2-indol-3-ylethyl thiocyanate | 75121-75-4

• 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: 2-indol-3-ylethyl thiocyanate
• 英文别名: 3-(2-thiocyanatoethyl)-1H-indole；Thiocyanic acid, 2-(1H-indol-3-yl)ethyl ester；2-(1H-indol-3-yl)ethyl thiocyanate
• CAS: 75121-75-4
• 化学式: C₁₁H₁₀N₂S
• 分子量: 202.28
• InChiKey: YQAYFJPGYPUGDY-UHFFFAOYSA-N

物化性质

• 熔点：
  40-41 °C
• 沸点：
  431.5±28.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-indol-3-ylethyl thiocyanate 在 sodium azide 、 zinc dibromide 作用下， 以 水 、 异丙醇 为溶剂， 反应 6.0h， 以73%的产率得到3-(2-(1H-tetrazol-5-ylthio)ethyl)-1H-indole
  参考文献：
  名称：

  Tryptophan 2,3-Dioxygenase (TDO) Inhibitors. 3-(2-(Pyridyl)ethenyl)indoles as Potential Anticancer Immunomodulators

  摘要：

  Tryptophan catabolism mediated by indoleamine 2,3-dioxygenase (IDO) is an important mechanism of peripheral immune tolerance contributing to tumoral immune resistance. IDO inhibition is thus an active area of research in drug development. Recently, our group has shown that tryptophan 2,3-dioxygenase (TDO), an unrelated hepatic enzyme also catalyzing the first step of tryptophan degradation, is also expressed in many tumors and that this expression prevents tumor rejection by locally depleting tryptophan. Herein, we report a structure- activity study on a series of 3-(2-(pyridyl)ethenyl)indoles. More than 70 novel derivatives were synthesized, and their TDO inhibitory potency was evaluated. The rationalization of the structure-activity relationships (SARs) revealed essential features to attain high TDO inhibition and notably a dense H-bond network mainly involving His(55) and Thr(254) residues. Our study led to the identification of a very promising compound (58) displaying good TDO inhibition (K-i = 5.5 mu M), high selectivity, and good oral bioavailability. Indeed, 58 was chosen for preclinical evaluation.

  DOI：

  10.1021/jm2006782
• 作为产物：
  描述：

  色醇 、 triphenylphosphine thiocyanogen 以 二氯甲烷 为溶剂， 以43%的产率得到2-indol-3-ylethyl thiocyanate
  参考文献：
  名称：

  Tamura, Yasumitsu; Adachi, Masahiro; Kawasaki, Tomomi, Journal of the Chemical Society. Perkin transactions I, 1980, p. 1132 - 1135

  摘要：

  DOI：

文献信息

• TAMURA Y.; ADACHI M.; KAWASAKI T.; YASUDA H.; KITA Y., J. CHEM. SOC. PERKIN TRANS., PART 1, 1980, NO 5, 1132-1135
  作者：TAMURA Y.、 ADACHI M.、 KAWASAKI T.、 YASUDA H.、 KITA Y.

  DOI：——

  日期：——