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Kawakami, Hiroshi’s team published research in Heterocycles in 1991 | CAS: 122567-97-9

((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9) belongs to pyrimidine. Pyrimidine nucleotide derivatives have a wide range of biological applications. For example, pyrimidine derivatives are useful in DNA repair studies involving cancer and epigenetics.Formula: C17H16N2O5

Kawakami, Hiroshi; Ebata, Takashi; Koseki, Koshi; Matsumoto, Katsuya; Matsushita, Hajime; Naoi, Yoshitake; Itoh, Kazuo published their research in Heterocycles on December 1 ,1991. The article was titled 《Synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides utilizing coupling reactions between nucleic bases and phenylthio-substituted 2,3-dideoxyribose》.Formula: C17H16N2O5 The article contains the following contents:

Stereoselectivities in coupling reactions between silylated pyrimidine bases I (X = O, R = H, Me; X = NAc, R = H) and 3- or 2-α-phenylthio-2,3-dideoxyribose derivatives, e.g., II (R1 = Cl, OAc) and III, resp., was examined In the former case, no stereoselectivities were observed when the coupling reactions were performed either with 1-chloro sugar in an SN2 mode or in the presence of Lewis acids as catalyst in an SN1 mode. Coupling reaction with 2-α-phenylthio-2,3-dideoxyribose in the presence of Lewis acids, especially SnCl4, proceeded with good stereoselectivity to give anomeric mixtures of nucleosides, e.g. IV, α:β = 1:9. All these nucleosides were converted to 2′,3′-didehydro-2′,3′-dideoxynucleosides, such as V, by oxidation to sulfoxides followed by thermal elimination of sulfenic acid. In the experimental materials used by the author, we found ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9Formula: C17H16N2O5)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

De Abrew, K. Nadira’s team published research in Toxicology in 2019 | CAS: 213743-31-8

7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine(cas: 213743-31-8) belongs to pyrimidine. Pyrimidine nucleotide derivatives have a wide range of biological applications. For example, pyrimidine derivatives are useful in DNA repair studies involving cancer and epigenetics.Application In Synthesis of 7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

De Abrew, K. Nadira; Shan, Yuqing K.; Wang, Xiaohong; Krailler, Jesse M.; Kainkaryam, Raghunandan M.; Lester, Cathy C.; Settivari, Raja S.; LeBaron, Matthew J.; Naciff, Jorge M.; Daston, George P. published an article in Toxicology. The title of the article was 《Use of connectivity mapping to support read across: A deeper dive using data from 186 chemicals, 19 cell lines and 2 case studies》.Application In Synthesis of 7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine The author mentioned the following in the article:

The authors previously demonstrated that the Connectivity Map (CMap) (Lamb et al., 2006) concept can be successfully applied to a predictive toxicol. paradigm to generate meaningful MoA-based connections between chems. (De Abrew et al., 2016). Here the authors expand both the chem. and biol. (cell lines) domain for the method and demonstrate two applications, both in the area of read across. In the first application the authors demonstrate CMap’s utility as a tool for testing biol. relevance of source chems. (analogs) during a chem. led read across exercise. In the second application CMap can be used to identify functionally relevant source chems. (analogs) for a structure of interest (SOI)/target chem. with minimal knowledge of chem. structure. Finally, the authors highlight four factors: promiscuity of chem., dose, cell line and timepoint as having significant impact on the output. The authors discuss the biol. relevance of these four factors and incorporate them into a work flow. The experimental part of the paper was very detailed, including the reaction process of 7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine(cas: 213743-31-8Application In Synthesis of 7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Chen, Bang-Chi’s team published research in Tetrahedron Letters in 1998 | CAS: 122567-97-9

Chen, Bang-Chi; Quinlan, Sandra L.; Reid, J. Gregory; Spector, Richard H. published an article on February 19 ,1998. The article was titled 《A new thymine free synthesis of the anti-AIDS drug d4T via regio/stereo controlled β-elimination of bromoacetates》, and you may find the article in Tetrahedron Letters.Formula: C17H16N2O5 The information in the text is summarized as follows:

