- Synthesis and anticancer activity of thiosubstituted purines
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New thiopurines with the propargylthio, pyrrolidinobutynylthio, sulfenamide, and sulfonamide groups in the pyrimidine ring were synthesized. The anticancer activity of these compounds and previously obtained 2- or 6-substituted azathioprine analogs and dialkylaminoalkylthiopurines were tested in vitro against three cell lines: glioblastoma SNB-19, melanoma C-32, and human ductal breast epithelial tumor T47D. 2-Chloro-7-methyl-6-pyrrolidinobutynylthiopurine (5b) was the most potent compound against SBN-19 and C-32 cell lines with the activity similar to cisplatin (EC50 = 5.00 and 7.58 μg/ml, respectively). The dialkylaminoalkylthio derivatives (4b, 4c, 4e, and 4f) showed good activity against SBN-19 cell line (EC50 10 μg/ml). The azathioprine analogs (2a, 2b, and 3a) were more active than azathioprine against SBN-19 and C-32 cell lines. The sulfenamide and sulfonamide derivatives of purine were very weak active against tested cell lines. All studied thiopurines were less toxic than cisplatin.
- Kowalska, Alicja,Latocha, Malgorzata,Pluta, Krystian
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- Pharmaceutical composition containing 2-dimethylamino-6-diethyleneimidophosphamido-7-methyl-purine
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2-Dimethylamino-6-diethyleneimidophosphamido-7-methylpurine having the formula STR1 A method for preparing 2-dimethylamino-6-diethyleneimido-phosphamido-7-methylpurine consisting of treating theo-bromine with heating to the boiling point and subsequently with phosphorus oxychloride and phosphorus pentachloride. The prepared 2,6-dichloro-7-methylpurine is heated to 50° - 60° C in an aqueous solution of ammonia and the resulting 2-chloro-6-amino-7-methylpurine is reacted, with heating, with a aqueous solution of dimethylamine. The obtained 2-dimethylamino-6-amino-7-methylpurine is reacted, at the boiling point, with either phosphorus oxychloride, or phosphorus pentachloride and formic acid. The resulting 2-dimethylamino-7-methylpurinyl-6-aminophosphoric dichloroanhydride is then treated with ethyleneimine in a medium of an organic solvent in the presence of an acceptor of hydrogen chloride, and the final product is then isolated. A preparation for treating malignant tumors of the haemopoietic system, containing 2-dimethylamino-6-diethyleneimidophosphamido-7-methylpurine as the active principle is provided.
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