(2S,3S,4R,5R)-5-[2-Chloro-6-[(3-Iodophenyl)Methylamino]Purin-9-Yl]-3,4-Dihydroxy-N-Methyloxolane-2-Carboxamide 2-Cl-IB-MECA游离态

CAS 163042-96-4 MFCD01323055

化学结构图

163042-96-4
SMILES: CNC(=O)[C@H]1O[C@@H](n2cnc3c(NCc4cccc(I)c4)nc(Cl)nc32)[C@H](O)[C@@H]1O

化学属性

Mol. Weight544.73079
Appearance Solid powder
SolubilitySoluble in DMSO, not in water

别名和识别编码

Chemical Name Translation2-Cl-IB-MECA游离态
Chemical Name(2S,3S,4R,5R)-5-[2-Chloro-6-[(3-Iodophenyl)Methylamino]Purin-9-Yl]-3,4-Dihydroxy-N-Methyloxolane-2-Carboxamide
FormulaC18H18ClIN6O4
Synonym CF102; CF-102; CF 102; Cl-IB-MECA; 2-Cl-IB-MECA; Namodenoson; Chloro-IB-MECA;
IUPAC Name(2S,3S,4R,5R)-5-(2-chloro-6-((3-iodobenzyl)amino)-9H-purin-9-yl)-3,4-dihydroxy-N-methyltetrahydrofuran-2-carboxamide
InChIKeyIPSYPUKKXMNCNQ-PFHKOEEOSA-N
InChIInChI=1S/C18H18ClIN6O4/c1-21-16(29)13-11(27)12(28)17(30-13)26-7-23-10-14(24-18(19)25-15(10)26)22-6-8-3-2-4-9(20)5-8/h2-5,7,11-13,17,27-28H,6H2,1H3,(H,21,29)(H,22,24,25)/t11-,12+,13-,17+/m0/s1
Canonical SMILESO[C@H]1[C@H](N2C=NC3=C(NCC4=CC=CC(I)=C4)N=C(Cl)N=C23)O[C@H](C(NC)=O)[C@H]1O
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产品应用

  • Namodenoson, also known as 2-Cl-IB-MECA and CF-102, is an orally bioavailable, synthetic, highly selective adenosine A3 receptor (A3AR) agonist with potential antineoplastic activity. Adenosine A3 receptor agonist CF102 selectively binds to and activates the cell surface-expressed A3AR, deregulating Wnt and NF-kB signal transduction pathways downstream, which may result in apoptosis of A3AR-expressing tumor cells. A3AR, a G protein-coupled receptor, is highly expressed on the cell surfaces of various solid tumor cell types, including hepatocellular carcinoma (HCC) cells, and plays an important role in cellular proliferation.

相关文献及参考

  • [2]. Jacobson KA et al. Adenosine A3 receptors: novel ligands and paradoxical effects. Trends Pharmacol Sci. 1998 May;19(5):184-91.
  • [1]. 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.
  • [1]. 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.
  • [2]. Jacobson KA et al. Adenosine A3 receptors: novel ligands and paradoxical effects. Trends Pharmacol Sci. 1998 May;19(5):184-91.

安全信息

Storage condition Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

系列性分类


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