3-((4-fluorophenyl)imino)indolin-2-one | 21231-47-0

• 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-((4-fluorophenyl)imino)indolin-2-one
• 英文别名: 3-(4-Fluoroanilino)indol-2-one；3-(4-fluorophenyl)imino-1H-indol-2-one
• CAS: 21231-47-0
• 化学式: C₁₄H₉FN₂O
• mdl: MFCD00442900
• 分子量: 240.237
• InChiKey: NXPXTHPLHCNMOJ-UHFFFAOYSA-N

物化性质

• 熔点：
  210-216 °C(Solv: ethanol (64-17-5))
• 密度：
  1.31±0.1 g/cm3(Predicted)
• 溶解度：
  >36 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  3-((4-fluorophenyl)imino)indolin-2-one 在 氢氧化钾 、 巯基乙酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 23.0h， 生成 3-(4-fluorophenyl)-1-methylspiro<3H-indole-3,2'-thiazolidine>-2,4'(1H)-dione
  参考文献：
  名称：

  Joshi; Dandia; Bhagat, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 8, p. 766 - 770

  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-((4-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

• Tin powder-promoted one-pot synthesis of 3-spiro-fused or 3,3′-disubstituted 2-oxindoles
  作者：Juanjuan Wang、Danfeng Huang、Ke-Hu Wang、Xiansha Peng、Yingpeng Su、Yulai Hu、Ying Fu

  DOI：10.1039/c6ob01487a

  日期：——

  oxindoles has been developed from one-pot reactions of isatins, hydrazides or aromatic amines, 2-(bromomethyl)acrylic ester and tin powder in the presence of a catalytic amount of Brønsted or Lewis acid. The method avoids the use of toxic stannanes and allows easy operation. It is also proved that hydrazides are more favorable for intramolecular cyclization than amines.

  在存在下，由靛红，酰肼或芳香胺，2-（溴甲基）丙烯酸酯和锡粉的一锅反应，开发了一种方便有效的3-螺氧并吲哚衍生物或3,3'-二取代的羟吲哚的结构方法。催化量的布朗斯台德酸或路易斯酸。该方法避免了使用有毒的锡烷，并且易于操作。还证明了酰肼比胺更有利于分子内环化。
• 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。
• 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。
• “On water” synthesis of spiro-indoles via Schiff bases
  作者：Siva S. Panda、Subhash C. Jain

  DOI：10.1007/s00706-011-0697-x

  日期：2012.8

  AbstractA fast, efficient, and clean “on water” synthesis of new Schiff bases and their conversion to spiro compounds under microwave irradiation, as well as in water, is reported. Indol-2,3-diones were reacted separately with various heterocyclic and aromatic amines in water at room temperature to obtain corresponding Schiff bases in high purity and yield. These were then converted into corresponding

  摘要据报道，新的席夫碱快速，有效，清洁的“水上”合成以及在微波辐射下以及在水中均可将其转化为螺环化合物。吲哚-2，3-二酮在室温下分别与各种杂环胺和芳族胺反应，以高纯度和高收率获得相应的席夫碱。然后使用巯基乙酸在纯净条件下以及在回流下的水中在微波辐射下将它们转化为相应的螺环化合物。因此，开发了绿色合成方案以在生态友好的条件下合成新的分子，其轮廓得到改善，其中不形成废物或副产物。 图形概要 。