737823-38-0

Basic information

• Product Name: Benzoic acid, 4-[(1Z)-2-[2-(acetylamino)-4-thiazolyl]ethenyl]-, methyl ester
• CAS NO: 737823-38-0
• Molecular Formula: C15H14N2O3S
• Molecular Weight: 302.354
• Mol File: 737823-38-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 4-[(1Z)-2-[2-(acetylamino)-4-thiazolyl]ethenyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-[(1Z)-2-[2-(acetylamino)-4-thiazolyl]ethenyl]-, methyl ester(737823-38-0)
• EPA Substance Registry System: Benzoic acid, 4-[(1Z)-2-[2-(acetylamino)-4-thiazolyl]ethenyl]-, methyl ester(737823-38-0)

Safety Data

• Hazardous Substances Data: 737823-38-0(Hazardous Substances Data)

Upstream product

• 16444-13-6 N-(4-formyl-1,3-thiazol-2-yl)acetamide 
• 1253-46-9 4-methoxycarbonylbenzyltriphenylphosphonium bromide 

Downstream Products

• 737823-39-1 methyl 4-[2-(2-acetamido-1,3-thiazol-4-yl)ethyl]benzoate 
• 1442469-21-7 tert-butyl (4-{4-[2-(2-acetamido-1,3-thiazol-4-yl)ethyl]phenyl}-1H-imidazol-2-yl)carbamate 
• 1030892-96-6 4-[2-(2-acetamido-1,3-thiazol-4-yl)ethyl]benzoic acid 

Relevant articles and documents

Novel 1H-imidazol-2-amine derivatives as potent and orally active vascular adhesion protein-1 (VAP-1) inhibitors for diabetic macular edema treatment

Novel thiazole derivatives were synthesized and evaluated as vascular adhesion protein-1 (VAP-1) inhibitors. Although we previously identified a compound (2) with potent VAP-1 inhibitory activity in rats, the human activity was relatively weak. Here, to improve the human VAP-1 inhibitory activity of compound 2, we first evaluated the structure-activity relationships of guanidine bioisosteres as simple small molecules and identified a 1H-benzimidazol-2-amine (5) with potent activity compared to phenylguanidine (1). Based on the structure of compound 5, we synthesized a highly potent VAP-1 inhibitor (37b; human IC50 = 0.019 μM, rat IC50 = 0.0051 μM). Orally administered compound 37b also markedly inhibited ocular permeability in streptozotocin-induced diabetic rats after oral administration, suggesting it is a promising compound for the treatment of diabetic macular edema.

THIAZOLE DERIVATIVES AND THEIR USE AS VAP-1 INHIBITORS

A compound of the formula (I): R1-NH-X-Y-Z (I) wherein R1 is acyl; X is a bivalent residue derived from optionally substituted thiazole; Y is a bond, lower alkylene or -COHN-; and Z is a groupe of the formulae (II) or (III) wherein R