Thio-IB-MECA | 1008705-32-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: Thio-IB-MECA
• 英文别名: N6-(3-iodobenzyl)-4'-thioadenosine-5'-N-methyluronamide；(2S,3S,4R,5R)-5-(6-(3-iodobenzylamino)-9H-purin-9-yl)-3,4-dihydroxy-N-methyl-tetrahydrothiophene-2-carboxamide；(2S,3S,4R,5R)-3,4-dihydroxy-5-[6-[(3-iodophenyl)methylamino]purin-9-yl]-N-methylthiolane-2-carboxamide
• CAS: 1008705-32-5
• 化学式: C₁₈H₁₉IN₆O₃S
• 分子量: 526.358
• InChiKey: GWXXZRJKZRKCOK-MOROJQBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 Thio-IB-MECA
  参考文献：
  名称：

  Design and synthesis of N6-substituted-4′-thioadenosine-5′-uronamides as potent and selective human A3 adenosine receptor agonists

  摘要：

  On the basis of a bioisosteric rationale, 4'-thionucleoside analogues of IB-MECA (N-6-(3-Iodo-benzyl)-9-(5'-methylaminocarbonyl-beta-D-ribofuranosyl)adenine), which is a potent and selective A(3) adenosine receptor (AR) agonist, were synthesized from D-gulonic acid gamma-lactone. The 4'-thio analogue (5h) of IB-MECA showed extremely high binding affinity (K-i = 0.25 nM) at the human A(3)AR and was more potent than IB-MECA (K-i = 1.4 nM). Bulky substituents at the 5'-uronamide position, such as cyclohexyl and 2-methylbenzyl, in this series of 2-H nucleoside derivatives were tolerated in A3AR binding, although small alkyl analogues were more potent. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.011