isopropyl 4-(pyridin-2-yl)-2-(pyrimidin-2-ylamino)thiazole-5-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: isopropyl 4-(pyridin-2-yl)-2-(pyrimidin-2-ylamino)thiazole-5-carboxylate
• 英文别名: Propan-2-yl 4-pyridin-2-yl-2-(pyrimidin-2-ylamino)-1,3-thiazole-5-carboxylate；propan-2-yl 4-pyridin-2-yl-2-(pyrimidin-2-ylamino)-1,3-thiazole-5-carboxylate
• 化学式: C₁₆H₁₅N₅O₂S
• 分子量: 341.393
• InChiKey: LFSZDBORWAVQDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  isopropyl 4-(pyridin-2-yl)-2-(pyrimidin-2-ylamino)thiazole-5-carboxylate 、 二叔丁基氯甲基磷酸酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.5h， 以12%的产率得到isopropyl 2-((((di-tert-butoxyphosphoryl)oxy)methyl)(pyrimidin-2-yl)amino)-4-(pyridin-2-yl)thiazole-5-carboxylate
  参考文献：
  名称：

  Novel substituted aminothiazoles as potent and selective anti-hepatocellular carcinoma agents

  摘要：

  Based on our previous identification of a disubstituted aminothiazole termed HBF-0079 with promising selective toxicity for HCC-derived cell lines versus non-HCC liver lines, a series of tri-substituted aminothiazole derivatives were prepared and evaluated. This work resulted in the discovery of isopropyl 4-(pyrazin-2-yl)-2-(pyrimidin-2-ylamino) thiazole-5-carboxylate, 14, which displayed EC50 value of 0.11 mu M and more than 450 times of selectivity, and its methyl carbonate prodrug 24 with improved solubility in organic solvents. Furthermore, 14, was shown to reduce the proliferation of several liver cancer cells derived directly from patients. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.10.015
• 作为产物：
  描述：

  C₁₁H₁₂BrNO₃ 、 1-(嘧啶-2-基)硫代脲 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以63%的产率得到isopropyl 4-(pyridin-2-yl)-2-(pyrimidin-2-ylamino)thiazole-5-carboxylate
  参考文献：
  名称：

  Novel substituted aminothiazoles as potent and selective anti-hepatocellular carcinoma agents

  摘要：

  Based on our previous identification of a disubstituted aminothiazole termed HBF-0079 with promising selective toxicity for HCC-derived cell lines versus non-HCC liver lines, a series of tri-substituted aminothiazole derivatives were prepared and evaluated. This work resulted in the discovery of isopropyl 4-(pyrazin-2-yl)-2-(pyrimidin-2-ylamino) thiazole-5-carboxylate, 14, which displayed EC50 value of 0.11 mu M and more than 450 times of selectivity, and its methyl carbonate prodrug 24 with improved solubility in organic solvents. Furthermore, 14, was shown to reduce the proliferation of several liver cancer cells derived directly from patients. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.10.015

文献信息

• [EN] SUBSTITUTED AMINOTHIAZOLES<br/>[FR] AMINOTHIAZOLES SUBSTITUÉS
  申请人：BARUCH S BLUMBERG INST

  公开号：WO2018013508A1

  公开（公告）日：2018-01-18

  Described herein are substituted aminothiazoles, compositions comprising same; and methods of making and using same.

  本文描述了替代氨基噻唑，包括相同成分的组合物；以及制备和使用相同的方法。
• Substituted aminothiazoles
  申请人：BARUCH S. BLUMBERG INSTITUTE

  公开号：US10913734B2

  公开（公告）日：2021-02-09

  Described herein are substituted aminothiazoles, compositions comprising same; and methods of making and using same.

  本文描述了取代的氨基噻唑、包含取代的氨基噻唑的组合物以及制造和使用取代的氨基噻唑的方法。
• SUBSTITUTED AMINOTHIAZOLES
  申请人：BARUCH S. BLUMBERG INSTITUTE

  公开号：US20190241552A1

  公开（公告）日：2019-08-08

  Described herein are substituted aminothiazoles, compositions comprising same; and methods of making and using same.