1027081-49-7

Basic information

• Product Name: 2-{(Z)-3-[2-Cyano-5-(thiophen-3-ylmethoxy)-phenyl]-2-phenyl-allyl}-malonic acid dimethyl ester
• Synonyms: 2-{(Z)-3-[2-Cyano-5-(thiophen-3-ylmethoxy)-phenyl]-2-phenyl-allyl}-malonic acid dimethyl ester
• CAS NO: 1027081-49-7
• Molecular Weight: 461.538
• Mol File: 1027081-49-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-{(Z)-3-[2-Cyano-5-(thiophen-3-ylmethoxy)-phenyl]-2-phenyl-allyl}-malonic acid dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-{(Z)-3-[2-Cyano-5-(thiophen-3-ylmethoxy)-phenyl]-2-phenyl-allyl}-malonic acid dimethyl ester(1027081-49-7)
• EPA Substance Registry System: 2-{(Z)-3-[2-Cyano-5-(thiophen-3-ylmethoxy)-phenyl]-2-phenyl-allyl}-malonic acid dimethyl ester(1027081-49-7)

Safety Data

• Hazardous Substances Data: 1027081-49-7(Hazardous Substances Data)

Upstream product

• 210109-78-7 (E)-3-[2-Cyano-5-(thiophen-3-ylmethoxy)-phenyl]-2-phenyl-acrylic acid 
• 210109-94-7 (Z)-2-phenyl-3-[2-cyano-5-(3-thiophen-3-yl)methyloxyphenyl]propenol 
• 210109-99-2 2-cyano-5-(3-thiophen-3-yl)methyloxybenzaldehyde 
• 210109-98-1 2-bromo-5-(3-thiophen-3-yl-methyloxy)benzaldehyde 
• 100-83-4 meta-hydroxybenzaldehyde 
• 2973-80-0 2-bromo-5-hydroxybenzaldehyde 
• 108-59-8 malonic acid dimethyl ester 
• 210110-05-7 2-((E)-3-Bromo-2-phenyl-propenyl)-4-(thiophen-3-ylmethoxy)-benzonitrile 

Relevant articles and documents

Selective endothelin a receptor antagonists. 4. Discovery and structure- activity relationships of stilbene acid and alcohol derivatives

This publication describes the synthesis and optimization of a novel series of stilbene endothelin antagonists. Analysis of the SAR established for previous papers in this series prompted the design and synthesis of (Z)- 4-phenyl-5-(3-benzyloxyphenyl)pent-4-enoic acid 3 which was found to be a moderately active inhibitor of the binding of [125I]ET-1 to ET(A) receptors with an IC50 of 6 μM. More interestingly, the intermediate compound (E)-2-phenyl-3-(3-benzyloxyphenyl)propenoic acid 5 was equiactive with 3. Optimization of 5 resulted in the preparation of (E)2-phenyl-3-(2- cyano-5-(thien-3-ylmethoxy))phenylpropenoic acid 18 (RPR111723) which had an IC50 in the binding assay of 80 nM on the ET(A) receptor and a pK(B) of 6.5 in the functional assay, measured on rat aortic strips. Reduction of the acid group of 5 gave the first nonacidic ET(A) antagonist in our series, (E)-2- phenyl-3-(3-benzyloxyphenoxy)prop2-enol 6 with an IC50 of 20 μM. Optimization of 6 resulted in the preparation of 2-(2-methylphenyl)-3-(2- cyano-5-(thien3-ylmethyl)phenyl)prop-2-enol 33 with an IC50 of 300 nM on the ET(A) receptor.