152918-18-8 | Ib-meca

Packsize	Purity	Availability	Price	Discounted Price
1mg	98%	in stock	$49.00	$35.00
25mg	98%	in stock	$108.00	$76.00
50mg	98%	in stock	$175.00	$122.00

Description

• Catalog Number: AE81481
• Chemical Name: Ib-meca
• CAS Number: 152918-18-8
• Molecular Formula: C18H19IN6O4
• Molecular Weight: 510.2857
• MDL Number: MFCD00671785
• SMILES: CNC(=O)[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2NCc1cccc(c1)I

Computed Properties

• Complexity: 589
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 4
• Heavy Atom Count: 29
• Hydrogen Bond Acceptor Count: 8
• Hydrogen Bond Donor Count: 4
• Rotatable Bond Count: 5
• XLogP3: 0.9

Literature

• Targeting the A3 adenosine receptor for glaucoma treatment (review).

  Molecular medicine reports 20130601

• Synthesis and structure-activity relationship studies in serotonin 5-HT(1A) receptor agonists based on fused pyrrolidone scaffolds.

  European journal of medicinal chemistry 20130501

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

  Journal of medicinal chemistry 20120628

• Treatment of plaque-type psoriasis with oral CF101: data from an exploratory randomized phase 2 clinical trial.

  Journal of the European Academy of Dermatology and Venereology : JEADV 20120301

• Molecular mechanisms of A3 adenosine receptor-induced G1 cell cycle arrest and apoptosis in androgen-dependent and independent prostate cancer cell lines: involvement of intrinsic pathway.

  Journal of cancer research and clinical oncology 20111001

• Inhibition of cyclooxygenase-2 promotes the stimulatory action of adenosine A₃ receptor agonist on hematopoiesis in sublethally γ-irradiated mice.

  Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20110901

• The role of adenosine receptors in rheumatoid arthritis.

  Autoimmunity reviews 20101201

• Activation of A1, A2A, or A3 adenosine receptors attenuates lung ischemia-reperfusion injury.

  The Journal of thoracic and cardiovascular surgery 20100801

• Activation of adenosine A(3) receptors supports hematopoiesis-stimulating effects of granulocyte colony-stimulating factor in sublethally irradiated mice.

  International journal of radiation biology 20100801

• Multivalent dendrimeric and monomeric adenosine agonists attenuate cell death in HL-1 mouse cardiomyocytes expressing the A(3) receptor.

  Biochemical pharmacology 20100715

• Induction of apoptosis by A3 adenosine receptor agonist N-(3-iodobenzyl)-adenosine-5'-N-methylcarboxamide in human leukaemia cells: a possible involvement of intracellular mechanism.

  Acta physiologica (Oxford, England) 20100601

• Synthesis and evaluation of new N6-substituted adenosine-5'-N-methylcarboxamides as A3 adenosine receptor agonists.

  Bioorganic & medicinal chemistry 20100501

• Compensatory upregulation of the adenosine system following phenylephrine-induced hypertrophy in cultured rat ventricular myocytes.

  American journal of physiology. Heart and circulatory physiology 20100201

• 2-Dialkynyl derivatives of (N)-methanocarba nucleosides: 'Clickable' A(3) adenosine receptor-selective agonists.

  Bioorganic & medicinal chemistry 20100115

• Activation of adenosine low-affinity A3 receptors inhibits the enteric short interplexus neural circuit triggered by histamine.

  American journal of physiology. Gastrointestinal and liver physiology 20091201

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

  Bioorganic & medicinal chemistry 20091201

• Adenosine A(3) receptor suppresses prostate cancer metastasis by inhibiting NADPH oxidase activity.

  Neoplasia (New York, N.Y.) 20091101

• Cardioprotection induced by adenosine A1 receptor agonists in a cardiac cell ischemia model involves cooperative activation of adenosine A2A and A2B receptors by endogenous adenosine.

  Journal of cardiovascular pharmacology 20090501

• Activation of adenosine A(3) receptors potentiates stimulatory effects of IL-3, SCF, and GM-CSF on mouse granulocyte-macrophage hematopoietic progenitor cells.

  Physiological research 20090101

• A3 adenosine receptor: pharmacology and role in disease.

  Handbook of experimental pharmacology 20090101

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

  Peptides 20081201

• cis-4-(Piperazin-1-yl)-5,6,7a,8,9,10,11,11a-octahydrobenzofuro[2,3-h]quinazolin-2-amine (A-987306), a new histamine H4R antagonist that blocks pain responses against carrageenan-induced hyperalgesia.

