(E)-N'-(benzo[d][1,3]dioxol-5-ylmethylidene)benzohydrazide | 5327-23-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (E)-N'-(benzo[d][1,3]dioxol-5-ylmethylidene)benzohydrazide
• 英文别名: (E)-N′-(benzo[d][1,3]dioxol-5-ylmethylene)benzohydrazide；piperonal-benzoylhydrazone；Piperonal-benzoylhydrazon；N'-[(E)-1,3-Benzodioxol-5-ylmethylidene]benzohydrazide；N-[(E)-1,3-benzodioxol-5-ylmethylideneamino]benzamide
• CAS: 5327-23-1
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: LDCJHBPONKAQST-CXUHLZMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  (E)-N'-(benzo[d][1,3]dioxol-5-ylmethylidene)benzohydrazide 在 sodium amalgam 、 乙醇 作用下， 生成 benzoic acid-(N'-piperonyl-hydrazide)
  参考文献：
  名称：

  Aggarwal; Darbari; Ray, Journal of the Chemical Society, 1929, p. 1944

  摘要：

  DOI：
• 作为产物：
  描述：

  胡椒醛 、 苯甲酰肼 以 乙醇 为溶剂， 反应 6.0h， 以85%的产率得到(E)-N'-(benzo[d][1,3]dioxol-5-ylmethylidene)benzohydrazide
  参考文献：
  名称：

  描述取代基对芳基hydr配体在PdII配合物中的配位行为的作用及其对水介质中Suzuki-Miyaura偶联的影响

  摘要：

  胡椒醛aroylhydrazone配体（反应的HL1 - HL4）与[的PdCl 2（PPH 3）2的CH] 3 OH和CHCl 3，得到四个新的Pd（II）配合物（1 - 4），具有不同的协调行为。这些配合物1 - 4进行了充分表征通过元素分析，UV /可见光，FT-IR和1个H / 13 C NMR光谱。通过单晶XRD研究明确证实了这些配合物中胡椒醛hydr配体与Pd（II）离子的不同配位模式。尽管配体HL1-HL4它们具有相似的性质，其中之一（HL4）在the的外围部分具有吸电子硝基作为取代基，显示出与钯离子的罕见连接。依次通过密度泛函理论（DFT）计算和自然键合分析（NBO）使实验观察的分子建筑师合理化。所有这些Pd（II）配合物在开罐条件下在低催化剂负载的水性介质中，对空间拥挤的芳基硼酸与（杂）芳基卤化物的Suzuki-Miyaura交叉偶联反应的催化潜力进行了评估。有利地，所选

  DOI：

  10.1002/ejic.201900781

文献信息

• Stereoselective, solvent free, highly efficient synthesis of aldo- and keto-N-acylhydrazones applying grindstone chemistry
  作者：José Maurício dos Santos Filho、Savio Moita Pinheiro

  DOI：10.1039/c7gc00730b

  日期：——

  A mild and efficient synthesis of N-acylhydrazones has been developed, applying a simple grindstone procedure, leading to a library of 51 examples exhibiting a broad variety of structural features, 21 of them described for the first time in this paper. This methodology works without any organic solvent under the catalysis of acetic acid at room temperature, promotes the formation of essentially pure

  已经开发出了温和而有效的N-酰基hydr酮合成方法，该方法采用了简单的磨石程序，从而产生了51个实例，这些实例均显示出多种结构特征，其中21个实例首次在本文中进行了描述。该方法在室温下在乙酸催化下无需任何有机溶剂即可工作，可促进形成基本纯净的粗产物，并避免繁琐的后处理和有害溶剂的使用以及能耗。另外，如NMR分析所支持的，其导致N-酰基hydr的立体选择性形成。
• 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.
• Delineating the Role of Substituents on the Coordination Behavior of Aroylhydrazone Ligands in Pd ^II Complexes and their Influence on Suzuki–Miyaura Coupling in Aqueous Media
  作者：Arumugam Vignesh、Chinnuswamy Shalini、Nallasamy Dharmaraj、Werner Kaminsky、Ramasamy Karvembu

  DOI：10.1002/ejic.201900781

  日期：2019.9.15

  piperonal aroylhydrazone ligands (HL1–HL4) with [PdCl2(PPh3)2] in CH3OH and CHCl3 afforded four new Pd(II) complexes (1–4) featuring diverse coordination behaviors. These complexes 1–4 were fully characterized by elemental analyses, UV/Visible, FT‐IR and 1H/13C NMR spectra. The variant coordination modes of piperonal aroylhydrazone ligands with Pd(II) ion in these complexes were unambiguously confirmed

  胡椒醛aroylhydrazone配体（反应的HL1 - HL4）与[的PdCl 2（PPH 3）2的CH] 3 OH和CHCl 3，得到四个新的Pd（II）配合物（1 - 4），具有不同的协调行为。这些配合物1 - 4进行了充分表征通过元素分析，UV /可见光，FT-IR和1个H / 13 C NMR光谱。通过单晶XRD研究明确证实了这些配合物中胡椒醛hydr配体与Pd（II）离子的不同配位模式。尽管配体HL1-HL4它们具有相似的性质，其中之一（HL4）在the的外围部分具有吸电子硝基作为取代基，显示出与钯离子的罕见连接。依次通过密度泛函理论（DFT）计算和自然键合分析（NBO）使实验观察的分子建筑师合理化。所有这些Pd（II）配合物在开罐条件下在低催化剂负载的水性介质中，对空间拥挤的芳基硼酸与（杂）芳基卤化物的Suzuki-Miyaura交叉偶联反应的催化潜力进行了评估。有利地，所选
• Aggarwal; Darbari; Ray, Journal of the Chemical Society, 1929, p. 1944
  作者：Aggarwal、Darbari、Ray

  DOI：——

  日期：——