740842-51-7

Basic information

• Product Name: 7H-Benzocyclohepten-7-one,2-amino-5,6,8,9-tetrahydro-(9CI)
• Synonyms: 7H-Benzocyclohepten-7-one,2-amino-5,6,8,9-tetrahydro-(9CI);2-amino-5,6,8,9-tetrahydro-benzocyclohepten-7-one;2-AMINO-8,9-DIHYDRO-5H-BENZO[7]ANNULEN-7(6H)-ONE
• CAS NO: 740842-51-7
• Molecular Formula: C₁₁H₁₃NO
• Molecular Weight: 175.22702
• Product Categories: CYCLOHEXANE
• Mol File: 740842-51-7.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7H-Benzocyclohepten-7-one,2-amino-5,6,8,9-tetrahydro-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 7H-Benzocyclohepten-7-one,2-amino-5,6,8,9-tetrahydro-(9CI)(740842-51-7)
• EPA Substance Registry System: 7H-Benzocyclohepten-7-one,2-amino-5,6,8,9-tetrahydro-(9CI)(740842-51-7)

Safety Data

• Hazardous Substances Data: 740842-51-7(Hazardous Substances Data)

Upstream product

• 740842-50-6 2-nitro-8,9-dihydro-5H-benzo[7]annulene-7(6H)-one 

Downstream Products

• 740842-52-8 (7-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yl)-carbamic acid benzyl ester 

Relevant articles and documents

Design, Synthesis, Pharmacological Evaluation and Docking Studies of GluN2B-Selective NMDA Receptor Antagonists with a Benzo[7]annulen-7-amine Scaffold

Antagonists that selectively target GluN2B-subunit-containing N-methyl-d-aspartate (NMDA) receptors are of major interest for the treatment of various neurological disorders. In this study, relationships between variously substituted benzo[7]annulen-7-amines and their GluN2B affinity were investigated. 2-Nitro-5,6,8,9-tetrahydrobenzo[7]annulen-7-one (8) represents the central building block for the introduction of various substituents at the 2-position and various 7-amino moieties. N-(3-Phenylpropyl)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-7-amines with a 2-NO2 (7 c), 2-Cl (15 c), or 2-OBn group (22 c) show very high GluN2B affinity (Ki=1.6–3.6 nm). Docking studies revealed the same binding poses for benzo[7]annulen-7-amines and ifenprodil at the interface of GluN1b and GluN2B subunits. The large 2-OBn moiety of 22 c occupies a previously unrecognized subpocket, which explains its high GluN2B affinity (Ki=3.6 nm). In two-electrode voltage clamp experiments and cytoprotection assays, the high-affinity GluN2B ligands 7 c, 15 c, and 22 c could not inhibit the glutamate-/glycine-evoked current and cytotoxic effects. However, the analogous phenols 16 c ((3-phenylpropyl)amino moiety) and 16 d ((4-phenylbutyl)amino moiety) with 10-fold lower GluN2B affinity (Ki=28 and 21 nm, respectively) showed promising inhibition of glutamate-/glycine-evoked effects in both assays. The presence of a phenolic hydroxy group seems to be essential for inducing conformational changes of the receptor protein, which finally results in closure of the ion conduction pathway.

OXAZOLIDINONE DERIVATIVES N-SUBSTITUTED BY A BICYCLIC RING, FOR USE AS ANTIBACTERIAL AGENTS

Compounds of formula (I) and methods for their preparation are disclosed. Further disclosed are methods of making biologically active compounds of formula (I) as well as pharmaceutically acceptable compositions comprising compounds of formula (I). Compoun