(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
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. Weight | 544.73079 |
|---|---|
| Appearance | Solid powder |
| Solubility | Soluble in DMSO, not in water |
别名和识别编码
| Chemical Name Translation | 2-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 |
| Formula | C18H18ClIN6O4 |
| 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 |
| InChIKey | IPSYPUKKXMNCNQ-PFHKOEEOSA-N |
| InChI | InChI=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 SMILES | O[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.
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