2-[1-(2-Hydroxyphenyl)ethylideneamino]guanidine | 239472-56-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[1-(2-Hydroxyphenyl)ethylideneamino]guanidine
• CAS: 239472-56-1
• 化学式: C₉H₁₂N₄O
• mdl: MFCD21101401
• 分子量: 192.22
• InChiKey: RRLOAHWSTJDIPD-UHFFFAOYSA-N

物化性质

• 沸点：
  337.7±44.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  97
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-肉桂酸苯酯 、 2-[1-(2-Hydroxyphenyl)ethylideneamino]guanidine 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以55.3%的产率得到(2E)-N-[{2-[1-(2-hydroxyphenyl)ethylidene]hydrazino}(imino)methyl]-3-phenylacrylamide
  参考文献：
  名称：

  Novel molecular hybrids of cinnamic acids and guanylhydrazones as potential antitubercular agents

  摘要：

  In an attempt to identify potential new agents active against tuberculosis, 20 novel phenylacrylamide derivatives incorporating cinnamic acids and guanylhydrazones were synthesized using microwave assisted synthesis. Activity of the synthesized compounds was evaluated using resazurin microtitre plate assay (REMA) against Mycobacterium tuberculosis H37Rv. Based on empirical structure-activity relationship data it was observed that both steric and electronic parameters play major role in the activity of this series of compounds. Compound 7s (2E)-N-((-2-(3,4-dimethoxybenzylidene) hydrazinyl) (imino) methyl)-3-(4-methoxyphenyl) acrylamide showed MIC of 6.49 mu M along with good safety profile of >50-fold in VERO cell line. Thus, this compound could act as a potential lead for further antitubercular studies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.031
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 肼甲酰亚胺酰胺一氯化氢 在 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 0.33h， 生成 2-[1-(2-Hydroxyphenyl)ethylideneamino]guanidine
  参考文献：
  名称：

  Novel molecular hybrids of cinnamic acids and guanylhydrazones as potential antitubercular agents

  摘要：

  In an attempt to identify potential new agents active against tuberculosis, 20 novel phenylacrylamide derivatives incorporating cinnamic acids and guanylhydrazones were synthesized using microwave assisted synthesis. Activity of the synthesized compounds was evaluated using resazurin microtitre plate assay (REMA) against Mycobacterium tuberculosis H37Rv. Based on empirical structure-activity relationship data it was observed that both steric and electronic parameters play major role in the activity of this series of compounds. Compound 7s (2E)-N-((-2-(3,4-dimethoxybenzylidene) hydrazinyl) (imino) methyl)-3-(4-methoxyphenyl) acrylamide showed MIC of 6.49 mu M along with good safety profile of >50-fold in VERO cell line. Thus, this compound could act as a potential lead for further antitubercular studies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.031