Home Amines 558447-26-0
558447-26-0,MFCD11977316
Catalog No.:AA00DB1X

558447-26-0 | (S)-N1-((1H-Benzo[d]imidazol-2-yl)methyl)-N1-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine

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5mg
≥95%
in stock  
$168.00   $117.00
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10mg
≥95%
in stock  
$266.00   $186.00
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25mg
95%
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$466.00   $326.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00DB1X
Chemical Name:
(S)-N1-((1H-Benzo[d]imidazol-2-yl)methyl)-N1-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine
CAS Number:
558447-26-0
Molecular Formula:
C21H27N5
Molecular Weight:
349.4726
MDL Number:
MFCD11977316
SMILES:
NCCCCN([C@H]1CCCc2c1nccc2)Cc1nc2c([nH]1)cccc2
Properties
Computed Properties
 
Complexity:
431  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
7  
XLogP3:
2.4  

Downstream Synthesis Route

[1]CurrentPatentAssignee:SANOFI-US2006/69122,2006,A1Locationinpatent:Page/Pagecolumn6

[1]Patent:US2006/69122,2006,A1.Locationinpatent:Page/Pagecolumn7

[1]Crawford,JasonB.;Chen,Gang;Gauthier,David;Wilson,Trevor;Carpenter,Bryon;Baird,IanR.;McEachern,Ernie;Kaller,Alan;Harwig,Curtis;Atsma,Bem;Skerlj,RenatoT.;Bridger,GaryJ.[OrganicProcessResearchandDevelopment,2008,vol.12,#5,p.823-830]

[1]CurrentPatentAssignee:X4PHARMACEUTICALSINC-US10548889,2020,B1Locationinpatent:Page/Pagecolumn76;82

Literature

Title: The molecular pharmacology of AMD11070: an orally bioavailable CXCR4 HIV entry inhibitor.

Journal: Biochemical pharmacology 20120215

Title: Combination of drug therapy in acute lymphoblastic leukemia with a CXCR4 antagonist.

Journal: Leukemia 20110801

Title: Design of novel CXCR4 antagonists that are potent inhibitors of T-tropic (X4) HIV-1 replication.

Journal: Bioorganic & medicinal chemistry letters 20110301

Title: HIV-1 tropism.

Journal: Protein & cell 20100601

Title: Synthesis and SAR of novel isoquinoline CXCR4 antagonists with potent anti-HIV activity.

Journal: Bioorganic & medicinal chemistry letters 20100515

Title: 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.

Journal: Journal of medicinal chemistry 20100422

Title: Amine substituted N-(1H-benzimidazol-2ylmethyl)-5,6,7,8-tetrahydro-8-quinolinamines as CXCR4 antagonists with potent activity against HIV-1.

Journal: Bioorganic & medicinal chemistry letters 20090901

Title: Comparison of the potential multiple binding modes of bicyclam, monocylam, and noncyclam small-molecule CXC chemokine receptor 4 inhibitors.

Journal: Molecular pharmacology 20081201

Title: Pharmacokinetic effect of AMD070, an Oral CXCR4 antagonist, on CYP3A4 and CYP2D6 substrates midazolam and dextromethorphan in healthy volunteers.

Journal: Journal of acquired immune deficiency syndromes (1999) 20080415

Title: Multiple-dose escalation study of the safety, pharmacokinetics, and biologic activity of oral AMD070, a selective CXCR4 receptor inhibitor, in human subjects.

Journal: Antimicrobial agents and chemotherapy 20070701

Title: Emerging anti-HIV drugs.

Journal: Expert opinion on emerging drugs 20050501

Title: The appealing story of HIV entry inhibitors : from discovery of biological mechanisms to drug development.

Journal: Drugs 20050101

Title: Emerging drug targets for antiretroviral therapy.

Journal: Drugs 20050101

Title: HIV co-receptor drugs on the horizon.

Journal: GMHC treatment issues : the Gay Men's Health Crisis newsletter of experimental AIDS therapies 20040101

Title: Skerlj RT, et al. 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. J Med Chem. 2010 Apr 22;53(8):3376-88.

Title: Chow LN, et al. Impact of a CXCL12/CXCR4 Antagonist in Bleomycin (BLM) Induced Pulmonary Fibrosis and Carbon Tetrachloride (CCl4) Induced Hepatic Fibrosis in Mice. PLoS One. 2016 Mar 21;11(3):e0151765.

Title: Uchida D, et al. Effect of a novel orally bioavailable CXCR4 inhibitor, AMD070, on the metastasis of oral cancer cells. Oncol Rep. 2018 Jul;40(1):303-308.

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Tags:558447-26-0 Molecular Formula|558447-26-0 MDL|558447-26-0 SMILES|558447-26-0 (S)-N1-((1H-Benzo[d]imidazol-2-yl)methyl)-N1-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine