5-(3-benzyloxybenzyl)-2',3'-bis-O-(tert-butyldimethylsilyl)-5'-deoxycytidine | 216449-54-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 5-(3-benzyloxybenzyl)-2',3'-bis-O-(tert-butyldimethylsilyl)-5'-deoxycytidine
• 英文别名: 4-amino-1-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-methyloxolan-2-yl]-5-[(3-phenylmethoxyphenyl)methyl]pyrimidin-2-one
• CAS: 216449-54-6
• 化学式: C₃₅H₅₃N₃O₅Si₂
• 分子量: 651.994
• InChiKey: ARXCTZBHJGMXQN-OHNBDJBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.69
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(3-benzyloxybenzyl)-2',3'-bis-O-(tert-butyldimethylsilyl)-5'-deoxycytidine 在 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以36%的产率得到5-(3-benzyloxybenzyl)-5'-deoxycytidine
  参考文献：
  名称：

  Design and synthesis of the tumor-activated prodrug of dihydropyrimidine dehydrogenase (DPD) inhibitor, RO0094889 for combination therapy with capecitabine

  摘要：

  A series of tumor-activated prodrugs of the inhibitors of dihydropyrimidine dehydrogenase (DPD), an enzyme catabolizing 5-fluorouracil (5-FU: 4g), has been designed and synthesized. RO0094889 (11c) is a prodrug of 5-vinyluracil (4c), a known DPD inhibitor, and was designed to generate 4c selectively in tumor tissues by sequential conversion of 11c by three enzymes: esterase, cytidine deaminase and thymidine phosphorylase, the latter two of which are known to be highly expressed in various tumor tissues. When capecitabine (1), a tumor-activated prodrug of 5-FU, was co-administered orally with 11c, 5-FU in tumor tissues was significantly increased with only a slight increase of 5-FU in plasma as compared with oral capecitabine alone. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)01082-x
• 作为产物：
  描述：

  5-苄氧基苄基尿嘧啶 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 硫酸氢铵 、 sodium hydroxide 、 六甲基二硅氮烷 、 三氯氧磷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 33.5h， 生成 5-(3-benzyloxybenzyl)-2',3'-bis-O-(tert-butyldimethylsilyl)-5'-deoxycytidine
  参考文献：
  名称：

  Design and synthesis of the tumor-activated prodrug of dihydropyrimidine dehydrogenase (DPD) inhibitor, RO0094889 for combination therapy with capecitabine

  摘要：

  A series of tumor-activated prodrugs of the inhibitors of dihydropyrimidine dehydrogenase (DPD), an enzyme catabolizing 5-fluorouracil (5-FU: 4g), has been designed and synthesized. RO0094889 (11c) is a prodrug of 5-vinyluracil (4c), a known DPD inhibitor, and was designed to generate 4c selectively in tumor tissues by sequential conversion of 11c by three enzymes: esterase, cytidine deaminase and thymidine phosphorylase, the latter two of which are known to be highly expressed in various tumor tissues. When capecitabine (1), a tumor-activated prodrug of 5-FU, was co-administered orally with 11c, 5-FU in tumor tissues was significantly increased with only a slight increase of 5-FU in plasma as compared with oral capecitabine alone. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)01082-x

文献信息

• Design and synthesis of the tumor-activated prodrug of dihydropyrimidine dehydrogenase (DPD) inhibitor, RO0094889 for combination therapy with capecitabine
  作者：Kazuo Hattori、Yasunori Kohchi、Nobuhiro Oikawa、Hitomi Suda、Masako Ura、Tohru Ishikawa、Masanori Miwa、Mika Endoh、Hiroyuki Eda、Hiromi Tanimura、Akira Kawashima、Ikuo Horii、Hideo Ishitsuka、Nobuo Shimma

  DOI：10.1016/s0960-894x(02)01082-x

  日期：2003.3

  A series of tumor-activated prodrugs of the inhibitors of dihydropyrimidine dehydrogenase (DPD), an enzyme catabolizing 5-fluorouracil (5-FU: 4g), has been designed and synthesized. RO0094889 (11c) is a prodrug of 5-vinyluracil (4c), a known DPD inhibitor, and was designed to generate 4c selectively in tumor tissues by sequential conversion of 11c by three enzymes: esterase, cytidine deaminase and thymidine phosphorylase, the latter two of which are known to be highly expressed in various tumor tissues. When capecitabine (1), a tumor-activated prodrug of 5-FU, was co-administered orally with 11c, 5-FU in tumor tissues was significantly increased with only a slight increase of 5-FU in plasma as compared with oral capecitabine alone. (C) 2003 Published by Elsevier Science Ltd.