Synthesis and Evaluation of Some New Aza-B-homocholestane Derivatives as Anticancer Agents

doi:10.3390/md12041715

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Mar. Drugs 2014, 12(4), 1715-1731; doi:10.3390/md12041715

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Synthesis and Evaluation of Some New Aza-B-homocholestane Derivatives as Anticancer Agents

Yanmin Huang¹, Jianguo Cui^1,* , Sijing Chen¹, Qifu Lin¹, Huacan Song², Chunfang Gan¹, Bin Su³ and Aimin Zhou³

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Received: 26 December 2013; in revised form: 24 February 2014 / Accepted: 26 February 2014 / Published: 25 March 2014

(This article belongs to the Special Issue Bioactivity-Focused Syntheses of Marine Natural Products and Congeners)

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract: Using analogues of some marine steroidal oximes as precursors, a series of aza-B-homocholestane derivatives possessing different substituted groups at the 3-position of the steroidal nucleus were synthesized. Their biological activity against cancer cell proliferation was determined with multiple cancer cell lines. Aza-B-homocholestane derivatives possessing 3-hydroxyl, 3-hydroximino and 3-thiosemicarbazone groups displayed remarkable cytotoxicity to cancer cells via apoptosis inducing mechanism. Compounds 5, 10, 12, 15 and 18 exhibited better potency to inhibit cancer cell proliferation. In addition, compound 15 was further evaluated with three dimensional (3D) multicellular spheroids assay to determine its potency against spheroid growth. The structure-activity relationship (SAR) generated in the studies is valuable for the design of novel chemotherapeutic agents.

Keywords: aza-B-homo-cholestane derivatives; anticancer agents; cytotoxicity; 3D multicellular spheroids screening; apoptosis

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MDPI and ACS Style

Huang, Y.; Cui, J.; Chen, S.; Lin, Q.; Song, H.; Gan, C.; Su, B.; Zhou, A. Synthesis and Evaluation of Some New Aza-B-homocholestane Derivatives as Anticancer Agents. Mar. Drugs 2014, 12, 1715-1731.

AMA Style

Huang Y, Cui J, Chen S, Lin Q, Song H, Gan C, Su B, Zhou A. Synthesis and Evaluation of Some New Aza-B-homocholestane Derivatives as Anticancer Agents. Marine Drugs. 2014; 12(4):1715-1731.

Chicago/Turabian Style

Huang, Yanmin; Cui, Jianguo; Chen, Sijing; Lin, Qifu; Song, Huacan; Gan, Chunfang; Su, Bin; Zhou, Aimin. 2014. "Synthesis and Evaluation of Some New Aza-B-homocholestane Derivatives as Anticancer Agents." Mar. Drugs 12, no. 4: 1715-1731.

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