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Tak-779

CAS No.:
229005-80-5
Catalog Number:
AG00BF4R
Molecular Formula:
C33H39ClN2O2
Molecular Weight:
531.1280
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
99%
1 week
United States
$229
- +
10mg
99%
1 week
United States
$365
- +
Product Description
Catalog Number:
AG00BF4R
Chemical Name:
Tak-779
CAS Number:
229005-80-5
Molecular Formula:
C33H39ClN2O2
Molecular Weight:
531.1280
MDL Number:
MFCD05662319
IUPAC Name:
dimethyl-[[4-[[3-(4-methylphenyl)-8,9-dihydro-7H-benzo[7]annulene-6-carbonyl]amino]phenyl]methyl]-(oxan-4-yl)azanium;chloride
InChI:
InChI=1S/C33H38N2O2.ClH/c1-24-7-11-27(12-8-24)28-14-13-26-5-4-6-29(22-30(26)21-28)33(36)34-31-15-9-25(10-16-31)23-35(2,3)32-17-19-37-20-18-32;/h7-16,21-22,32H,4-6,17-20,23H2,1-3H3;1H
InChI Key:
VDALIBWXVQVFGZ-UHFFFAOYSA-N
SMILES:
Cc1ccc(cc1)c1ccc2c(c1)C=C(CCC2)C(=O)Nc1ccc(cc1)C[N+](C1CCOCC1)(C)C.[Cl-]
UNII:
BQW1Y9KIIP
Properties
Complexity:
769  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
530.27g/mol
Formal Charge:
0
Heavy Atom Count:
38  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
531.137g/mol
Monoisotopic Mass:
530.27g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
38.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
Title Journal
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The blocking of CXCR3 and CCR5 suppresses the infiltration of T lymphocytes in rat renal ischemia reperfusion. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20121001
Structure activity relationship studies of natural product chemokine receptor CCR5 antagonist anibamine toward the development of novel anti prostate cancer agents. European journal of medicinal chemistry 20120901
CCR5 antagonist TD-0680 uses a novel mechanism for enhanced potency against HIV-1 entry, cell-mediated infection, and a resistant variant. The Journal of biological chemistry 20120511
Baseline susceptibility of primary HIV-2 to entry inhibitors. Antiviral therapy 20120101
Allosteric and orthosteric sites in CC chemokine receptor (CCR5), a chimeric receptor approach. The Journal of biological chemistry 20111028
Effects of a calcineurin inhibitor, FK506, and a CCR5/CXCR3 antagonist, TAK-779, in a rat small intestinal transplantation model. Transplant immunology 20110701
Discovery of 4-[4-({(3R)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid hydrochloride: a highly potent orally available CCR5 selective antagonist. Bioorganic & medicinal chemistry 20110701
CCL5 neutralization restricts cancer growth and potentiates the targeting of PDGFRβ in colorectal carcinoma. PloS one 20110101
C-C chemokine receptor type 5 (CCR5) utilization of transmitted and early founder human immunodeficiency virus type 1 envelopes and sensitivity to small-molecule CCR5 inhibitors. The Journal of general virology 20101201
Evolution of CCR5 antagonist resistance in an HIV-1 subtype C clinical isolate. Journal of acquired immune deficiency syndromes (1999) 20101201
Tricyclononene carboxamide derivatives as novel anti-HIV-1 agents. European journal of medicinal chemistry 20100901
Different selection patterns of resistance and cross-resistance to HIV-1 agents targeting CCR5. The Journal of antimicrobial chemotherapy 20100301
Ex vivo comparison of microbicide efficacies for preventing HIV-1 genomic integration in intraepithelial vaginal cells. Antimicrobial agents and chemotherapy 20100201
The chemokine receptor antagonist, TAK-779, decreased experimental autoimmune encephalomyelitis by reducing inflammatory cell migration into the central nervous system, without affecting T cell function. British journal of pharmacology 20091201
Elucidation of binding sites of dual antagonists in the human chemokine receptors CCR2 and CCR5. Molecular pharmacology 20090601
Design, synthesis, and structure-activity relationship of novel CCR2 antagonists. Bioorganic & medicinal chemistry letters 20090315
[Viral entry as therapeutic target. Current situation of entry inhibitors]. Enfermedades infecciosas y microbiologia clinica 20081001
Inhibition of HIV fusion with multivalent gold nanoparticles. Journal of the American Chemical Society 20080604
Molecular interactions of CCR5 with major classes of small-molecule anti-HIV CCR5 antagonists. Molecular pharmacology 20080301
HIV-1 escape to CCR5 coreceptor antagonism through selection of CXCR4-using variants in vitro. AIDS (London, England) 20080102
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1. Antimicrobial agents and chemotherapy 20080101
