(+/-)-1-<(2α,2β,3β,4α)-2,3-dihydroxy-4-(hydroxymethyl)-cyclopentyl>-5-fluoro-2,4(1H,3H)pyrimidinedione | 78336-05-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (+/-)-1-<(2α,2β,3β,4α)-2,3-dihydroxy-4-(hydroxymethyl)-cyclopentyl>-5-fluoro-2,4(1H,3H)pyrimidinedione
• 英文别名: 1-[(1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]-5-fluoro-pyrimidine-2,4-dione；1-[(1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]-5-fluoropyrimidine-2,4-dione
• CAS: 78336-05-7
• 化学式: C₁₀H₁₃FN₂O₅
• 分子量: 260.222
• InChiKey: IXEMCZVSTHJQAY-JBBNEOJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  110
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (+/-)-1-<(1α,2β,3β,4α)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl>-2,4-(1H,3H)pyrimidinedione 在 fluorine 作用下， 以 溶剂黄146 为溶剂， 反应 0.17h， 生成 (+/-)-1-<(2α,2β,3β,4α)-2,3-dihydroxy-4-(hydroxymethyl)-cyclopentyl>-5-fluoro-2,4(1H,3H)pyrimidinedione
  参考文献：
  名称：

  Carbocyclic analogs of 5-fluorouracil nucleosides

  摘要：

  The carbocyclic analogues of 5-fluoro-2'-deoxyuridine (5-FdUrd, 1), 5-fluorouridine, and 5-fluoro-3 alpha-deoxyuridine were prepared by fluorination of the uracil nucleoside analogues with elemental fluorine. The 5-FdUrd analogue (C-5-F-2'-dUrd, 6) was enzymatically phosphorylated to the analogue of 5-FdUrd 5'-phosphate and inhibited the incorporation of 2'-deoxyuridine into DNA of murine colon 26 tumor cells and L-1210 cells in culture. Biochemical studies also indicated that C-5-F-2'-Urd (6) was a less potent inhibitor of DNA synthesis in tumor cells than was 5-FdUrd (1). C-5-F-2'-dUrd was cytotoxic (ED50 = 2.5 mcg/mL) to L-1210 cells in culture; the other two analogues were less cytotoxic. C-5-F-2'-dUrd was inactive--or, at best, borderline active--in tests against P-388 leukemia in vivo.

  DOI：

  10.1021/jm00141a013

文献信息

• Carbocyclic analogs of 5-fluorouracil nucleosides
  作者：Y. Fulmer Shealy、Jerry L. Frye、Nancy F. DuBois、Sue C. Shaddix、R. Wallace Brockman

  DOI：10.1021/jm00141a013

  日期：1981.9

  The carbocyclic analogues of 5-fluoro-2'-deoxyuridine (5-FdUrd, 1), 5-fluorouridine, and 5-fluoro-3 alpha-deoxyuridine were prepared by fluorination of the uracil nucleoside analogues with elemental fluorine. The 5-FdUrd analogue (C-5-F-2'-dUrd, 6) was enzymatically phosphorylated to the analogue of 5-FdUrd 5'-phosphate and inhibited the incorporation of 2'-deoxyuridine into DNA of murine colon 26 tumor cells and L-1210 cells in culture. Biochemical studies also indicated that C-5-F-2'-Urd (6) was a less potent inhibitor of DNA synthesis in tumor cells than was 5-FdUrd (1). C-5-F-2'-dUrd was cytotoxic (ED50 = 2.5 mcg/mL) to L-1210 cells in culture; the other two analogues were less cytotoxic. C-5-F-2'-dUrd was inactive--or, at best, borderline active--in tests against P-388 leukemia in vivo.