(S)-N-(2-azido-1-phenylethyl)-2-(2-(methylamino)pyrimidin-4-yl)thiazole-5-carboxamide | 1357194-16-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-N-(2-azido-1-phenylethyl)-2-(2-(methylamino)pyrimidin-4-yl)thiazole-5-carboxamide
• CAS: 1357194-16-1
• 化学式: C₁₇H₁₆N₈OS
• 分子量: 380.433
• InChiKey: IGOZVRAAWITTEZ-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  128.56
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-N-(2-azido-1-phenylethyl)-2-(2-(methylamino)pyrimidin-4-yl)thiazole-5-carboxamide 在 palladium 10% on activated carbon 、 氢气 作用下， 反应 5.0h， 以71%的产率得到(S)-N-(2-amino-1-phenylethyl)-2-(2-(methylamino)pyrimidin-4-yl)thiazole-5-carboxamide
  参考文献：
  名称：

  New thiazole carboxamides as potent inhibitors of Akt kinases

  摘要：

  A new series of 2-substituted thiazole carboxamides were identified as potent pan inhibitors against all three isoforms of Akt (Akt1, Akt2 and Akt3) by systematic optimization of weak screening hit N-(1-amino-3-phenylpropan-2-yl)-2-phenylthiazole-5-carboxamide (1). One of the most potent compounds, 5m, inhibited the kinase activities of Akt1, Akt2 and Akt3 with IC50 values of 25, 196 and 24 nM, respectively. The compound also potently inhibited the phosphorylation of downstream MDM2 and GSK3 beta proteins, and displayed strongly antiproliferative activity in prostate cancer cells. The inhibitors might serve as lead compounds for further development of novel effective anticancer agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.080
• 作为产物：
  描述：

  methyl 2-(3-(dimethylamino)acryloyl)thiazole-5-carboxylate 在 sodium ethanolate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 (S)-N-(2-azido-1-phenylethyl)-2-(2-(methylamino)pyrimidin-4-yl)thiazole-5-carboxamide
  参考文献：
  名称：

  New thiazole carboxamides as potent inhibitors of Akt kinases

  摘要：

  A new series of 2-substituted thiazole carboxamides were identified as potent pan inhibitors against all three isoforms of Akt (Akt1, Akt2 and Akt3) by systematic optimization of weak screening hit N-(1-amino-3-phenylpropan-2-yl)-2-phenylthiazole-5-carboxamide (1). One of the most potent compounds, 5m, inhibited the kinase activities of Akt1, Akt2 and Akt3 with IC50 values of 25, 196 and 24 nM, respectively. The compound also potently inhibited the phosphorylation of downstream MDM2 and GSK3 beta proteins, and displayed strongly antiproliferative activity in prostate cancer cells. The inhibitors might serve as lead compounds for further development of novel effective anticancer agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.080