Species selectivity of small-molecular antagonists for the CCR5 chemokine receptor. International immunopharmacology 20071205
Synergistic inhibition of HIV-1 infection by combinations of soluble polyanions with other potential microbicides. Antiviral research 20070901
Isolation and characterization of human immunodeficiency virus type 1 resistant to the small-molecule CCR5 antagonist TAK-652. Antimicrobial agents and chemotherapy 20070201
An anti-CCR5 monoclonal antibody and small molecule CCR5 antagonists synergize by inhibiting different stages of human immunodeficiency virus type 1 entry. Virology 20060901
Interaction of small molecule inhibitors of HIV-1 entry with CCR5. Virology 20060525
Highly potent and orally active CCR5 antagonists as anti-HIV-1 agents: synthesis and biological activities of 1-benzazocine derivatives containing a sulfoxide moiety. Journal of medicinal chemistry 20060323
T-cell line for HIV drug screening using EGFP as a quantitative marker of HIV-1 replication. BioTechniques 20060101
Role of CCR1 and CCR5 in homing and growth of multiple myeloma and in the development of osteolytic lesions: a study in the 5TMM model. Clinical & experimental metastasis 20060101
HIV entry inhibitor TAK-779 attenuates atherogenesis in low-density lipoprotein receptor-deficient mice. Arteriosclerosis, thrombosis, and vascular biology 20051201
Replicative fitness of historical and recent HIV-1 isolates suggests HIV-1 attenuation over time. AIDS (London, England) 20051014
Selection of human immunodeficiency virus type 1 R5 variants with augmented replicative capacity and reduced sensitivity to entry inhibitors during severe immunodeficiency. The Journal of general virology 20051001
The CCR5 receptor-based mechanism of action of 873140, a potent allosteric noncompetitive HIV entry inhibitor. Molecular pharmacology 20050401
Kinetic factors control efficiencies of cell entry, efficacies of entry inhibitors, and mechanisms of adaptation of human immunodeficiency virus. Journal of virology 20050401
Variants of human immunodeficiency virus type 1 that efficiently use CCR5 lacking the tyrosine-sulfated amino terminus have adaptive mutations in gp120, including loss of a functional N-glycan. Journal of virology 20050401
CCR5 antagonists: host-targeted antivirals for the treatment of HIV infection. Antiviral chemistry & chemotherapy 20050101
Impact of mutations in the coreceptor binding site on human immunodeficiency virus type 1 fusion, infection, and entry inhibitor sensitivity. Journal of virology 20040501
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CCR2: characterization of the antagonist binding site from a combined receptor modeling/mutagenesis approach. Journal of medicinal chemistry 20030911
Rapamycin causes down-regulation of CCR5 and accumulation of anti-HIV beta-chemokines: an approach to suppress R5 strains of HIV-1. Proceedings of the National Academy of Sciences of the United States of America 20030902
Development of a novel high-throughput surrogate assay to measure HIV envelope/CCR5/CD4-mediated viral/cell fusion using BacMam baculovirus technology. Journal of biomolecular screening 20030801
Binding of 2-aryl-4-(piperidin-1-yl)butanamines and 1,3,4-trisubstituted pyrrolidines to human CCR5: a molecular modeling-guided mutagenesis study of the binding pocket. Biochemistry 20030218
Sensitivity of HIV-1 to entry inhibitors correlates with envelope/coreceptor affinity, receptor density, and fusion kinetics. Proceedings of the National Academy of Sciences of the United States of America 20021210
Inhibitory effects of small-molecule CCR5 antagonists on human immunodeficiency virus type 1 envelope-mediated membrane fusion and viral replication. Antimicrobial agents and chemotherapy 20011201
Potent, broad-spectrum inhibition of human immunodeficiency virus type 1 by the CCR5 monoclonal antibody PRO 140. Journal of virology 20010101
Discovery of novel, potent, and selective small-molecule CCR5 antagonists as anti-HIV-1 agents: synthesis and biological evaluation of anilide derivatives with a quaternary ammonium moiety. Journal of medicinal chemistry 20000518
A binding pocket for a small molecule inhibitor of HIV-1 entry within the transmembrane helices of CCR5. Proceedings of the National Academy of Sciences of the United States of America 20000509
A small-molecule, nonpeptide CCR5 antagonist with highly potent and selective anti-HIV-1 activity. Proceedings of the National Academy of Sciences of the United States of America 19990511
Properties