Molecules 2000, 5(10), 1101-1112; doi:10.3390/51001101
Article

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

1 Chemistry Department (Girls), Al-Azhar University, Nasr City, Cairo, Egypt 2 Faculty of Science and Faculty of Pharmacy, Al-Azhar University, Nasr City, Cairo, Egypt 3 Medicinal Chemistry Department, National Research Center, Cairo, Egypt 4 Chemistry of Natural and Microbial Products Department, National Research Center, Cairo, Egypt
* Author to whom correspondence should be addressed.
Received: 22 February 2000; in revised form: 21 July 2000 / Accepted: 28 August 2000 / Published: 31 October 2000
PDF Full-text Download PDF Full-Text [53 KB, uploaded 9 October 2008 11:44 CEST]
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

Article Statistics

Load and display the download statistics.

Citations to this Article

Cite This Article

MDPI and ACS Style

Shmeiss, N.A.M.M.; Ismail, M.M.; Soliman, A.M.; El-Diwani, H.I. Synthesis of Novel 1-Substituted and 1,9-Disubstituted-1,2,3,4-tetrahydro-9H-Carbazole Derivatives as Potential Anticancer Agents. Molecules 2000, 5, 1101-1112.

AMA Style

Shmeiss NAMM, Ismail MM, Soliman AM, El-Diwani HI. Synthesis of Novel 1-Substituted and 1,9-Disubstituted-1,2,3,4-tetrahydro-9H-Carbazole Derivatives as Potential Anticancer Agents. Molecules. 2000; 5(10):1101-1112.

Chicago/Turabian Style

Shmeiss, N. A.M.M.; Ismail, M. M.; Soliman, A. M.; El-Diwani, H. I. 2000. "Synthesis of Novel 1-Substituted and 1,9-Disubstituted-1,2,3,4-tetrahydro-9H-Carbazole Derivatives as Potential Anticancer Agents." Molecules 5, no. 10: 1101-1112.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert