298181-76-7

Basic information

• Product Name: 6,7,8,9-Tetrahydro-5H-cyclohepta[b]pyridin-9-ylamine
• Synonyms: 6,7,8,9-Tetrahydro-5H-cyclohepta[b]pyridin-9-ylamine;6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-amine
• CAS NO: 298181-76-7
• Molecular Formula: C₁₀H₁₄N₂
• Molecular Weight: 162.23156
• Mol File: 298181-76-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 6,7,8,9-Tetrahydro-5H-cyclohepta[b]pyridin-9-ylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7,8,9-Tetrahydro-5H-cyclohepta[b]pyridin-9-ylamine(298181-76-7)
• EPA Substance Registry System: 6,7,8,9-Tetrahydro-5H-cyclohepta[b]pyridin-9-ylamine(298181-76-7)

Safety Data

• Hazardous Substances Data: 298181-76-7(Hazardous Substances Data)

Upstream product

• 558442-15-2 9-azido-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine 
• 7197-96-8 2,3-cycloheptenopyridine 

Downstream Products

• 298181-92-7 N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N'-(6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl)-1,4-benzenedimethanamine 

Relevant articles and documents

Discovery of novel small molecule orally bioavailable C-X-C chemokine receptor 4 antagonists that are potent inhibitors of T-tropic (X4) HIV-1 replication

The redesign of azamacrocyclic CXCR4 chemokine receptor antagonists resulted in the discovery of novel, small molecule, orally bioavailable compounds that retained T-tropic (CXCR4 using, X4) anti-HIV-1 activity. A structure-activity relationship (SAR) was determined on the basis of the inhibition of replication of X4 HIV-1 NL4.3 in MT-4 cells. As a result of lead optimization, we identified (S)-N′-((1H-benzo[d]imidazol-2-yl)methyl)- N′-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine (AMD070) 2 as a potent and selective antagonist of CXCR4 with an IC50 value of 13 nM in a CXCR4 125I-SDF inhibition binding assay. Compound 2 inhibited the replication of T-tropic HIV-1 (NL4.3 strain) in MT-4 cells and PBMCs with an IC50 of 2 and 26 nM, respectively, while remaining noncytotoxic to cells at concentrations exceeding 23 μM. The pharmacokinetics of 2 was evaluated in rat and dog, and good oral bioavailability was observed in both species. This compound represents the first small molecule orally bioavailable CXCR4 antagonist that was developed for the treatment of HIV-1 infection.

Chemokine receptor binding heterocyclic compounds with enhanced efficacy

The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).