2-chloro-N'-(nonan-5-yl)benzohydrazide | 1156004-47-5

• 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-chloro-N'-(nonan-5-yl)benzohydrazide
• 英文别名: 2-chloro-N'-nonan-5-ylbenzohydrazide
• CAS: 1156004-47-5
• 化学式: C₁₆H₂₅ClN₂O
• 分子量: 296.84
• InChiKey: ZCRVIYULMASNDU-UHFFFAOYSA-N

物化性质

• 熔点：
  36.2-37.5 °C
• 沸点：
  382.0±34.0 °C(predicted)
• 密度：
  1.048±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-N'-(nonan-5-yl)benzohydrazide 、 甲氧基苯甲酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到2-chloro-N'-(2-methoxybenzoyl)-N'-(nonan-5-yl)benzohydrazide
  参考文献：
  名称：

  Diacylhydrazine derivatives as novel potential chitin biosynthesis inhibitors: Design, synthesis, and structure–activity relationship

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2009.01.004
• 作为产物：
  描述：

  2-chloro-N'-(nonan-5-ylidene)benzohydrazide 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到2-chloro-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

文献信息

• Novel 4H-1,3,4-oxadiazin-5(6H)-ones with hydrophobic and long alkyl chains: Design, synthesis, and bioactive diversity on inhibition of monoamine oxidase, chitin biosynthesis and tumor cell
  作者：Shao-Yong Ke、Xu-Hong Qian、Feng-Yi Liu、Ni Wang、Qing Yang、Zhong Li

  DOI：10.1016/j.ejmech.2008.10.015

  日期：2009.5

  chains were designed and synthesized by direct cyclization reaction of N′-alkylation substituted aroylhydrazines with chloroacetyl chloride. The preliminary assays showed that some of the compounds displayed moderate to good inhibitory activities toward monoamine oxidase (MAO) at the concentration of 10−5–10−3 M, and antitumor activities against human lung cancer A-549 and human prostate cancer PC-3 cell

  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。
• 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.