Home Other Building Blocks 163042-96-4
163042-96-4,MFCD01861178
Catalog No.:AA001TK8

163042-96-4 | 2-Cl-ib-meca

Pack Size
Purity
Availability
Price(USD)
Quantity
  
5mg
≥98%
in stock  
$158.00   $110.00
- +
10mg
>98.0%(HPLC)
in stock  
$167.00   $117.00
- +
50mg
95%
in stock  
$190.00   $133.00
- +
100mg
95%
in stock  
$258.00   $181.00
- +
250mg
95%
in stock  
$446.00   $312.00
- +
  • Technical Information
  • Properties
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA001TK8
Chemical Name:
2-Cl-ib-meca
CAS Number:
163042-96-4
Molecular Formula:
C18H18ClIN6O4
Molecular Weight:
544.7308
MDL Number:
MFCD01861178
SMILES:
CNC(=O)[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(Cl)nc2NCc1cccc(c1)I
Properties
Computed Properties
 
Complexity:
623  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
5  
XLogP3:
1.9  

Literature

Title: Resveratrol 3-O-D-glucuronide and resveratrol 4'-O-D-glucuronide inhibit colon cancer cell growth: evidence for a role of A3 adenosine receptors, cyclin D1 depletion, and G1 cell cycle arrest.

Journal: Molecular nutrition & food research 20131001

Title: Adenosine A(3) receptor-induced proliferation of primary human coronary smooth muscle cells involving the induction of early growth response genes.

Journal: Journal of molecular and cellular cardiology 20121101

Title: Medicinal chemistry of A₃ adenosine receptor modulators: pharmacological activities and therapeutic implications.

Journal: Journal of medicinal chemistry 20120628

Title: Anti-ischemic effects of multivalent dendrimeric A₃ adenosine receptor agonists in cultured cardiomyocytes and in the isolated rat heart.

Journal: Pharmacological research 20120301

Title: 3-aryl-[1,2,4]triazino[4,3-a]benzimidazol-4(10H)-one: a novel template for the design of highly selective A₂B adenosine receptor antagonists.

Journal: Journal of medicinal chemistry 20120223

Title: P-glycoprotein mediates resistance to A3 adenosine receptor agonist 2-chloro-N6-(3-iodobenzyl)-adenosine-5'-n-methyluronamide in human leukemia cells.

Journal: Journal of cellular physiology 20120201

Title: Protection from myocardial ischemia/reperfusion injury by a positive allosteric modulator of the A₃ adenosine receptor.

Journal: The Journal of pharmacology and experimental therapeutics 20120101

Title: A3 adenosine receptor-mediated p53-dependent apoptosis in Lu-65 human lung cancer cells.

Journal: Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20120101

Title: Adenosine induces apoptosis in SBC-3 human lung cancer cells through A(3) adenosine receptor-dependent AMID upregulation.

Journal: Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20120101

Title: Adoptive immunotherapy with Cl-IB-MECA-treated CD8+ T cells reduces melanoma growth in mice.

Journal: PloS one 20120101

Title: CF102 an A3 adenosine receptor agonist mediates anti-tumor and anti-inflammatory effects in the liver.

Journal: Journal of cellular physiology 20110901

Title: Cl-IB-MECA enhances TNF-α release in peritoneal macrophages stimulated with LPS.

Journal: Cytokine 20110501

Title: NK1.1 cells and CD8 T cells mediate the antitumor activity of Cl-IB-MECA in a mouse melanoma model.

Journal: Neoplasia (New York, N.Y.) 20110401

Title: A2A and A3 adenosine receptor expression in rheumatoid arthritis: upregulation, inverse correlation with disease activity score and suppression of inflammatory cytokine and metalloproteinase release.

Journal: Arthritis research & therapy 20110101

Title: Adenosine receptor A3 is a critical mediator in LPS-induced pulmonary inflammation.

Journal: American journal of physiology. Lung cellular and molecular physiology 20101001

Title: Control of enteric neuromuscular functions by purinergic A(3) receptors in normal rat distal colon and experimental bowel inflammation.

