5755-07-7

Usage

Uses

A tetrahydrobenzodiazepine derivative as arginine vasopressin antagonist.

InChI:InChI=1/C9H10N2O/c12-9-5-6-10-7-3-1-2-4-8(7)11-9/h1-4,10H,5-6H2,(H,11,12)

Upstream product

• 4295-36-7 2,3-dihydroquinolin-4(1H)-one 
• 930-21-2 2-azetidinone 
• 615-43-0 2-iodophenylamine 
• 615-36-1 2-bromoaniline 

Downstream Products

• 104310-01-2 5-formyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one 
• 104310-03-4 5-(3,4,5-Trimethoxybenzoyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one 
• 202537-03-9 5-Benzyl-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one 
• 168045-47-4 2,6-diaza-6-<(4-nitrophenyl)carbonyl>bicyclo<5.4.0>undeca-1(7),8,10-trien-3-one 
• 7647-01-0 hydrogenchloride 
• 65533-78-0 1-nitroso-2,3-dihydro<1,5>benzodiazepin-4-one 
• 37040-46-3 8-bromo-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one 
• 159588-63-3 (4-amino-phenyl)-(5-pyridin-3-ylmethyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-methanone 
• 159588-62-2 (4-amino-phenyl)-(5-pyridin-2-ylmethyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-methanone 
• 159588-64-4 (4-amino-phenyl)-(5-pyridin-4-ylmethyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-methanone 
• 159588-91-7 1-(2-dimethylaminoethyl)-5-(4-nitrobenzoyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine 
• 159588-60-0 (4-nitro-phenyl)-(5-pyridin-3-ylmethyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-methanone 
• 159588-61-1 (4-nitro-phenyl)-(5-pyridin-4-ylmethyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-methanone 
• 159588-59-7 1-(4-nitrobenzoyl)-5-(2-pyridylmethyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine 

Relevant academic research and scientific papers

Synthesis of Medium Ring Nitrogen Heterocycles via a Tandem Copper-Catalyzed C-N Bond Formation-Ring-Expansion Process

A simple method for the preparation of medium ring heterocycles (7-, 8-, 9-, and 10-membered) has been developed. The process employs a Cu-catalyzed coupling of a β-lactam with an aryl bromide or iodide followed by intramolecular attack of a pendant amino group. In some instances, the intermediate β-lactam is observable but can be converted to the aza-heterocycle by catalysis. Acetic acid was found to be superior to transition metal complexes as a catalyst for this ring-expansion process.

Effect of ring size or an additional heteroatom on the potency and selectivity of bicyclic benzylamine-type inhibitors of phenylethanolamine N- methyltransferase

In the search for potent and selective inhibitors of the enzyme phenylethanolamine N-methyltransferase (PNMT; EC 2.1.1.28), we examined the effect of ring size or an additional heteroatom in the conformationally- restricted benzylamine-type PNMT inhibitors. Based on semiempirical calculations (MNDO) and molecular modeling studies, PNMT-inhibitory activity of these compounds seemed to be dependent on (a) the torsion angle between the plane of the aromatic ring and the endo N atom lone pair (τ2 angle), with the optimal value of τ2 being about -75°, and (b) the amount of steric bulk about the 3-position of 1,2,3,4-tetrahydroisoquinoline (5, THIQ). 2,3,4,5-Tetrahydro-1H-2-benzazepine (6) was found to have the highest selectivity (PNMT K(i) = 3.34 μM, α2 K(i) = 11 μM, selectivity = 3.2) as compared to other homologues of THIQ (PNMT K(i) = 9.67 μM, α2 K(i) = 0.35 μM, selectivity = 0.036). The higher PNMT-inhibitory activity of 6 was attributed to favorable steric interactions of the puckered methylene groups in the putative bioactive conformation of 6 at the PNMT active site, whereas unfavorable interactions of these puckered methylene groups at the α2- adrenoceptor were thought to be the cause of reduced α2 affinity of 6. No further enhancement of the selectivity of the benzazepine ring system could be obtained via introduction of a second heteroatom (N, O, S) at the 5- position in this ring system.