3-((3-nitrophenyl)imino)indolin-2-one | 78662-39-2

• 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: 3-((3-nitrophenyl)imino)indolin-2-one
• 英文别名: 3-(3-Nitroanilino)indol-2-one；3-(3-nitrophenyl)imino-1H-indol-2-one
• CAS: 78662-39-2
• 化学式: C₁₄H₉N₃O₃
• mdl: MFCD00422725
• 分子量: 267.244
• InChiKey: PIUWEYFCGBZZMB-UHFFFAOYSA-N

物化性质

• 熔点：
  224-225 °C
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯甲醛肟 、 3-((3-nitrophenyl)imino)indolin-2-one 在 吡啶 、 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到4-(3-nitrophenyl)-3-phenylspiro[1,2,4-oxadiazole-5,3'-1H-indole]-2'-one
  参考文献：
  名称：

  One Pot Synthesis of Some New Spiro[3H-Indol-3,5′(4′H)-[1,2,4] Oxadiazol]-2-Ones and Bis[Spiro[3H-Indol-3,5′(4′H)-[1,2,4] Oxadiazol]-2-Ones]

  摘要：

  A facile preparation of the title compound by 1,3-dipolar cycloaddition reaction of benzonitrile oxides with isatin imines or isatin diimines, in excellent yield, are reported.

  DOI：

  10.1080/00397910008086871
• 作为产物：
  描述：

  间硝基苯胺 在 盐酸 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 生成 3-((3-nitrophenyl)imino)indolin-2-one
  参考文献：
  名称：

  通过aza-Wittig反应方便的E-非对映选择性合成NH-靛红N'-芳基亚胺

  摘要：

  NH -靛红N' -芳基亚胺的一般合成涉及靛红和芳基叠氮化物的氮杂维蒂希反应，与先前描述的方法相比，提供更高的E -非对映选择性。该程序甚至适用于不直接与靛红反应的苯胺。

  DOI：

  10.1016/j.mencom.2022.09.022

文献信息

• Leucine rich repeat kinase 2 (LRRK2) inhibitors based on indolinone scaffold: Potential pro-neurogenic agents
  作者：Irene G. Salado、Josefa Zaldivar-Diez、Víctor Sebastián-Pérez、Lingling Li、Larissa Geiger、Silvia González、Nuria E. Campillo、Carmen Gil、Aixa V. Morales、Daniel I. Perez、Ana Martinez

  DOI：10.1016/j.ejmech.2017.06.060

  日期：2017.9

  design, synthesis, biological evaluation, SAR and potential binding mode of indoline-like LRRK2 inhibitors and their preliminary neurogenic effect in neural precursor cells isolated from adult mice ventricular-subventricular zone. These results open new therapeutic horizons for the use of LRRK2 inhibitors as neuroregenerative agents. Moreover, the indolinone derivatives here prepared, inhibitors of the

  富含亮氨酸的重复激酶2（LRRK2）是帕金森氏病（PD）治疗中最受欢迎的靶标之一。此外，它最近已经描述了其在调节Wnt信号传导中的作用，因此，它可能与成人神经发生有关。这一新假设可能首先通过抑制LRRK2的益处，其次通过促进成年神经发生而产生双重疾病改良剂。在这里，我们报告的设计，合成，生物学评估，合成孔径雷达和潜在的结合模式的LRRK2抑制剂及其在成年小鼠心室-室下区分离的神经前体细胞中的初步神经源性作用。这些结果为LRRK2抑制剂作为神经再生剂的使用开辟了新的治疗前景。此外，这里制备的吲哚啉酮衍生物是LRRK2激酶活性的抑制剂，
• Design, synthesis and biological activity of novel tacrine-isatin Schiff base hybrid derivatives
  作者：E. Riazimontazer、H. Sadeghpour、H. Nadri、A. Sakhteman、T. Tüylü Küçükkılınç、R. Miri、N. Edraki

