2'-O-tert-butyldimethylsilyl-3'-deoxy-3'-[(ethoxycarbonyl)methyl]-5'-(N-methylcarbamoyl)adenosine | 1202513-89-0

• 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: 2'-O-tert-butyldimethylsilyl-3'-deoxy-3'-[(ethoxycarbonyl)methyl]-5'-(N-methylcarbamoyl)adenosine
• 英文别名: ethyl 2-[(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-(methylcarbamoyloxymethyl)oxolan-3-yl]acetate
• CAS: 1202513-89-0
• 化学式: C₂₂H₃₆N₆O₆Si
• 分子量: 508.65
• InChiKey: FEHHCHOFLJZAHM-PNQCTFMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  153
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2'-O-tert-butyldimethylsilyl-3'-deoxy-3'-[(ethoxycarbonyl)methyl]-5'-(N-methylcarbamoyl)adenosine 、 异氰酸苯酯 以 二氯甲烷 为溶剂， 反应 72.0h， 以96%的产率得到2'-O-tert-butyldimethylsilyl-3'-deoxy-3'-[(ethoxycarbonyl)methyl]-5'-(N-methylcarbamoyl)-N6-(N-phenylcarbamoyl)adenosine
  参考文献：
  名称：

  Preliminary SAR analysis of novel antiproliferative N6,5′-bis-ureidoadenosine derivatives

  摘要：

  A preliminary library of novel N-6,5'-bis-ureidoadenosine analogs and related derivatives was prepared and tested for activity against the NCI 60 panel of human cancers. A 2'-O-TBS group was found to be necessary, but not sufficient, for optimal antiproliferative activity. Neither the N-6-nor 5'-ureido substituents were sufficient to achieve significant antiproliferative effects when present in the absence of the other. The 2'-O-TBS, and N-6,5'-bis-ureido substitution patterns were found to be necessary for optimal antiproliferative activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.083
• 作为产物：
  描述：

  4-硝基苯基氨基甲酸乙酯 、 2'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-[(ethoxycarbonyl)methyl]adenosine 在 二异丙胺 作用下， 以 乙腈 为溶剂， 反应 168.0h， 以96%的产率得到2'-O-tert-butyldimethylsilyl-3'-deoxy-3'-[(ethoxycarbonyl)methyl]-5'-(N-methylcarbamoyl)adenosine
  参考文献：
  名称：

  Preliminary SAR analysis of novel antiproliferative N6,5′-bis-ureidoadenosine derivatives

  摘要：

  A preliminary library of novel N-6,5'-bis-ureidoadenosine analogs and related derivatives was prepared and tested for activity against the NCI 60 panel of human cancers. A 2'-O-TBS group was found to be necessary, but not sufficient, for optimal antiproliferative activity. Neither the N-6-nor 5'-ureido substituents were sufficient to achieve significant antiproliferative effects when present in the absence of the other. The 2'-O-TBS, and N-6,5'-bis-ureido substitution patterns were found to be necessary for optimal antiproliferative activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.083