2'-deoxy-2'-methylene-β-L-cytidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2'-deoxy-2'-methylene-β-L-cytidine
• 英文别名: 4-amino-1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)-3-methylideneoxolan-2-yl]pyrimidin-2-one
• 化学式: C₁₀H₁₃N₃O₄
• 分子量: 239.231
• InChiKey: PULHLIOPJXPGJN-ZQARSLAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(β-L-arabinofuranosyl)uracil 在 chromium(VI) oxide 、 ammonium hydroxide 、 四丁基氟化铵 、 乙酸酐 、 sodium hydride 、 4-氯苯基二氯磷酸酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 二甲基亚砜 为溶剂， 反应 124.5h， 生成 2'-deoxy-2'-methylene-β-L-cytidine
  参考文献：
  名称：

  Synthesis of 1-β-L-Arabinofuranosylcytosine (β-L-Ara-C) and 2′-Deoxy-2′-methylene-β-L-cytidine (β-L-DMDC) as Potential Antineoplastic Agents

  摘要：

  1-beta-L-Arabinofuranosylcytosine (beta-L-Ara-C, 7) and 2'-deoxy-2'-methylene-beta-L-cytidine (beta-L-DMDC, 14) have been synthesized via a multi-step synthesis from L-arabinose. These compounds were tested in vitro against L1210, P388, Sarcoma 180, and CEM cells, and found not to be active at a concentration up to 100 mu M. beta-L-Ara-C and beta-L-DMDC were also tested against HSV-1 and HSV-2 and yielded ID50 values of >100 mu M.

  DOI：

  10.1080/15257779408010669

文献信息

• Synthesis of 1-β-L-Arabinofuranosylcytosine (β-L-Ara-C) and 2′-Deoxy-2′-methylene-β-L-cytidine (β-L-DMDC) as Potential Antineoplastic Agents
  作者：Tai-Shun Lin、Mei-Zhen Luo、Mao-Chin Liu

  DOI：10.1080/15257779408010669

  日期：1994.9

  1-beta-L-Arabinofuranosylcytosine (beta-L-Ara-C, 7) and 2'-deoxy-2'-methylene-beta-L-cytidine (beta-L-DMDC, 14) have been synthesized via a multi-step synthesis from L-arabinose. These compounds were tested in vitro against L1210, P388, Sarcoma 180, and CEM cells, and found not to be active at a concentration up to 100 mu M. beta-L-Ara-C and beta-L-DMDC were also tested against HSV-1 and HSV-2 and yielded ID50 values of >100 mu M.