  DOI：10.1016/j.bioorg.2019.103006

  日期：2019.8

  ranging from 0.42 nM to 79.66 nM. Amongst them, 7k, 7m and 7p, all with a 6 carbon linker between tacrine and isatin Schiff base exhibited the strongest inhibitory activity against AChE with IC50 values of 0.42 nM, 0.62 nM and 0.95 nM, respectively. They were 92-, 62- and 41-fold more active than tacrine (IC50 = 38.72 nM) toward AChE. Most of the compounds also showed a potent BuChE inhibition among

  设计，合成和评估了一系列新颖的他克林-依斯汀-希夫汀席夫碱杂合衍生物（7a-p），作为对抗阿尔茨海默氏病（AD）的多目标候选药物。生物学测定表明，这些化合物大多数对乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BuChE）表现出有效的抑制活性，并且对AChE的选择性高于BuChE。还发现它们充当出色的金属螯合剂。发现化合物7k和7m是AChE诱导的淀粉样β（Aβ）聚集的良好抑制剂。大多数化合物以0.42 nM至79.66 nM的IC50值抑制AChE。其中7k，7m和7p都在他克林和isatin Schiff碱之间具有6个碳连接基，对AChE表现出最强的抑制活性，IC50值分别为0.42 nM，0.62 nM和0.95 nM，分别。它们对他汀AChE的活性比他克林（IC50 = 38.72 nM）高92倍，62倍和41倍。大多数化合物还显示出有效的BuChE抑制作用，其中7d的BuChE的IC50值为0
• Mechanistic insight of cell anti-proliferative activity of fluoroquinolone drug-based Cu(II) complexes
  作者：Divyang H. Gandhi、Foram U. Vaidya、Chandramani Pathak、Tushar N. Patel、Bhupesh S. Bhatt

  DOI：10.1007/s11030-021-10199-2

  日期：2022.4

  Pefloxacin-based mixed ligand Cu(II) complexes with substituted isatin of type [Cu(Isatin)(Pefloxacin)Cl] were synthesized, and characterized by EPR, mass, FT-IR, electronic spectrometry, metal content, magnetic moment, and conductance measurement. The g factors g $$\parallel $$ > g $$\perp $$ > 2.0023 observed in EPR suggest a square-pyramidal environment of ligands around the copper metal. The compounds were screened for diverse biological activities. The compounds inhibit efficiently the cell proliferation of HCT 116 cancer cells. To take the insight of anticancer activity mechanism, we investigated compound—1 for further cellular assay-based biological activities like trypan blue assay, cell morphological alteration assay, colony formation assay, cell apoptosis, and cell necrosis assay. The compound—1 induced distinct morphological alteration in cells, inhibits cell viability, decreases % plating efficiency, and decreases the clonogenic ability of the HCT 116 cells. The cell death mechanism was confirmed by annexin V-FITC / PI assay and LDH release assay. The positive annexin V/PI stained cells in presence of compound-1 and the absence of a significant amount of lactate dehydrogenase suggest cell apoptosis mechanism for anticancer activity of compounds. We also screened compounds for in vitro antibacterial and cytotoxic activities. Synthesis, characterization, antibacterial, anticancer, and cytotoxicity activities of pefloxacin based Cu(II) complexes were studied. The compound -1 is more potent than standard anticancer drugs and it induced apoptosis to the HCT 116 cells.

