116495-73-9

Basic information

• Product Name: Benzoic acid, 3-(2-phenoxyethoxy)-
• Synonyms: 3-(2-phenoxyethoxy)benzoic acid
• CAS NO: 116495-73-9
• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.27
• Mol File: 116495-73-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzoic acid, 3-(2-phenoxyethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 3-(2-phenoxyethoxy)-(116495-73-9)
• EPA Substance Registry System: Benzoic acid, 3-(2-phenoxyethoxy)-(116495-73-9)

Safety Data

• Hazardous Substances Data: 116495-73-9(Hazardous Substances Data)

Upstream product

• 2788-70-7 3-(2-phenoxy-ethoxy)-benzoic acid methyl ester 
• 56101-99-6 phenoxyethyl alcohol 
• 589-10-6 phenoxyethyl bromide 
• 19438-10-9 methyl 3-hydroxybenzoate 

Relevant articles and documents

2,5-diamino-3,4-disubstituted-1,6-diphenylhexane isosteres comprising benzamide, sulfonamide and anthranilamide subunits and methods of using same

The present invention provides 2,5-diamino-3,4-disubstituted-1,6-diphenylhexane (DAD) isosteres comprising benzamide, sulfonamide and anthranilamide subunits, a pharmaceutical composition comprising such compounds, a method of using such compounds to treat retroviral, specifically HIV and more specifically HIV-1 and HIV-2, infections in mammals, particularly humans, a method of synthesizing asymmetric DAD isosteres comprising benzamide, sulfonamide and anthranilamide subunits, and a method of using such compounds to assay new compounds for antiretroviral activity.

Structure-based design of achiral, nonpeptidic hydroxybenzamide as a novel P2/P2' replacement for the symmetry-based HIV protease inhibitors

A combination of structure-activity studies, kinetic analysis, X-ray crystallographic analysis, and modeling were employed in the design of a novel series of HIV-1 protease (HIV PR) inhibitors. The crystal structure of a complex of HIV PR with SRSS-2,5-bis[N-(tert-butyloxycarbonyl)amino]-3,4-dihydroxy-1,6-diphenylhexane (1) delineated a crucial water-mediated hydrogen bond between the tert-butyloxy group of the inhibitor and the amide hydrogen of Asp29 of the enzyme. Achiral, nonpeptidic 2-hydroxy/phenylacetamide and 3-hydroxybenzamide groups were modeled as novel P2/P2' ligands to replace the crystallographic water molecules and to provide direct interactions with the NH groups of the Asp29/129 residues. Indeed, the symmetry-based inhibitors 7 and 19, possessing 3-hydroxy and 3-aminobenzamide, respectively, as a P2/P2' ligand, were potent inhibitors of HIV PR. The benzamides were superior in potency to the phenylacetamides and have four fewer rotatable bonds. An X-ray crystal structure of the HIV PR/7 complex at 2.1 A resolution revealed an asymmetric mode of binding, in which the 3-hydroxy group of the benzamide ring makes the predicted interaction with the backbone NH of Asp29 on one side of the active site only. An unexpected hydrogen bond with the Gly148 carbonyl group, resulting from rotation of the aromatic ring out of the amide plane, was observed on the other side. The inhibitory potencies of the benzamide compounds were found to be sensitive to the nature and position of substituents on the benzamide ring, and can be rationalized on the basis of the structure of the HIV PR/7 complex. These results partly confirm our initial hypothesis and suggest that optimal inhibitor designs should satisfy a requirement for providing polar interactions with Asp29 NH, and should minimize the conformational entropy loss on binding by reducing the number of freely rotatable bonds in inhibitors.