N'-((5-nitrofuran-2-yl)methylene)cyclohexanecarbohydrazide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: N'-((5-nitrofuran-2-yl)methylene)cyclohexanecarbohydrazide
• 英文别名: N-[(5-nitrofuran-2-yl)methylideneamino]cyclohexanecarboxamide
• 化学式: C₁₂H₁₅N₃O₄
• 分子量: 265.269
• InChiKey: ADQLSTKWWHWFMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  环己甲酸 在 硫酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 4.5h， 生成 N'-((5-nitrofuran-2-yl)methylene)cyclohexanecarbohydrazide
  参考文献：
  名称：

  Designing and exploring active N′-[(5-nitrofuran-2-yl) methylene] substituted hydrazides against three Trypanosoma cruzi strains more prevalent in Chagas disease patients

  摘要：

  Chagas disease affects around 8 million people worldwide and its treatment depends on only two nitroheterocyclic drugs, benznidazole (BZD) and nifurtimox (NFX). Both drugs have limited curative power in chronic phase of disease. Nifuroxazide (NF), a nitroheterocyclic drug, was used as lead to design a set of twenty one compounds in order to improve the anti-Trypanosoma cruzi activity. Lipinski's rules were considered in order to support drug-likeness designing. The set of N'-[(5-nitrofuran-2-yl) methylene] substituted hydrazides was assayed against three T. cruzi strains, which represent the discrete typing units more prevalent in human patients: Y (TcII), Silvio X10 cl1 (TcI), and Bug 2149 cl10 (TcV). All the derivatives, except one, showed enhanced trypanocidal activity against the three strains as compared to BZD. In the Y strain 62% of the compounds were more active than NFX. The most active compound was N'((5-nitrofuran-2-yl) methylene)biphenyl-4-carbohydrazide (C20), which showed IC50 values of 1.17 +/- 0.12 mu M; 3.17 +/- 0.32 mu M; and 1.81 +/- 0.18 mu M for Y, Silvio X10 cl1, and Bug 2149 cl10 strains, respectively. Cytotoxicity assays with human fibroblast cells have demonstrated high selectivity indices for several compounds. Exploratory data analysis indicated that primarily topological, steric/geometric, and electronic properties have contributed to the discrimination of the set of investigated compounds. The findings can be helpful to drive the designing, and subsequently, the synthesis of additional promising drugs against Chagas disease. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.066