In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called The antimalarial activity of 1,2-dimethoxy-4-[bis(diethylaminoethyl)amino]-5-bromobenzene, published in 1966, which mentions a compound: 148-51-6, mainly applied to , Application of 148-51-6.
Oral administration of 1,2-dimethoxy-4-[bis(diethylaminoethyl)amino]-5-bromobenzene (I) (6.25 mg./kg. by stomach tube 1 day prior to sporozoite inoculation, the day of inoculation, and for 7 days afterwards) completely protected rhesus monkeys from Plasmodium cynomolgi infections; although dose-for-dose I was less active than primaquine, it was less toxic also. Doses as high as 100 mg./kg. were tolerated by 4 of 5 monkeys, while the 5th died of convulsive seizures 30 min. after administration of I; 200 mg./kg. produced fatal convulsions. Vacuolization of the circulating lymphocytes was the only noncentral nervous system reaction to administration of I, either alone or in combination with chloroquine, and the vacuolization was not associated with either hypertropy or involution of the spleen or lymph nodes; simultaneous administration of I and chloroquine did not enhance the toxicity of the former. Although administration of 100 mg. I/kg. for 7 days cured only 3 of 6 monkeys with parasite levels of 10-50/1000 erythrocytes, subsequent treatment with chloroquine was 100% successful. Administration of 25 mg. I/kg. for 14 days with chloroquine (2.5 mg./kg.) for the 1st 7 days produced cures in 21 of 22 monkeys; however, the curative activity of I was inferior to that of primaquine. I also showed prophylactic activity towards plasmodia resistant to chlorguanide and pyrimethamine. Doses of I spaced 7 days apart were ≤50% protective, but 7 days treatment in combination with chloroquine was as effective as the same does of I administered for 14 days. Schizontoidal activity was equal to that of quinine, but I was slower in achieving clearance of parasitemia. Although I per se is not highly effective as a schizontocidal or suppressive drug, it may be used as a prophylactic or radical curative agent when the combination of chloroquine and primaquine is not effective in causal prophylaxis, when a curative agent is required which is effective in less than 10-14 days, and when enhanced susceptibility to the hematotoxicity of primaquine is apparent.
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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia