2-疏基-4-三氟甲基-5,6,7,8-四氢喹啉-3-甲腈 | 306935-92-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-疏基-4-三氟甲基-5,6,7,8-四氢喹啉-3-甲腈
• 英文名称: 2-Mercapto-4-(trifluoromethyl)-5,6,7,8-tetrahydroquinoline-3-carbonitrile
• 英文别名: 2-sulfanylidene-4-(trifluoromethyl)-5,6,7,8-tetrahydro-1H-quinoline-3-carbonitrile
• CAS: 306935-92-2
• 化学式: C₁₁H₉F₃N₂S
• 分子量: 258.267
• InChiKey: VRDUDTDTFZCTHJ-UHFFFAOYSA-N

物化性质

• 熔点：
  216 °C
• 沸点：
  316.2±52.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• 海关编码：
  2933499090
• 危险品运输编号：
  UN 3276

反应信息

• 作为产物：
  描述：

  2-氰基硫代乙酰胺 、 2,2,2-三氟乙醛 、 环己酮 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 2-疏基-4-三氟甲基-5,6,7,8-四氢喹啉-3-甲腈
  参考文献：
  名称：

  3-Amino-thieno[2,3-b]pyridines as microtubule-destabilising agents: Molecular modelling and biological evaluation in the sea urchin embryo and human cancer cells

  摘要：

  A series of 3-amino-thieno[2,3-b]pyridines was prepared and tested in a phenotypic sea urchin embryo assay to identify potent and specific molecules that affect tubulin dynamics. The most active compounds featured a tricyclic core ring system with a fused cycloheptyl or cyclohexyl substituent and unsubstituted or alkyl-substituted phenyl moiety tethered via a carboxamide. Low nano-molar potency was observed in the sea urchin embryos for the most active compounds (1-5) suggestive of a microtubule-destabilising effect. The molecular modelling studies indicated that the tubulin colchicine site is inhibited, which often leads to microtubule-destabilisation in line with the sea urchin embryo results. Finally, the identified hits displayed a robust growth inhibition (GI(50) of 50-250 nM) of multidrug-resistant melanoma MDA-MB-435 and breast MDA-MB-468 human cancer cell lines. This work demonstrates that for the thieno[2,3-b]pyridines the most effective mechanism of action is microtubule-destabilisation initiated by binding to the colchicine pocket. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.11.041

文献信息

• 3-Amino-thieno[2,3-b]pyridines as microtubule-destabilising agents: Molecular modelling and biological evaluation in the sea urchin embryo and human cancer cells
  作者：Chatchakorn Eurtivong、Victor Semenov、Marina Semenova、Leonid Konyushkin、Olga Atamanenko、Jóhannes Reynisson、Alex Kiselyov

  DOI：10.1016/j.bmc.2016.11.041

  日期：2017.1

  A series of 3-amino-thieno[2,3-b]pyridines was prepared and tested in a phenotypic sea urchin embryo assay to identify potent and specific molecules that affect tubulin dynamics. The most active compounds featured a tricyclic core ring system with a fused cycloheptyl or cyclohexyl substituent and unsubstituted or alkyl-substituted phenyl moiety tethered via a carboxamide. Low nano-molar potency was observed in the sea urchin embryos for the most active compounds (1-5) suggestive of a microtubule-destabilising effect. The molecular modelling studies indicated that the tubulin colchicine site is inhibited, which often leads to microtubule-destabilisation in line with the sea urchin embryo results. Finally, the identified hits displayed a robust growth inhibition (GI(50) of 50-250 nM) of multidrug-resistant melanoma MDA-MB-435 and breast MDA-MB-468 human cancer cell lines. This work demonstrates that for the thieno[2,3-b]pyridines the most effective mechanism of action is microtubule-destabilisation initiated by binding to the colchicine pocket. (C) 2016 Elsevier Ltd. All rights reserved.