title: Stereoselective synthesis of novel antiproliferative steroidal (E, E) dienamides through a cascade aldol/cyclization process.
abstract: The stereoselective and metal-free protocol involving a cascade aldol/cyclization process for the synthesis of steroidal (E, E) dienamides from steroidal α, α-dicyanoalkene was reported. This protocol efficiently achieved the construction of C=C bond and selective conversion of cyano group into carboxamide in one-pot procedure under mild condition. Further biological evaluation showed that some of these compounds had moderate to excellent cytotoxic activities against all the tested cancer cell lines and were more potent than well-known drug 5-fluorouracil. Particularly, compound 3c represented excellent inhibitory effect against MCF-7 (IC50=0.76 μM), which was about 10-fold more potent than 5-fluorouracil.
authors: School of Pharmaceutical Sciences and New Drug Research & Development Center, Zhengzhou University, Zhengzhou 450001, PR China.
authors: Bin
authors: B
authors: Yu
authors: Xiao-Nan
authors: XN
authors: Sun
authors: Xiao-Jing
authors: XJ
authors: Shi
authors: Ping-Ping
authors: PP
authors: Qi
authors: Yuan
authors: Y
authors: Fang
authors: En
authors: E
authors: Zhang
authors: De-Quan
authors: DQ
authors: Yu
authors: Hong-Min
authors: HM
authors: Liu
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D003500:Cyclization; D006801:Humans; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013379:Substrate Specificity
chemical_list: D000447:Aldehydes; D000577:Amides; D000970:Antineoplastic Agents; D013256:Steroids; C116609:3-hydroxybutanal
keywords: Cytotoxic activities; Dienamides; Pregnenolone; Stereoselective synthesis