  合成了[Cu(Isatin)(Pefloxacin)Cl]型取代isatin的培氟沙星基混合配体铜(II)配合物，并通过 EPR、质谱、傅立叶变换红外光谱、电子能谱、金属含量、磁矩和电导测量对其进行了表征。在 EPR 中观察到的 g 因子 g $$\parallel $$ > g $$\perp $$ > 2.0023 表明配体在铜金属周围具有方阵环境。对这些化合物进行了多种生物活性筛选。这些化合物能有效抑制 HCT 116 癌细胞的增殖。为了深入了解化合物的抗癌活性机制，我们对化合物-1 进行了进一步的细胞检测，包括胰蓝试验、细胞形态改变试验、集落形成试验、细胞凋亡和细胞坏死试验。结果表明，化合物-1能诱导细胞发生明显的形态改变，抑制细胞活力，降低细胞培养率，并降低 HCT 116 细胞的克隆生成能力。细胞死亡机制通过附件素 V-FITC / PI 检测和 LDH 释放检测得到了证实。化合物-1存在时，细胞的附件素V/PI染色呈阳性，且没有大量乳酸脱氢酶，这表明化合物的抗癌活性具有细胞凋亡机制。我们还对化合物进行了体外抗菌和细胞毒性活性筛选。我们研究了培氟沙星铜(II)配合物的合成、表征、抗菌、抗癌和细胞毒性活性。化合物-1 比标准抗癌药物更有效，而且能诱导 HCT 116 细胞凋亡。
• Catalyst‐free straightforward synthesis of 3‐cyano‐3‐arylamino‐2‐oxindoles through hydrocyanation with benzoyl cyanide
  作者：Xiao Chen、Zheng Li

  DOI：10.1002/jhet.3809

  日期：2020.2

  The effective hydrocyanation of 3‐(arylimino)indolin‐2‐ones with benzoyl cyanide under catalyst‐free condition at room temperature to synthesize 3‐cyano‐3‐arylamino‐2‐oxindoles is described. This protocol benefits from low toxicity, inexpensive, and easy‐to‐handle cyanating agent, no catalysts, no additives, mild conditions, good substrate tolerance, and simple work‐up procedure. This reaction successfully

  描述了在室温下在无催化剂条件下用苯甲酰基氰化物将3-（芳基）吲哚-2-酮进行有效的氢氰化反应以合成3-氰基-3-芳基氨基-2-氧吲哚的过程。该方案得益于低毒性，廉价且易于处理的氰化剂，无催化剂，无添加剂，条件温和，底物耐受性好以及后处理程序简单的优点。该反应成功地为结构上多样化的3,3-二取代的羟吲哚提供了替代方法。
• Cell apoptosis induced by ciprofloxacin based Cu(II) complexes: cytotoxicity, SOD mimic and antibacterial studies
  作者：Bhupesh S. Bhatt、Divyang H. Gandhi、Foram U. Vaidya、Chandramani Pathak、Tushar N. Patel

  DOI：10.1080/07391102.2020.1776641

  日期：2021.8.13

  The current cancer research focuses on the design and synthesis of chemical compounds that can modulate cell apoptosis or programmed cell death. So we synthesized and characterized ciprofloxacin based copper(II) complexes and studied their anticancer activity against HCT 116 cancer cells by MTT assay. We further investigated the influence of compound-2 (better IC(50)value than cisplatin) on cancer cells to know the exact mechanism of anticancer activity. The distinct morphological change of cells due to compound-2 was observed in bright field microscopy. The trypan blue assay clearly demonstrated inhibition of cell viability. The clonogenic ability inhibition assay showed a low percentage of the plating efficiency of HCT 116 cells. The mechanism of cell death, either apoptotic or necrotic was distinguished by annexin V-FITC/PI (propidium iodide) staining assay and LDH (lactate dehydrogenase) release assay. The positive annexinV/PI cells in presence of compound-2 and absence of LDH in the LDH release assay confirmed the cell apoptotic mechanism of cell death. We also checkedin vitroantibacterial activity of compounds against Gram((-ve))and Gram((+ve))bacteria in terms of MIC (minimum inhibitory concentration) and the data were in good agreement with the standard drug data. SOD mimic activity of synthesized Cu(II) complexes was also studied in terms of IC(50)value. The brine shrimp lethality bioassay was also performed to evaluate the cytotoxic properties of the Cu(II) complexes. Communicated by Ramaswamy H. Sarma