4-amino-6-(1H-pyrrol-2-yl)-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine | 1350887-26-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 4-amino-6-(1H-pyrrol-2-yl)-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine
• CAS: 1350887-26-1
• 化学式: C₃₇H₂₈N₆O₇
• 分子量: 668.665
• InChiKey: CFSFOAPBPGVYRX-OBSQGUSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  50.0
• 可旋转键数：
  9.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  184.44
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  4-amino-6-(1H-pyrrol-2-yl)-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以76%的产率得到4-amino-6-(1H-pyrrol-2-yl)-5-cyano-7-(β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Synthesis of 6-(het) ary Xylocydine analogues and evaluating their inhibitory activities of CDK1 and CDK2 in vitro

  摘要：

  A series of purine nucleoside analogues bearing an aryl and hetaryl group in position 6 were prepared and their biological activities were assessed by in vitro CDK1/Cyclin B1 and CDK2/Cyclin A2 kinase assay. From the synthesized chemicals, three Xylocydine derivatives 3h, 3i, and 3j exhibited specific inhibitory activities on CDK2/Cyclin A2 with IC50 values of 4.6, 4.8, and 55 mu M, respectively. Those three compounds all induced G1/S phase arrest in Human epithelial carcinoma cell line (HeLa), and the results suggested they may inhibit CDK2 activity in vitro. Furthermore, molecular modeling study, their docking into Cyclin Dependant Kinase 2 (CDK2) active site showed high docking scores. Taken together, these data suggest that, those three compounds are good inhibitors of CDK2 for studying this kinase signal transduction pathway in cell system. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.003
• 作为产物：
  描述：

  2-氨基-5-溴-1H-吡咯-3,4-二甲腈 在 bis-triphenylphosphine-palladium(II) chloride 、 N,O-双三甲硅基乙酰胺 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 41.67h， 生成 4-amino-6-(1H-pyrrol-2-yl)-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Synthesis of 6-(het) ary Xylocydine analogues and evaluating their inhibitory activities of CDK1 and CDK2 in vitro

  摘要：

  A series of purine nucleoside analogues bearing an aryl and hetaryl group in position 6 were prepared and their biological activities were assessed by in vitro CDK1/Cyclin B1 and CDK2/Cyclin A2 kinase assay. From the synthesized chemicals, three Xylocydine derivatives 3h, 3i, and 3j exhibited specific inhibitory activities on CDK2/Cyclin A2 with IC50 values of 4.6, 4.8, and 55 mu M, respectively. Those three compounds all induced G1/S phase arrest in Human epithelial carcinoma cell line (HeLa), and the results suggested they may inhibit CDK2 activity in vitro. Furthermore, molecular modeling study, their docking into Cyclin Dependant Kinase 2 (CDK2) active site showed high docking scores. Taken together, these data suggest that, those three compounds are good inhibitors of CDK2 for studying this kinase signal transduction pathway in cell system. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.003