q 7. Variations of the alkylamino group on the cresol portion of camoquin were studied: α-amino-4-(7-chloro-4-quinolylamino)-ο-cresol (VII) (2HCl.0.5H2O, SN 1603, m. 325°, 80%, Q 6); analogs of VII (substituents on the α-amino group): benzoyl (HCl, SN. 11,557, m. 289°, 80%, Q 0.15); Et (2HCl, m. 280°, Q 40, 4% conversion, prepared by the Mannich reaction of EtNH2, (HCHO)x, and 7-chloro-4-(4-hydroxyanilino)quinoline (HCl, m. above 320°, 94%)); Pr(2HCl.0.5H2O, m. 244°, 24%, Q 30); iso-Pr (2HCl, m. 287° 50%, Q 40); Bu (2HCl, m. 254°, 6%, Q 30); sec-Bu (2HCl.H2O, m. 252°, 3%, Q 50); iso-Bu (2HCl, m. 256°, 65%, Q 75); tert-Bu (2HCl, m. 285°, 36%, Q 40); Am (2HCl, m. 266°, 15%, Q 50); (1-methylbutyl 2HCl, m. 231°, 22%, Q 40); iso-Am (2HCl, m. 279°, 20%, Q 50); hexyl (2HCl, m. 280°, 56%, Q 25); (2-ethylbutyl (2HCl, m. 263°, 15%, Q 50)); heptyl (2HCl, m. 278°, 29%, Q 15); octyl, m. 150°, 15%, Q 2.5; allyl (2HCl, m. 257°, 3%, Q 20); 1-methylallyl (2HCl.1.75H2O, m. 95°); cyclohexyl (2HCl.0.25H2O, m. 252°, 30%, Q 30); 2-hydroxyethyl (2HCl.H2O, m. 182°, 15%, Q 3); 2-methoxyethyl (2HCl, m. 271°, Q 25); benzyl (2HCl, m. 270°, Q 16); (α-methylphenethyl) (2HCl.0.25H2O, m. 243°, 31%, Q 25); di-Me (2HCl, m. 290°, 85%, Q 6); N-ethyl-N-butyl(2HCl, m. 240°, 65%, Q 30); di-Pr, SN 13,835, m. 181°, 11%, Q 25; di-Bu, SN 14,105, m. 164°, 20%, Q 35; diiso-Bu (0.5H2O, m. 166°, 38%); diiso-Am (0.5H2O, m. 135°); dihexyl (2HCl, m. 220°, 40%, Q 0.5); diheptyl (2HCl, m. 203°, 52%, Q 1); dioctyl (2HCl, m. 192°, 46%, Q 0.2); bis(2-ethylhexyl) (2HCl.H2O, m. 154°, 1%, Q 3); methyl(2-hydroxyethyl) (2HCl, SN 12,363, m. 250°, 63%, Q 3); butyl(2-hydroxyethyl), SN 14,824, m. 149°, 22%, Q 12; bis(2-hydroxyethyl), m. 193°, 25%, Q 0.6; dibenzyl (2HCl, m. 235°, 74%, Q 2.5); N-methyl-N-Ph (H2O, m. 140°, 39%, Q 0.07); N-ethyl-N-Ph, m. 131°, 54%, Q <0.05. Further analogs of VII: α-1-piperidyl (2HCl.2.5H2O, SN 11,636, m. 302°, 77.5%, Q 25); α-(2-methyl-1-piperidyl) (2HCl, SN 12,357, m. 288°, 66%, Q 20); α-4-morpholinyl (2HCl, SN 11,987, m. 292°, 60-5%, Q 4). Compounds containing heterocyclic nuclei other than the 4-quinolyl include the following 4-(heterocyclic amino)-α-diethylamino-ο-cresols: 9-acridyl (2HCl, SN 12,356, m. 265°, 45%, Q 1.5); (3-chloro-9-acridyl) (2HCl, SN 12,355, m. 267°, 52%, Q 3); (4-methoxy-9-acridyl) (2HCl, SN 12,164, m. 245°, 50%, Q 0.15); (3-chloro-5-methyl-9-acridyl) (2HCl, SN 11,988, m. 275°, 40%, Q 0.25); 2-quinolyl (2HCl, SN 9559, m. 230°, 48%, Q 0.12); (6-methoxy-2-quinolyl) (2HCl, SN 11,537, m. 237°, 20.5%, Q 0.7); (5-nitro-2-quinolyl) (2HCl, SN 9307, m. 245°, 33%, Q <0.07); (2-amino-4-pyrimidyl) (2HCl, SN 9591, m. 258°, 41%, Q 1.1); [2-(1-piperidyl)-4-pyrimidyl], SN 10,177, m. 156°, 31%, Q 0.4; (2-amino-6-methyl-4-pyrimidyl) (2HCl, m. 245°, 55%); (4-methoxy-2-benzothiazolyl) (2HCl, SN 11,189, m. 163°, 47%, Q <0.07); (6-chloro-2-methoxy-9-acridyl) (VIII), SN 8617, m. 175°, 50% (H2O, m. 117°; 2HCl, m. 280°, 76%, Q 4; 2HCl.2H2O, m. 180°); analogs of VIII: α-(ethylbutylamino) (2HCl, m. 252°, 36%, Q 5); α-dibutylamino (2HCl, SN 11,599, m. 246°, 69%, Q 2.5); α-diallylamino, SN 13,163, m. 158°, 16%, Q 0.5; α-dihexylamino (2HCl, m. 254°, 23%, Q 0.4); α-dioctylamino (2HCl, m. 285°, 20%, Q <0.06); α-1-piperidylamino (2HCl, SN 11,536, m. 287°, Q 0.6); α-hexylamino (2HCl.H2O, m. 226°, 7%, Q 1); α-(2-hydroxyethylamino) (2HCl.H2O, SN 11,233, m. 284°, 90%, Q 0.2); α-benzamido (HCl.0.5H2O, SN 11,589, m. 294°, 95%, Q <0.04). 