(Z)-3-(4-(dimethylamino)benzylidene)-1-methylindolin-2-one | 50793-69-6

• 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: (Z)-3-(4-(dimethylamino)benzylidene)-1-methylindolin-2-one
• 英文别名: 3-(4-dimethylamino-benzylidene)-1-methyl-indolin-2-one；3-(4-Dimethylamino-benzyliden)-1-methyl-indolin-2-on；3-[1-(4-Dimethylamino-phenyl)-meth-(Z)-ylidene]-1-methyl-1,3-dihydro-indol-2-one；(3Z)-3-[[4-(dimethylamino)phenyl]methylidene]-1-methylindol-2-one
• CAS: 50793-69-6
• 化学式: C₁₈H₁₈N₂O
• 分子量: 278.354
• InChiKey: TUNFCKFZFPSXAU-VBKFSLOCSA-N

物化性质

• 熔点：
  155 °C
• 沸点：
  429.9±45.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 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：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基吲哚酮 、 对二甲氨基苯甲醛 在 哌啶 、 乙醇 作用下， 生成 (Z)-3-(4-(dimethylamino)benzylidene)-1-methylindolin-2-one
  参考文献：
  名称：

  Porter et al., Journal of the Chemical Society, 1941, p. 620,621

  摘要：

  DOI：

文献信息

• 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
• Design, Synthesis, and Characterization of 3-(Benzylidene)indolin-2-one Derivatives as Ligands for α-Synuclein Fibrils
  作者：Wenhua Chu、Dong Zhou、Vrinda Gaba、Jialu Liu、Shihong Li、Xin Peng、Jinbin Xu、Dhruva Dhavale、Devika P. Bagchi、André d’Avignon、Naomi B. Shakerdge、Brian J. Bacskai、Zhude Tu、Paul T. Kotzbauer、Robert H. Mach

  DOI：10.1021/acs.jmedchem.5b00571

  日期：2015.8.13

  A series of 3-(benzylidine)indolin-2-one derivatives were synthesized and evaluated for their in vitro binding to alpha synuclein (alpha-syn), beta amyloid (A beta), and tau fibrils. Compounds with a single double bond in the 3-position had only a modest affinity for alpha-syn and no selectivity for alpha-syn versus A beta or tau fibrils. Homologation to the corresponding diene analogues yielded a mixture of Z,E and E,E isomers; substitution of the indoline nitrogen with an N-benzyl group resulted in increased binding to alpha-syn and reasonable selectivity for alpha-syn versus and tau. Introduction of a para-nitro group into the benzene ring of the diene enabled separation of the Z,E and E,E isomers and led to the identification of the Z,E configuration as the more active regioisomer. The data described here provide key structural information in the design of probes which bind preferentially to alpha-syn versus A beta or tau fibrils.
• Porter et al., Journal of the Chemical Society, 1941, p. 620,621
  作者：Porter et al.

  DOI：——

  日期：——