The anti-AIDS drug d4T was prepared without contamination of the nucleoside bond cleaved byproduct thymine from the readily available ribonucleoside 5-methyluridine. This was accomplished by using a new strategy which involved a regio/stereo controlled β-elimination of trans-bromoacetates. The experimental process involved the reaction of ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9Formula: C17H16N2O5)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Chen, Bang-Chi’s team published research in Tetrahedron Letters in 1995 | CAS: 122567-97-9

Recommanded Product: ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoateOn October 30, 1995 ,《5′-Benzoyl-2’α-bromo-3′-O-methanesulfonylthymidine: a superior nucleoside for the synthesis of the anti-AIDS drug D4T (stavudine)》 was published in Tetrahedron Letters. The article was written by Chen, Bang-Chi; Quinlan, Sandra L.; Stark, Derron R.; Reid, J. Gregory; Audia, Vicki H.; George, Jacqueline G.; Eisenreich, Emerich; Brundidge, Steve P.; Racha, Saibaba; Spector, Richard H.. The article contains the following contents:

The anti-AIDS drug d4T is prepared in 75% overall yield starting from the readily available ribonucleoside 5-methyluridine. The key step in this new synthesis is the zinc-induced reductive elimination of the bromomesylate I, which affords d4T without nucleoside bond cleavage. A facile procedure for the deprotection/isolation of this highly water soluble product is also described. After reading the article, we found that the author used ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9Recommanded Product: ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Xie, Ting’s team published research in Nature Chemical Biology in 2014 | CAS: 213743-31-8

Xie, Ting; Lim, Sang Min; Westover, Kenneth D.; Dodge, Michael E.; Ercan, Dalia; Ficarro, Scott B.; Udayakumar, Durga; Gurbani, Deepak; Tae, Hyun Seop; Riddle, Steven M.; Sim, Taebo; Marto, Jarrod A.; Janne, Pasi A.; Crews, Craig M.; Gray, Nathanael S. published their research in Nature Chemical Biology on December 31 ,2014. The article was titled 《Pharmacological targeting of the pseudokinase Her3》.Application of 213743-31-8 The article contains the following contents:

Her3 (also known as ErbB3) belongs to the epidermal growth factor receptor tyrosine kinases and is well credentialed as an anti-cancer target but is thought to be ‘undruggable’ using ATP-competitive small mols. because it lacks appreciable kinase activity. Here we report what is to our knowledge the first selective Her3 ligand, TX1-85-1, that forms a covalent bond with Cys721 located in the ATP-binding site of Her3. We demonstrate that covalent modification of Her3 inhibits Her3 signaling but not proliferation in some Her3-dependent cancer cell lines. Subsequent derivatization with a hydrophobic adamantane moiety demonstrates that the resultant bivalent ligand (TX2-121-1) enhances inhibition of Her3-dependent signaling. Treatment of cells with TX2-121-1 results in partial degradation of Her3 and serendipitously interferes with productive heterodimerization between Her3 with either Her2 or c-Met. These results suggest that small mols. will be capable of perturbing the biol. function of Her3 and ∼60 other pseudokinases found in human cells. The results came from multiple reactions, including the reaction of 7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine(cas: 213743-31-8Application of 213743-31-8)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Deschamps, Joshua D.’s team published research in Biochemistry in 2016 | CAS: 213743-31-8

COA of Formula: C23H22N4OOn June 14, 2016, Deschamps, Joshua D.; Ogunsola, Abiola F.; Jameson, J. Brian; Yasgar, Adam; Flitter, Becca A.; Freedman, Cody J.; Melvin, Jeffrey A.; Nguyen, Jason V. M. H.; Maloney, David J.; Jadhav, Ajit; Simeonov, Anton; Bomberger, Jennifer M.; Holman, Theodore R. published an article in Biochemistry. The article was 《Biochemical and Cellular Characterization and Inhibitor Discovery of Pseudomonas aeruginosa 15-Lipoxygenase》. The article mentions the following:

