5-methoxy-2-((pyridin-2-ylmethyl)thio)-1H-benzo[d]imidazole | 64948-80-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-methoxy-2-((pyridin-2-ylmethyl)thio)-1H-benzo[d]imidazole
• 英文别名: 5-methoxy-2-pyridin-2-ylmethylsulfanyl-1(3)H-benzoimidazole；2-[2-pyridylmethylthio]-(5-methoxy)benzimidazole；5-methoxy-2-[(pyridin-2-ylmethyl)thio]-1H-benzimidazole；6-methoxy-2-(pyridin-2-ylmethylsulfanyl)-1H-benzimidazole
• CAS: 64948-80-7
• 化学式: C₁₄H₁₃N₃OS
• 分子量: 271.343
• InChiKey: ASVPNBDOVHTUEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-巯基-5-甲氧基苯并咪唑 、 2-三氟乙酰氧基甲基吡啶 在 四丁基溴化铵 作用下， 以 甲苯 为溶剂， 以770 mg的产率得到5-methoxy-2-((pyridin-2-ylmethyl)thio)-1H-benzo[d]imidazole
  参考文献：
  名称：

  2-甲基吡啶N-氧化物中甲基C（sp 3）-H键的无金属和无碱区域选择性硫醇化

  摘要：

  通过TFAA介导的吡啶N-氧化物的[3,3]-σ重排和TBAB催化的三氟乙酸盐在金属和金属催化下直接转化为三氟乙酸的反应，可以开发一锅两步的吡啶-2-基甲基硫醚合成方法无碱条件。这种方法可以使未活化的甲基C（sp 3硫醇化）–2-甲基吡啶与硫醇的氢键。该方法的显着特征包括区域选择性高，阶跃和原子经济，条件温和，操作简单，底物范围广和可扩展性。此外，该方法已成功地用于合成奥美拉唑硫化物和雷贝拉唑硫化物，而无需TBAB催化。全面的绿色化学指标分析表明，该方法比报道的雷贝拉唑硫化物更有效，更环保。

  DOI：

  10.1039/c8gc03072c

文献信息

• Ligand-Based Design of a Potent and Selective Inhibitor of Cytochrome P450 2C19
  作者：Robert S. Foti、Dan A. Rock、Xiaogang Han、Robert A. Flowers、Larry C. Wienkers、Jan L. Wahlstrom

  DOI：10.1021/jm201346g

  日期：2012.2.9

  A series of omeprazole-based analogues was synthesized and assessed for inhibitory activity against CYP2C19. The data was used to build a CYP2C19 inhibition pharmacophore model for the series. The model was employed to design additional analogues with inhibitory potency against CYP2C19. Upon identifying inhibitors of CYP2C19, ligand-based design shifted to attenuating the rapid clearance observed for many of the inhibitors. While most analogues underwent metabolism on their aliphatic side chain, metabolite identification indicated that for analogues such as compound 30 which contain a heterocycle adjacent to the sulfur moiety, metabolism primarily occurred on the benzimidazole moiety. Compound 30 exhibited improved metabolic stability (Cl-int = 12.4 mL/min/nmol) and was selective in regard to inhibition of CYP2C19-catalyzed (S)-mephenytoin hydroxylation in human liver microsomes. Finally, representative compounds were docked into a homology model of CYP2C19 in an effort to understand the favorable inhibition or metabolism properties.
• INHIBITORS OF H+K+ -ATPASE
  申请人：Advanced Medicine, Inc.

  公开号：EP1143991A2

  公开（公告）日：2001-10-17
• US4045564A
  申请人：——

  公开号：US4045564A

  公开（公告）日：1977-08-30
• [EN] INHIBITORS OF HK-ATPase<br/>[FR] INHIBITEURS DE HK-ATPASE
  申请人：——

  公开号：WO1999063940A2

  公开（公告）日：1999-12-16

  [EN] Disclosed are multibinding compounds which inhibit H<+>/K<+>-ATPase, an enzyme which is involved in the control of acid secretion in the stomach. The multibinding compounds of this invention containing from 2 to 10 ligands covalently attached to one or more linkers. Each ligand is an inhibitor of H<+>/K<+>-ATPase. The multibinding compounds of this invention are useful in the treatment gastroesophageal reflux disease ("GERD").
  [FR] L'invention concerne des composés multiliaisons qui inhibent la H<+>/K<+>-ATPase, une enzyme qui intervient dans la régulation de la sécrétion d'acide dans l'estomac. Les composés multiliaisons de l'invention contiennent de 2 à 10 ligands fixés de manière covalente à un ou à plusieurs lieurs. Chaque ligand constitue un inhibiteur de H<+>/K<+>-ATPase. Les composés multiliaisons de l'invention sont utiles dans le traitement de reflux gastro-oesophagien pathologique (RGO).
• Metal- and base-free regioselective thiolation of the methyl C(sp³)–H bond in 2-picoline <i>N</i>-oxides
  作者：Dong Wang、Zhenlin Liu、Zhentao Wang、Xinyue Ma、Peng Yu

  DOI：10.1039/c8gc03072c

  日期：——

  A one-pot, two-step synthesis of pyridine-2-ylmethyl thioethers is developed through a TFAA-mediated [3,3]-sigmatropic rearrangement of pyridine N-oxides and TBAB-catalyzed direct conversion of trifluoroacetates into thioethers under metal- and base-free conditions. This methodology enables thiolation of the unactivated methyl C(sp3)–H bond in 2-picolines with thiols. Remarkable features of the method

  通过TFAA介导的吡啶N-氧化物的[3,3]-σ重排和TBAB催化的三氟乙酸盐在金属和金属催化下直接转化为三氟乙酸的反应，可以开发一锅两步的吡啶-2-基甲基硫醚合成方法无碱条件。这种方法可以使未活化的甲基C（sp 3硫醇化）–2-甲基吡啶与硫醇的氢键。该方法的显着特征包括区域选择性高，阶跃和原子经济，条件温和，操作简单，底物范围广和可扩展性。此外，该方法已成功地用于合成奥美拉唑硫化物和雷贝拉唑硫化物，而无需TBAB催化。全面的绿色化学指标分析表明，该方法比报道的雷贝拉唑硫化物更有效，更环保。