Heterocyclic ring extension of androstenedione: Synthesis and cytotoxicity of fused pyran, pyrimidine and thiazole derivatives

• Heterocyclization ring extension of androstenedione through ring E.
• Fused pyran, pyrimidine and thiazole derivatives were produced.
• Cytotoxicity of the newly synthesized products were measured against human cancer and normal cell lines.

The reaction of androstenedione with either malononitrile or ethyl cyanoacetate and aromatic aldehydes 2a-c gave the pyran derivatives 4a-f, respectively. On the other hand, the reaction of androstenedione with thiourea and the aromatic aldehydes 2a-c gave the pyrimidine derivatives 6a-c, respectively. Compound 6b reacted with 2-bromo-1-arylethanone derivatives 7a-d to give the indeno[2,1-e]thiazole derivatives 8a-d. Some of the produced compounds were used for further heterocyclization reactions. The cytotoxicity of the newly obtained products was evaluated against some cancer cell lines and a normal cell line.

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