3-Phenyl-2-indolin-thion-2 | 33689-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-Phenyl-2-indolin-thion-2
• 英文别名: 3-Phenyl-2-indolinthion；3-phenyl-1,3-dihydro-indole-2-thione；3-phenyl-indoline-2-thione；3-Phenyl-indolin-2-thion；3-Phenyl-1,3-dihydroindole-2-thione
• CAS: 33689-22-4
• 化学式: C₁₄H₁₁NS
• 分子量: 225.314
• InChiKey: NGLOJOSCXCGWKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  44.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Phenyl-2-indolin-thion-2 、 2-溴苯乙酮 在 三乙胺 、 三苯基膦 、 sodium iodide 作用下， 以 乙腈 为溶剂， 以29%的产率得到2-benzoylmethylthio-3-phenylindole
  参考文献：
  名称：

  从二氢吲哚-2-硫酮开始的吲哚和吲哚衍生物的合成

  摘要：

  在3位上具有至少一个氢的二氢吲哚啉-2-硫酮1a-b，d，f，h与α-卤代酯2a-d，α-卤代酮2e-f和a-溴乙腈2g反应生成得到2-烷基硫代吲哚衍生物3-11。以类似的方式处理3,3-二取代的二氢吲哚-2-硫酮的1C，电子与α卤代酯2A，C，d和α卤代酮2E，得到2- alkylthioindolenines 12-16。用溴乙酸乙酯2a处理1，3，3-三取代的二氢吲哚-2-硫酮1g，i导致原料的回收。假吲哚的脱硫14与三苯基膦得到2-亚烷基二氢吲哚19。

  DOI：

  10.1002/jhet.5570380115
• 作为产物：
  描述：

  bis(3-phenyl-2-indolyl) disulfide 在 溶剂黄146 、 锌 作用下， 生成 3-Phenyl-2-indolin-thion-2
  参考文献：
  名称：

  Wieland et al., Justus Liebigs Annalen der Chemie, 1954, vol. 587, p. 146,151

  摘要：

  DOI：

文献信息

• Tyrosine Kinase Inhibitors. 4. Structure-Activity Relationships among N- and 3-Substituted 2,2'-Dithiobis(1H-indoles) for in vitro Inhibition of Receptor and Nonreceptor Protein Tyrosine Kinases
  作者：Brian D. Palmer、Gordon W. Rewcastle、Andrew M. Thompson、Maruta Boyd、H. D. Hollis Showalter、Anthony D. Sercel、David W. Fry、Alan J. Kraker、William A. Denny

  DOI：10.1021/jm00001a011

  日期：1995.1

  A series of S-substituted 2,2'-dithiobis(1H-indoles) were synthesized and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60(v-src) tyrosine kinase, to extend the available structure-activity relationships for this series. The majority of the compounds were prepared either by reaction of 2-chloro-1-methylindole-3-carbonyl chloride with amines, followed by thiomethylation, demethylation, and oxidative dimerization, or by reaction of isocyanates with the anion of 1-methyl-2-indolinethione followed by dimerization. Overall, inhibitory activity is retained by analogues having a wide variety of side chains. A series of 3-carboxamide analogues had moderate to good activity against isolated EGFR (IC(50)s 1-20 mu M), with monoalkyl substitution of the carboxamide being optimal. Polar side chains were generally less effective than lipophilic ones, with benzyl being particularly effective. However, N,N-disubstitution was the most effective pattern for inhibition of pp60(v-src). A variety of substituted N-phenylcarboxamides had lower activity against EGFR than the parent derivative, and a N-thienylcarboxamide also had low activity. A series of 3-ketones, including methyl, phenyl, and furyl derivatives, showed moderate activity against the pp60(v-src) kinase, but were less effective against EGFR. The mechanism of inhibition of both kinases by these drugs was shown to be noncompetitive with respect to both ATP and peptide substrate. Selected compounds inhibited the growth of Swiss 3T3 cells with IC(50)s in the low micromolar range and inhibited bFGF-mediated intracellular tyrosine phosphorylation in the same cell line. Thiol inhibits the effects of the compounds, suggesting that one possible mechanism of inhibition is thiol-disulfide exchange with thiol-containing residues in the catalytic sites. Crystal structures of two representative compounds show a folded, V-shaped structure, with the disulfide bridge exposed, consistent with this hypothesis.