132225-51-5

Basic information

• Product Name: Benzamide, 4-cyano-N-[2-(3,4-dihydroxyphenyl)-2-oxoethyl]-N-methyl-
• CAS NO: 132225-51-5
• Molecular Formula: C17H14N2O4
• Molecular Weight: 310.309
• Mol File: 132225-51-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Benzamide, 4-cyano-N-[2-(3,4-dihydroxyphenyl)-2-oxoethyl]-N-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, 4-cyano-N-[2-(3,4-dihydroxyphenyl)-2-oxoethyl]-N-methyl-(132225-51-5)
• EPA Substance Registry System: Benzamide, 4-cyano-N-[2-(3,4-dihydroxyphenyl)-2-oxoethyl]-N-methyl-(132225-51-5)

Safety Data

• Hazardous Substances Data: 132225-51-5(Hazardous Substances Data)

Upstream product

• 62-13-5 1-(3,4-dihydroxyphenyl)-1-oxo-2-methylamino-ethan-hydrochlorid 
• 6068-72-0 4-cyanobenzoyl chlorIde 
• 67-56-1 methanol 

Downstream Products

• 132224-05-6 dimethyl <<4-<(p-amidino-N-methylbenzamido)acetyl>-o-phenylene>dioxy>diacetate 
• 1025821-85-5 (2-Methoxycarbonylmethoxy-5-{2-[methyl-(4-methylsulfanylcarbonimidoyl-benzoyl)-amino]-acetyl}-phenoxy)-acetic acid methyl ester 
• 1027171-23-8 (2-Methoxycarbonylmethoxy-5-{2-[methyl-(4-thiocarbamoyl-benzoyl)-amino]-acetyl}-phenoxy)-acetic acid methyl ester 
• 132224-71-6 [[[4-(4-aminoiminomethyl-N-methylbenzamino)acetyl]-o-phenylene]dioxy]diacetic acid 
• 132224-06-7 dimethyl <<4-<(p-cyano-N-methylbenzamido)acetyl>-o-phenylene>dioxy>diacetate 

Relevant articles and documents

Low molecular weight, non-peptide fibrinogen receptor antagonists

The tetrapeptide H-Arg-Gly-Asp-Ser-OH (1) (RGDS), representing a recognition sequence of fibrinogen for its platelet receptor GP IIb-IIIa (integrin α(IIb)β3), served as lead compound for the development of highly potent and selective fibrinogen receptor antagonists. Replacement of the N- terminal arginine by p-amidinophenylalanine or the Gly moiety by m- aminobenzoic acid led to compounds which are superior to the lead peptide with regard to activity and selectivity for GP IIb-IIIa vs the closely related vitronectin receptor α(v)β3. By random screening [(p- amidinobenzenesulfonamido)ethyl]-p-phenoxyacetic acid derivatives have been identified as fibrinogen receptor antagonists. Further structure-activity relationship studies culminated in the preparation of N-[N-[N-(p- amidinobenzoyl)-β-alanyl]-L-α-aspartyl]-3-phenyl-L-alanine (29h, Ro 43- 5054) and [[1-[N-(p-amidinobenzoyl)-L-tyrosyl]-4-piperidinyl]oxy]acetic acid (37f, Ro 44-9883), which exhibit very high activity as platelet aggregation inhibitors (IC50s 0.06 and 0.03 μM, respectively, human PRP/ADP) as well as marked selectivity for GP IIb-IIIa vs α(v)β3. Since the activity of 37f in dogs declines according to a two-compartment model with an initial phase having a t( 1/2 ) of 8 min and a second phase with a t( 1/2 ) of 110 min, this compound is a suitable candidate for the development as iv platelet inhibitor.