5'-deoxy-5-iodouridine | 573671-41-7

• 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'-deoxy-5-iodouridine
• 英文别名: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-iodopyrimidine-2,4-dione
• CAS: 573671-41-7
• 化学式: C₉H₁₁IN₂O₅
• 分子量: 354.101
• InChiKey: OSPWDMZLKBWHML-ZIYNGMLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5'-deoxy-5-iodouridine 在 Lindlar catalyst 咪唑 、 喹啉 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-methyl-tetrahydro-furan-2-yl)-5-((Z)-styryl)-1H-pyrimidine-2,4-dione
  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-iodo-5'-deoxyuridine-2',3'-diacetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 5'-deoxy-5-iodouridine
  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.