N-[(E)-(3-oxido-2,1,3-benzoxadiazol-3-ium-5-yl)methylideneamino]-1,3-benzodioxole-5-carboxamide | 1361949-62-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: N-[(E)-(3-oxido-2,1,3-benzoxadiazol-3-ium-5-yl)methylideneamino]-1,3-benzodioxole-5-carboxamide
• CAS: 1361949-62-3
• 化学式: C₁₅H₁₀N₄O₅
• 分子量: 326.268
• InChiKey: HSTYXKYAROJMSF-FRKPEAEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4-亚甲基二氧苄肼 、 6-formylbenzofuroxan 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 以98%的产率得到N-[(E)-(3-oxido-2,1,3-benzoxadiazol-3-ium-5-yl)methylideneamino]-1,3-benzodioxole-5-carboxamide
  参考文献：
  名称：

  Discovery of new orally effective analgesic and anti-inflammatory hybrid furoxanyl N-acylhydrazone derivatives

  摘要：

  We report the design, the synthesis and the biological evaluation of the analgesic and anti-inflammatory activities of furoxanyl N-acylhydrazones (furoxanyl-NAH) by applying molecular hybridization approach. Hybrid compounds with IL-8-release inhibition capabilities were identified. Among them, furoxanyl-NAH, 17, and benzofuroxanyl-derivative, 24, together with furoxanyl-NAH derivative, 31, without IL-8 inhibition displayed both orally analgesic and anti-inflammatory activities. These hybrid derivatives do not have additional LOX- or COX-inhibition activities. For instance, LOX-inhibition by furoxanyl-NAH derivative, 42, emerged as a structural lead to develop new inhibitors. The lack of mutagenicity of the active derivatives 17, 31, and 42, allow us to propose them as candidates for further clinical studies. These results confirmed the success in the exploitation of hybridization strategy for identification of novel N-acylhydrazones (NAH) with optimized activities. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.034

文献信息

• Discovery of new orally effective analgesic and anti-inflammatory hybrid furoxanyl N-acylhydrazone derivatives
  作者：Paola Hernández、Mauricio Cabrera、María Laura Lavaggi、Laura Celano、Inés Tiscornia、Thiago Rodrigues da Costa、Leonor Thomson、Mariela Bollati-Fogolín、Ana Luisa P. Miranda、Lidia M. Lima、Eliezer J. Barreiro、Mercedes González、Hugo Cerecetto

  DOI：10.1016/j.bmc.2012.01.034

  日期：2012.3

  We report the design, the synthesis and the biological evaluation of the analgesic and anti-inflammatory activities of furoxanyl N-acylhydrazones (furoxanyl-NAH) by applying molecular hybridization approach. Hybrid compounds with IL-8-release inhibition capabilities were identified. Among them, furoxanyl-NAH, 17, and benzofuroxanyl-derivative, 24, together with furoxanyl-NAH derivative, 31, without IL-8 inhibition displayed both orally analgesic and anti-inflammatory activities. These hybrid derivatives do not have additional LOX- or COX-inhibition activities. For instance, LOX-inhibition by furoxanyl-NAH derivative, 42, emerged as a structural lead to develop new inhibitors. The lack of mutagenicity of the active derivatives 17, 31, and 42, allow us to propose them as candidates for further clinical studies. These results confirmed the success in the exploitation of hybridization strategy for identification of novel N-acylhydrazones (NAH) with optimized activities. (C) 2012 Elsevier Ltd. All rights reserved.