Journal: British journal of pharmacology 20101001

Title: Adenosine A3 receptor agonist reduces early brain injury in subarachnoid haemorrhage.

Journal: Neuroreport 20100915

Title: A(3) adenosine receptor activation during reperfusion reduces infarct size through actions on bone marrow-derived cells.

Journal: Journal of molecular and cellular cardiology 20100801

Title: Post exposure administration of A(1) adenosine receptor agonists attenuates noise-induced hearing loss.

Journal: Hearing research 20100201

Title: The A3 adenosine receptor attenuates the calcium rise triggered by NMDA receptors in retinal ganglion cells.

Journal: Neurochemistry international 20100101

Title: Nucleoside-derived antagonists to A3 adenosine receptors lower mouse intraocular pressure and act across species.

Journal: Experimental eye research 20100101

Title: Design and synthesis of N(6)-substituted-4'-thioadenosine-5'-uronamides as potent and selective human A(3) adenosine receptor agonists.

Journal: Bioorganic & medicinal chemistry 20091201

Title: Cl-IB-MECA enhances TRAIL-induced apoptosis via the modulation of NF-kappaB signalling pathway in thyroid cancer cells.

Journal: Journal of cellular physiology 20091101

Title: Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.

Journal: Nature chemical biology 20091001

Title: Structure-activity relationships of truncated adenosine derivatives as highly potent and selective human A3 adenosine receptor antagonists.

Journal: Bioorganic & medicinal chemistry 20090515

Title: Novel 2- and 4-substituted 1H-imidazo[4,5-c]quinolin-4-amine derivatives as allosteric modulators of the A3 adenosine receptor.

Journal: Journal of medicinal chemistry 20090409

Title: Topological descriptors in modeling the agonistic activity of human A3 adenosine receptor ligands: the derivatives of 2-chloro-N(6)-substituted-4'-thioadenosine-5'-uronamide.

Journal: European journal of medicinal chemistry 20090401

Title: Stimulation of ANP secretion by 2-Cl-IB-MECA through A(3) receptor and CaMKII.

Journal: Peptides 20081201

Title: Adenosine A1 and A3 receptors protect astrocytes from hypoxic damage.

Journal: European journal of pharmacology 20081031

Title: Structure-activity relationships of truncated D- and l-4'-thioadenosine derivatives as species-independent A3 adenosine receptor antagonists.

Journal: Journal of medicinal chemistry 20081023

Title: Selective A(3) adenosine receptor antagonists derived from nucleosides containing a bicyclo[3.1.0]hexane ring system.

Journal: Bioorganic & medicinal chemistry 20080915

Title: The A3 adenosine receptor agonist CF102 induces apoptosis of hepatocellular carcinoma via de-regulation of the Wnt and NF-kappaB signal transduction pathways.

Journal: International journal of oncology 20080801

Title: Short- and long-term A3 adenosine receptor activation inhibits the Na+/H+ exchanger NHE3 activity and expression in opossum kidney cells.

Journal: Journal of cellular physiology 20080701

Title: Design of (N)-methanocarba adenosine 5'-uronamides as species-independent A3 receptor-selective agonists.

Journal: Bioorganic & medicinal chemistry letters 20080501

Title: Derivatives of 4-amino-6-hydroxy-2-mercaptopyrimidine as novel, potent, and selective A3 adenosine receptor antagonists.

Journal: Journal of medicinal chemistry 20080327

Title: Structure-activity relationships of 2-chloro-N6-substituted-4'-thioadenosine-5'-N,N-dialkyluronamides as human A3 adenosine receptor antagonists.

Journal: Bioorganic & medicinal chemistry letters 20080301

Title: Cl-IB-MECA inhibits human thyroid cancer cell proliferation independently of A3 adenosine receptor activation.

Journal: Cancer biology & therapy 20080201

Title: Dual purinergic synaptic transmission in the human enteric nervous system.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20080201

Title: Flexible modulation of agonist efficacy at the human A3 adenosine receptor by the imidazoquinoline allosteric enhancer LUF6000.