  Journal of medicinal chemistry 20081127

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

  Journal of medicinal chemistry 20081023

• Adenosine A(2A) receptor dynamics studied with the novel fluorescent agonist Alexa488-APEC.

  European journal of pharmacology 20080820

• Identification of a potent, selective, and orally active leukotriene a4 hydrolase inhibitor with anti-inflammatory activity.

  Journal of medicinal chemistry 20080724

• Homeostatic action of adenosine A3 and A1 receptor agonists on proliferation of hematopoietic precursor cells.

  Experimental biology and medicine (Maywood, N.J.) 20080701

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

  Bioorganic & medicinal chemistry letters 20080501

• The anti-inflammatory effect of A3 adenosine receptor agonists: a novel targeted therapy for rheumatoid arthritis.

  Expert opinion on investigational drugs 20071001

• Adenosine A(3) receptor agonist acts as a homeostatic regulator of bone marrow hematopoiesis.

  Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20070701

• Rapid stimulation of presynaptic serotonin transport by A(3) adenosine receptors.

  The Journal of pharmacology and experimental therapeutics 20070701

• Structure-activity relationship study of prion inhibition by 2-aminopyridine-3,5-dicarbonitrile-based compounds: parallel synthesis, bioactivity, and in vitro pharmacokinetics.

  Journal of medicinal chemistry 20070111

• Overexpression of A3 adenosine receptor in peripheral blood mononuclear cells in rheumatoid arthritis: involvement of nuclear factor-kappaB in mediating receptor level.

  The Journal of rheumatology 20070101

• Expression of adenosine receptors in cardiac fibroblasts as a function of insulin and glucose level.

  Archives of biochemistry and biophysics 20061101

• Modulation of cardiac sarcoplasmic reticulum calcium release by aenosine: a protein kinase C- dependent pathway.

  Molecular and cellular biochemistry 20060801

• ADOA3R as a therapeutic target in experimental colitis: proof by validated high-density oligonucleotide microarray analysis.

  Inflammatory bowel diseases 20060801

• N6-(3-iodobenzyl)-adenosine-5'-N-methylcarboxamide confers cardioprotection at reperfusion by inhibiting mitochondrial permeability transition pore opening via glycogen synthase kinase 3 beta.

  The Journal of pharmacology and experimental therapeutics 20060701

• Effects of adenosine A(3) receptor agonist on bone marrow granulocytic system in 5-fluorouracil-treated mice.

  European journal of pharmacology 20060524

• The synthesis of highly potent, selective, and water-soluble agonists at the human adenosine A3 receptor.

  Bioorganic & medicinal chemistry letters 20060501

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

  Bioorganic & medicinal chemistry letters 20060501

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

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

• Radioligand binding and functional responses of ligands for human recombinant adenosine A(3) receptors.

  Autonomic & autacoid pharmacology 20060401

• Adenosine receptors as therapeutic targets.

  Nature reviews. Drug discovery 20060301

• The PI3K-NF-kappaB signal transduction pathway is involved in mediating the anti-inflammatory effect of IB-MECA in adjuvant-induced arthritis.

  Arthritis research & therapy 20060101

• IB-MECA, an A3 adenosine receptor agonist prevents bone resorption in rats with adjuvant induced arthritis.

  Clinical and experimental rheumatology 20060101

• Methotrexate enhances the anti-inflammatory effect of CF101 via up-regulation of the A3 adenosine receptor expression.

  Arthritis research & therapy 20060101

• IB-MECA and cardioprotection.

  Cardiovascular drug reviews 20060101

• 2-n-Butyl-9-methyl-8-[1,2,3]triazol-2-yl-9H-purin-6-ylamine and analogues as A2A adenosine receptor antagonists. Design, synthesis, and pharmacological characterization.

  Journal of medicinal chemistry 20051103

• G(i)-protein-dependent inhibition of IL-12 production is mediated by activation of the phosphatidylinositol 3-kinase-protein 3 kinase B/Akt pathway and JNK.

  Journal of immunology (Baltimore, Md. : 1950) 20050901

• Induction of apoptosis by the adenosine derivative IB-MECA in parental or multidrug-resistant HL-60 leukemia cells: possible relationship to the effects on inhibitor of apoptosis protein levels.

  Chemotherapy 20050801

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

  Journal of medicinal chemistry 20050324

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

  Journal of medicinal chemistry 20050310

• Inhibition of phenylephrine-induced cardiomyocyte hypertrophy by activation of multiple adenosine receptor subtypes.

