3-((2-chlorophenyl)imino)indolin-2-one

• 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-chlorophenyl)imino)indolin-2-one
• 英文别名: 3-(2-Chloro-phenylimino)-1,3-dihydro-indol-2-one；3-(2-chlorophenyl)imino-1H-indol-2-one
• 化学式: C₁₄H₉ClN₂O
• 分子量: 256.691
• InChiKey: NCIYCSASBSFDJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 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：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-((2-chlorophenyl)imino)indolin-2-one 在 silver tetrafluoroborate 、 正丁基锂 、 三苯基膦氯金 作用下， 以 四氢呋喃 为溶剂， 反应 7.92h， 生成 methyl (2-(8-chloro-4-phenylquinolin-2-yl)phenyl)carbamate
  参考文献：
  名称：

  通过一锅法弗瑞德-克拉夫茨反应/氧化 Umpolung Aza-Grob 断裂序列合成 (2-(Quinolin-2-yl)phenyl) carbamates

  摘要：

  利用由靛红、末端炔烃和苯胺制备的容易获得的靛红基炔丙基胺，通过一锅法依次制备（2-（喹啉-2-基）苯基）氨基甲酸酯，结合金催化的 Friedel-工艺环化、氧化 umpolung aza-Grob 碎裂和亲核加成。在这个过程中，金催化的靛红基炔丙基胺环化得到 1' H-螺[二氢吲哚-3,2'-喹啉]-2-酮，其通过 aza-Grob 裂解被高价碘原位氧化成得到异氰基中间体2-(2-异氰酸基苯基)喹啉。随后与醇溶剂进行亲核加成，合成了(2-(喹啉-2-基)苯基)氨基甲酸酯。该程序具有操作简单、底物范围广、条件温和等特点。

  DOI：

  10.1021/acs.joc.2c00502
• 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-chlorophenyl)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

文献信息

• Preparation and antiplasmodial activity of 3',4'‐dihydro‐1' <i>H</i> ‐spiro(indoline‐3,2'‐quinolin)‐2‐ones
  作者：Bakolise Mathebula、Kamogelo Rosinah Butsi、Robyn Lynne van Zyl、Natasha Colleen Jansen van Vuuren、Heinrich Carl Hoppe、Joseph Philip Michael、Charles Bernard de Koning、Amanda Louise Rousseau

  DOI：10.1111/cbdd.13598

  日期：2019.10

  A series of 3',4'-dihydro-1'H-spiro(indoline-3,2'-quinolin)-2-ones were prepared by the inverse-electron-demand aza-Diels-Alder reaction (Povarov reaction) of imines derived from isatin and substituted anilines, and the electron-rich alkenes trans-isoeugenol and 3,4-dihydro-2H-pyran. These compounds were assessed for in vitro antiplasmodial activity against drug-sensitive and drug-resistant forms of

  通过反电子需求的氮杂-Diels-Alder反应（Povarov反应）制备了一系列的3'，4'-二氢-1'H-螺（吲哚啉-3,2'-喹啉）-2-酮。亚胺衍生自Isatin和取代的苯胺，以及富含电子的烯烃反式异丁香酚和3,4-二氢-2H-吡喃。评估了这些化合物对恶性疟原虫寄生虫的药物敏感性和耐药性形式的体外抗血浆活性。衍生自3,4-二氢-2H-吡喃的三种化合物和衍生自反异丁香酚的四种化合物在低微摩尔范围内对耐药FCR-3菌株（1.52-4.20 µM）表现出抗血浆活性。仅衍生自反式异丁香酚的化合物显示出对药物敏感的3D7菌株（1.31-1.80 µM）的抗血浆活性。
• Stereocontrolled [3+2] Cycloaddition of Donor–Acceptor Cyclopropanes to Iminooxindoles: Access to Spiro[oxindole-3,2′-pyrrolidines]
  作者：Andrey A. Akaev、Stanislav I. Bezzubov、Victor G. Desyatkin、Nataliya S. Vorobyeva、Alexander G. Majouga、Mikhail Ya. Melnikov、Ekaterina M. Budynina

  DOI：10.1021/acs.joc.8b03208

  日期：2019.3.15

  with ester, keto, nitro, cyano etc. groups, and N-unprotected iminooxindoles. The stereospecificity of the initial SN2-like imine attack on a cyclopropane molecule together with a high diastereoselectivity of further C–C bond formation facilitate a rapid access to spiro[oxindole-3,2′-pyrrolidines] in their optically active forms. Preliminary in vitro testing of the synthesized compounds against LNCaP

  通过将供体-受体环丙烷的[3 + 2]-环加成到电子贫乏的酮亚胺（亚氨基氧吲哚）上，开发了螺环[oxindole-3,2'-吡咯烷]的新型立体控制组装。该方法可有效利用常用的供体-受体环丙烷，它们经酯，酮，硝基，氰基等基团和N-未保护的亚氨基吲哚官能化。最初的S N 2样亚胺攻击环丙烷分子的立体定向性以及进一步C-C键形成的高非对映选择性，有助于快速接近其光学活性形式的螺[oxindole-3,2'-吡咯烷]。初步体外 对合成的化合物针对LNCaP（p53 +）和PC-3（p53-）细胞的测试显示，对于几种化合物作为MDM2-p53相互作用的抑制剂，它们具有很好的抗增殖活性和p53选择性指数。
• Indium/Fe(<scp>iii</scp>) – mediated regioselective β-cross-coupling aldol type addition reaction of activated alkenes with isatins/isatinimines in aqueous media
  作者：A. Sanjeeva Kumar、Palakuri Ramesh、G. Santosh Kumar、Jagadeesh Babu Nanubolu、T. Prabhakar Rao、H. M. Meshram

  DOI：10.1039/c5ra07216f

  日期：——

  A highly efficient and regioselective β-cross coupling aldol type addition reaction of activated alkenes with isatin/isatinimine derivatives in the presence of Indium/Fe(iii) in THF/H₂O at room temperature is described.

  描述了在THF/H₂O中，室温下活化烯烃与异喹啉/异喹啉亚胺衍生物在铟/Fe(iii)存在下高效和区域选择性的β-交叉偶联醛缩加反应。
• 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。