2'-脱氧-N,5-二甲基-胞苷 | 25406-44-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 2'-脱氧-N,5-二甲基-胞苷
• 英文名称: N,5-dimethyl-2’-deoxycytidine
• 英文别名: 5,N⁴-dimethyl-2'-deoxy-cytidine；5,N⁴-Dimethyl-2'-desoxy-cytidin；2'-deoxy-N,5-dimethylCytidine；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-4-(methylamino)pyrimidin-2-one
• CAS: 25406-44-4
• 化学式: C₁₁H₁₇N₃O₄
• 分子量: 255.274
• InChiKey: SUURDKULGPGHGO-DJLDLDEBSA-N

物化性质

• 溶解度：
  乙醇（微溶）、甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  94.4
• 氢给体数：
  3
• 氢受体数：
  4

制备方法与用途

2'-脱氧-5,N4-二甲基胞苷是一种嘌呤核苷类似物，具有广泛的抗肿瘤活性，尤其针对惰性淋巴系统恶性肿瘤。其抗癌机制主要通过抑制DNA合成和诱导细胞凋亡来实现。

反应信息

• 作为产物：
  描述：

  beta-胸苷 在 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 溶剂黄146 、 三乙胺 、 乙腈 为溶剂， 反应 12.0h， 生成 2'-脱氧-N,5-二甲基-胞苷
  参考文献：
  名称：

  Convenient Intermediates for the Preparation ofC-4 Modified Derivatives of Pyrimidine Nucleosides

  摘要：

  4-(4-Nitrophenoxy)-1-(beta-D-ribofuranosyl)pyrimidin-2(1H)-one 15, 5-methyl-4-(1,2,4-triazol-1-yl)-1-(beta-D-2-deoxyribofuranosyl 7a and 4-(4-nitrophenoxy)-1-(beta-D-2-deoxyribofuranosyl)pyrimidin-2(1H)-one 17a, respectively, have been prepared and are recommended as reactive intermediates for the preparation of derivatives of uridine, thymidine and 2'-deoxyuridine which are modified at C-4.

  DOI：

  10.1080/07328319708002521

文献信息

• Transformations of thiopyrimidine and thiopurine nucleosides following oxidation with dimethyldioxirane
  作者：Raffaele Saladino、Enrico Mincione、Claudia Crestini、Maurizio Mezzetti

  DOI：10.1016/0040-4020(96)00289-x

  日期：1996.5

  and convenient method for the synthesis of several pyrimidine and purine nucleosides by selective oxidation of thionucleosides with dimethyldioxirane is reported. Thioketo moieties in the C-4 position of the pyrimidine ring, and in the C-6, and C-8 positions of the purine ring are the domain of oxidative nucleophilic substitution. Thioketo moieties in the C-2 position of both purine and pyrimidine rings

  报道了通过用二甲基二环氧乙烷选择性氧化硫代核苷来合成几种嘧啶和嘌呤核苷的通用且方便的方法。嘧啶环的C-4位，嘌呤环的C-6和C-8位的Thioketo部分是氧化亲核取代的结构域。嘌呤和嘧啶环的C-2位的Thioketo部分是脱硫或二硫化物形成的区域。
• Facile functionalization at the C4 position of pyrimidine nucleosides via amide group activation with (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and biological evaluations of the products
  作者：Hari K. Akula、Hariprasad Kokatla、Graciela Andrei、Robert Snoeck、Dominique Schols、Jan Balzarini、Lijia Yang、Mahesh K. Lakshman

  DOI：10.1039/c6ob02334g

  日期：——

  transformations. In the course of these investigations, the formation of 1-(4-pyrimidinyl)-1H-benzotriazole-3-oxide derivatives from the pyrimidine nucleosides was identified. However, these too underwent conversion to the desired products. Products obtained from AZT were converted to the 3′-amino derivatives by catalytic reduction. All products were assayed for their abilities to inhibit cancer cell proliferation

  Ot-丁基二甲基甲硅烷基保护的胸苷、2'-脱氧尿苷和 3'-叠氮胸苷 (AZT) 与 (苯并三唑-1-基氧基)三(二甲氨基)鏻六氟磷酸盐 (BOP) 的反应导致 C4 酰胺羰基活化，形成推定的O 4 -(苯并三唑-1-基)衍生物。随后用烷基和芳基胺、硫醇和醇取代导致该位置容易官能化。与胺和硫醇的反应可以两步一锅转化或一步转化的方式进行。与醇的反应以两步一锅转化的方式进行。在这些研究过程中，鉴定出从嘧啶核苷形成1-(4-嘧啶基)-1H-苯并三唑-3-氧化物衍生物。然而，这些也经历了转化为所需的产品。通过催化还原将AZT获得的产物转化为3'-氨基衍生物。所有产品均经过检测其抑制癌细胞增殖和抗病毒活性的能力。许多药物被发现对 HIV-1 和 HIV-2 具有活性，其中一种对单纯疱疹病毒 1 (HSV-1) 具有活性。
• Thiation of Nucleosides. II. Synthesis of 5-Methyl-2'-deoxycytidine and Related Pyrimidine Nucleosides¹
  作者：Jack J. Fox、Dina Van Praag、Iris Wempen、Iris L. Doerr、Loretta Cheong、Joseph E. Knoll、Maxwell L. Eidinoff、Aaron Bendich、George Bosworth Brown

  DOI：10.1021/ja01510a042

  日期：1959.1
• Convenient Intermediates for the Preparation of<i>C</i>-4 Modified Derivatives of Pyrimidine Nucleosides
  作者：Anwar Miah、Colin B. Reese、Quanlai Song

  DOI：10.1080/07328319708002521

  日期：1997.1

  4-(4-Nitrophenoxy)-1-(beta-D-ribofuranosyl)pyrimidin-2(1H)-one 15, 5-methyl-4-(1,2,4-triazol-1-yl)-1-(beta-D-2-deoxyribofuranosyl 7a and 4-(4-nitrophenoxy)-1-(beta-D-2-deoxyribofuranosyl)pyrimidin-2(1H)-one 17a, respectively, have been prepared and are recommended as reactive intermediates for the preparation of derivatives of uridine, thymidine and 2'-deoxyuridine which are modified at C-4.