  The Journal of pharmacology and experimental therapeutics 20050101

• CF101, an agonist to the A3 adenosine receptor, enhances the chemotherapeutic effect of 5-fluorouracil in a colon carcinoma murine model.

  Neoplasia (New York, N.Y.) 20050101

• Mesangial cell apoptosis induced by stimulation of the adenosine A3 receptor: signaling and apoptotic events.

  Journal of investigative medicine : the official publication of the American Federation for Clinical Research 20050101

• Activation of A3 adenosine receptor provides lung protection against ischemia-reperfusion injury associated with reduction in apoptosis.

  American journal of transplantation : official journal of the American Society of Transplantation and the American Society of Transplant Surgeons 20041201

• Activation of A3 adenosine receptors attenuates lung injury after in vivo reperfusion.

  Anesthesiology 20041101

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

  Journal of medicinal chemistry 20041021

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

  Bioorganic & medicinal chemistry letters 20041004

• Negative chronotropic response to adenosine receptor stimulation in rat right atria after run training.

  Clinical and experimental pharmacology & physiology 20041001

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

  Journal of medicinal chemistry 20040909

• Role of adenosine A1 receptor in the regulation of gastrin release.

  The Journal of pharmacology and experimental therapeutics 20040801

• An adenosine analog (IB-MECA) inhibits anchorage-dependent cell growth of various human breast cancer cell lines.

  The international journal of biochemistry & cell biology 20040801

• A2A adenosine receptor activation improves survival in mouse models of endotoxemia and sepsis.

  The Journal of infectious diseases 20040515

• An agonist to the A3 adenosine receptor inhibits colon carcinoma growth in mice via modulation of GSK-3 beta and NF-kappa B.

  Oncogene 20040401

• Effects of stable adenosine receptor agonists on bone marrow hematopoietic cells as inferred from the cytotoxic action of 5-fluorouracil.

  Physiological research 20040101

• A3 adenosine receptor activation in melanoma cells: association between receptor fate and tumor growth inhibition.

  The Journal of biological chemistry 20031024

• Inhibition of primary colon carcinoma growth and liver metastasis by the A3 adenosine receptor agonist CF101.

  British journal of cancer 20031020

• An adenosine analogue, IB-MECA, down-regulates estrogen receptor alpha and suppresses human breast cancer cell proliferation.

  Cancer research 20031001

• Protection from myocardial stunning by ischaemia and hypoxia with the adenosine A3 receptor agonist, IB-MECA.

  European journal of pharmacology 20030923

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

  Journal of medicinal chemistry 20030828

• A3 adenosine receptor agonist IB-MECA reduces myocardial ischemia-reperfusion injury in dogs.

  American journal of physiology. Heart and circulatory physiology 20030801

• Protein kinase C-delta mediates adenosine A3 receptor-induced delayed cardioprotection in mouse.

  American journal of physiology. Heart and circulatory physiology 20030701

• Activation of murine lung mast cells by the adenosine A3 receptor.

  Journal of immunology (Baltimore, Md. : 1950) 20030701

• Adenosine affects expression of membrane molecules, cytokine and chemokine release, and the T-cell stimulatory capacity of human dendritic cells.

  Blood 20030515

• The adenosine A3 receptor agonist, N6-(3-iodobenzyl)-adenosine-5'-N-methyluronamide, is protective in two murine models of colitis.

  European journal of pharmacology 20030418

• The influence of adenosine A3 receptor agonist: IB-MECA, on scopolamine- and MK-801-induced memory impairment.

  Behavioural brain research 20030417

• A3 adenosine receptor knockout mice are protected against ischemia- and myoglobinuria-induced renal failure.

  American journal of physiology. Renal physiology 20030201

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

  Molecular pharmacology 20030201

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

  Journal of medicinal chemistry 20030130

• Positive coupling of atypical adenosine A3 receptors on human eosinophils to adenylyl cyclase.

  Biochemical and biophysical research communications 20030117

• Targeting the A3 adenosine receptor for cancer therapy: inhibition of prostate carcinoma cell growth by A3AR agonist.

  Anticancer research 20030101

• Contractile responses to adenosine, R-PIA and ovalbumen in passively sensitized guinea-pig isolated airways.

  British journal of pharmacology 20021101

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

  Journal of medicinal chemistry 20020926

• Knockout of A3 adenosine receptors reduces mouse intraocular pressure.

  Investigative ophthalmology & visual science 20020901

• Evidence for involvement of Wnt signaling pathway in IB-MECA mediated suppression of melanoma cells.