Journal: BMC pharmacology 20080101

Title: Protective roles of adenosine A1, A2A, and A3 receptors in skeletal muscle ischemia and reperfusion injury.

Journal: American journal of physiology. Heart and circulatory physiology 20071201

Title: Involvement of COX-1 in A3 adenosine receptor-mediated contraction through endothelium in mice aorta.

Journal: American journal of physiology. Heart and circulatory physiology 20071201

Title: 5-amino-2-phenyl[1,2,3]triazolo[1,2-a][1,2,4]benzotriazin-1-one: a versatile scaffold to obtain potent and selective A3 adenosine receptor antagonists.

Journal: Journal of medicinal chemistry 20071115

Title: Discovery of a new nucleoside template for human A3 adenosine receptor ligands: D-4'-thioadenosine derivatives without 4'-hydroxymethyl group as highly potent and selective antagonists.

Journal: Journal of medicinal chemistry 20070712

Title: Barrier qualities of the mouse eye to topically applied drugs.

Journal: Experimental eye research 20070701

Title: Adenosine receptors in colon carcinoma tissues and colon tumoral cell lines: focus on the A(3) adenosine subtype.

Journal: Journal of cellular physiology 20070601

Title: The protective effect of prior ischemia reperfusion adenosine A1 or A3 receptor activation in the normal and hypertrophied heart.

Journal: Interactive cardiovascular and thoracic surgery 20070601

Title: Cl-IB-MECA inhibits human erythropoiesis.

Journal: British journal of haematology 20070501

Title: N6-methoxy-2-alkynyladenosine derivatives as highly potent and selective ligands at the human A3 adenosine receptor.

Journal: Journal of medicinal chemistry 20070322

Title: Contractile effects of adenosine, coronary flow and perfusion pressure in murine myocardium.

Journal: Pflugers Archiv : European journal of physiology 20070101

Title: Docking studies of agonists and antagonists suggest an activation pathway of the A3 adenosine receptor.

Journal: Journal of molecular graphics & modelling 20061201

Title: Cl-IB-MECA [2-chloro-N6-(3-iodobenzyl)adenosine-5'-N-methylcarboxamide] reduces ischemia/reperfusion injury in mice by activating the A3 adenosine receptor.

Journal: The Journal of pharmacology and experimental therapeutics 20061201

Title: The impact of adenosine and A(2B) receptors on glucose homoeostasis.

Journal: The Journal of pharmacy and pharmacology 20061201

Title: Identification of the A3 adenosine receptor in rat retinal ganglion cells.

Journal: Molecular vision 20060816

Title: N6-ethyl-2-alkynyl NECAs, selective human A3 adenosine receptor agonists.

Journal: Bioorganic & medicinal chemistry letters 20060501

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Activation of adenosine A3 receptor suppresses lipopolysaccharide-induced TNF-alpha production through inhibition of PI 3-kinase/Akt and NF-kappaB activation in murine BV2 microglial cells.

Journal: Neuroscience letters 20060320

Title: Adenosine receptors as therapeutic targets.

Journal: Nature reviews. Drug discovery 20060301

Title: The role of adenosine A2A and A3 receptors on the differential modulation of norepinephrine and neuropeptide Y release from peripheral sympathetic nerve terminals.

Journal: Journal of neurochemistry 20060301

Title: Antitumor effect of cordycepin (3'-deoxyadenosine) on mouse melanoma and lung carcinoma cells involves adenosine A3 receptor stimulation.

Journal: Anticancer research 20060101

Title: Different roles of adenosine A1, A2A and A3 receptors in controlling kainate-induced toxicity in cortical cultured neurons.

Journal: Neurochemistry international 20051001

Title: A3 adenosine receptor activation inhibits cell proliferation via phosphatidylinositol 3-kinase/Akt-dependent inhibition of the extracellular signal-regulated kinase 1/2 phosphorylation in A375 human melanoma cells.

