ethyl (5-benzyl-1,3,4-thiadiazol-2-ylcarbamoyl)formate | 600147-86-2

• 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: ethyl (5-benzyl-1,3,4-thiadiazol-2-ylcarbamoyl)formate
• 英文别名: ethyl 2-((5-benzyl-1,3,4-thiadiazol-2-yl)amino)-2-oxoacetate；Ethyl [(5-benzyl-1,3,4-thiadiazol-2-yl)amino](oxo)acetate；ethyl 2-[(5-benzyl-1,3,4-thiadiazol-2-yl)amino]-2-oxoacetate
• CAS: 600147-86-2
• 化学式: C₁₃H₁₃N₃O₃S
• mdl: MFCD03930096
• 分子量: 291.331
• InChiKey: YUDWLNZLKXYXEL-UHFFFAOYSA-N

物化性质

• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (5-benzyl-1,3,4-thiadiazol-2-ylcarbamoyl)formate 在 羟胺 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以91%的产率得到N1-(5-benzyl-1,3,4-thiadiazol-2-yl)-N2-hydroxyoxalamide
  参考文献：
  名称：

  Design, synthesis and preliminary bioactivity studies of 1,3,4-thiadiazole hydroxamic acid derivatives as novel histone deacetylase inhibitors

  摘要：

  Histone deacetylase (HDAC) inhibitors have emerged as a new class of anticancer agents, targeting the biological processes including cell cycle, apoptosis and differentiation. In the present study, a series of 1,3,4-thiadiazole based hydroxamic acids were developed as potent HDAC inhibitors. Some of them showed good inhibitory activity in HDAC enzyme assay and potent growth inhibition in some tumor cell lines. Among them, compound 6i (IC50 = 0.089 mu M), exhibited better inhibitory effect compared with SAHA (IC50 = 0.15 mu M). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.032
• 作为产物：
  描述：

  苯乙酸 在 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 ethyl (5-benzyl-1,3,4-thiadiazol-2-ylcarbamoyl)formate
  参考文献：
  名称：

  Design, synthesis and preliminary bioactivity studies of 1,3,4-thiadiazole hydroxamic acid derivatives as novel histone deacetylase inhibitors

  摘要：

  Histone deacetylase (HDAC) inhibitors have emerged as a new class of anticancer agents, targeting the biological processes including cell cycle, apoptosis and differentiation. In the present study, a series of 1,3,4-thiadiazole based hydroxamic acids were developed as potent HDAC inhibitors. Some of them showed good inhibitory activity in HDAC enzyme assay and potent growth inhibition in some tumor cell lines. Among them, compound 6i (IC50 = 0.089 mu M), exhibited better inhibitory effect compared with SAHA (IC50 = 0.15 mu M). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.032

文献信息

• One-pot synthesis of 4-ethyl 2,3-dimethyl 1-(5-aryl-1,3,4-thiadiazol-2-yl)-5-oxo-2,5-dihydro-1<i>H</i>-pyrrole-2,3,4-tricarboxylate derivatives via intramolecular Wittig reaction
  作者：Samin Iravani、Abbas Ali Esmaeili

  DOI：10.1177/1747519820903291

  日期：2020.7

  A facile one-pot synthesis of highly functionalized dialkyl 1-(5-aryl-1,3,4-thiadiazol-2-yl)-4-ethoxy-5-oxo-2,5-dihydro-1H-pyrrole-2,3-dicarboxylate derivatives via the reaction between acetylenic esters, triphenylphosphine, and ethyl 2-[(5-aryl-1,3,4-thiadiazol-2-yl)amino]-2-oxoacetate is developed. The structure of the products is confirmed by spectroscopic methods.

  高度官能化的二烷基 1-(5-aryl-1,3,4-thiadiazol-2-yl)-4-ethoxy-5-oxo-2,5-dihydro-1H-pyrrole-2 的简便一锅合成，通过炔酸酯、三苯基膦和 2-[(5-芳基-1,3,4-噻二唑-2-基)氨基]-2-氧代乙酸乙酯之间的反应，开发了 3-二羧酸衍生物。产物的结构通过光谱方法确认。