(E)-N'-(naphthalen-2-ylmethylene)benzohydrazide | 24091-07-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-N'-(naphthalen-2-ylmethylene)benzohydrazide
• 英文别名: N'-(2-naphthylmethylene)benzohydrazide；N-[(E)-naphthalen-2-ylmethylideneamino]benzamide
• CAS: 24091-07-4
• 化学式: C₁₈H₁₄N₂O
• 分子量: 274.322
• InChiKey: PELFDAIRBMAVCL-CPNJWEJPSA-N

物化性质

• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  三甲基氰硅烷 、 (E)-N'-(naphthalen-2-ylmethylene)benzohydrazide 在 甲醇 、 [(S)-PhPYBOX]ErCl₃ 作用下， 以 氯仿 为溶剂， 反应 72.0h， 生成 Benzoic acid N'-((R)-cyano-naphthalen-2-yl-methyl)-hydrazide 、 Benzoic acid N'-((S)-cyano-naphthalen-2-yl-methyl)-hydrazide
  参考文献：
  名称：

  Asymmetric Hydrocyanation of Hydrazones Catalyzed by Lanthanide−PYBOX Complexes

  摘要：

  [GRAPHICS]The asymmetric addition of HCN to hydrazones is catalyzed in high yield and good-to-excellent enantioselectivity by the easily prepared (PhPYBOX)ErCl3 complex. This constitutes the first example of asymmetric catalytic hydrocyanation of hydrazones.

  DOI：

  10.1021/ol035844c
• 作为产物：
  描述：

  苯甲酰肼 、 2-萘甲醛 反应 1.0h， 以100%的产率得到(E)-N'-(naphthalen-2-ylmethylene)benzohydrazide
  参考文献：
  名称：

  Solvent-free synthesis of hydrazones and their subsequent N-alkylation in a Ball-mill

  摘要：

  A large variety of Boc-, Bz-, Ts-, and Fmoc- protected hydrazones were prepared via condensation of an equimolar amount of carbonyl-compound and the corresponding hydrazine using a ball-mill. Hydrazones were always obtained in a quantitative yield and no solvents were used at any step. In a second step, we realized the first solvent-free N-allylation and N-benzylation of these hydrazones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.056

文献信息

• Solvent-free synthesis of hydrazones and their subsequent N-alkylation in a Ball-mill
  作者：Pierrick Nun、Charlotte Martin、Jean Martinez、Frédéric Lamaty

  DOI：10.1016/j.tet.2011.07.056

  日期：2011.10

  A large variety of Boc-, Bz-, Ts-, and Fmoc- protected hydrazones were prepared via condensation of an equimolar amount of carbonyl-compound and the corresponding hydrazine using a ball-mill. Hydrazones were always obtained in a quantitative yield and no solvents were used at any step. In a second step, we realized the first solvent-free N-allylation and N-benzylation of these hydrazones. (C) 2011 Elsevier Ltd. All rights reserved.
• N-(1′-naphthyl)-3,4,5-trimethoxybenzohydrazide as microtubule destabilizer: Synthesis, cytotoxicity, inhibition of cell migration and in vivo activity against acute lymphoblastic leukemia
  作者：Lívia B. Salum、Alessandra Mascarello、Rafael R. Canevarolo、Wanessa F. Altei、Angelo B.A. Laranjeira、Patrícia D. Neuenfeldt、Taisa R. Stumpf、Louise D. Chiaradia-Delatorre、Laura L. Vollmer、Hikmat N. Daghestani、Carolina P. de Souza Melo、André B. Silveira、Paulo C. Leal、Marisa J.S. Frederico、Leandro F. do Nascimento、Adair R.S. Santos、Adriano D. Andricopulo、Billy W. Day、Rosendo A. Yunes、Andreas Vogt、José A. Yunes、Ricardo J. Nunes

  DOI：10.1016/j.ejmech.2015.02.041

  日期：2015.5

  Tubulin-interacting agents, like vinca alkaloid and taxanes, play a fundamental role in cancer chemotherapy, making cellular microtubules (MT), one of the few validated anticancer targets. Cancer resistance to classical MT inhibitors has motivated the development of novel molecules with increased efficacy and lower toxicity. Aiming at designing structurally-simple inhibitors of MT assembly, we synthesized a series of thirty-one 3,4,5-trimethoxy-hydrazones and twenty-five derivatives or analogs. Docking simulations suggested that a representative N-acylhydrazone could adopt an appropriate stereochemistry inside the colchicine-binding domain of tubulin. Several of these compounds showed anti-leukemia effects in the nanomolar concentration range. Interference with MT polymerization was validated by the compounds' ability to inhibit MT assembly at the biochemical and cellular level. Selective toxicity investigations done with the most potent compound, a 3,4,5-trimethoxy-hydrazone with a 1-naphthyl group, showed remarkably selective toxicity against leukemia cells in comparison with stimulated normal lymphocytes, and no acute toxicity in vivo. Finally, this molecule was as active as vincristine in a murine model of human acute lymphoblastic leukemia at a weekly dose of 1 mg/kg. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Asymmetric Hydrocyanation of Hydrazones Catalyzed by Lanthanide−PYBOX Complexes
  作者：John M. Keith、Eric N. Jacobsen

  DOI：10.1021/ol035844c

  日期：2004.1.1

  [GRAPHICS]The asymmetric addition of HCN to hydrazones is catalyzed in high yield and good-to-excellent enantioselectivity by the easily prepared (PhPYBOX)ErCl3 complex. This constitutes the first example of asymmetric catalytic hydrocyanation of hydrazones.