diethyl 2-(4-(2-(3-(3-oxo-3-(2-(propylthio)benzo[d]thiazol-6-ylamino)propyl)ureido)ethyl)benzyl)malonate | 1391621-92-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl 2-(4-(2-(3-(3-oxo-3-(2-(propylthio)benzo[d]thiazol-6-ylamino)propyl)ureido)ethyl)benzyl)malonate
• CAS: 1391621-92-3
• 化学式: C₃₀H₃₈N₄O₆S₂
• 分子量: 614.787
• InChiKey: OUTMPBUHZCLGRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  42.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  135.72
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  diethyl 2-(4-(2-(3-(3-oxo-3-(2-(propylthio)benzo[d]thiazol-6-ylamino)propyl)ureido)ethyl)benzyl)malonate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 32.0h， 以29 mg的产率得到2-(4-(2-(3-(3-oxo-3-(2-(propylthio)benzo[d]thiazol-6-ylamino)propyl)ureido)ethyl)benzyl)malonic acid
  参考文献：
  名称：

  Design and Synthesis of Novel Lactate Dehydrogenase A Inhibitors by Fragment-Based Lead Generation

  摘要：

  Lactate dehydrogenase A (LDHA) catalyzes the conversion of pyruvate to lactate, utilizing NADH as a cofactor. It has been identified as a potential therapeutic target in the area of cancer metabolism. In this manuscript we report our progress using fragment-based lead generation (FBLG), assisted by X-ray crystallography to develop small molecule LDHA inhibitors. Fragment hits were identified through NMR and SPR screening and optimized into lead compounds with nanomolar binding affinities via fragment linking. Also reported is their modification into cellular active compounds suitable for target validation work.

  DOI：

  10.1021/jm201734r
• 作为产物：
  描述：

  tert-butyl 2-(propylthio)benzo[d]thiazol-6-ylcarbamate 在 盐酸 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N-甲基吡咯烷酮 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 107.0h， 生成 diethyl 2-(4-(2-(3-(3-oxo-3-(2-(propylthio)benzo[d]thiazol-6-ylamino)propyl)ureido)ethyl)benzyl)malonate
  参考文献：
  名称：

  Design and Synthesis of Novel Lactate Dehydrogenase A Inhibitors by Fragment-Based Lead Generation

  摘要：

  Lactate dehydrogenase A (LDHA) catalyzes the conversion of pyruvate to lactate, utilizing NADH as a cofactor. It has been identified as a potential therapeutic target in the area of cancer metabolism. In this manuscript we report our progress using fragment-based lead generation (FBLG), assisted by X-ray crystallography to develop small molecule LDHA inhibitors. Fragment hits were identified through NMR and SPR screening and optimized into lead compounds with nanomolar binding affinities via fragment linking. Also reported is their modification into cellular active compounds suitable for target validation work.

  DOI：

  10.1021/jm201734r