(2E)-3-(4-hydroxy-3-methoxy-5-nitrophenyl)acrylohydrazide | 1394115-41-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (2E)-3-(4-hydroxy-3-methoxy-5-nitrophenyl)acrylohydrazide
• 英文别名: (E)-3-(4-hydroxy-3-methoxy-5-nitrophenyl)prop-2-enehydrazide
• CAS: 1394115-41-3
• 化学式: C₁₀H₁₁N₃O₅
• 分子量: 253.214
• InChiKey: MZDYXNSUFSMCQO-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2E)-3-(4-hydroxy-3-methoxy-5-nitrophenyl)acrylohydrazide 、 苯甲醛 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以81%的产率得到(2E)-3-(4-hydroxy-3-methoxy-5-nitrophenyl)-N'-[(1E)-benzylidene]acrylohydrazide
  参考文献：
  名称：

  Design and synthesis of new (E)-cinnamic N-acylhydrazones as potent antitrypanosomal agents

  摘要：

  We report herein the synthesis and trypanocidal profile of new (E)-cinnamic N-acylhydrazones (NAHs) designed by exploiting molecular hybridization between the potent cruzain inhibitors (E)-1-(benzo[d] 11,3)dioxol-5-yl)-3-(4-bromophenyl)prop-2-en-1-one and (E)-3-hydroxy-N'-((2-hydroxynaphthalen-1-yl)methylene)-7-methoxy-2-naphthohydrazide. These derivatives were evaluated against both amastigote and trypomastigote forms of Trypanosoma cruzi and lead us to identify two compounds that were approximately two times more active than the reference drug, benznidazole, and with good cytotoxic index. Although designed as cruzain inhibitors, the weak potency displayed by the best cinnamyl NAH derivatives indicated that another mechanism of action was likely responsible for their trypanocide action. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.041
• 作为产物：
  描述：

  5-硝基香兰素 在 哌啶 、 吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 (2E)-3-(4-hydroxy-3-methoxy-5-nitrophenyl)acrylohydrazide
  参考文献：
  名称：

  Design and synthesis of new (E)-cinnamic N-acylhydrazones as potent antitrypanosomal agents

  摘要：

  We report herein the synthesis and trypanocidal profile of new (E)-cinnamic N-acylhydrazones (NAHs) designed by exploiting molecular hybridization between the potent cruzain inhibitors (E)-1-(benzo[d] 11,3)dioxol-5-yl)-3-(4-bromophenyl)prop-2-en-1-one and (E)-3-hydroxy-N'-((2-hydroxynaphthalen-1-yl)methylene)-7-methoxy-2-naphthohydrazide. These derivatives were evaluated against both amastigote and trypomastigote forms of Trypanosoma cruzi and lead us to identify two compounds that were approximately two times more active than the reference drug, benznidazole, and with good cytotoxic index. Although designed as cruzain inhibitors, the weak potency displayed by the best cinnamyl NAH derivatives indicated that another mechanism of action was likely responsible for their trypanocide action. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.041

文献信息

• Design and synthesis of new (E)-cinnamic N-acylhydrazones as potent antitrypanosomal agents
  作者：Samir A. Carvalho、Larisse O. Feitosa、Márcio Soares、Thadeu E.M.M. Costa、Maria G. Henriques、Kelly Salomão、Solange L. de Castro、Marcel Kaiser、Reto Brun、James L. Wardell、Solange M.S.V. Wardell、Gustavo H.G. Trossini、Adriano D. Andricopulo、Edson F. da Silva、Carlos A.M. Fraga

  DOI：10.1016/j.ejmech.2012.05.041

  日期：2012.8

  We report herein the synthesis and trypanocidal profile of new (E)-cinnamic N-acylhydrazones (NAHs) designed by exploiting molecular hybridization between the potent cruzain inhibitors (E)-1-(benzo[d] 11,3)dioxol-5-yl)-3-(4-bromophenyl)prop-2-en-1-one and (E)-3-hydroxy-N'-((2-hydroxynaphthalen-1-yl)methylene)-7-methoxy-2-naphthohydrazide. These derivatives were evaluated against both amastigote and trypomastigote forms of Trypanosoma cruzi and lead us to identify two compounds that were approximately two times more active than the reference drug, benznidazole, and with good cytotoxic index. Although designed as cruzain inhibitors, the weak potency displayed by the best cinnamyl NAH derivatives indicated that another mechanism of action was likely responsible for their trypanocide action. (C) 2012 Elsevier Masson SAS. All rights reserved.