N-dodecyl-4-ethyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazine-2-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: N-dodecyl-4-ethyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazine-2-carboxamide
• 英文别名: N-dodecyl-4-ethyl-3-oxo-1,4-benzothiazine-2-carboxamide
• 化学式: C₂₃H₃₆N₂O₂S
• 分子量: 404.617
• InChiKey: LCCGUZDAJGGKET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2H)1,4-苯并噻嗪-3(4H)-酮 在 水 、 sodium hydride 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-dodecyl-4-ethyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazine-2-carboxamide
  参考文献：
  名称：

  The discovery of novel benzothiazinones as highly selective non-ATP competitive glycogen synthase kinase 3β inhibitors for the treatment of ovarian cancer

  摘要：

  Glycogen synthase kinase 3 beta (GSK 3 beta) is a highly conserved serine/threonine kinase, and its roles in cancer remain controversial. Cumulative evidence supported that GSK 3 beta inhibitors could suppress ovarian cancer (OC) development in vitro and made a new direction for ovarian cancer treatment. Here, we reported a series of novel substituted benzothiazinones as non-ATP competitive inhibitors of GSK 3 beta. Further studies showed that most of them had antiproliferative activities in ovarian cancer cell lines in vitro. As the most promising candidate of them, compound 20g induced cells apoptosis, arrested the cell cycle at the G1 phase in the A2780 cell line and showed moderate suppression efficacy in a female BALB/C nude mice model. All of the results demonstrated that compound 20g, as the first reported non ATP competitive small molecule inhibitor of GSK 3 beta with suppression efficacy on ovarian cancer both in vitro and in vivo, might represent a potential candidate for the treatment of OC. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.04.039

文献信息

• The discovery of novel benzothiazinones as highly selective non-ATP competitive glycogen synthase kinase 3β inhibitors for the treatment of ovarian cancer
  作者：Yang Gao、De-Yong Ye、Wei-Cheng Zhou、Yong Chu

  DOI：10.1016/j.ejmech.2017.04.039

  日期：2017.7

  Glycogen synthase kinase 3 beta (GSK 3 beta) is a highly conserved serine/threonine kinase, and its roles in cancer remain controversial. Cumulative evidence supported that GSK 3 beta inhibitors could suppress ovarian cancer (OC) development in vitro and made a new direction for ovarian cancer treatment. Here, we reported a series of novel substituted benzothiazinones as non-ATP competitive inhibitors of GSK 3 beta. Further studies showed that most of them had antiproliferative activities in ovarian cancer cell lines in vitro. As the most promising candidate of them, compound 20g induced cells apoptosis, arrested the cell cycle at the G1 phase in the A2780 cell line and showed moderate suppression efficacy in a female BALB/C nude mice model. All of the results demonstrated that compound 20g, as the first reported non ATP competitive small molecule inhibitor of GSK 3 beta with suppression efficacy on ovarian cancer both in vitro and in vivo, might represent a potential candidate for the treatment of OC. (C) 2017 Elsevier Masson SAS. All rights reserved.