442563-32-8

Usage

Chemical structure

A bicyclic compound consisting of a pyrrolo azepine ring system.

Versatility

Serves as a building block for the synthesis of various pharmaceuticals and biologically active molecules.

Potential applications

Studied for its potential as an antipsychotic and anxiolytic agent.

Reactivity

Its structure and reactivity make it a valuable intermediate in organic synthesis and medicinal chemistry.

Pharmacological applications

Has interesting pharmacological properties due to its unique structure.

Synthetic applications

Used in the development of new compounds with potential therapeutic benefits.

Upstream product

• 27866-27-9 1,5,6,7-tetrahydro-indol-4-one oxime 
• 13754-86-4 1,5,6,7-tetrahydro-indol-4-one 

Downstream Products

• 186808-28-6 (4-Nitro-phenyl)-(5,6,7,8-tetrahydro-1H-pyrrolo[3,2-b]azepin-4-yl)-methanone 
• 186808-30-0 (1-Methyl-5,6,7,8-tetrahydro-1H-pyrrolo[3,2-b]azepin-4-yl)-(4-nitro-phenyl)-methanone 

Relevant academic research and scientific papers

Synthesis and Structure-Activity Relationships of 5,6,7,8-Tetrahydro-4H-thieno[3,2-b]azepine Derivatives: Novel Arginine Vasopressin Antagonists

A variety of novel heterocyclic compounds having thienoazepine, pyrroloazepine, furoazepine, and thienodiazepine skeletons were synthesized, most of which exhibited potent antagonism of [3H]-AVP specific binding in assays using rat liver (V1), rat kidney (V2), human platelet plasma membranes, and recombinant human CHO cells (V2), as well as antagonizing AVP-induced hypertension in rats (V1, intravenous) and showing a diuretic effect in rats (V2, oral). By detailed studies of the structure-activity relationships of these compounds, the thienoazepine derivative 1 was found to be a very potent combined V1 and V2 antagonist. After further pharmacological and toxicological evaluation as well as physical properties, the hydrochloride 2 (JTV-605) of compound 1 was selected for clinical studies as a potent AVP antagonist with a long duration of action.

Regioselective synthesis of several heterocyclic fused azepines using diisobutylaluminum hydride

5,6,7,8-Tetrahydrothieno[3,2-b]azepine,5,6,7,8-tetrahydro-1H-furo[3,2-b] azepine, and 1,4,5,6,7,8-hexahydropyrrolo[3,2-b]azepine were synthesized by the ring expansion reaction of heterocyclic fused cyclohexanone oximes with diisobutylaluminum hydride (DIBAH). The mechanism of the reaction was different from that of Beckmann rearrangement.