1,3-dihydro-1,3-dimethyl-2H-indole-2-thione | 13637-41-7

• 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: 1,3-dihydro-1,3-dimethyl-2H-indole-2-thione
• 英文别名: 1,3-Dimethyl-2-thioxo-2,3-dihydroindole；1,3-Dimethyl-indolin-2-thion；1,3-Dimethyl-2-indolinthion；1,3-Dimethyl-2-thioxo-indolin；1,3-dimethyl-1,3-dihydro-indole-2-thione；2H-Indole-2-thione, 1,3-dihydro-1,3-dimethyl-；1,3-dimethyl-3H-indole-2-thione
• CAS: 13637-41-7
• 化学式: C₁₀H₁₁NS
• 分子量: 177.27
• InChiKey: TYFJUZPJHYOUES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  异氰酸苯酯 、 1,3-dihydro-1,3-dimethyl-2H-indole-2-thione 在 sodium hydride 作用下， 生成 1,3-dihydro-1,3-dimethyl-N-phenyl-2-thioxo-2H-indole-3-carboxamide
  参考文献：
  名称：

  Tyrosine Kinase Inhibitors. 3. Structure-Activity Relationships for Inhibition of Protein Tyrosine Kinases by Nuclear-Substituted Derivatives of 2,2'-Dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamide)

  摘要：

  A series of indole-substituted 2,2'-dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamides) were prepared 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. The compounds were synthesized by conversion of appropriate 1-methyloxindoles to 1-methyl-2-indolinethiones with P2S5 followed by subsequent reaction with NaH and phenyl isocyanate and oxidative dimerization of the resulting 2,3-dihydro-N-phenyl-2-thioxo-1H-indole-3-carboxamides. The parent compound and many of the substituted analogues were moderately potent inhibitors of both kinase enzymes, but no clear relationships were seen between substitution on the indole ring and inhibitory activity, While 4-substituted compounds were generally inactive, 5-substituted derivatives with electron-withdrawing groups showed inhibitory activity. However, none of the substituted compounds showed significantly better activity than the unsubstituted parent compound. There was generally a good correlation between activity against the EGFR and pp60(v-src) kinases, but several compounds did show some specificity (>20-fold) of inhibition; 5-Cl and 5-Br derivatives preferentially inhibited pp60(v-src), while the 5-CF3 compound preferentially inhibited EGFR. Selected compounds from the series were found to inhibit the growth of Swiss 3T3 fibroblasts with IC(50)s in the range 2-25 mu M, the most active being 4-substituted derivatives. The compounds inhibited bFGF-mediated protein tyrosine phosphorylation in intact cells more effectively than EGFR- or PDGF-mediated phosphorylation.

  DOI：

  10.1021/jm00039a016
• 作为产物：
  描述：

  N-Methyl-N-(1-propynylthio)-benzenamine 以 苯 为溶剂， 反应 3.0h， 以68%的产率得到1,3-dihydro-1,3-dimethyl-2H-indole-2-thione
  参考文献：
  名称：

  Thermal Rearrangements ofN-Aryl-1-alkynesulphenamides into Indoline-2-thiones

  摘要：

  溴镁苯甲酰胺与 1-炔基硫氰酸盐反应生成了标题中的磺酰胺。在苯中加热时，这些苯磺酰胺会发生[3.3]-对位重排，然后中间硫酮环化，生成吲哚啉-2-硫酮。

  DOI：

  10.1055/s-1985-31400

文献信息

• Isatin products
  申请人：The Regents of the University of Minnesota

  公开号：US04186132A1

  公开（公告）日：1980-01-29

  An aniline is converted to a 3-lower hydrocarbonthiooxindole by processes already known in the art, the product converted to a 3-halo-3-lower hydrocarbonthiooxindole by oxidative halogenation, and the product subjected to hydrolysis to form the desired isatins.

  一种苯胺通过已知的方法转化为3-较低碳氢基硫代吲哚，该产物通过氧化卤代反应转化为3-卤代-3-较低碳氢基硫代吲哚，然后将产物进行水解反应形成所需的吲哚酮。
• Isatin process and products
  申请人：Regents of University of Minnesota

  公开号：US04188325A1

  公开（公告）日：1980-02-12

  An aniline is converted to a 3-lower hydrocarbonthiooxindole by processes already known in the art, the product converted to a 3-halo-3-lower hydrocarbonthiooxindole by oxidative halogenation, and the product subjected to hydrolysis to form the desired isatins.

  一种苯胺通过已知的工艺转化为3-较低碳氢基硫代吲哚，该产物通过氧化卤代反应转化为3-卤代-3-较低碳氢基硫代吲哚，然后将产物经过水解作用形成所需的吲哚。
• Rewcastle Gordon W., Palmer Brian D., Dobrusin Ellen M., Fry David W., Kr+, J. Med. Chem, 37 (1994) N 13, S 2033-2042
  作者：Rewcastle Gordon W., Palmer Brian D., Dobrusin Ellen M., Fry David W., Kr+

  DOI：——

  日期：——
• BAUDIN, J. -B.;BEKHAZI, M.;JULIA, S. A.;RUEL, O.;JONG, R. L. P. DE;BRANDS+, SYNTHESIS, BRD, 1985, N 10, 956-958
  作者：BAUDIN, J. -B.、BEKHAZI, M.、JULIA, S. A.、RUEL, O.、JONG, R. L. P. DE、BRANDS+

  DOI：——

  日期：——
• US4186132A
  申请人：——

  公开号：US4186132A

  公开（公告）日：1980-01-29