6-(2-Methoxy-phenyl)-3-methyl-imidazo[2,1-b]thiazole | 92754-12-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-(2-Methoxy-phenyl)-3-methyl-imidazo[2,1-b]thiazole
• 英文别名: 6-(2-Methoxyphenyl)-3-methylimidazo[2,1-b][1,3]thiazole
• CAS: 92754-12-6
• 化学式: C₁₃H₁₂N₂OS
• mdl: MFCD08815583
• 分子量: 244.317
• InChiKey: FHUAMYVHSOYXNL-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C(Solv: ethanol (64-17-5))
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(2-Methoxy-phenyl)-3-methyl-imidazo[2,1-b]thiazole 在 盐酸 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 8-hydroxy-8-(2-methoxyphenyl)-5-methyl-8H-[1,2,4]-oxadiazolo[3,4-c][1,4]thiazin-3-one
  参考文献：
  名称：

  Understanding Oxadiazolothiazinone Biological Properties: Negative Inotropic Activity versus Cytochrome P450-Mediated Metabolism

  摘要：

  We present a series of oxadiazolothiazinones, selective inotropic agents on isolated cardiac tissues, devoid of chronotropy and vasorelaxant activity. Functional and binding data for the precursor of the series (compound 1) let us hypothesize LTCC blocking activity and the existence of a recognition site specific for this scaffold. We synthesized and tested 22 new derivatives: introducing a para-methoxyphenyl at C-8 led to compound 12 (EC50 = 0.022 mu M), twice as potent as its para-bromo analogue (1). For 10 analogues, we extended the characterization of the biological properties by including the assessment of metabolic stability in human liver microsomes and cytochrome P450 inhibition potential. We observed that the methoxy group led to active compounds with low metabolic stability and high CYP inhibition, whereas the protective effect of bromine resulted in enhanced metabolic stability and reduced CYP inhibition. Thus, we identified two para-bromo benzothiazino-analogues as candidates for further studies.

  DOI：

  10.1021/acs.jmedchem.6b00030
• 作为产物：
  描述：

  邻甲氧基-2-溴苯乙酮 在 氢溴酸 作用下， 以 丙酮 为溶剂， 反应 1.17h， 生成 6-(2-Methoxy-phenyl)-3-methyl-imidazo[2,1-b]thiazole
  参考文献：
  名称：

  Andreani; Rambaldi; Bonazzi, European Journal of Medicinal Chemistry, 1984, vol. 19, # 3, p. 219 - 222

  摘要：

  DOI：

文献信息

• Asymmetric Mannich reactions of imidazo[2,1-b]thiazole-derived nucleophiles with (SS)-N-tert-butanesulfinyl (3,3,3)-trifluoroacetaldimine
  作者：Haibo Mei、Chen Xie、Lingmin Wu、Vadim A. Soloshonok、Jianlin Han、Yi Pan

  DOI：10.1039/c3ob41785a

  日期：——

  reasonably good yields (55%–79%) and exceptionally high stereoselectivity (>99 : 1 dr). This method presents a general approach for the preparation of a new type of biologically relevant compounds containing pharmacophoric imidazo[2,1-b]thiazole and (trifluoro)ethylamine groups.

  咪唑并[2,1-的不对称曼尼希反应b ]噻唑衍生的亲核试剂与（S小号） - N-叔-butanesulfinyl（3,3,3-）-trifluoroacetaldimine发现具有相当好的产率继续进行（55％-79％ ）和极高的立体选择性（> 99：1 dr）。该方法为制备含有药效基咪唑并[2，1- b ]噻唑和（三氟）乙胺基团的新型生物相关化合物提供了一种通用方法。
• ANDREANI, A.;RAMBALDI, M.;BONAZZI, D.;LELLI, G.;BOSSA, R.;GALATULAS, I., EUR. J. MED. CHEM., 1984, 19, N 3, 219-222
  作者：ANDREANI, A.、RAMBALDI, M.、BONAZZI, D.、LELLI, G.、BOSSA, R.、GALATULAS, I.

  DOI：——

  日期：——