2,4-dichloro-N'-(nonan-5-ylidene)benzohydrazide | 1071432-69-3

• 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: 2,4-dichloro-N'-(nonan-5-ylidene)benzohydrazide
• 英文别名: 2,4-dichloro-N-(nonan-5-ylideneamino)benzamide
• CAS: 1071432-69-3
• 化学式: C₁₆H₂₂Cl₂N₂O
• 分子量: 329.269
• InChiKey: AFBATGPAFGWLIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-dichloro-N'-(nonan-5-ylidene)benzohydrazide 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到2,4-dichloro-N'-(nonan-5-yl)benzohydrazide
  参考文献：
  名称：

  具有疏水性和长烷基链的新型4 H -1,3,4-恶二嗪-5（6 H）-ones ：抑制单胺氧化酶，甲壳质生物合成和肿瘤细胞的设计，合成和生物活性多样性

  摘要：

  通过N'-烷基化取代的芳酰肼与氯乙酰氯的直接环化反应，设计合成了一系列具有疏水性和长链性的含氮杂环4 H -1,3,4-恶二嗪-5（6 H）-ones衍生物。初步分析表明，某些化合物在10 -5 –10 -3  M的浓度下对单胺氧化酶（MAO）表现出中等至良好的抑制活性，并且对人肺癌A-549和人前列腺癌PC-具有抗肿瘤活性。 3个μM水平的细胞系，可能为抗癌药物提供新的支架。此外，化合物5i和5m 在几丁质生物合成中显示出显着的抑制活性，这可能代表了一类新型的几丁质合成抑制剂。

  DOI：

  10.1016/j.ejmech.2008.10.015
• 作为产物：
  描述：

  5-壬酮 、 2,4-二氯苯酰肼 以 乙醇 为溶剂， 生成 2,4-dichloro-N'-(nonan-5-ylidene)benzohydrazide
  参考文献：
  名称：

  具有疏水性和长烷基链的新型4 H -1,3,4-恶二嗪-5（6 H）-ones ：抑制单胺氧化酶，甲壳质生物合成和肿瘤细胞的设计，合成和生物活性多样性

  摘要：

  通过N'-烷基化取代的芳酰肼与氯乙酰氯的直接环化反应，设计合成了一系列具有疏水性和长链性的含氮杂环4 H -1,3,4-恶二嗪-5（6 H）-ones衍生物。初步分析表明，某些化合物在10 -5 –10 -3  M的浓度下对单胺氧化酶（MAO）表现出中等至良好的抑制活性，并且对人肺癌A-549和人前列腺癌PC-具有抗肿瘤活性。 3个μM水平的细胞系，可能为抗癌药物提供新的支架。此外，化合物5i和5m 在几丁质生物合成中显示出显着的抑制活性，这可能代表了一类新型的几丁质合成抑制剂。

  DOI：

  10.1016/j.ejmech.2008.10.015

文献信息

• 1,3,4-Oxadiazoline derivatives as novel potential inhibitors targeting chitin biosynthesis: Design, synthesis and biological evaluation
  作者：Shaoyong Ke、Fengyi Liu、Ni Wang、Qing Yang、Xuhong Qian

  DOI：10.1016/j.bmcl.2008.11.095

  日期：2009.1

  Two series of 1,3,4-oxadiazoline heterocycle derivatives were designed, synthesized and identified. Bioactivity assays showed that all synthesized compounds inhibited chitin synthesis in yeast, suggesting they might be a novel class of potential inhibitors against chitin biosynthesis. The structure-activity relationships (SAR) of these compounds are discussed. (C) 2008 Elsevier Ltd. All rights reserved.
• 1,3,4-Oxadiazole-3(2H)-carboxamide derivatives as potential novel class of monoamine oxidase (MAO) inhibitors: Synthesis, evaluation, and role of urea moiety
  作者：Shaoyong Ke、Zhong Li、Xuhong Qian

  DOI：10.1016/j.bmc.2008.07.026

  日期：2008.8

  A new series of 1,3,4-oxadiazole-3(2H)-carboxamide derivatives have been synthesized by direct heterocyclization reaction of substituted benzoylisocyanate with various aroylhydrazones as novel monoamine oxidase inhibitors (MAOIs). The target molecules have been identified on the basis of satisfactory analytical and spectra ( IR, (1)H NMR, (13)C NMR, and HR-MS) data. The newly synthesized compounds were evaluated for their MAO inhibitory activity by kynuramine fluorimetric assay method. The preliminary results showed that most of the compounds have moderate inhibitory activities toward MAO at the concentration of 10(5)-10(3) M. This work may provide a novel class of lead compounds with potential MAO inhibitions for further optimization. (C) 2008 Elsevier Ltd. All rights reserved.
• Diacylhydrazine derivatives as novel potential chitin biosynthesis inhibitors: Design, synthesis, and structure–activity relationship
  作者：Shaoyong Ke、Xuhong Qian、Fengyi Liu、Ni Wang、Feng Fan、Zhong Li、Qing Yang

  DOI：10.1016/j.ejmech.2009.01.004

  日期：2009.7

  A series of diacylhydrazine derivatives containing hydrophobic alkyl chains have been designed and synthesized. The target molecules have been identified on the basis of analytical spectral (IR, H-1 NMR, C-13 NMR, and HRMS) data. All synthesized compounds have been screened for their potential inhibition in vitro against chitin synthesis using yeast cell extracts. The preliminary assays indicate that some of the compounds display moderate to good inhibitory activity. Structure-activity relationship (SAR) is also discussed based on the experimental data, and the further analysis of the quantitative structure-activity relationship (QSAR) indicates that the electronic parameter is the main factor to affect inhibition activities. (C) 2009 Elsevier Masson SAS. All rights reserved.