161455-90-9

Basic information

• Product Name: Acetamide, N-(1-methylethyl)-N-phenyl-2-[[2-(phenylamino)phenyl]amino]-
• CAS NO: 161455-90-9
• Molecular Formula: C23H25N3O
• Molecular Weight: 359.471
• Mol File: 161455-90-9.mol

Chemical Properties

• CAS DataBase Reference: Acetamide, N-(1-methylethyl)-N-phenyl-2-[[2-(phenylamino)phenyl]amino]-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetamide, N-(1-methylethyl)-N-phenyl-2-[[2-(phenylamino)phenyl]amino]-(161455-90-9)
• EPA Substance Registry System: Acetamide, N-(1-methylethyl)-N-phenyl-2-[[2-(phenylamino)phenyl]amino]-(161455-90-9)

Safety Data

• Hazardous Substances Data: 161455-90-9(Hazardous Substances Data)

Upstream product

• 161455-97-6 2-bromo-N-isopropyl-N-phenyl-acetamide 
• 534-85-0 N-phenyl-1,2-benzenediamine 
• 768-52-5 N-Isopropylaniline 

Downstream Products

• 161455-91-0 2-[2,4-Dioxo-5-phenyl-3-(phenyl-hydrazono)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-phenyl-acetamide 
• 174180-28-0 2-(2,4-Dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl acetamide 
• 184945-06-0 2-{3-[3-(3-Amino-phenyl)-ureido]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl}-N-isopropyl-N-phenyl-acetamide 
• 1060663-00-4 4-(2-{1-[(Isopropyl-phenyl-carbamoyl)-methyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamoyl}-indol-1-yl)-butyric acid tert-butyl ester 
• 184944-89-6 [3-(3-{1-[(Isopropyl-phenyl-carbamoyl)-methyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl}-ureido)-phenoxy]-acetic acid tert-butyl ester 
• 161455-98-7 (2-{1-[(Isopropyl-phenyl-carbamoyl)-methyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamoyl}-indol-1-yl)-acetic acid tert-butyl ester 
• 161455-82-9 3-{3-[1-(Isopropyl-phenyl-carbamoylmethyl)-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-3-yl]-ureido}benzoic acid ethyl ester 
• 184945-28-6 N-Isopropyl-2-{3-[3-(3-nitro-phenyl)-ureido]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl}-N-phenyl-acetamide 

Relevant articles and documents

Use of 1,5-benzo?b!1,4-diazepines to control gastric emptying

A method of controlling gastric emptying in patients having an early non-insulin-dependent diabetic condition and exhibiting rapid gastric emptying comprising the administration of an effective gastric emptying controlling amount of a compound of Formula

Optimization of 3-(1H-Indazol-3-ylmethyl)-1,5-benzodiazepines as potent, orally active CCK-A agonists

We previously described a series of 3-(1H-indazol-3-ylmethyl)-1,5- benzodiazepine CCK-A agonists exemplified by compound 1 (GW 5823), which is the first reported binding selective CCK-A full agonist demonstrating oral efficacy in a rat feeding model. In this report we describe analogs of compound 1 designed to explore changes to the CS and N1 pharmacophores and their effect on agonist activity and receptor selectivity. Agonist efficacy in this series was affected by stereoelectronic factors within the C3 moiety. Binding affinity for the CCK-A vs CCK-B receptor showed little dependence on the structure of the C3 moiety but was affected by the nature of the second substituent at CS. Structure-activity relationships at the N1- anilidoacetamide 'trigger' moiety within the C3 indazole series were also investigated. Both agonist efficacy and binding affinity within this series were modulated by variation of substituents on the Nl-anilidoacetamide moiety. Evaluation of several analogs in an in vivo mouse gallbladder emptying assay revealed compound 1 to be the most potent and efficacious of all the analogs tested. The pharmacokinetic and pharmacodynamic profile of 1 in rats is also discussed.

3-[2-(N-phenylacetamide)]-1,5-benzodiazepines: Orally active, binding selective CCK-A agonists

A series of modifications were made to the C-3 substituent of the 1,5- benzodiazepine CCK-A agonist 1. Replacement of the inner urea NH and addition of a methyl group to generate a C-3 quaternary carbon resulted in acetamide 6, which showed CCK-A receptor

Discovery of 1,5-benzodiazepines with peripheral cholecystokinin (CCK-A) receptor agonist activity (II): Optimization of the C3 amino substituent

Analogs of the previously reported 1,5-benzodiazepine peripheral cholecystokinin (CCK-A) receptor agonist 1 were prepared which explore substitution and/or replacement of the C-3 phenyl urea moiety. Agonist efficacy on the isolated guinea pig gallbladder (GPGB) was retained with a variety of substituted ureas and amide analogs. Three compounds were identified which were orally active in the mouse gallbladder emptying assay (MGBE). The 2-indolamide (52) and N-(carboxymethyl)-2-indolamide (54) derivatives had improved affinity for the human CCK-A receptor but reduced agonist efficacy on the GPGB. Neither indolamide was orally active in a rat feeding assay. In contrast, the (3-carboxyphenyl)urea derivative (29, GW7854) had moderately increased affinity for the human CCK-B receptor but was a potent full agonist on the GPGB and was orally active in both the MGBE and rat feeding assays. GW7854 was a full agonist (EC50 = 60 nM) for calcium mobilization on CHO K1 cells expressing hCCK-A receptors and a potent antagonist of CCK-8 (pA2 = 9.1) on CHO K1 cells expressing hCCK-B receptors. GW7854 is a potent mixed CCK-A agonist/CCK-B antagonist which is orally active in two in vivo models of CCK-A-mediated agonist activity.