1-((2R,4S,5S)-4-hydroxy-5-((S)-5-oxo-1,2-dithiolan-3-yl)-tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione | 722493-06-3

• 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: 1-((2R,4S,5S)-4-hydroxy-5-((S)-5-oxo-1,2-dithiolan-3-yl)-tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
• 英文别名: 1-[(2R,4S,5S)-4-hydroxy-5-(5-oxodithiolan-3-yl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 722493-06-3
• 化学式: C₁₂H₁₄N₂O₅S₂
• 分子量: 330.386
• InChiKey: XSYUHHYIWWZJEP-MZGKANMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-((2R,4S,5S)-4-hydroxy-5-((S)-5-oxo-1,2-dithiolan-3-yl)-tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 在 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以96%的产率得到1-((2R,4S,5S)-4-hydroxy-5-((S)-[5-(2,5-dioxo-1,2-dithiolan-3-yl)]-tetrahydrofuran-2-yl))-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Incorporation of the bioactive moiety of leinamycin into thymidine

  摘要：

  A simple synthesis of 1,2-dithiolan-3-ones from alpha,beta-unsaturated thiophenyl esters has been elaborated. With the aim of introducing the biologically active 1,2-dithiolan-3-one-1-oxide moiety of leinamycin into a nucleoside, the method was successfully applied to thymidine-5'-aldehyde. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.011
• 作为产物：
  描述：

  3'-O-(叔丁基二甲基硅烷基)胸苷 在 硫化氢 、 戴斯-马丁氧化剂 、 三乙胺 、 三氟乙酸 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 72.0h， 生成 1-((2R,4S,5S)-4-hydroxy-5-((S)-5-oxo-1,2-dithiolan-3-yl)-tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and Cytotoxicity of Leinamycin Antibiotic Analogues

  摘要：

  A simple synthesis of 1,2-dithiolan-3-ones from alpha,beta-unsaturated thiophenyl esters is reported. Introduction of the biologically active 1,2-dithiolan-3-one-1-oxide moiety of leinamycin into aldehydo-D-arabinose 11, the uridine derivative 16, and the deoxythymidine 21 was established. An extended bioactive part of leinamycin carrying a carbon-carbon triple bond was also synthesized. All of these analogues of leinamycin showed cytotoxic activity against HeLa3 tumor cells. Interestingly, the lipophilic, silyl group-containing derivatives proved to be more active than the hydrophilic counterparts.

  DOI：

  10.1021/jm060471h

文献信息

• Incorporation of the bioactive moiety of leinamycin into thymidine
  作者：Ákos Szilágyi、István F. Pelyvás、Orsolya Majercsik、Pál Herczegh

  DOI：10.1016/j.tetlet.2004.04.011

  日期：2004.5

  A simple synthesis of 1,2-dithiolan-3-ones from alpha,beta-unsaturated thiophenyl esters has been elaborated. With the aim of introducing the biologically active 1,2-dithiolan-3-one-1-oxide moiety of leinamycin into a nucleoside, the method was successfully applied to thymidine-5'-aldehyde. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and Cytotoxicity of Leinamycin Antibiotic Analogues
  作者：Ákos Szilágyi、Ferenc Fenyvesi、Orsolya Majercsik、István F. Pelyvás、Ildikó Bácskay、Pálma Fehér、Judit Váradi、Miklós Vecsernyés、Pál Herczegh

  DOI：10.1021/jm060471h

  日期：2006.9.1

  A simple synthesis of 1,2-dithiolan-3-ones from alpha,beta-unsaturated thiophenyl esters is reported. Introduction of the biologically active 1,2-dithiolan-3-one-1-oxide moiety of leinamycin into aldehydo-D-arabinose 11, the uridine derivative 16, and the deoxythymidine 21 was established. An extended bioactive part of leinamycin carrying a carbon-carbon triple bond was also synthesized. All of these analogues of leinamycin showed cytotoxic activity against HeLa3 tumor cells. Interestingly, the lipophilic, silyl group-containing derivatives proved to be more active than the hydrophilic counterparts.