Synthesis of Novel 1-Substituted and 1,9-Disubstituted-1,2,3,4-tetrahydro-9H-Carbazole Derivatives as Potential Anticancer Agents

Abstract

Condensation of 1-acetyl-1,2,3,4-tetrahydro-9H-carbazole (2) with some amino compounds furnished the corresponding imino derivatives 3a-e. Compound 3a reacted with chloroacetic acid and underwent cyclization to give the thiazolidine derivative 5. Also, treatment of 3c with thionyl chloride caused cyclization to yield the [1,2,6]thiadiazino derivative 6, which gave the corresponding N-formyl derivative 7 upon heating with ethyl formate. In addition, interaction of 3d with ethyl cyanoacetate yielded the monoamide of malonic acid derivative 8. Acylation of carbazole 1 with succinoyl chloride or phenylacetyl choride produced the corresponding azepine (11) and 1,9-diphenyl acetyl derivatives (14), respectively. Compounds 11, 14 were further reacted to give the carbazole derivatives 12, 13 and 15a,b. The cytotoxic activity for some of the prepared compounds against breast cancer B20 is discussed.

Keywords

• Carbazole derivatives
• thiadiazino derivatives
• cytotoxic activity