178239-00-4

Upstream product

• 134-96-3 syringic aldehyde 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 1916-07-0 3,4,5-trimethoxybenzoic acid methyl ester 
• 3840-31-1 (3,4,5-trimethoxyphenyl)methanol 
• 6527-32-8 4-(benzyloxy)-3,5-dimethoxybenzaldehyde 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 1048005-06-6 C₂₇H₂₇NO₇ 
• 14897-77-9 3,5-dimethoxy-4-benzyloxycinnamic acid 

Relevant academic research and scientific papers

Synthesis, biological evaluation, and structure-activity relationship study of novel cytotoxic aza-caffeic acid derivatives

Three series of aza-caffeic acid derivatives with different linkers were designed and synthesized. Each of the synthesized derivatives was then used in cytotoxicity screening on either 8 or 12 human cancer cell lines. The structure-activity relationships on three structural regions A, B, and C are analyzed in detail, indicating that a nine bond linker B, containing a piperazine unit, is the most favorable linker leading to the generation of molecules with potent cytotoxicities. Compound (E)-1-(4-(3,4-dichlorobenzyl) piperazin-1-yl)-3-(4-(4-ethoxybenzyloxy)-3,5-dimethoxyphenyl)prop-2-en-1-one (80) exhibited the most significant and selective cytotoxicity to KB, BEL7404, K562, and Eca109 cell lines, with IC50 values of 0.2, 2.0, 1.7, and 1.1 μM, respectively, stronger than that seen for caffeic acid phenethyl ester (CAPE) and cisplatin (CDDP). Flow cytometric and western blot analysis indicate that compound 80 plays a role in mitochondria-dependent apoptosis activity by suppressing K562 cell proliferation in a concentration- and time-dependent manner.

Design, synthesis, and SAR analysis of cytotoxic sinapyl alcohol derivatives

Five series totalling 51 of sinapyl alcohol derivatives were designed and synthesized. Their cytotoxicity analyses were performed on six human tumor cell lines such as PC-3, CNE, KB, A549, BEL-7404, and HeLa. Certain sinapyl alcohol derivatives showed significant cytotoxic activities. Compound 14d exhibited especially potent cytotoxicity against the BEL-7404 cell line with an IC 50 value of 0.7 μM, which showed more cytotoxic activity than the positive control, cisplatin. The structure-cytotoxicity relationships were discussed and the CoMFA analysis was performed using the cytotoxic data against HeLa cells as a template.