4-n-Hexylcyclohexancarbonsaeurehydrazid | 113423-43-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-n-Hexylcyclohexancarbonsaeurehydrazid
• 英文别名: 4-hexylcyclohexane-1-carbohydrazide
• CAS: 113423-43-1
• 化学式: C₁₃H₂₆N₂O
• 分子量: 226.362
• InChiKey: XYXOPRRYYDGTHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.12
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-己基苯甲酰氯 、 4-n-Hexylcyclohexancarbonsaeurehydrazid 在 2.) P₂S₁₀ 作用下， 生成 2-(4-Hexyl-cyclohexyl)-5-(4-hexyl-phenyl)-[1,3,4]thiadiazole
  参考文献：
  名称：

  Schaefer, W.; Rosenfeld, U.; Zaschke, H., Journal fur praktische Chemie (Leipzig 1954), 1989, vol. 331, # 4, p. 631 - 636

  摘要：

  DOI：
• 作为产物：
  描述：

  4-n-hexylcyclohexanecarboxylic acid 在 硫酸 、 hydrazine hydrate 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 4-n-Hexylcyclohexancarbonsaeurehydrazid
  参考文献：
  名称：

  Investigating the structure-activity relationships of N’ -[(5-nitrofuran-2-yl) methylene] substituted hydrazides against Trypanosoma cruzi to design novel active compounds

  摘要：

  Chagas disease, caused by the protozoan Trypanosoma cruzi, is a neglected chronic tropical infection endemic in Latin America. New and effective treatments are urgently needed because the two available drugs - benznidazole (BZD) and nifurtimox (NFX) - have limited curative power in the chronic phase of the disease. We have previously reported the design and synthesis of N'-[(5-nitrofuran-2-yl) methylene] substituted hydrazides that showed high trypanocidal activity against axenic epimastigote forms of three T cruzi strains. Here we show that these compounds are also active against a BZD- and NFX-resistant strain. Herein, multivariate approaches (hierarchical cluster analysis and principal component analysis) were applied to a set of thirty-six formerly characterized compounds. Based on the findings from exploratory data analysis, novel compounds were designed and synthesized. These compounds showed two-to three-fold higher trypanocidal activity against epimastigote forms than the previous set and were 25-30-fold more active than BZD. Their activity was also evaluated against intracellular amastigotes by high content screening (HCS). The most active compounds (BSF-38 to BSF-40) showed a selective index (SI') greater than 200, in contrast to the SI' values of reference drugs (NFX, 16.45; BZD, > 3), and a 70-fold greater activity than BZD. These findings indicate that nitrofuran compounds designed based on the activity against epimastigote forms show promising trypanocidal activity against intracellular amastigotes, which correspond to the predominant parasite stage in the chronic phase of Chagas disease. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.12.011

文献信息

• DEMUS, D.;KRESSE, H.;ZASCHKE, H.;SCHAFER, W.;ROSENFELD, U.;STETTIN, H.
  作者：DEMUS, D.、KRESSE, H.、ZASCHKE, H.、SCHAFER, W.、ROSENFELD, U.、STETTIN, H.

  DOI：——

  日期：——