(E)-3-(4-isopropylbenzylidene)indolin-2-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-3-(4-isopropylbenzylidene)indolin-2-one
• 英文别名: (3E)-3-[(4-propan-2-ylphenyl)methylidene]-1H-indol-2-one
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: IRQQWCZKCUQNSO-LFIBNONCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-吲哚酮 、 4-异丙基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 (E)-3-(4-isopropylbenzylidene)indolin-2-one
  参考文献：
  名称：

  Natural α-methylenelactam analogues: Design, synthesis and evaluation of α-alkenyl-γ and δ-lactams as potential antifungal agents against Colletotrichum orbiculare

  摘要：

  In our continued efforts to improve the potential utility of the alpha-methylene-gamma-lactone scaffold, 62 new and 59 known natural alpha-methylenelactam analogues including alpha-methylene-gamma- lactams, alpha-arylidene- gamma and delta-lactams, and 3-arylideneindolin-2-ones were synthesized as the bioisosteric analogues of the amethylenelactone scaffold. The results of antifungal and cytotoxic activity indicated that among these derivatives compound (E)-1-(2, 6-dichlorobenzyl)-3-(2-fluorobenzylidene) pyrrolidin-2-one (Py51) possessed good selectivity with the highest antifungal activity against Colletotrichum orbiculare with IC50 - 10.4 mu M but less cytotoxic activity with IC50 - 141.2 mu M (against HepG2 cell line) and 161.2 mu M ( against human hepatic L02 cell line). Ultrastructural change studies performed by transmission electron microscope showed that Py51 could cause important cell morphological changes in C. orbiculare, such as plasma membrane detached from cell wall, cell wall thickening, mitochondria disruption, a dramatic increase in vacuolation, and eventually a complete loss in the integrity of organelles. Significantly, mitochondria appeared one of the primary targets, as confirmed by their remarkably aberrant morphological changes. Analysis of structureeactivity relationships revealed that incorporation of the aryl group into the alpha-exo methylene and the N-benzyl substitution increased the activity. Meanwhile, the alpha-arylidene-gamma-lactams have superiority in selectivity over the 3-arylideneindolin-2-ones. Based on the results, the N- benzyl substituted a-(2-fluorophenyl)-gamma-lactam was identified as the most promising natural- based scaffold for further discovering and developing improved crop- protection agents. (c) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.050

文献信息

• Oxindole synthesis by palladium-catalysed aromatic C–H alkenylation
  作者：Satoshi Ueda、Takahiro Okada、Hideko Nagasawa

  DOI：10.1039/b926560k

  日期：——

  A strategy involving palladium-catalysed aromatic C-H functionalisation/intramolecular alkenylation provides a convenient and direct synthesis of 3-alkylideneoxindoles. In the presence of 5 mol% of PdCl(2)MeCN(2) and AgOCOCF(3), a wide variety of N-cinnamoylanilines gave 3-alkylideneoxindoles in moderate to good yield.

  涉及钯催化的芳族CH官能化/分子内烯基化的策略提供了3-亚烷基亚氧吲哚的方便和直接的合成。在5 mol％的PdCl（2）MeCN（2）和AgOCOCF（3）的存在下，各种各样的N-肉桂酰基苯胺以中等至良好的收率得到3-亚烷基亚甲基吲哚。
• Synthesis and Biological Evaluations of 3-Substituted Indolin-2-ones:  A Novel Class of Tyrosine Kinase Inhibitors That Exhibit Selectivity toward Particular Receptor Tyrosine Kinases
  作者：Li Sun、Ngoc Tran、Flora Tang、Harald App、Peter Hirth、Gerald McMahon、Cho Tang

  DOI：10.1021/jm980123i

  日期：1998.7.1

  analysis for these compounds and their relative potency and selectivity to inhibit particular RTKs has determined that (1) 3-[(five-membered heteroaryl ring)methylidenyl]indolin-2-ones are highly specific against the VEGF (Flk-1) RTK activity, (2) 3-(substituted benzylidenyl)indolin-2-ones containing bulky group(s) in the phenyl ring at the C-3 position of indolin-2-ones showed high selectivity toward

  已经设计并合成了3-取代的吲哚-2-酮，作为一类新型的酪氨酸激酶抑制剂，该抑制剂对不同的受体酪氨酸激酶（RTK）具有选择性。已经评估了这些化合物对完整细胞中一组RTK的相对抑制特性。通过修饰3-取代的吲哚-2-酮，我们鉴定了在亚微摩尔水平下显示选择性抑制各种RTK的配体依赖性自磷酸化的化合物。这些化合物的结构活性分析及其抑制特定RTK的相对效能和选择性已确定（1）3-[（（五元杂芳基环）亚甲基]茚满-2-酮对VEGF（Flk-1 ）RTK活动，（2）在吲哚-2-酮的C-3位的C-3位置的苯环中含有庞大基团的3-（取代的苄基）吲哚啉-2-酮显示出对EGF和Her-2 RTK的高选择性，并且（ 3）在针对PDGF和VEGF（Flk-1）RTK进行测试时，在吲哚-2-酮（16）的C-3位置包含延伸的侧链的化合物表现出较高的效价和选择性。这些3-取代的吲哚-2-酮中的两个的最近公布的晶体学数据提供
• Synthesis of ( <i>E</i> )‐3‐Alkylideneindolin‐2‐ones by an Iron‐Catalyzed Aerobic Oxidative Condensation of Csp ³ –H Bonds of Oxindoles and Benzylamines
  作者：Kovuru Gopalaiah、Ankit Tiwari

  DOI：10.1002/ejoc.202001300

  日期：2020.12.13

  An iron‐catalyzed direct access to (E)‐3‐alkylideneindolin‐2‐ones through oxidative condensation of oxindoles with benzylamines is described. The procedure utilizes molecular oxygen as a clean and terminal oxidant.

  描述了铁催化的氧吲哚与苄基胺的氧化缩合直接生成（E）-3-亚烷基亚吲哚啉-2-酮的方法。该程序利用分子氧作为清洁的终端氧化剂。
• [EN] INDOLINONE COMPOUNDS FOR THE TREATMENT OF DISEASE<br/>[FR] COMPOSES D'INDOLINONE POUR LE TRAITEMENT DE MALADIES
  申请人：SUGEN, INC.

  公开号：WO1996040116A1

  公开（公告）日：1996-12-19

  (EN) The present invention relates to organic molecules capable of modulating tyrosine kinase signal transduction in order to regulate, modulate and/or inhibit abnormal cell proliferation.(FR) Molécules organiques aptes à moduler la transduction de signaux de la tyrosine-kinase afin de réguler, de moduler et/ou d'inhiber une prolifération cellulaire anormale.

  本发明涉及有机分子，能够调节酪氨酸激酶信号传导，以调节、调制和/或抑制异常细胞增殖。
• CRYSTALLINE FORMS OF C21H22Cl2N4O2
  申请人：BIOMED VALLEY DISCOVERIES, INC.

  公开号：US20170320851A1

  公开（公告）日：2017-11-09

  The present invention provides crystalline forms of a compound of formula (I): Also provided are pharmaceutical compositions that include the provided crystalline forms and methods of using the provided crystalline forms and pharmaceutical compositions for the treatment of cancer.

  本发明提供了公式（I）化合物的晶体形式。还提供包含所提供晶体形式的药物组合物以及使用所提供的晶体形式和药物组合物治疗癌症的方法。