101284-14-4

Basic information

• Product Name: methyl 2-[(phenoxyacetyl)amino]benzoate
• Synonyms: methyl 2-[(phenoxyacetyl)amino]benzoate
• CAS NO: 101284-14-4
• Molecular Formula: C₁₆H₁₅NO₄
• Molecular Weight: 285.2946
• Mol File: 101284-14-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: methyl 2-[(phenoxyacetyl)amino]benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-[(phenoxyacetyl)amino]benzoate(101284-14-4)
• EPA Substance Registry System: methyl 2-[(phenoxyacetyl)amino]benzoate(101284-14-4)

Safety Data

• Hazardous Substances Data: 101284-14-4(Hazardous Substances Data)

Upstream product

• 134-20-3 2-carbomethoxyaniline 
• 701-99-5 Phenoxyacetyl chloride 
• 122-59-8 2-phenoxyacetic acid 
• 108-95-2 phenol 

Downstream Products

• 1150095-01-4 2-chloro-N-(4-oxo-2-(phenoxymethyl)quinazolin-3(4H)-yl)acetamide 
• 100880-66-8 2-phenoxymethyl-3H-quinazolin-4-one 
• 276687-49-1 3-amino-2-(phenoxymethyl)quinazolin-4(3H)-one 
• 52910-87-9 N-phenoxyacetyl-anthranilic acid amide 
• 1026638-84-5 N-(2-hydrazinocarbonyl-phenyl)-2-phenoxy-acetamide 

Relevant articles and documents

Synthesis and Caco-2 cell permeability of N-substituted anthranilamide esters as ADP inhibitor in platelets

Twelve N-substituted anthranilamide esters (1-5, 8, 9, 12, 13, and 15-17) were synthesized and evaluated for their ability to inhibit the in vitro aggregation by washed human platelets induced by adenosine 5′-diphosphate (10 μM). The antiplatelet activity of DL-n-butyl 5-hydroxy-N-(2-phenoxypropionyl)anthranilate (9, IC50 = 10.5 μM) was most active among the tested compounds and ethyl ester 8 (IC50 = 11.2 μM) showed the second most activity. DL-Ethyl and DL-n-butyl 5-(p-toluenesulfonyloxy)-N-(2-phenoxypropionyl)anthranilate (12, IC50 = 13.1 μM and 13, IC50 = 14.0 μM), DL-methyl N-(2-phenoxybutyryl)anthranilate (2, IC50 = 12.7 μM), DL-N-(2-phenoxypropionyl)anthranilic acid (5, IC50 = 13.7 μM) displayed lower antiplatelet activity than 8 and 9. Compound 5 was more active than methyl ester prodrug 1. n-Butyl 5-hydroxy-N-(4′-acetoxybenzoyl)anthranilate (15, IC50 = 28.3 μM) showed moderate activity. Compounds 1 (IC50 = 42.8 μM), 4 (IC50 = 56.7 μM), 16 (IC50 = 51.0 μM), and 17 (IC50 = 49.8 μM) exhibited low antiplatelet activity. Methyl N-phenoxyacetylanthranilate (3, IC50 = 78.0 μM) showed the lowest antiplatelet activity. The compounds with branched alkyl chain (2 and 5) were more active than compounds with straight chain (3 and 4). The apparent permeability coefficient (Papp, cm/s) values of compounds 2 and 9 were determined as 45.34 ± 4.67 and 33.17 ± 5.15 × 10-6 cm/s by Caco-2 cell permeability assay.

Design, synthesis and antihistaminic (H1) activity of some condensed 3- aminopyrimidin-4(3H)-ones

A novel series of condensed 3-amino-2-(substituted)methylpyrimidin- 4(3H)-ones is reported with potential H1 receptor antagonistic activity. The IC50 values for 23 compounds were found to be in the micromolar range. Five lead compounds (10c, e, g, r and t), when evaluated by the in vivo method were found to protect guinea-pigs from the histamine induced asphyxia and antagonized histamine in a competitive and reversible manner. With a pA2 value of 8.7 and protection time of 9.5 min (in vivo test), compound 10g was the most active amongst these five compounds. The isosteric replacement of the side chain -NH- in series 1, by oxygen and -NHSO2- functions, was undertaken to investigate the role of two amino functions in the receptor binding. This isosteric replacement with -O- does not affect the antihistaminic activity and the sedative potential of the series. Preliminary molecular modelling, studies indicate that the compounds with -NHSO2- in the side chain exhibit a closer fit with temelastine than their -O- isosteres. (C) 2000 Editions scientifiques et medicales Elsevier SAS.