Pseudomonas aeruginosa is an opportunistic pathogen that can cause nosocomial and chronic infections in immunocompromised patients. P. aeruginosa secretes a lipoxygenase, LoxA, but the biol. role of this enzyme is currently unknown. LoxA is poorly similar in sequence to both soybean LOX-1 (s15-LOX-1) and human 15-LOX-1 (37 and 39%, resp.) yet has kinetics comparably fast vs. those of s15-LOX-1 (at pH 6.5, Kcat = 181 ± 6 s-1 and Kcat/KM = 16 ± 2 μM-1 s-1). LoxA is capable of efficiently catalyzing the peroxidation of a broad range of free fatty acid (FA) substrates (e.g., AA and LA) with high positional specificity, indicating a 15-LOX. Its mechanism includes hydrogen atom abstraction [a kinetic isotope effect (KIE) of >30], yet LoxA is a poor catalyst against phosphoester FAs, suggesting that LoxA is not involved in membrane decomposition LoxA also does not react with 5- or 15-HETEs, indicating poor involvement in lipoxin production A LOX high-throughput screen of the LOPAC library yielded a variety of low-micromolar inhibitors; however, none selectively targeted LoxA over the human LOX isoenzymes. With respect to cellular activity, the level of LoxA expression is increased when P. aeruginosa undergoes the transition to a biofilm mode of growth, but LoxA is not required for biofilm growth on abiotic surfaces. However, LoxA does appear to be required for biofilm growth in association with the host airway epithelium, suggesting a role for LoxA in mediating bacterium-host interactions during colonization. In the experimental materials used by the author, we found 7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine(cas: 213743-31-8COA of Formula: C23H22N4O)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Marcotte, Douglas J.’s team published research in Protein Science in 2010 | CAS: 213743-31-8

Computed Properties of C23H22N4OOn March 31, 2010, Marcotte, Douglas J.; Liu, Yu-Ting; Arduini, Robert M.; Hession, Catherine A.; Miatkowski, Konrad; Wildes, Craig P.; Cullen, Patrick F.; Hong, Victor; Hopkins, Brian T.; Mertsching, Elisabeth; Jenkins, Tracy J.; Romanowski, Michael J.; Baker, Darren P.; Silvian, Laura F. published an article in Protein Science. The article was 《Structures of human Bruton’s tyrosine kinase in active and inactive conformations suggest a mechanism of activation for TEC family kinases》. The article mentions the following:

Bruton’s tyrosine kinase (BTK), a member of the TEC family of kinases, plays a crucial role in B-cell maturation and mast cell activation. Although the structures of the unphosphorylated mouse BTK kinase domain and the unphosphorylated and phosphorylated kinase domains of human ITK are known, understanding the kinase selectivity profiles of BTK inhibitors has been hampered by the lack of availability of a high resolution, ligand-bound BTK structure. Here, we report the crystal structures of the human BTK kinase domain bound to either Dasatinib (BMS-354825) at 1.9 Å resolution or to 4-amino-5-(4-phenoxyphenyl)-7H-pyrrolospyrimidin-7-yl-cyclopentane at 1.6 Å resolution This data provides information relevant to the development of small mol. inhibitors targeting BTK and the TEC family of nonreceptor tyrosine kinases. Anal. of the structural differences between the TEC and Src families of kinases near the Trp-Glu-Ile motif in the N-terminal region of the kinase domain suggests a mechanism of regulation of the TEC family members. In the experimental materials used by the author, we found 7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine(cas: 213743-31-8Computed Properties of C23H22N4O)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Al-Ali, Hassan’s team published research in ACS Chemical Biology in 2013 | CAS: 213743-31-8

7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine(cas: 213743-31-8) belongs to pyrimidine. The pyrimidine ring system has wide occurrence in nature as substituted and ring fused compounds and derivatives, including the nucleotides cytosine, thymine and uracil, thiamine (vitamin B1) and alloxan. HPLC of Formula: 213743-31-8

