N’-(2-oxo-1,2-dihydro-indol-3-ylidene)-4-nitrobenzohydrazide | 70181-28-1

• 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-nitrobenzohydrazide
• 英文别名: 4-nitro-N'-[2-oxo-1,2-dihydro-3H-indol-3-ylidene]benzohydrazide；3-(4-Nitrobenzoylhydrazono)-2-indolinon
• CAS: 70181-28-1
• 化学式: C₁₅H₁₀N₄O₄
• 分子量: 310.269
• InChiKey: LJXZDNQLJYUNRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  113.7
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N’-(2-oxo-1,2-dihydro-indol-3-ylidene)-4-nitrobenzohydrazide 在 氢氧化钾 作用下， 以 水 为溶剂， 以72%的产率得到3-(4-Nitro-phenyl)-[1,3,4]oxadiazino[6,5-b]indole
  参考文献：
  名称：

  Ruab, Ali; Mishra, Bharati; Nizamuddin, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 526 - 528

  摘要：

  DOI：
• 作为产物：
  描述：

  对硝基苯甲醛 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-nitrobenzohydrazide
  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。
• Efficient synthesis of new 2,3-dihydrooxazole-spirooxindoles hybrids as antimicrobial agents
  作者：Shailendra Tiwari、Poonam Pathak、Ram Sagar

  DOI：10.1016/j.bmcl.2016.03.093

  日期：2016.5

  Two series of new 2,3-dihydrooxazole-spirooxindole derivatives were efficiently synthesized starting from N′-(2-oxoindolin-3-ylidene) benzohydrazide/N′-(2-oxoindolin-3-ylidene)-2-phenoxyacetohydrazide using designed synthetic route. Newly synthesized 2,3-dihydrooxazole-spirooxindole derivatives were screened for their antibacterial and antifungal activity against different pathogenic strain of bacteria

  使用设计的合成方法，从N '-（2-氧代吲哚-3-亚基）苯甲酰肼/ N '-（2-氧代吲哚-3-亚基）-2-苯氧基乙酰肼开始有效合成了两个系列的新的2,3-二氢恶唑-螺氧并恶唑衍生物。路线。筛选了新合成的2,3-二氢恶唑-螺氧并恶唑衍生物对不同病原菌的细菌和真菌的抗菌和抗真菌活性。确定了测试化合物和参考标准品的最小抑菌浓度（MIC），最小杀菌浓度（MBC）和最小杀菌浓度（MFC）。化合物4e，4g，7g表现出良好的抗菌活性，而化合物4f，7b，7d显示出更好的抗真菌活性。
• ISATIN DERIVATIVES, PHARMACEUTICAL COMPOSITIONS THEREOF, AND METHODS OF USE THEREOF
  申请人：Horne David A.

  公开号：US20130225637A1

  公开（公告）日：2013-08-29

  One aspect of the invention relates to novel isatin derivative compounds and the pharmaceutical composition thereof. Another aspect of the invention relates to methods of using the isatin derivative compounds disclosed herein and the pharmaceutical compositions thereof. In certain embodiments, the method is used to treat a cancer or a tumor in a subject including, without limitation, prostate cancer, melanoma, pancreatic cancer, ovarian cancer, and lymphoma. In certain embodiment, the method is used to treat a condition in a subject that can be regulated by the activation of one or more proteins such as EGFR, Erk1/2, Her2/Neu, Jak2, Src, Stat3, Akt, Cyclin B1, and Cdc25C. In certain embodiment, the method is used to treat a condition in a subject that can be regulated by the disruption of microtubule formations.

  该发明的一个方面涉及新型异喹啉衍生物化合物及其药物组合物。该发明的另一个方面涉及使用本文披露的异喹啉衍生物化合物和其药物组合物的方法。在某些实施例中，该方法用于治疗受试者中的癌症或肿瘤，包括但不限于前列腺癌、黑色素瘤、胰腺癌、卵巢癌和淋巴瘤。在某些实施例中，该方法用于治疗受试者中可以通过激活EGFR、Erk1/2、Her2/Neu、Jak2、Src、Stat3、Akt、Cyclin B1和Cdc25C等一个或多个蛋白质来调节的疾病。在某些实施例中，该方法用于治疗受试者中可以通过破坏微管形成来调节的疾病。
• Synthetic and Spectroscopic Investigations of bis(cyclopentadienyl)Titanium(IV)/Zirconium(IV) Derivatives with Isatin Hydrazones
  作者：Akhilesh Kumar Srivastava、Om Prakash Pandey、Soumitra Kumar Sengupta

  DOI：10.1080/00945710009351842

  日期：2000.9
• 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：——