1-(4'-C-methyl-β-D-arabinofuranosyl)cytosine | 175545-37-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4'-C-methyl-β-D-arabinofuranosyl)cytosine
• 英文别名: 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-5-methyl-tetrahydrofuran-2-yl]pyrimidin-2-one；4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-5-methyloxolan-2-yl]pyrimidin-2-one
• CAS: 175545-37-6
• 化学式: C₁₀H₁₅N₃O₅
• 分子量: 257.246
• InChiKey: MUBNRBNWTUDOEJ-QHOPCYEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 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：
  129
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4'-C-methyl-β-D-arabinofuranosyl)cytosine 在 三氯氧磷 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成
  参考文献：
  名称：

  Antileukemic Activities and Mechanism of Action of 2′-Deoxy-4′-methylcytidine and Related Nucleosides

  摘要：

  Antileukemic activity of several analogues containing 2'-deoxy-4'-methylcytidine and its araC counterpart were evaluated against murine leukemic P388 cells in vitro and in vivo. Both compounds showed significant cytostatic activity (both IC50 = 0.4 mu M) in vitro and the former compound administered intraperitoneally at a dose of 3 mg/kg/day x 5 showed high activity (T/C = 175%) in vivo. The mechanism of action of these 5'-triphosphates on DNA polymerases in detail will be also described.

  DOI：

  10.1080/07328319708006185
• 作为产物：
  描述：

  1-(2',3',5'-tri-O-acetyl-4'-C-methyl-β-D-arabinofuranosyl)uracil 在 ammonium hydroxide 、 ClPhPOCl₂ 作用下， 以 吡啶 为溶剂， 生成 1-(4'-C-methyl-β-D-arabinofuranosyl)cytosine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 4′-C-Methyl Nucleosides

  摘要：

  A series of 2'-deoxy, 2',3'-unsaturated and 2',3'-dideoxynucleoside analogues, which have an additional methyl group at the 4'-position, have been synthesized. When evaluated for their inhibitory activity against HIV in MT-4 cell, 2'-deoxy-4'-C-methyl nucleosides exhibited potent activity.

  DOI：

  10.1080/07328319608002385

文献信息

• [EN] NUCLEOSIDES FOR TREATING CANCER<br/>[FR] NUCLÉOSIDES POUR LE TRAITEMENT DU CANCER
  申请人：PRIMEFOUR THERAPEUTICS INC

  公开号：WO2023192499A1

  公开（公告）日：2023-10-05

  The present disclosure provides DNA damage repair enzyme inhibitors and methods of treating or preventing a cancer in a subject by administering a DNA damage repair enzyme inhibitor to the subject.

  本公开提供了DNA损伤修复酶抑制剂以及通过给受试者施用DNA损伤修复酶抑制剂来治疗或预防癌症的方法。
• Synthesis and Biological Evaluation of 4′-<i>C</i>-Methyl Nucleosides
  作者：Toshiaki Waga、Hiroshi Ohrui、Hiroshi Meguro

  DOI：10.1080/07328319608002385

  日期：1996.1

  A series of 2'-deoxy, 2',3'-unsaturated and 2',3'-dideoxynucleoside analogues, which have an additional methyl group at the 4'-position, have been synthesized. When evaluated for their inhibitory activity against HIV in MT-4 cell, 2'-deoxy-4'-C-methyl nucleosides exhibited potent activity.
• Antileukemic Activities and Mechanism of Action of 2′-Deoxy-4′-methylcytidine and Related Nucleosides
  作者：Toyofumi Yamaguchi、Aki Tomikawa、Toshiaki Hirai、Takeo Kawaguchi、Hiroshi Ohrui、Mineo Saneyoshi

  DOI：10.1080/07328319708006185

  日期：1997.7

  Antileukemic activity of several analogues containing 2'-deoxy-4'-methylcytidine and its araC counterpart were evaluated against murine leukemic P388 cells in vitro and in vivo. Both compounds showed significant cytostatic activity (both IC50 = 0.4 mu M) in vitro and the former compound administered intraperitoneally at a dose of 3 mg/kg/day x 5 showed high activity (T/C = 175%) in vivo. The mechanism of action of these 5'-triphosphates on DNA polymerases in detail will be also described.