Journal: The Journal of biological chemistry 20050520

Title: (N)-methanocarba 2,N6-disubstituted adenine nucleosides as highly potent and selective A3 adenosine receptor agonists.

Journal: Journal of medicinal chemistry 20050324

Title: The role of adenosine A2A and A2B receptors in the regulation of TNF-alpha production by human monocytes.

Journal: Biochemical pharmacology 20050315

Title: Synthesis, biological evaluation, and molecular modeling of ribose-modified adenosine analogues as adenosine receptor agonists.

Journal: Journal of medicinal chemistry 20050310

Title: Development of potent and selective human A3 adenosine receptor agonists.

Journal: Nucleic acids symposium series (2004) 20050101

Title: Analysis of calcium responses mediated by the A3 adenosine receptor in cultured newborn rat cardiac myocytes.

Journal: Cell calcium 20041101

Title: Activation of protein kinase B by adenosine A1 and A3 receptors in newborn rat cardiomyocytes.

Journal: Journal of molecular and cellular cardiology 20041101

Title: Synthesis and biological evaluation of novel N6-[4-(substituted)sulfonamidophenylcarbamoyl]adenosine-5'-uronamides as A3 adenosine receptor agonists.

Journal: Journal of medicinal chemistry 20041021

Title: Design and synthesis of 3'-ureidoadenosine-5'-uronamides: effects of the 3'-ureido group on binding to the A3 adenosine receptor.

Journal: Bioorganic & medicinal chemistry letters 20041004

Title: 2-Pyrazolyl-N(6)-substituted adenosine derivatives as high affinity and selective adenosine A(3) receptor agonists.

Journal: Journal of medicinal chemistry 20040909

Title: Adenosine A3 receptor-induced CCL2 synthesis in cultured mouse astrocytes.

Journal: Glia 20040501

Title: Role of adenosine receptor activation in antioxidant enzyme regulation during ischemia-reperfusion in the isolated rat heart.

Journal: Antioxidants & redox signaling 20040401

Title: The A3 adenosine receptor agonist 2-Cl-IB-MECA facilitates epileptiform discharges in the CA3 area of immature rat hippocampal slices.

Journal: Epilepsy research 20040101

Title: N6-substituted D-4'-thioadenosine-5'-methyluronamides: potent and selective agonists at the human A3 adenosine receptor.

Journal: Journal of medicinal chemistry 20030828

Title: Functional expression of adenosine A2A and A3 receptors in the mouse dendritic cell line XS-106.

Journal: European journal of pharmacology 20030801

Title: Characterization of adenosine receptor(s) involved in adenosine-induced bronchoconstriction in an allergic mouse model.

Journal: American journal of physiology. Lung cellular and molecular physiology 20030601

Title: Design, synthesis and binding affinity of 3'-fluoro analogues of Cl-IB-MECA as adenosine A3 receptor ligands.

Journal: Bioorganic & medicinal chemistry letters 20030310

Title: Pharmacological analysis of calcium responses mediated by the human A3 adenosine receptor in monocyte-derived dendritic cells and recombinant cells.

Journal: Molecular pharmacology 20030201

Title: 3'-Aminoadenosine-5'-uronamides: discovery of the first highly selective agonist at the human adenosine A3 receptor.

Journal: Journal of medicinal chemistry 20030130

Title: Design and synthesis of A3 adenosine receptor ligands, 3'-fluoro analogues of Cl-IB-MECA.

Journal: Nucleosides, nucleotides & nucleic acids 20030101

Title: Design and synthesis of A3 adenosine receptor ligands, 2'-fluoro analogues of Cl-IB-MECA.

Journal: Nucleosides, nucleotides & nucleic acids 20030101

Title: A role for histamine in cytokine modulation by the adenosine A(3) receptor agonist, 2-Cl-IB-MECA.

Journal: European journal of pharmacology 20021213

Title: Adenosine A(3) receptor activation protects the myocardium from reperfusion/reoxygenation injury.

Journal: American journal of physiology. Heart and circulatory physiology 20021001

Title: Structural determinants of A(3) adenosine receptor activation: nucleoside ligands at the agonist/antagonist boundary.

