Synthesis and evaluation of some steroidal oximes as cytotoxic agents: structure/activity studies (II).
Hydroximinosteroids isolated from marine sponges display a variety of biological functions including cytotoxicity and anti-virus. In this study, we synthesized a series of hydroximinosteroid derivatives with a different functional group on the ring A or B and various side chains at position 17, and analyzed the cytotoxicity of these compounds against sk-Hep-1, H-292, PC-3 and Hey-1B cancer cells. Our results revealed that although a cholesterol-type side chain at position 17 is required for the biological activity of the compounds as we previously confirmed, elimination of the 4,5-double bond augmented the cytotoxic activity for the steroidal oximes. In addition, the presence of a hydroxy on 3- or 6-position of the steroidal nucleus resulted in a remarkable increase of cytotoxic activity. Our findings present more evidence showing the relationship between the chemical structure and biological function.
Cui
Jianguo
J
College of Chemistry and Life Science, Guangxi Teachers Education University, Nanning 530001, China. cuijg1954@126.com
Fan
Lei
L
Huang
Yanmin
Y
Xin
Yi
Y
Zhou
Aimin
A
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D010091:Oximes / Q000737:chemistry*; D013256:Steroids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D010091:Oximes; D013256:Steroids