| 1472646-47-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• CAS: 1472646-47-1
• 化学式: C₁₇H₁₄ClN₃O₄
• 分子量: 359.769
• InChiKey: AMJUPPRUMTUSTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  96.04
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 sodium dithionite 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 1-(5-(2-mercapto-7-chlorobenzoxazol-5-yl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)ethanone
  参考文献：
  名称：

  Discovery of new antitubercular agents by combining pyrazoline and benzoxazole pharmacophores: design, synthesis and insights into the binding interactions

  摘要：

  The present study is aimed at combining two well-known pharmacophores (pyrazoline and benzoxazole nucleus) to design and synthesize a series of new benzoxazole-based pyrazoline derivatives. In vitro antitubercular evaluation against Mycobacterium tuberculosis H(37)Rv and multidrug-resistant TB (MDR-TB) strains showed that most of the target compounds displayed potent activity (MIC similar to 0.625-25 mu g/mL). Few compounds were found to be better than isoniazid against MDR-TB (MIC = 3.25 mu g/mL). In order to gain insights into the plausible binding motifs, the target compounds were docked into enoyl-acyl carrier protein (ACP) reductase, a molecular target of isoniazid. Many compounds were successfully docked into the active site of enoyl-ACP reductase and all the docked compounds occupied the same hydrophobic binding pocket and interacted mostly by dispersion interactions with the neighboring residues Met103, Met155, Tyr158, Met199, Ile202, Ile215, and Leu218. Contribution of the three pharmacophoric fragments (pyrazoline, benzoxazole and aryl ring) towards protein-ligand binding was evaluated at semi-empirical quantum mechanics level. The interaction energies suggested that most of the binding was governed by the benzoxazole moiety followed by pyrazoline and aryl rings.

  DOI：

  10.1007/s00044-013-0815-x
• 作为产物：
  描述：

  苯乙酮 在 hydrazine hydrate 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 23.0h， 生成
  参考文献：
  名称：

  Discovery of new antitubercular agents by combining pyrazoline and benzoxazole pharmacophores: design, synthesis and insights into the binding interactions

  摘要：

  The present study is aimed at combining two well-known pharmacophores (pyrazoline and benzoxazole nucleus) to design and synthesize a series of new benzoxazole-based pyrazoline derivatives. In vitro antitubercular evaluation against Mycobacterium tuberculosis H(37)Rv and multidrug-resistant TB (MDR-TB) strains showed that most of the target compounds displayed potent activity (MIC similar to 0.625-25 mu g/mL). Few compounds were found to be better than isoniazid against MDR-TB (MIC = 3.25 mu g/mL). In order to gain insights into the plausible binding motifs, the target compounds were docked into enoyl-acyl carrier protein (ACP) reductase, a molecular target of isoniazid. Many compounds were successfully docked into the active site of enoyl-ACP reductase and all the docked compounds occupied the same hydrophobic binding pocket and interacted mostly by dispersion interactions with the neighboring residues Met103, Met155, Tyr158, Met199, Ile202, Ile215, and Leu218. Contribution of the three pharmacophoric fragments (pyrazoline, benzoxazole and aryl ring) towards protein-ligand binding was evaluated at semi-empirical quantum mechanics level. The interaction energies suggested that most of the binding was governed by the benzoxazole moiety followed by pyrazoline and aryl rings.

  DOI：

  10.1007/s00044-013-0815-x