The synthesis and biological evaluation of some caffeic acid amide derivatives: E-2-cyano-(3-substituted phenyl)acrylamides.
A series of caffeic acid amide derivatives 2-cyano-(3-substituted phenyl)acrylamides were synthesized via Knoevenogal condensation of substituted benzaldehydes with cyanoacetamides. The structure of compound 1f was determined as E-isomer by X-ray diffractive analysis. The biological screening tests in vitro showed that compound 1b has obvious inhibitory activities against human gastric carcinoma cell line BGC-823, human nasopharyngeal carcinoma cell line KB and human hepatoma cell line BEL-7402 with IC(50) values of 5.6 microg/mL, 13.1 microg/mL and 12.5 microg/mL, respectively. Some preliminary structure-activity relationships (SAR) were also proposed which may provide a direction for further study.
Zhou
Wei
W
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310014, PR China.
Li
Hai-bo
HB
Xia
Chun-nian
CN
Zheng
Xian-ming
XM
Hu
Wei-xiao
WX
D000178:Acrylamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002109:Caffeic Acids / Q000737:chemistry*; D045744:Cell Line, Tumor; D018360:Crystallography, X-Ray; D006801:Humans; D020128:Inhibitory Concentration 50; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000178:Acrylamides; D002109:Caffeic Acids; D009570:Nitriles