SYNTHESIS AND ANTICANCER ACTIVITY OF SOME NOVEL 3-[(2-SUBSTITUTED-6,7,8,9-TETRAHYDRO-5H-CYCLOHEPTA[B]THIENO [2,3-D]PYRIMIDIN-4-YL)AMINO]PROPAN-1-OL DERIVATIVES.
Santhoshi Rekha Gunda, Srikanth Lingala* and Venkatesham Allenki
The chemistry of pyrimidines and its derivatives has been studied for over a century due to their diverse biological activities. They possess antibacterial, antiviral, antitumor, antihypertensive and antiinflammatory pharmacological activities. Thienopyrimidines formed by the fusion of thiophene moiety with pyrimidine ring, have been reported to be chemotherapeutically active. In view of various biological activities and its enormous importance of thienopyrimidines, we have made an attempt to synthesize and characterize some new 3-[(2-substituted-6,7,8,9-tetrahydro-5h-cyclohepta[b]thieno [2,3-d]pyrimidin-4-yl)amino]propan-1-ol derivatives and evaluate them for anticancer activity. Ethyl 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate was treated with acetonitrile in presence of hydrochloric acid gas to give 2-methyl-3,5,6,7,8,9-hexahydro-4H-cyclohepta[b]thieno[2,3-d]pyrimidin-4-one, which was reacted with excess POCl3 and then refluxed with dioxane, Triehtylamine and aminopropanol to give 3-[(2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]thieno[2,3-d]pyrimidin-4-yl)amino]propan-1-ol. All the intermediate and final compounds were purified and their chemical structures have been confirmed by IR, 1H NMR and Mass spectral data. All the newly synthesized compounds were screened for their anticancer activity by MTT assay and analyzed statistically. Compounds showed considerable anticancer activity when compared with cyclophosphamide.
Keywords: Pyrimidines, thienopyrimidines, thiophene, anticancer activity, cyclophosphamide.
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