methyl 6-methyl-2-(methylsulfanyl)thieno[2,3-d]thiazole-5-carboxylate | 1443015-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻唑类
• 英文名称: methyl 6-methyl-2-(methylsulfanyl)thieno[2,3-d]thiazole-5-carboxylate
• 英文别名: Methyl 6-methyl-2-methylsulfanylthieno[2,3-d][1,3]thiazole-5-carboxylate；methyl 6-methyl-2-methylsulfanylthieno[2,3-d][1,3]thiazole-5-carboxylate
• CAS: 1443015-07-3
• 化学式: C₉H₉NO₂S₃
• 分子量: 259.374
• InChiKey: CBDCYZAUCNEFTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  吗啉 、 methyl 6-methyl-2-(methylsulfanyl)thieno[2,3-d]thiazole-5-carboxylate 以39%的产率得到methyl 6-methyl-2-morpholinothieno[2,3-d]thiazole-5-carboxylate
  参考文献：
  名称：

  4-Bromo-2-(piperidin-1-yl)thiazol-5-yl-phenyl methanone (12b) inhibits Na+/K+-ATPase and Ras oncogene activity in cancer cells

  摘要：

  The in vitro growth inhibitory activity of 26 thiazoles (including 4-halogeno-2,5-disubtituted-1,3-thiazoles) and 5 thienothiazoles was assessed on a panel of 6 human cancer cell lines, including glioma cell lines. (4-Chloro-2-(piperidin-1-yl)thiazol-5-yl)(phenyl)methanone (12a) and (4-bromo-2-(piperidin-1-yl)thiazol-5-yl)(phenyl)methanone (12b) displayed similar to 10 times greater in vitro growth inhibitory activity than perillyl alcohol (POH), which therapeutically benefits glioma patients through the inhibition of both alpha-1 Na+/K+-ATPase (NAK) and Ras oncogene activity. The in vitro cytostatic activities (as revealed by quantitative videomicroscopy) displayed by 12a and 12b were independent of the intrinsic resistance to pro-apoptotic stimuli associated with cancer cells. Compounds 12a and 12b displayed relatively similar inhibitory activities on purified guinea pig brain preparations that mainly express NAK alpha-2 and alpha-3 subunits, whereas only compound 12b was efficacious against purified guinea pig kidney preparations that mainly express the NAK alpha-1 subunit, which is also expressed in gliomas, melanomas and non-small-cell lung cancers NSCLCs. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.046
• 作为产物：
  描述：

  1-(4-bromo-2-(methylsulfanyl)-1,3-thiazol-5-yl)ethanone 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 6.25h， 生成 methyl 6-methyl-2-(methylsulfanyl)thieno[2,3-d]thiazole-5-carboxylate
  参考文献：
  名称：

  4-Bromo-2-(piperidin-1-yl)thiazol-5-yl-phenyl methanone (12b) inhibits Na+/K+-ATPase and Ras oncogene activity in cancer cells

  摘要：

  The in vitro growth inhibitory activity of 26 thiazoles (including 4-halogeno-2,5-disubtituted-1,3-thiazoles) and 5 thienothiazoles was assessed on a panel of 6 human cancer cell lines, including glioma cell lines. (4-Chloro-2-(piperidin-1-yl)thiazol-5-yl)(phenyl)methanone (12a) and (4-bromo-2-(piperidin-1-yl)thiazol-5-yl)(phenyl)methanone (12b) displayed similar to 10 times greater in vitro growth inhibitory activity than perillyl alcohol (POH), which therapeutically benefits glioma patients through the inhibition of both alpha-1 Na+/K+-ATPase (NAK) and Ras oncogene activity. The in vitro cytostatic activities (as revealed by quantitative videomicroscopy) displayed by 12a and 12b were independent of the intrinsic resistance to pro-apoptotic stimuli associated with cancer cells. Compounds 12a and 12b displayed relatively similar inhibitory activities on purified guinea pig brain preparations that mainly express NAK alpha-2 and alpha-3 subunits, whereas only compound 12b was efficacious against purified guinea pig kidney preparations that mainly express the NAK alpha-1 subunit, which is also expressed in gliomas, melanomas and non-small-cell lung cancers NSCLCs. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.046