2-[4-[(4-Amino-2-cyclopropylpyrimidin-5-yl)methyl]-3-methylthiophen-2-yl]ethanol | 1012795-30-0

• 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-[4-[(4-Amino-2-cyclopropylpyrimidin-5-yl)methyl]-3-methylthiophen-2-yl]ethanol
• CAS: 1012795-30-0
• 化学式: C₁₅H₁₉N₃OS
• 分子量: 289.401
• InChiKey: GDKTUPHEYPDPSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[4-[(4-Amino-2-cyclopropylpyrimidin-5-yl)methyl]-3-methylthiophen-2-yl]ethanol 在 thiamine pyrophosphate 作用下， 生成
  参考文献：
  名称：

  Non-charged thiamine analogs as inhibitors of enzyme transketolase

  摘要：

  Inhibition of the thiamine-utilizing enzyme transketolase (TK) has been linked with diminished tumor cell proliferation. Most thiamine antagonists have a permanent positive charge on the B-ring, and it has been suggested that this charge is required for diphosphorylation by thiamine pyrophosphokinase (TPPK) and binding to TK. We sought to make neutral thiazolium replacements that would be substrates for TPPK, while not necessarily needing thiamine transporters (ThTr1 and ThTr2) for cell penetration. The synthesis, SAR, and structure-based rationale for highly potent non-thiazolium TK antagonists are presented. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.098
• 作为产物：
  描述：

  环丙烷甲脒盐酸盐 、 3-(2-Cyano-3-phenylaminoprop-2-en-1-yl)-5-(2-hydroxyethyl)-4-methylthiophene 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以52%的产率得到2-[4-[(4-Amino-2-cyclopropylpyrimidin-5-yl)methyl]-3-methylthiophen-2-yl]ethanol
  参考文献：
  名称：

  Non-charged thiamine analogs as inhibitors of enzyme transketolase

  摘要：

  Inhibition of the thiamine-utilizing enzyme transketolase (TK) has been linked with diminished tumor cell proliferation. Most thiamine antagonists have a permanent positive charge on the B-ring, and it has been suggested that this charge is required for diphosphorylation by thiamine pyrophosphokinase (TPPK) and binding to TK. We sought to make neutral thiazolium replacements that would be substrates for TPPK, while not necessarily needing thiamine transporters (ThTr1 and ThTr2) for cell penetration. The synthesis, SAR, and structure-based rationale for highly potent non-thiazolium TK antagonists are presented. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.098

文献信息

• Non-charged thiamine analogs as inhibitors of enzyme transketolase
  作者：Allen A. Thomas、J. De Meese、Y. Le Huerou、Steven A. Boyd、Todd T. Romoff、Steven S. Gonzales、Indrani Gunawardana、Tomas Kaplan、Francis Sullivan、Kevin Condroski、Joseph P. Lyssikatos、Thomas D. Aicher、Josh Ballard、Bryan Bernat、Walter DeWolf、May Han、Christine Lemieux、Darin Smith、Solly Weiler、S. Kirk Wright、Guy Vigers、Barb Brandhuber

  DOI：10.1016/j.bmcl.2007.11.098

  日期：2008.1

  Inhibition of the thiamine-utilizing enzyme transketolase (TK) has been linked with diminished tumor cell proliferation. Most thiamine antagonists have a permanent positive charge on the B-ring, and it has been suggested that this charge is required for diphosphorylation by thiamine pyrophosphokinase (TPPK) and binding to TK. We sought to make neutral thiazolium replacements that would be substrates for TPPK, while not necessarily needing thiamine transporters (ThTr1 and ThTr2) for cell penetration. The synthesis, SAR, and structure-based rationale for highly potent non-thiazolium TK antagonists are presented. (c) 2007 Elsevier Ltd. All rights reserved.