73108-79-9

Usage

InChI:InChI=1/C15H12ClNO/c16-13-8-4-5-9-14(13)17-15(18)11-10-12-6-2-1-3-7-12/h1-11H,(H,17,18)/b11-10+

Upstream product

• 93696-65-2 α,β-dibromohydrocinnamic acid chloride 
• 6286-30-2 2,3-dibromo-3-phenylpropanoic acid 
• 621-82-9 Cinnamic acid 
• 95-51-2 o-chloroaniline 
• 102-92-1 cinnamoyl chloride 

Downstream Products

• 1095715-33-5 1-(2-chloro-phenyl)-2-((E)-styryl)-1H-benzimidazole 
• 23981-25-1 8-chloroquinolin-2(1H)-one 
• 19358-30-6 8-chloro-4-phenyl-3,4-dihydro-1H-quinolin-2-one 
• 1453188-53-8 2-(2-chlorophenyl)-5-phenyl-1,2,4,5-tetrahydro-2-benzazepin-3-one 

Relevant academic research and scientific papers

Heterocoumarins Are Selective Carbonic Anhydrase IX and XII Inhibitors with Cytotoxic Effects against Cancer Cells Lines

We have synthesized a new series of coumarin-based compounds demonstrating high selectivity and potent effects with low nanomolar affinity against the tumor associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA IX and XII. A number of these compounds were evaluated ex vivo against human prostate (PC3) and breast (MDA-MB-231) cancer cell lines. Compounds 4b and 15 revealed effective cytotoxic effects after 48 h of incubation in both normoxic and hypoxic conditions with PC3 cancer cell line. However, compound 3 showed selective cytotoxic effects against MDA-MB-231 in hypoxic condition. These results may be of particular importance for the choice of future drug candidates targeting hypoxic tumors and metastases, considering the fact that a selective carbonic anhydrase CA IX inhibitor (SLC-0111) is presently in phase II clinical trials.

Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors

Four series of acid amides were synthesized, and through measurement using a fluorogenic substrate assay with human recombinant MMP-1, MMP-2 and MMP-9, compound 3f showed considerable inhibitory activities against MMP-2, MMP-9 and the best selectivity over MMP-1. Preliminary structure-activity relationship analysis indicated that caffeic acid amides with electron-donating groups at para-position of amino phenyl group showed better inhibitory activities and selectivity than those with electron-withdrawing groups, and the presence of adjacent dihydroxy in the caffeoyl group was very important for the MMP-2 and MMP-9 inhibitory activities.

Photochemical debromination of vic-dibromides

Photochemical debromination of dibromohydro cinnamamides gave the carbon-carbon double bond compounds.