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

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

Uses

Used in Cancer Treatment:
AMD 070 is used as an anti-cancer agent for its ability to inhibit the migration of cancer cells by blocking the CXCR4 receptor, which is involved in cancer metastasis. This makes it a potential therapeutic option for various types of cancer.
Used in HIV Treatment:
AMD 070 is used as an antiretroviral agent for its capacity to inhibit HIV infection by targeting the CXCR4 receptor, which the virus uses to enter host cells.
Used in Inflammatory and Autoimmune Disease Treatment:
AMD 070 is used as an immunomodulatory agent for its potential to treat inflammatory and autoimmune diseases by regulating immune cell trafficking and potentially reducing inflammation.
Used in Pharmaceutical Research and Development:
AMD 070 is used as a target for drug development in the pharmaceutical industry due to its multifaceted potential in treating various diseases by modulating the CXCR4 receptor pathway.

Upstream product

• 1044264-94-9 C₃₄H₃₇N₅O₄ 
• 4857-04-9 2-chloromethyl-1H-benzimidazole 
• 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 
• 865202-96-6 C₂₃H₃₇N₃O₄*ClH 
• 865202-97-7 C₃₆H₅₁N₅O₆ 

Downstream Products

• 880549-26-8 (S)-(N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl))-1,4-butanediamine benzoate 
• 880549-24-6 (S)-(N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl))-1,4-butanediamine 4-aminobenzenesulfonate 
• 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 

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.

AMD070, a CXCR4 chemokine receptor antagonist: Practical large-scale laboratory synthesis

An efficient and convergent four-step synthetic route to the CXCR4 chemokine receptor antagonist AMD070 (1) has been developed which employs only a single chromatographic step in the entire sequence. Novel reductive amination methods have been developed for the coupling of 2 and 3 in which a dehydrative imine formation is followed by reduction with an attenuated borohydride reagent (zinc chloride and sodium borohydride). Selective extraction methods were employed to purify synthetic intermediates and remove reagents and impurities. A procedure has also been developed to isolate 1 in a pure crystalline form.

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.

Chemokine-binding heterocyclic compound salts, and methods of use thereof

The present invention relates to chemokine-binding heterocyclic compound salts, methods of use thereof, and methods for preparing the same.

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′