Synthesis and cytotoxic activity of 3- O-acyl/3-hydrazine /2-bromo/20,29-dibromo betulinic acid derivatives

Graphic A series of 3- O-acyl, 3-hydrazine, 2-bromo, and 20,29-dibromo betulinic acid derivatives ( 1– 27) have been synthesized and screened for in vitro cytotoxic activity on human cancer cell lines MOLT-4, JurkatE6.1, CEM.CM3, BRISTOL8, U937, DU145, PA-1, A549, and L132. A number of compounds hav...

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Published in:Bioorganic & medicinal chemistry letters 2004-08, Vol.14 (15), p.4087-4091
Main Authors: Mukherjee, Rama, Jaggi, Manu, Siddiqui, Mohammad J.A, Srivastava, Sanjay K, Rajendran, Praveen, Vardhan, Anand, Burman, Anand C
Format: Article
Language:English
Subjects:
Antineoplastic Agents - toxicity
Cell Line
Cell Line, Tumor
Cell Survival - drug effects
Humans
Hydrazines
Jurkat Cells
Models, Molecular
Molecular Conformation
Triterpenes - chemical synthesis
Triterpenes - chemistry
Triterpenes - toxicity
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Summary:Graphic A series of 3- O-acyl, 3-hydrazine, 2-bromo, and 20,29-dibromo betulinic acid derivatives ( 1– 27) have been synthesized and screened for in vitro cytotoxic activity on human cancer cell lines MOLT-4, JurkatE6.1, CEM.CM3, BRISTOL8, U937, DU145, PA-1, A549, and L132. A number of compounds have shown ED 50 < 1 μg/mL against the cancer cell lines tested and have shown better cytotoxicity than betulinic acid. Compounds 13, 19, 20, 23, and 27 were the best derivatives and were selected as lead molecules for further development. The structure–activity relationship has been described.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2004.05.034