(2S,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3-ureido-tetrahydro-furan-2-carboxylic acid methylamide | 786666-17-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: (2S,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3-ureido-tetrahydro-furan-2-carboxylic acid methylamide
• CAS: 786666-17-9
• 化学式: C₂₅H₃₄ClIN₈O₄Si
• 分子量: 701.039
• InChiKey: LERXJGVBQJBJOD-OQYZPLRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  158.31
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3-ureido-tetrahydro-furan-2-carboxylic acid methylamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以73%的产率得到(2S,3S,4R,5R)-3-(carbamoylamino)-5-[2-chloro-6-[(3-iodophenyl)methylamino]purin-9-yl]-4-hydroxy-N-methyloxolane-2-carboxamide
  参考文献：
  名称：

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

  摘要：

  On the basis of high binding affinity at the A(3) adenosine receptor of 3'-aminoadenosine derivatives with hydrogen bonding donor ability, novel 3'-ureidoadenosine analogues were synthesized from 1,2:5,6-di-O-isopropylidene-D-glucose in order to lead to stronger hydrogen bonding than the corresponding 3'-aminoadeno sine derivatives. However, the synthesized 3'-ureidoadenosine analogues were totally devoid of binding affinity, because 3'-urea moiety caused steric and electrostatic repulsions at the binding site of the A(3) adenosine receptor, leading to conformational distortion. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.042
• 作为产物：
  描述：

  (2S,3S,4R,5R)-3-Azido-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-4-hydroxy-tetrahydro-furan-2-carboxylic acid methylamide 在 咪唑 、 ammonium hydroxide 、 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 63.0h， 生成 (2S,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3-ureido-tetrahydro-furan-2-carboxylic acid methylamide
  参考文献：
  名称：

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

  摘要：

  On the basis of high binding affinity at the A(3) adenosine receptor of 3'-aminoadenosine derivatives with hydrogen bonding donor ability, novel 3'-ureidoadenosine analogues were synthesized from 1,2:5,6-di-O-isopropylidene-D-glucose in order to lead to stronger hydrogen bonding than the corresponding 3'-aminoadeno sine derivatives. However, the synthesized 3'-ureidoadenosine analogues were totally devoid of binding affinity, because 3'-urea moiety caused steric and electrostatic repulsions at the binding site of the A(3) adenosine receptor, leading to conformational distortion. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.042