5-(6-Chloro-2-methoxy-9-acridylamino)-α-diethylamino-ο-cresol (2HCl.0.5H2O, SN 9614, m. 237°, 50%, Q 1); 4-tert-butyl-6-(6-chloro-2-methoxy-9-acridylamino)-α-diethylamino-ο-cresol (IX) (2HCl, SN 11,544, m. 271°, 98%, Q 0.6); 4-Ph analog of IX (2HCl, SN 11,553, m. 274°, 84%, Q 0.5); 4-diethylaminomethyl analog of IX (3HCl.H2O, SN 11,550, m. 257°, 73%, Q 2); 6-allyl-4-(6-chloro-2-methoxy-9-acridylamino)-α-diethylaminο-ο-cresol (X) (2HCl, SN 11,234, m. 233°, 65%, Q 3); α-diallylamino analog of X (2HCl.H2O, SN 13,399, m. 188°, 12%, Q 0.3); and α-1-piperidyl analog of X, SN 12,701, m. 164°, 44%, Q 2. A series of nitrobenzylamines was prepared by condensation of the nitrobenzyl chloride with the amine in absolute EtOH. During the course of this work, 2-(chloromethyl)-4-nitrophenetole,m. 72-5°, was obtained in 75% yield from the chloromethylation of 4-nitrophenetole. The nitrobenzylamines were reduced catalytically in absolute EtOH and the resulting aminobenzylamines without isolation were condensed with the chloroheterocycle. Thus were obtained: N,N-diethyl-3-nitrobenzylamine, b6 145-8°, 60%; 4-nitro isomer (XI) (HCl, m. 162°, 45%); analogs of XI: N,N-di-Pr (HCl, m. 138°, 68%); N-monoisopropyl (HCl, m. 232°, 82%); N-monoisobutyl (HCl, m. 214°, 64%). N,N-Diethyl-5-nitro-2-methoxybenzylamine (XII) (HCl, m. 178°, 72%); analogs of XII: N-monoisobutyl (HCl, m. 176°, 63%); N-monoamyl (HCl salt could not be separated from an impurity of AmNH2.HCl). N,N-Diethyl-5-nitro-2-ethoxybenzylamine (HCl, m. 182°, 56%). 3-(7-Chloro-4-quinolylamino)-N,N-diethylbenzylamine (2HCl.2H2O, SN 11,590, m. 128° (all these HCl salts m. with decomposition), 85%, Q 1); 4-(7-chloro-4-quinolylamino)-N,N-diethylbenzylamine (XIII) (2HCl, SN 12,455, m. 261°, Q 4); N,N-di-Pr analog of XIII (2HCl, m. 255°, 60%, Q 4); the N-monoisopropyl analog of XIII (2HCl salt, m. 303°, 23%, Q 10); N-monoisobutyl analog of XIII (2HCl.H2O, m. 288°, 76%); 5-(7-chloro-4-quinolylamino)-N,N-diethyl-2-methoxybenzylamine (XIV), m. 203°, 64%, Q 25; N-monoisobutyl analog of XIV (2HCl.0.25H2O, m. 194°, 76%, Q 17); N-monoamyl analog of XIV (2HCl, m. 288°, 42%, Q 15); 2-ethoxy analog of XIV (2HCl.2H2O, m. 247°, 73%, Q 8); 3-(6-chloro-2-methoxy-9-acridylamino)-N,N-diethylbenzylamine (XV) (2HCl.0.75H2O, SN 10,984, m. 278°, 55%, Q 0.5); the 4-substituted benzyl isomer of XV (2HCl.0.5H2O, SN 10,028, m. 260°, 92%, Q 0.4); and 5-(6-chloro-2-methoxy-9-acridylamino)-2-methoxy-N,N-diethylbenzylamine (2HCl.0.5H2O, m. 212°, 67%, Q 3). 6-Chloro-9-(4-hydroxyanilino)-2-methoxyacridine, m. 266° (decomposition) (HCl, orange, m. above 300°, prepared in 98% yield from p-NH2C6H4OH and 6,9-dichloro-2-methoxyacridine on the steam bath), failed to undergo the usual Mannich reaction. Failure of this reaction led to the development of the method of synthesis used for all of the heterocyclic derivatives reported in this paper. In some applications, this compound(18436-73-2)Recommanded Product: 4-Chloro-8-methylquinoline is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 4-Chloro-8-methylquinoline. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 4-Chloro-8-methylquinoline, is researched, Molecular C10H8ClN, CAS is 18436-73-2, about Hypoxia-selective antitumor agents. 6. 4-(Alkylamino)nitroquinolines: a new class of hypoxia-selective cytotoxins.

