N’-(2-oxo-1,2-dihydro-indol-3-ylidene)-4-methylbenzohydrazide

• 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: N’-(2-oxo-1,2-dihydro-indol-3-ylidene)-4-methylbenzohydrazide
• 化学式: C₁₆H₁₃N₃O₂
• 分子量: 279.298
• InChiKey: ATRAFOVJHWFHEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  70.56
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N’-(2-oxo-1,2-dihydro-indol-3-ylidene)-4-methylbenzohydrazide 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Singh, Kumud; Tiwari, Nirupama; Nizamuddin, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1086 - 1089

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲基苯甲醛 在 N-氯代丁二酰亚胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 N’-(2-oxo-1,2-dihydro-indol-3-ylidene)-4-methylbenzohydrazide
  参考文献：
  名称：

  Facile synthesis of ninhydrin and isatin based hydrazones in water using PEG-OSO3H as a highly efficient and homogeneous polymeric acid-surfactant combined catalyst

  摘要：

  The synthesis of a series of biologically important ninhydrin and isatin based hydrazones has been carried out by refluxing easily synthesized novel N'-(chloro-aryl-methylene)-tert-butylcarbazates with ninhydrin and isatins in the presence of PEG-OSO3H as catalyst in water medium. The dual characteristic of PEG-OSO3H as a Bronsted acid as well as a phase-transfer catalyst is successfully exploited in this synthesis. Reduced reaction time, operational simplicity, excellent yields of the products with high purity, and more importantly, easy recoverability, and reusability of the homogeneous polymeric catalyst make the reaction an attractive, economic, and sustainable green synthetic methodology. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.105

文献信息

• Synthesis, in silico, in vitro and in vivo evaluations of isatin aroylhydrazones as highly potent anticonvulsant agents
  作者：Saeed Emami、Mehdi Valipour、Fatemeh Kazemi Komishani、Fatemehsadat Sadati-Ashrafi、Maria Rasoulian、Majid Ghasemian、Mahmood Tajbakhsh、Patrick Honarchian Masihi、Aidin Shakiba、Hamid Irannejad、Nematollah Ahangar

  DOI：10.1016/j.bioorg.2021.104943

  日期：2021.7

  In this study, a series of new isatin aroylhydrazones (5a-e and 6a-e) was synthesized and evaluated for their anticonvulsant activities. The (Z)-configuration of compounds was confirmed by 1H NMR. In vivo studies using maximal electroshock (MES) and pentylenetetrazole (PTZ) models of epilepsy in mice revealed that while most of compounds had no effect on chemically-induced seizures at the higher dose

  在这项研究中，合成了一系列新的靛红芳酰腙（5a-e和6a-e）并评估了它们的抗惊厥活性。化合物的 ( Z )-构型通过1 H NMR确认。使用最大电击 (MES) 和戊四唑 (PTZ) 小鼠癫痫模型进行的体内研究表明，虽然大多数化合物在 100 mg/kg 的较高剂量下对化学诱发的癫痫发作没有影响，但对电诱发的癫痫发作具有显着保护作用低剂量 5 mg/kg 时癫痫发作。当然，N-甲基类似物6a和6e被发现是最有效的化合物，在 5 mg/kg 的剂量下显示出 100% 的保护作用。还通过实验确定 了所选化合物（6a和6e）的蛋白质结合和亲脂性（logP）。标题化合物的计算机模拟评估显示可接受的 ADME 参数和药物相似特性。所选化合物与不同靶点的距离映射和对接提出了它们对 VGSC 和 GABA A受体的可能作用。6a和6e对 SH-SY5Y 和 Hep-G2 细胞系的细胞毒性评估表明化合物对神经元和肝细胞的安全性。
• Tin powder-promoted one-pot synthesis of 3-spiro-fused or 3,3′-disubstituted 2-oxindoles
  作者：Juanjuan Wang、Danfeng Huang、Ke-Hu Wang、Xiansha Peng、Yingpeng Su、Yulai Hu、Ying Fu

  DOI：10.1039/c6ob01487a

  日期：——

  oxindoles has been developed from one-pot reactions of isatins, hydrazides or aromatic amines, 2-(bromomethyl)acrylic ester and tin powder in the presence of a catalytic amount of Brønsted or Lewis acid. The method avoids the use of toxic stannanes and allows easy operation. It is also proved that hydrazides are more favorable for intramolecular cyclization than amines.

  在存在下，由靛红，酰肼或芳香胺，2-（溴甲基）丙烯酸酯和锡粉的一锅反应，开发了一种方便有效的3-螺氧并吲哚衍生物或3,3'-二取代的羟吲哚的结构方法。催化量的布朗斯台德酸或路易斯酸。该方法避免了使用有毒的锡烷，并且易于操作。还证明了酰肼比胺更有利于分子内环化。
• Isatin based Schiff bases as inhibitors of α-glucosidase: Synthesis, characterization, in vitro evaluation and molecular docking studies
  作者：Fazal Rahim、Fazal Malik、Hayat Ullah、Abdul Wadood、Fahad Khan、Muhammad Tariq Javid、Muhammad Taha、Wajid Rehman、Ashfaq Ur Rehman、Khalid Mohammed Khan

  DOI：10.1016/j.bioorg.2015.03.005

  日期：2015.6

  Isatin base Schiff bases (1-20) were synthesized, characterized by H-1 NMR and EI/MS and evaluated for alpha-glucosidase inhibitory potential. Out of these twenty (20) compounds only six analogs showed potent alpha-glucosidase inhibitory potential with IC50 value ranging in between 2.2 +/- 0.25 and 83.5 +/- 1.0 mu M when compared with the standard acarbose (IC50 = 840 +/- 1.73 mu M). Among the series compound 2 having IC50 value (18.3 +/- 0.56 mu M), 9 (83.5 +/- 1.0 mu M), 11 (3.3 +/- 0.25 mu M), 12 (2.2 +/- 0.25 mu M), 14 (11.8 +/- 0.15 mu M), and 20 (3.0 +/- 0.15 mu M) showed excellent inhibitory potential many fold better than the standard acarbose. The binding interactions of these active analogs were confirmed through molecular docking. (C) 2015 Elsevier Inc. All rights reserved.
• Facile synthesis of ninhydrin and isatin based hydrazones in water using PEG-OSO3H as a highly efficient and homogeneous polymeric acid-surfactant combined catalyst
  作者：Kamalesh Debnath、Sudipta Pathak、Animesh Pramanik

  DOI：10.1016/j.tetlet.2013.05.105

  日期：2013.7

  The synthesis of a series of biologically important ninhydrin and isatin based hydrazones has been carried out by refluxing easily synthesized novel N'-(chloro-aryl-methylene)-tert-butylcarbazates with ninhydrin and isatins in the presence of PEG-OSO3H as catalyst in water medium. The dual characteristic of PEG-OSO3H as a Bronsted acid as well as a phase-transfer catalyst is successfully exploited in this synthesis. Reduced reaction time, operational simplicity, excellent yields of the products with high purity, and more importantly, easy recoverability, and reusability of the homogeneous polymeric catalyst make the reaction an attractive, economic, and sustainable green synthetic methodology. (C) 2013 Elsevier Ltd. All rights reserved.
• Singh, Kumud; Tiwari, Nirupama; Nizamuddin, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1086 - 1089
  作者：Singh, Kumud、Tiwari, Nirupama、Nizamuddin

  DOI：——

  日期：——