3-((2-methoxyphenyl)imino)indolin-2-one | 34042-60-9

• 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-((2-methoxyphenyl)imino)indolin-2-one
• 英文别名: (3E)-3-[(2-Methoxyphenyl)imino]-2,3-dihydro-1H-indol-2-one；3-(2-methoxyphenyl)imino-1H-indol-2-one
• CAS: 34042-60-9
• 化学式: C₁₅H₁₂N₂O₂
• mdl: MFCD01883929
• 分子量: 252.272
• InChiKey: XPSLHXXSARQIJF-UHFFFAOYSA-N

物化性质

• 熔点：
  177-179 °C
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-((2-methoxyphenyl)imino)indolin-2-one 在 盐酸羟胺 、 sodium acetate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Sahu; Mishra; Banerjee, Journal of the Indian Chemical Society, 2006, vol. 83, # 7, p. 725 - 727

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羟基亚氨基-n-苯乙酰胺 在 硫酸 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 3-((2-methoxyphenyl)imino)indolin-2-one
  参考文献：
  名称：

  Practical Synthesis, Antidepressant, and Anticonvulsant Activity of 3-Phenyliminoindolin-2-one Derivatives

  摘要：

  Herein, a series of 3‐phenyliminoindolin‐2‐one derivatives were designed, synthesized, and screened for their antidepressant and anticonvulsant activities. The IR spectra of the compounds afforded NH stretching (3340–3346 cm−1) bands and C=O stretching (1731–1746 cm−1). In the 1H‐NMR spectra of the compounds, N‐H protons of indoline ring were observed at 10.65–10.89 ppm generally as broad bands, and 13C‐NMR spectra of the compounds C=O were seen at 161.72–169.27 ppm. Interestingly, compounds 3o, 3p and 3r significantly shortened immobility time in the The forced swimming test (FST) and The tail suspension test (TST) at 50 mg/kg dose levels. In addition, compound 3r exhibited higher levels of efficacy than the reference standard fluoxetine but had no effect on locomotor activity in the open‐field test. Compound 3r significantly increased serotonin and norepinephrine and the metabolite 5‐hydroxyindoleacetic acid in mouse brain, suggesting that the effects of compound 3r may be mediated through these neurotransmitters. In the seizure screen, 15 compounds showed some degree against PTZ‐induced seizure at a dose of 100 mg/kg, and the tested compounds did not show any neurotoxicity at a dose of 300 mg/kg in the rotarod test.

  DOI：

  10.1111/cbdd.12668
• 作为试剂：
  描述：

  2-乙基苯胺 、 靛红 在 3-((2-methoxyphenyl)imino)indolin-2-one 作用下， 以 甲醇 为溶剂， 生成 3-(2-ethylphenyl)imino-1H-indol-2-one
  参考文献：
  名称：

  A simple entry to novel spiro dihydroquinoline-oxindoles using Povarov reaction between 3-N-aryliminoisatins and isoeugenol

  摘要：

  An easy, fast, and cheap way for the synthesis of the new 4 '-(4-hydroxy-3-methoxyphenyl)-3 '-methyl-3 ',4 '-dihydro-1 ' H-spiro[indoline-3,2 '-quinolin-2-ones using BF3 center dot OEt(2-)promoted imino Diels-Alder cycloaddition between ketimine-isatin derivatives and trans-isoeugenol. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.096

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，
• 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。
• Theoretical Molecular Properties Prediction, Docking and Antimicrobial Studies on Anisidine-Isatin Schiff Bases
  作者：G.K. Ayyadurai、R. Jayaprakash、S. Rathika

  DOI：10.14233/ajchem.2021.23467

  日期：——

  antibiotic for diseases is continuously reducing the immunity of the human in course of time, which includes Covid-19 treatment. Recent research on Schiff bases shows the promising biological activities and good antibacterial results. In this study, three Schiff bases with lactam ring using isatin and three different anisidines in presence of acetic acid were synthesized and characterized. Drug likeness was

  随着时间的推移，持续摄入针对疾病的特定抗生素会不断降低人类的免疫力，其中包括 Covid-19 治疗。席夫碱的最新研究表明其具有良好的生物活性和良好的抗菌效果。在本研究中，在乙酸存在下，使用靛红和三种不同的茴香胺合成了三种具有内酰胺环的席夫碱并对其进行了表征。使用 Molsoft 检查药物相似性，并与 5J6R、3L9L、5HVY、covid 主要蛋白酶和 3ZBO 蛋白等靶蛋白对接，以确保药物适用性。对金黄色葡萄球菌、枯草芽孢杆菌、表皮葡萄球菌等革兰氏阳性菌株具有实验抗菌活性。在合成的化合物中，三种席夫碱邻位和间位取代的化合物与对位化合物相比表现出良好的结果，其中观察到甲氧基位置效应。
• A convenient -diastereoselective synthesisof -isatin arylimines the aza-Wittig reaction
  作者：Vadim E. Filatov、Dmitrii A. Iuzabchuk、Boris N. Tarasevich、Nikolai V. Zyk、Elena K. Beloglazkina

  DOI：10.1016/j.mencom.2022.09.022

  日期：2022.9

  A general synthesis of NH-isatin N′-arylimines involves the aza-Wittig reaction of isatin and aryl azides, providing higher E-diastereoselectivity as compared to previously described methods. The procedure is applicable even to anilines which do not directly react with isatins.

  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。
• Khan, Khalid Mohammed; Mughal, Uzma Rasool; Ambreen, Nida, Letters in drug design and discovery, 2010, vol. 7, # 10, p. 716 - 720
  作者：Khan, Khalid Mohammed、Mughal, Uzma Rasool、Ambreen, Nida、Rama, Nasim Hasan、Naz, Farzana、Perveen, Shahnaz、Choudhary, Muhammad Iqbal

  DOI：——

  日期：——