A series of isomeric 4-[[3-(dimethylamino)propyl]amino]nitroquinolines, e.g., I [Rn = H, 3-, 5-, 6-, 7-, 8-NO2, 2,5-Me(O2N), 3,5-Me(O2N), 6,5-Me(O2N), 8,5-Me(O2N), 7,8-Me(O2N), 7,6-Me(O2N), 2,3-Me(O2N)], has been synthesized and evaluated as hypoxia-selective cytotoxins and as radiosensitizers of hypoxic cells. The compounds showed widely-differing hypersensitivity factors (ratios of cytotoxicity against wild-type and repair-deficient mammalian cells). Many compounds showed oxygen-sensitive bioreduction resulting in DNA alkylation, while others show oxygen-insensitive modes of action. Of the nitro isomers studied, the 5-nitro showed the greatest hypoxic selectivity. A series of ring-substituted analogs were then prepared, in an effort to lower its reduction potential of -286 mV. Structure-activity studies showed that the effects of substitution on reduction potential were complex, being mediated by electronic and steric effects on the nitro group, as well as by effects on quinoline pKa. Two compounds of lower reduction potential, the 3- and 8-Me analogs, showed improved selectivity (47- and 60-fold in a clonogenic assay). These two compounds also showed the highest in vitro therapeutic indexes of the series as hypoxic cell radiosensitizers. Despite these favorable in vitro properties, neither compound had activity against hypoxic cells in SCCVII tumors when administered at 60% of the maximum tolerated dose.

In some applications, this compound(18436-73-2)Reference of 4-Chloro-8-methylquinoline is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Formula: C10H8ClN. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 4-Chloro-8-methylquinoline, is researched, Molecular C10H8ClN, CAS is 18436-73-2, about Synthesis of bicyclic N-arylmethyl-substituted iminoribitol derivatives as selective nucleoside hydrolase inhibitors.

The purine metabolism of Trypanosoma and Leishmania spp. provides a good target in the search for new selective drugs. Bicyclic N-arylmethyl-substituted iminoribitols were developed as inhibitors of T. vivax nucleoside hydrolase, a key enzyme of the purine salvage pathway. The obtained results and structure-activity data confirmed our model for inhibitor binding with a hydrogen bond between a nitrogen atom of the nucleobase mimetic and the protonated Asp40 from the enzyme. This interaction depends on an optimal pKa value, which can be influenced by the electronic properties of the substituents. These compounds are potent, selective inhibitors of nucleoside hydrolase and are inactive toward human nucleoside phosphorylase.

In some applications, this compound(18436-73-2)Formula: C10H8ClN is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia