161455-96-5

Basic information

• Product Name: Acetamide, 2-bromo-N-(4-methoxyphenyl)-N-(1-methylethyl)-
• CAS NO: 161455-96-5
• Molecular Formula: C12H16BrNO2
• Molecular Weight: 286.169
• Mol File: 161455-96-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Acetamide, 2-bromo-N-(4-methoxyphenyl)-N-(1-methylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetamide, 2-bromo-N-(4-methoxyphenyl)-N-(1-methylethyl)-(161455-96-5)
• EPA Substance Registry System: Acetamide, 2-bromo-N-(4-methoxyphenyl)-N-(1-methylethyl)-(161455-96-5)

Safety Data

• Hazardous Substances Data: 161455-96-5(Hazardous Substances Data)

Upstream product

• 104-94-9 4-methoxy-aniline 
• 16495-67-3 4-(isopropylamino)anisole 
• 598-21-0 2-Bromoacetyl bromide 

Downstream Products

• 161455-95-4 N-isopropyl-N-(4-methoxy-phenyl)-2-(2-phenylamino-phenylamino)-acetamide 
• 179083-22-8 (R)-4-tert-Butoxycarbonylamino-4-({[isopropyl-(4-methoxy-phenyl)-carbamoyl]-methyl}-phenyl-carbamoyl)-butyric acid tert-butyl ester 
• 179083-47-7 (S)-4-tert-Butoxycarbonylamino-4-({[isopropyl-(4-methoxy-phenyl)-carbamoyl]-methyl}-phenyl-carbamoyl)-butyric acid tert-butyl ester 
• 351421-31-3 N-isopropyl-N-(4-methoxy-phenyl)-2-(2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)-acetamide 
• 173459-68-2 2-[3-(N-benzyloxycarbonyl-amino)-2-oxo-5-cyclohexyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide 
• 875552-48-0 (R)-2-[3-amino-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)acetamide 
• 875552-49-1 (S)-2-[3-amino-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)acetamide 
• 161455-94-3 2-[2,4-dioxo-5-phenyl-3-(phenylhydrazono)-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)acetamide 
• 161455-93-2 2-[3-amino-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)acetamide 
• 220493-41-4 2-{3-[3-(4-benzoylphenyl)ureido]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl}-N-isopropyl-N-(4-methoxyphenyl)acetamide 
• 174180-45-1 2-(2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide 
• 174181-60-3 2-[3-(1H-Indol-3-ylmethyl)-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide 
• 174181-69-2 GW₅₈₂₃ 
• 174181-81-8 N-Isopropyl-N-(4-methoxy-phenyl)-2-[3-(1-methyl-1H-indazol-3-ylmethyl)-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]acetamide 

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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.