Document Type
Article
Publication Date
11-1-2011
Publication Title
Steroids
Abstract
Using cholesterol as starting material, a series of 6-substituted-3-aza-A-homo-3-oxycholestanes and 6-substituted-4-aza-A-homo-3-oxycholestanes were synthesized by the oxidation, reduction, oximation, Beckman rearrangement and condensation reaction. These synthesized compounds displayed a distinct cytotoxicity against MGC 7901, HeLa and SMMC 7404 cancer cells. Our results revealed that the structures of functional groups at position-6 on the steroidal ring are crucial for the IC50 value of antiproliferative activities of these compounds and the cytotoxic activity against MGC 7901 and SMMC 7404 cells was not significantly different between 4-N-lactams and 3-N-lactams when its 6-substituted group was a carbonyl or a hydroximino, but all 3-N-lactams showed a higher cytotoxicity against HeLa cells than 4-N-lactams. In particular, compounds 6, 8, 9 (IC506: 6.5 μmol/L; 8: 7.7 μmol/L; 9: 5.6 μmol/L) were even more cytotoxic than cisplatin to HeLa cells (positive contrast, 10.1 μmol/L). The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs.
Recommended Citation
Huang, Yanmin; Cui, Jianguo; Chen, Sijing; Gan, Chunfang; and Zhou, Aimin, "Synthesis and Antiproliferative Activity of Some Steroidal Lactams" (2011). Chemistry Faculty Publications. 412.
https://engagedscholarship.csuohio.edu/scichem_facpub/412
Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-No Derivative Works 4.0 International License.
DOI
10.1016/j.steroids.2011.06.013
Version
Postprint
Volume
76
Issue
12
Comments
The authors acknowledge the financial support of the Natural Science Foundation of Guangxi Province (Nos. 2010GXNSFD013019 and 0832106).