  Oncogene 20020606

• Effects of adenosine receptor agonists on guinea-pig isolated working hearts and the role of endothelium and NO.

  The Journal of pharmacy and pharmacology 20020601

• Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

  The Journal of biological chemistry 20020419

• Adenosine A(3) receptor-mediated potentiation of mucociliary transport and epithelial ciliary motility.

  American journal of physiology. Lung cellular and molecular physiology 20020301

• Late preconditioning elicited by activation of adenosine A(3) receptor in heart: role of NF- kappa B, iNOS and mitochondrial K(ATP) channel.

  Journal of molecular and cellular cardiology 20020301

• Regulation of glycogen metabolism in hepatocytes through adenosine receptors. Role of Ca2+ and cAMP.

  European journal of pharmacology 20020222

• A(3) adenosine receptors in human neutrophils and promyelocytic HL60 cells: a pharmacological and biochemical study.

  Molecular pharmacology 20020201

• Apparent activation of cardiovascular A1 adenosine receptors by A3 agonists.

  American journal of physiology. Heart and circulatory physiology 20020201

• Binding thermodynamics at the human A(3) adenosine receptor.

  Biochemical pharmacology 20020115

• Inhibition of human mast cell activation with the novel selective adenosine A(2B) receptor antagonist 3-isobutyl-8-pyrrolidinoxanthine (IPDX)(2).

  Biochemical pharmacology 20011101

• Adenosine-mediated hypotension in in vivo guinea-pig: receptors involved and role of NO.

  British journal of pharmacology 20011001

• The plasma protein extravasation induced by adenosine and its analogues in the rat dorsal skin: evidence for the involvement of capsaicin sensitive primary afferent neurones and mast cells.

  British journal of pharmacology 20010901

• Pharmacological characterization of adenosine receptors in PGT-beta mouse pineal gland tumour cells.

  British journal of pharmacology 20010901

• Role of adenosine in ischemic preconditioning in rats depends critically on the duration of the stimulus and involves both A(1) and A(3) receptors.

  Cardiovascular research 20010901

• Protection of IB-MECA against myocardial stunning in conscious rabbits is not mediated by the A1 adenosine receptor.

  Basic research in cardiology 20010901

• Right thing at a wrong time? Adenosine A3 receptors and cerebroprotection in stroke.

  Annals of the New York Academy of Sciences 20010601

• Regulation of p42/p44 mitogen-activated protein kinase by the human adenosine A3 receptor in transfected CHO cells.

  European journal of pharmacology 20010518

• A3 adenosine receptor stimulation modulates sarcoplasmic reticulum Ca(2+) release in rat heart.

  Cardiovascular research 20010401

• Adenosine inhibits neutrophil vascular endothelial growth factor release and transendothelial migration via A2B receptor activation.

  Shock (Augusta, Ga.) 20010401

• A(1) or A(3) adenosine receptors induce late preconditioning against infarction in conscious rabbits by different mechanisms.

  Circulation research 20010316

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

  Molecular pharmacology 20010101

• [(3)H]MRE 3008F20: a novel antagonist radioligand for the pharmacological and biochemical characterization of human A(3) adenosine receptors.

  Molecular pharmacology 20000501

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

  Naunyn-Schmiedeberg's archives of pharmacology 20000301

• Characterization of human A(2B) adenosine receptors: radioligand binding, western blotting, and coupling to G(q) in human embryonic kidney 293 cells and HMC-1 mast cells.

  Molecular pharmacology 19991001

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

  Journal of medicinal chemistry 19980813

• 2'-C-Methyl analogues of selective adenosine receptor agonists: synthesis and binding studies.

  Journal of medicinal chemistry 19980507

• Comparative pharmacology of human adenosine receptor subtypes - characterization of stably transfected receptors in CHO cells.

  Naunyn-Schmiedeberg's archives of pharmacology 19980101

• Canine mast cell adenosine receptors: cloning and expression of the A3 receptor and evidence that degranulation is mediated by the A2B receptor.

  Molecular pharmacology 19971101

• Site-directed mutagenesis identifies residues involved in ligand recognition in the human A2a adenosine receptor.

  The Journal of biological chemistry 19950609

• The effects of adenosine A3 receptor stimulation on seizures in mice.

  European journal of pharmacology 19950224

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

  Journal of medicinal chemistry 19941014

• Structure-activity relationships of N6-benzyladenosine-5'-uronamides as A3-selective adenosine agonists.

  Journal of medicinal chemistry 19940304