174181-06-7

Usage

Uses

Used in Pharmaceutical Industry:
1H-Indazole-1-carboxylic acid, 3-[[1-[2-[(1,1-dimethylethyl)phenylamino]-2-oxoethyl]-2,3,4,5-tetrahydro-2,4-dioxo-5-phenyl-1H-1,5-benzodiazepin-3-yl]methyl]-, 1,1-dimethylethyl ester is used as a potential active pharmaceutical ingredient for the development of psychoactive or anxiolytic drugs due to the presence of the benzodiazepin-3-yl moiety, which is commonly found in such medications. Further research and testing are needed to explore its therapeutic potential and efficacy.

Upstream product

• 937-33-7 N-tert-butylaniline 
• 174181-40-9 N-(2-nitrophenyl)-N-phenylmalonamic acid methyl ester 
• 194278-28-9 N-(2-aminophenyl)-N-phenylmalonamic acid methyl ester 
• 174180-72-4 2-methyl-2-propanyl 3-methyl-1H-indazole-1-carboxylate 
• 174181-07-8 2-Bromo-N-tert-butyl-N-phenyl-acetamide 
• 22316-50-3 1-phenyl 1,2,4,5-tetrahydro 2,4-dioxo 3H-1,5-benzodiazepine 
• 119-75-5 2-nitro-N-phenylaniline 
• 445-27-2 2'-Fluoroacetophenone 
• 24424-99-5 di-tert-butyl dicarbonate 
• 174180-42-8 2-methyl-2-propanyl 3-(bromomethyl)-1H-indazole-1-carboxylate 

Relevant academic research and scientific papers

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.