Journal: Journal of medicinal chemistry 20020926

Title: Targeted deletion of adenosine A(3) receptors augments adenosine-induced coronary flow in isolated mouse heart.

Journal: American journal of physiology. Heart and circulatory physiology 20020601

Title: Differential aspects in ratio measurements of [Ca(2+)](i) relaxation in cardiomyocyte contraction following various drug treatments.

Journal: Cell calcium 20020601

Title: p53-Independent induction of Fas and apoptosis in leukemic cells by an adenosine derivative, Cl-IB-MECA.

Journal: Biochemical pharmacology 20020301

Title: Roles of BCL-2 and caspase 3 in the adenosine A3 receptor-induced apoptosis.

Journal: Journal of molecular neuroscience : MN 20011201

Title: Neoceptor concept based on molecular complementarity in GPCRs: a mutant adenosine A(3) receptor with selectively enhanced affinity for amine-modified nucleosides.

Journal: Journal of medicinal chemistry 20011122

Title: The A3 adenosine receptor as a new target for cancer therapy and chemoprotection.

Journal: Experimental cell research 20011001

Title: Constitutive activation of A(3) adenosine receptors by site-directed mutagenesis.

Journal: Biochemical and biophysical research communications 20010615

Title: Adenosine A(1) receptor-mediated inhibition of protein kinase A-induced calcitonin gene-related peptide release from rat trigeminal neurons.

Journal: Molecular pharmacology 20010601

Title: Activation of A(3)adenosine receptor protects against doxorubicin-induced cardiotoxicity.

Journal: Journal of molecular and cellular cardiology 20010601

Title: The A3 adenosine receptor induces cytoskeleton rearrangement in human astrocytoma cells via a specific action on Rho proteins.

Journal: Annals of the New York Academy of Sciences 20010601

Title: A functional role for adenosine A3 receptors: modulation of synaptic plasticity in the rat hippocampus.

Journal: Neuroscience letters 20010413

Title: Adenosine inhibits norepinephrine release in the postischemic rat heart: the mechanism of neuronal stunning.

Journal: Cardiovascular research 20010301

Title: A3 adenosine receptor activation triggers phosphorylation of protein kinase B and protects rat basophilic leukemia 2H3 mast cells from apoptosis.

Journal: Molecular pharmacology 20010101

Title: Cardioprotective effects of adenosine A1 and A3 receptor activation during hypoxia in isolated rat cardiac myocytes.

Journal: Molecular and cellular biochemistry 20010101

Title: Induction of apoptosis in rat cardiocytes by A3 adenosine receptor activation and its suppression by isoproterenol.

Journal: Experimental cell research 20000525

Title: Activation of the A3 adenosine receptor affects cell cycle progression and cell growth.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20000301

Title: Structure-activity relationships and molecular modeling of 3, 5-diacyl-2,4-dialkylpyridine derivatives as selective A3 adenosine receptor antagonists.

Journal: Journal of medicinal chemistry 19980813

Title: Pharmacological characterization of novel A3 adenosine receptor-selective antagonists.

Journal: Neuropharmacology 19970901

Title: 2-Substitution of N6-benzyladenosine-5'-uronamides enhances selectivity for A3 adenosine receptors.

Journal: Journal of medicinal chemistry 19941014

Title: Van Schaick EA et al. Hemodynamic effects and histamine release elicited by the selective adenosine A3 receptor agonist 2-Cl-IB-MECA in conscious rats. Eur J Pharmacol. 1996 Jul 25;308(3):311-4.

Title: Jacobson KA et al. Adenosine A3 receptors: novel ligands and paradoxical effects. Trends Pharmacol Sci. 1998 May;19(5):184-91.

Quotation Request
Company Name:
*
Contact Person:
*
Email:
*
Quantity Required:
*
Country:
Additional Info:
SDS
Tags:163042-96-4 Molecular Formula|163042-96-4 MDL|163042-96-4 SMILES|163042-96-4 2-Cl-ib-meca