2-[(2-methylphenyl)methylene]hydrazinecarboximidamide | 13308-86-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(2-methylphenyl)methylene]hydrazinecarboximidamide
• 英文别名: 2-[(2-methylphenyl)methylideneamino]guanidine
• CAS: 13308-86-6
• 化学式: C₉H₁₂N₄
• 分子量: 176.221
• InChiKey: NAFYBNDPHKSYLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 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：
  76.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(2-methylphenyl)methylene]hydrazinecarboximidamide 、 1,1,1-trifluoro-4-methoxypent-3-en-2-one 以 乙醇 为溶剂， 反应 4.0h， 以88%的产率得到2-(N'-2-methyl-benzylidenehydrazino)-6-methyl-4-trifluoromethyl-pyrimidine
  参考文献：
  名称：

  Convergent synthesis and cruzain inhibitory activity of novel 2-(N′-benzylidenehydrazino)-4-trifluoromethyl-pyrimidines

  摘要：

  To search for new cruzain inhibitors, the synthesis of a series of novel 2-(N'-benzylidenehydrazino)-4-trifluoromethyl-pyrimidines in a convergent manner is presented. The cruzain inhibitory activity of some of these compounds was evaluated and a binding model was proposed. All derivatives tested were active and the most significant inhibitory effect (80% at 100 mu M) and IC(50) value (85 mu M) were obtained from the 2-(N'-4-chloro-benzylidenehydrazino)-4-trifluoromethyl-pyrimidine. Although further structural optimization to improve solubility is necessary, the molecular docking studies suggest that these inhibitors occupy the S2 pocket without irreversible enzyme inactivation, through hydrophobic interactions, thus, indicating a desirable mode of interaction for the design of novel inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.052
• 作为产物：
  描述：

  肼甲酰亚胺酰胺一氯化氢 、 2-甲基苯甲醛 在 potassium hydroxide 作用下， 生成 2-[(2-methylphenyl)methylene]hydrazinecarboximidamide
  参考文献：
  名称：

  Molecular hybrids integrated with imidazole and hydrazone structural motifs: Design, synthesis, biological evaluation, and molecular docking studies

  摘要：

  DOI：

  10.1016/j.molliq.2023.123242

文献信息

• Potential antisecretory antidiarrheals. 1. .alpha.2-Adrenergic aromatic aminoguanidine hydrazones
  作者：Barnett S. Pitzele、Alan E. Moormann、Gary W. Gullikson、David Albin、Robert G. Bianchi、Prima Palicharla、Elizabeth L. Sanguinetti、D. Eric Walters

  DOI：10.1021/jm00396a020

  日期：1988.1

  using a rabbit ileum preparation. A number of compounds, including members of each structural class, were active upon subcutaneous administration in the rat. Active compounds were determined to be alpha 2-adrenergic agonists by yohimbine reversals of their Ussing chamber activities. The compound displaying the best separation of activities was the aminoguanidine hydrazone of 2,6-dimethyl-4-hydroxybenzaldehyde

  瓜纳本斯，一种中枢性降压药，已显示具有肠道抗分泌特性。为了分离抗分泌和心血管活性，制备了一系列芳香族氨基胍and。合成了苯甲醛，萘醛和四氢萘酮衍生物。使用兔回肠制剂，在霍乱毒素治疗的大鼠结扎空肠中和Ussing室中评估化合物。在大鼠皮下给药后，许多化合物（包括每个结构类别的成员）均具有活性。通过育亨宾逆转其Ussing室活动，确定活性化合物为α2-肾上腺素能激动剂。表现出最佳分离活性的化合物是2,6-二甲基-4-羟基苯甲醛的氨基胍（20）。