(2S,3S,4R,5R)-5-{6-[(4-氨基-3-碘苄基)氨基]-9H-嘌呤-9-基}-3,4-二羟基-N-甲基四氢-2-呋喃甲酰胺 | 152918-27-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: (2S,3S,4R,5R)-5-{6-[(4-氨基-3-碘苄基)氨基]-9H-嘌呤-9-基}-3,4-二羟基-N-甲基四氢-2-呋喃甲酰胺
• 英文名称: (2S,3S,4R,5R)-5-[6-(4-Amino-3-iodo-benzylamino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid methylamide
• 英文别名: N⁶-(4-amino-3-iodobenzyl)-adenosine-5'-(N-methyluronamide)；AB-MECA；I-AB-MECA；(2S,3S,4R,5R)-5-[6-[(4-amino-3-iodophenyl)methylamino]purin-9-yl]-3,4-dihydroxy-N-methyloxolane-2-carboxamide
• CAS: 152918-27-9
• 化学式: C₁₈H₂₀IN₇O₄
• 分子量: 525.306
• InChiKey: LOGOEBMHHXYBID-MOROJQBDSA-N

物化性质

• 密度：
  2.06±0.1 g/cm3(Predicted)
• 溶解度：
  在45%(w/v)aq2-羟丙基-β-环糊精溶解度为：0.2 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  30
• 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：
  160
• 氢给体数：
  5
• 氢受体数：
  9

安全信息

• WGK Germany：
  3

反应信息

• 作为产物：
  描述：

  1-(6-氯-9H-嘌呤-9-基)-1-脱氧-N-甲基-2,3-O-异亚丙基-beta-D-呋喃核糖酰胺 在 盐酸 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (2S,3S,4R,5R)-5-{6-[(4-氨基-3-碘苄基)氨基]-9H-嘌呤-9-基}-3,4-二羟基-N-甲基四氢-2-呋喃甲酰胺
  参考文献：
  名称：

  Structure-Activity Relationships of N6-Benzyladenosine-5'-uronamides as A3-Selective Adenosine Agonists

  摘要：

  Adenosine analogues modified at the 5'-position as uronamides and/or as N-6-benzyl derivatives were synthesized. These derivatives were examined for affinity in radioligand binding assays at the newly discovered rat brain A(3) adenosine receptor and at rat brain A(1) and Az, receptors. 5'Uronamide substituents favored AS selectivity in the order N-methyl > N-ethyl approximate to unsubstituted carboxamide > N-cyclopropyl. 5'-(N-Methylcarboxamido)-N-6-benzyladenosine was 37-56-fold more selective for Ag receptors. Potency at A(3) receptors was enhanced upon substitution of the benzyl substituent with nitro and other groups. 5'-N-Methyluronamides and N-6-(3-substituted-benzyl) adenosines are optimal for potency and selectivity at A(3) receptors. A series of 3-(halobenzyl)5'-N-ethyluronamide derivatives showed the order of potency at A(1) and A(2)a receptors of I similar to Br > Cl > F. At A(3) receptors the 3-F derivative was weaker than the other halo derivatives. 5'-N-Methyl-N-6- (3-iodobenzyl) adenosine displayed a K-i value of 1.1 nM at A(3) receptors and selectivity versus A(1) and A(2a), receptors of 50-fold. A series of methoxybenzyl derivatives showed that a C-methoxy group best favored A(3) selectivity. A 4-sulfobenzyl derivative was a specific ligand at A(3) receptors of moderate potency. An aryl amino derivative was prepared as a probe for radioiodination and receptor cross-linking.

  DOI：

  10.1021/jm00031a014

文献信息

• Structure-Activity Relationships of N6-Benzyladenosine-5'-uronamides as A3-Selective Adenosine Agonists
  作者：Carola Gallo-Rodriguez、Xiao-duo Ji、Neli Melman、Barry D. Siegman、Lawrence H. Sanders、Jeraldine Orlina、Bilha Fischer、Quanlong Pu、Mark E. Olah

  DOI：10.1021/jm00031a014

  日期：1994.3

  Adenosine analogues modified at the 5'-position as uronamides and/or as N-6-benzyl derivatives were synthesized. These derivatives were examined for affinity in radioligand binding assays at the newly discovered rat brain A(3) adenosine receptor and at rat brain A(1) and Az, receptors. 5'Uronamide substituents favored AS selectivity in the order N-methyl > N-ethyl approximate to unsubstituted carboxamide > N-cyclopropyl. 5'-(N-Methylcarboxamido)-N-6-benzyladenosine was 37-56-fold more selective for Ag receptors. Potency at A(3) receptors was enhanced upon substitution of the benzyl substituent with nitro and other groups. 5'-N-Methyluronamides and N-6-(3-substituted-benzyl) adenosines are optimal for potency and selectivity at A(3) receptors. A series of 3-(halobenzyl)5'-N-ethyluronamide derivatives showed the order of potency at A(1) and A(2)a receptors of I similar to Br > Cl > F. At A(3) receptors the 3-F derivative was weaker than the other halo derivatives. 5'-N-Methyl-N-6- (3-iodobenzyl) adenosine displayed a K-i value of 1.1 nM at A(3) receptors and selectivity versus A(1) and A(2a), receptors of 50-fold. A series of methoxybenzyl derivatives showed that a C-methoxy group best favored A(3) selectivity. A 4-sulfobenzyl derivative was a specific ligand at A(3) receptors of moderate potency. An aryl amino derivative was prepared as a probe for radioiodination and receptor cross-linking.