3-((2-fluorophenyl)imino)indolin-2-one | 100108-78-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-((2-fluorophenyl)imino)indolin-2-one
• 英文别名: 3-(2-fluorophenyl)imino-1H-indol-2-one
• CAS: 100108-78-9
• 化学式: C₁₄H₉FN₂O
• 分子量: 240.237
• InChiKey: IOYBXOWARYWTAJ-UHFFFAOYSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-甲氧基-4-(1-丙烯基苯酚) 、 3-((2-fluorophenyl)imino)indolin-2-one 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 72.25h， 以25%的产率得到8'‐fluoro‐4'‐(4‐hydroxy‐3‐methoxyphenyl)‐3'‐methyl‐3',4'‐dihydro‐1'H‐spiro[indoline‐3,2'‐quinolin]‐2‐one
  参考文献：
  名称：

  3'，4'-二氢-1'H-螺（吲哚啉-3,2'-喹啉）-2-酮的制备及其抗血浆活性。

  摘要：

  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。

  DOI：

  10.1111/cbdd.13598
• 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-fluorophenyl)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

• 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，
• Synthesis of 1,3-diaryl-spiro[azetidine-2,3′-indoline]-2′,4-diones<i>via</i>the Staudinger reaction:<i>cis</i>- or<i>trans</i>-diastereoselectivity with different addition modes
  作者：Vadim Filatov、Maksim Kukushkin、Juliana Kuznetsova、Dmitry Skvortsov、Viktor Tafeenko、Nikolay Zyk、Alexander Majouga、Elena Beloglazkina

  DOI：10.1039/d0ra02374d

  日期：——

  A new synthetic approach for realizing biologically relevant bis-aryl spiro[azetidine-2,3′-indoline]-2′,4-diones was developed based on Staudinger ketene–imine cycloaddition through the one-pot reaction of substituted acetic acids and Schiff bases in the presence of oxalyl chloride and an organic base. A series of [azetidine-2,3′-indoline]-2′,4-diones were synthesized using this method. For comparison

  基于 Staudinger 烯酮-亚胺环加成反应，通过取代乙酸与 Schiff 的一锅反应，开发了一种实现生物学相关双芳基螺[氮杂环丁烷-2,3'-二氢吲哚]-2',4-二酮的新合成方法碱在草酰氯和有机碱的存在下。使用该方法合成了一系列[氮杂环丁烷-2,3'-二氢吲哚]-2',4-二酮。为了比较，使用已知技术获得相同的化合物，其中乙烯酮是由预合成的酰氯产生的。结果表明，与先前描述的程序不同，在室温下在一锅反应中使用草酰氯生成乙烯酮可以逆转螺内酰胺形成的非对映选择性。
• 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。
• FACILE SYNTHESIS OF SOME NEW FLUORINE CONTAINING SPIRO [3H-INDOLE-3,2′TETRAHYDRO-1,3-THIAZINE].2,4′(1H)-DIONES
  作者：Anshu Dandia、C. S. Sharma、Mitali Saha

  DOI：10.1080/10426509808035677

  日期：1998.8.1

  Attempts have been made to synthesize exclusively 5',b'-dihydro-spiro [3H-indol-3,2'-[2H-1,3] thiazine]-2,4'(1H.3'H)-diones (V) under varying reaction conditions such as temperature, reaction period and molar ratio of the two reactants, by the reaction of fluorinated indole-2,3-diones (I) with fluorinated anilines (II) and 3-mercaptopropanoic acid (IV). The reaction of 3-indolylimines (III) with a slight excess of IV at room temperature, resulted in the formation of an acidic compound (VI), instead of expected spiro product (V), which has been further subjected to acetylation and chloroacetylation. The compounds have been characterized on the basis of elemental and spectral studies.
• An ultrasound assisted synthesis of spirooxindolo-1,2,4-oxadiazoles via [3+2] cycloaddition reaction and their anti-cancer activity
  作者：Madhu Kanchrana、Bhargava Sai Allaka、Gamidi Rama Krishna、Srinivas Basavoju

  DOI：10.24820/ark.5550190.p011.940

  日期：——