558447-26-0

Basic information

• Product Name: AMD 070
• Synonyms: AMD 070;N-(1H-benzimidazol-2-ylmethyl)-N-[(8S)-5,6,7,8-tetrahydro-8-quinolinyl]- (9CI);N'-(1H-Benzimidazol-2-ylmethyl)-N'-((S)-5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine;AMD 070 N-(1H-benziMidazol-2-ylMethyl)-N-[(8S)-5,6,7,8-tetrahydro-8-quinolinyl]- (9CI);1,4-ButanediaMine, N-(1H-benziMidazol-2-ylMethyl)-N-[(8S)-5,6,7,8-tetrahydro-8-quinolinyl]-;(S)-N1-((1H-benzo[d]iMidazol-2-yl)Methyl)-N1-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diaMine;AMD070/AMD-070;(S)-N1-((1H-Benzo[d]imidazol-2-yl)methyl)-N1-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diami
• CAS NO: 558447-26-0
• Molecular Formula: C₂₁H₂₇N₅
• Molecular Weight: 349.479
• Mol File: 558447-26-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 108-110℃
• Boiling Point: 597.0±50.0 °C(Predicted)
• Appearance: /
• Density: 1.21
• Solubility: ≥17.45 mg/mL in DMSO; ≥44.5 mg/mL in EtOH; ≥7.47 mg/mL in H2O with gentle warming
• PKA: 11.65±0.10(Predicted)
• CAS DataBase Reference: AMD 070(CAS DataBase Reference)
• NIST Chemistry Reference: AMD 070(558447-26-0)
• EPA Substance Registry System: AMD 070(558447-26-0)

Safety Data

• Hazardous Substances Data: 558447-26-0(Hazardous Substances Data)

Usage

General Description

AMD 070 is a potent inhibitor of the C-X-C chemokine receptor type 4 (CXCR4), which plays a crucial role in the regulation of immune cell trafficking and is involved in cancer metastasis and HIV infection. By targeting CXCR4, AMD 070 blocks the activation of downstream signaling pathways and inhibits the migration of cancer cells and immune cells. This makes it a promising candidate for the treatment of various cancers and HIV, and it has been the subject of preclinical and clinical studies. Additionally, AMD 070 has shown potential for the treatment of inflammatory and autoimmune diseases, making it an exciting target for further research and drug development.

Upstream product

• 865202-96-6 C₂₃H₃₇N₃O₄*ClH 
• 163798-87-6 1-Boc-2-chloromethylbenzimidazole 
• 558444-72-7 (S)-2-[4-(5,6,7,8-tetrahydro-quinolin-8-ylamino)-butyl]-isoindole-1,3-dione 
• 4857-04-9 2-chloromethyl-1H-benzimidazole 
• 1044264-94-9 C₃₄H₃₇N₅O₄ 
• 865202-97-7 C₃₆H₅₁N₅O₆ 

Downstream Products

• 880549-21-3 (S)-(N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl))-1,4-butanediamine 4-hydroxybenzoate 
• 880549-23-5 (S)-(N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl))-1,4-butanediamine 4-hydroxybenzenesulfonate 
• 880549-22-4 (S)-(N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl))-1,4-butanediamine 4-aminobenzoate 
• 880549-25-7 (S)-(N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl))-1,4-butanediamine benzenesulfonate 
• 880549-24-6 (S)-(N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl))-1,4-butanediamine 4-aminobenzenesulfonate 
• 880549-26-8 (S)-(N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl))-1,4-butanediamine benzoate 

Relevant articles and documents

Compositions of CXCR4 inhibitors and methods of preparation and use

The present invention provides compositions and methods of use for treating, preventing, or ameliorating a disease, disorder, or condition associated with a chemokine receptor such as CXCR4.

Chemokine combinations to mobilize progenitor/stem cells

Methods to elevate progenitor and stem cell counts in animal subjects using compounds which bind to the chemokine receptor CXCR4 in combination with the CXCR2 chemokine GROβ, including its modified forms, are disclosed.

Process for the synthesis of CXCR4 antagonist

This invention relates to a process for synthesizing heterocyclic pharmaceutical compound which binds to the CXCR4 chemokine receptor. In one embodiment, the process comprises: a) reacting a 5,6,7,8-tetrahydroquinolinylamine and an alkyl aldehyde bearing a phthalimide or a di-tertiary-butoxycarbonyl (di-BOC) protecting group to form an imine; b) reducing the imine to form a secondary amine; c) reacting the secondary amine with a haloalkyl substituted heterocyclic compound, to form a phthalimido-protected or di-tert-butoxycarbonyl protected tertiary amine; and d) hydrolyzing the protected amine to obtain a compound having Formula I′