HPLC of Formula: 213743-31-8On May 17, 2013 ,《Chemical Interrogation of the Neuronal Kinome Using a Primary Cell-Based Screening Assay》 appeared in ACS Chemical Biology. The author of the article were Al-Ali, Hassan; Schurer, Stephan C.; Lemmon, Vance P.; Bixby, John L.. The article conveys some information:

A fundamental impediment to functional recovery from spinal cord injury (SCI) and traumatic brain injury is the lack of sufficient axonal regeneration in the adult central nervous system. There is thus a need to develop agents that can stimulate axon growth to re-establish severed connections. Given the critical role played by protein kinases in regulating axon growth and the potential for pharmacol. intervention, small mol. protein kinase inhibitors present a promising therapeutic strategy. Here, the authors report a robust cell-based phenotypic assay, utilizing primary rat hippocampal neurons, for identifying small mol. kinase inhibitors that promote neurite growth. The assay is highly reliable and suitable for medium-throughput screening, as indicated by its Z’-factor of 0.73. A focused structurally diverse library of protein kinase inhibitors was screened, revealing several compound groups with the ability to strongly and consistently promote neurite growth. The best performing bioassay hit robustly and consistently promoted axon growth in a postnatal cortical slice culture assay. This study can serve as a jumping-off point for structure activity relationship (SAR) and other drug discovery approaches toward the development of drugs for treating SCI and related neurol. pathologies. In the part of experimental materials, we found many familiar compounds, such as 7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine(cas: 213743-31-8HPLC of Formula: 213743-31-8)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Becouarn, Stefan’s team published research in Nucleosides & Nucleotides in 1995 | CAS: 122567-97-9

《Efficient transformation of thymidine into 2′,3′-didehydro-2′,3′-dideoxythymidine (D4T) involving opening of a 2,3′-anhydro derivative by phenylselenol》 was written by Becouarn, Stefan; Czernecki, Stanislas; Valery, Jean-Marc. Application In Synthesis of ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate And the article was included in Nucleosides & Nucleotides on August 31 ,1995. The article conveys some information:

A high-yielding method for the introduction of the phenylselenyl residue at the 3′-position of thymidine is reported. This reaction avoided any strongly basic or reductive reagent, thus allowing the use of benzoate ester as a protective group at O-5′. Further oxidation-elimination sequence followed by basic deprotection afforded D4T in 67.5% overall yield from thymidine. In the experimental materials used by the author, we found ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9Application In Synthesis of ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Srinivasan, Prakash’s team published research in Nature Communications in 2013 | CAS: 213743-31-8

In 2013,Nature Communications included an article by Srinivasan, Prakash; Yasgar, Adam; Luci, Diane K.; Beatty, Wandy L.; Hu, Xin; Andersen, John; Narum, David L.; Moch, J. Kathleen; Sun, Hongmao; Haynes, J. David; Maloney, David J.; Jadhav, Ajit; Simeonov, Anton; Miller, Louis H.. Computed Properties of C23H22N4O. The article was titled 《Disrupting malaria parasite AMA1-RON2 interaction with a small molecule preventserythrocyte invasion》. The information in the text is summarized as follows:

Plasmodium falciparum resistance to artemisinin derivatives, the first-line antimalarial drug, drives the search for new classes of chemotherapeutic agents. Current discovery is primarily directed against the intracellular forms of the parasite. However, late schizont-infected red blood cells (RBCs) may still rupture and cause disease by sequestration; consequently targeting invasion may reduce disease severity. Merozoite invasion of RBCs requires interaction between two parasite proteins AMA1 and RON2. Here we identify the first inhibitor of this interaction that also blocks merozoite invasion in genetically distinct parasites by screening a library of over 21,000 compounds We demonstrate that this inhibition is mediated by the small mol. binding to AMA1 and blocking the formation of AMA1-RON complex. Electron microscopy confirms that the inhibitor prevents junction formation, a critical step in invasion that results from AMA1-RON2 binding. This study uncovers a strategy that will allow for highly effective combination therapies alongside existing antimalarial drugs. In the experiment, the researchers used many compounds, for example, 7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine(cas: 213743-31-8Computed Properties of C23H22N4O)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia