(+/-)-1-<(1β,2α,4β)-2-hydroxy-4-(hydroxymethyl)cyclopentyl>-2,4-(1H,3H)-pyrimidinedione | 62102-31-2

• 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-<(1β,2α,4β)-2-hydroxy-4-(hydroxymethyl)cyclopentyl>-2,4-(1H,3H)-pyrimidinedione
• 英文别名: (+/-)-1-<(1α,2β,4α)-2-hydroxy-4-(hydroxymethyl)cyclopentyl>-2,4-(1H,3H)pyrimidinedione；1-[(1R,2R,4S)-2-hydroxy-4-(hydroxymethyl)cyclopentyl]pyrimidine-2,4-dione
• CAS: 62102-31-2
• 化学式: C₁₀H₁₄N₂O₄
• 分子量: 226.232
• InChiKey: DPWHBIMKUXLNPO-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  16
• 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：
  89.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-1-<(1β,2α,4β)-2-hydroxy-4-(hydroxymethyl)cyclopentyl>-2,4-(1H,3H)-pyrimidinedione 在 溴 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 生成 (+/-)-5-bromo-1-<(1α,2β,4α)-2-hydroxy-4-(hydroxymethyl)cyclopentyl>-2,4(1H,3H)-pyrimidinedione diacetate
  参考文献：
  名称：

  5-取代的尿嘧啶核苷的碳环类似物：合成和抗病毒活性。

  摘要：

  3'-脱氧尿苷，3'-脱氧尿苷和尿嘧啶在尿嘧啶部分第5位具有取代基的碳环类似物是通过直接卤化（5-溴和5-碘基）并通过氨基置换5-溴基制备的和取代的氨基。5-（羟甲基）尿苷的类似物是通过尿苷类似物的亚丙基衍生物与多聚甲醛反应制备的。胸苷和5-溴-，5-碘-和5-（甲基氨基）-2'-脱氧尿苷的碳环类似物在体外对1型和2型单纯疱疹病毒具有很高的活性。5-取代的相应类似物3'-脱氧尿苷和5-取代的尿苷在该测定中没有活性。

  DOI：

  10.1021/jm00356a008
• 作为产物：
  描述：

  (+/-)-3-ethoxy-N-carbamoyl>propenamide 在 硫酸 作用下， 反应 0.5h， 以75%的产率得到(+/-)-1-<(1β,2α,4β)-2-hydroxy-4-(hydroxymethyl)cyclopentyl>-2,4-(1H,3H)-pyrimidinedione
  参考文献：
  名称：

  Hronowski, Lucjan J. J.; Szarek, Walter A., Canadian Journal of Chemistry, 1986, vol. 64, p. 1620 - 1629

  摘要：

  DOI：

文献信息

• Carbocyclic analogs of cytosine nucleosides
  作者：Y. Fulmer Shealy、C. Allen O'Dell

  DOI：10.1002/jhet.5570170228

  日期：1980.3

  cytosine derivatives were frequently accompanied by small amounts of the corresponding N,N-dimethylcytosine derivatives, which could be removed by ion-exchange chromatography. Carbodine (VIa), the carbocyclic analog of cytidine, was obtained in 84% yield from the pure 4-chloropyrimidinone intermediate, after the latter was prepared by deoxychlorination in carbon tetrachloride. Carbodine has antileukemic

  由类似的尿嘧啶衍生物合成了胞苷，2'-脱氧胞苷和3'-脱氧胞苷的碳环类似物。该途径包括尿嘧啶衍生物的完全苯甲酰化，选择性除去连接在嘧啶环上的苯甲酰基，用二甲基甲酰胺-亚硫酰氯试剂将4-氧代转化为4-氯基以及用氯代氨酯取代氯基。甲醇氨中的氨基 当使用脱氧氯化反应的总产物时，所需的胞嘧啶衍生物常常伴随着少量的相应的N，N-二甲基胞嘧啶衍生物，可以通过离子交换色谱法除去。从纯的4-氯嘧啶酮中间体通过在四氯化碳中进行脱氧氯化制备后，以84％的收率获得了胞嘧啶核苷的类似物卡铂（VIa）。卡博定具有抗白血病，抗病毒和抗菌活性。
• 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.