2-[(4-ethoxy-3-methylpyridin-2-yl)-methylthio]-1H-benzimidazole | 206990-37-6

• 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: 2-[(4-ethoxy-3-methylpyridin-2-yl)-methylthio]-1H-benzimidazole
• 英文别名: 2-[[(3-Methyl-4-ethoxy-2-pyridyl)methyl]thio]-1H-benzimidazole；2-[(4-ethoxy-3-methylpyridin-2-yl)methylsulfanyl]-1H-benzimidazole
• CAS: 206990-37-6
• 化学式: C₁₆H₁₇N₃OS
• 分子量: 299.396
• InChiKey: SCPCJSHPLBJOPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(4-ethoxy-3-methylpyridin-2-yl)-methylthio]-1H-benzimidazole 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 lansoprazole
  参考文献：
  名称：

  Structure-Activity Relationship of Omeprazole and Analogs as Helicobacter pylori Urease Inhibitors

  摘要：

  Helicobacter pylori urease belongs to a family of highly conserved urea-hydrolyzing enzymes. A common feature of these enzymes is the presence of two Lewis acid nickel ions and a reactive cysteine residue in the active site. The H+/K(+)-ATPase inhibitor omeprazole is a prodrug of a sulfenamide which covalently modifies cysteine residues on the luminal side of the H+/K(+)-ATPase of gastric parietal cells. Omeprazole and eight analogues were selected based on their chemical, electronic, and kinetic properties, and each was incubated with viable H. pylori in phosphate-buffered saline at pH 7.4 for 30 min, after which 100 mM urea was added and the amount of ammonia formed analyzed after a further 10 min. Inhibition between 0% and 100% at a 0.1 mM concentration was observed for the different analogues and could be expressed as a function of the pKa-value of the pyridine, the pKa-value of the benzimidazole, the overall lipophilicity, and, most importantly, the rate of sulfenamide formation, in a quantitative structure-activity relationship. The inhibition was potentiated by a lower pH (favoring the formation of the sulfenamide) but abolished in the presence of beta-mercaptoethanol (a scavenger of the sulfenamide). Structural analogues incapable of yielding the sulfenamide did not inhibit ammonia production. Treatment of Helicobacter felis-infected mice with 230 mumol/kg flurofamide b.i.d. for 4 weeks, known to potently inhibit urease activity in vivo, as a means of eradicating the infection, was tested and compared with the effect of 125 mumol/kg omeprazole b.i.d. for 4 weeks. Neither treatment proved efficacious.

  DOI：

  10.1021/jm00025a008
• 作为产物：
  描述：

  2,3-二甲基-4-氯吡啶-N-氧化物 在 氯化亚砜 、 sodium hydride 作用下， 以 氯仿 、 二甲基亚砜 为溶剂， 反应 9.0h， 生成 2-[(4-ethoxy-3-methylpyridin-2-yl)-methylthio]-1H-benzimidazole
  参考文献：
  名称：

  HELICOBACTER PYLORI ERADICATING AGENT HAVING INHIBITORY ACTIVITY ON GASTRIC ACID SECRETION

  摘要：

  公开号：

  EP2103608B1

文献信息

• NOVEL SOLVATE OF DEXLANSOPRAZOLE
  申请人：Reguri Buchi Reddy

  公开号：US20130012714A1

  公开（公告）日：2013-01-10

  The present invention provides novel solvate of dexlansoprazole (or R-lansoprazole), particularly diol solvate and its hydrate form of dexlansoprazole (or R-lansoprazole) which is chemically known as (R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole compound of the formula (I), as well as processes for the preparation thereof. The said solvates are useful in the preparation of dexlansoprazole with enhanced chiral purity and better HPLC purity with less sulphone impurity content.

  本发明提供了新型的地塞拉唑（或R-兰索拉唑）溶剂化物，特别是地塞拉唑（或R-兰索拉唑）的二醇溶剂化物及其水合物形式，其化学名称为（R）-2-[[[3-甲基-4-(2,2,2-三氟乙氧基)-2-吡啶基]甲基]亚磺酰基]-1H-苯并咪唑化合物式（I），以及其制备方法。所述溶剂化物在地塞拉唑的制备中具有增强的手性纯度和更好的高效液相色谱纯度，同时硫酮杂质含量更少。
• Helicobacter pylori eradicating agent having inhibitory activity on gastric acid secretion
  申请人：Ito Masaharu

  公开号：US08778975B2

  公开（公告）日：2014-07-15

  Disclosed are: a compound which is stable in an acid, has an antibacterial effect against a bacterium Helicobacter pylori, can exert a satisfactory level of an antibacterial effect when used singly, does not affect an enteric bacterium, has an antibacterial effect against a bacterium resistant to an antibacterial agent, and has an inhibitory effect on gastric acid secretion; and a pharmaceutical composition comprising the compound. Specifically disclosed are: a compound represented by the general formula (I) or a salt thereof; and a pharmaceutical composition comprising the compound or the salt thereof: wherein R represents a linear alkyl group having 4 to 8 carbon atoms, preferably 5 to 7 carbon atoms.

  本发明涉及一种在酸性条件下稳定，对幽门螺杆菌具有抗菌作用，单独使用时能够发挥满意的抗菌作用，不影响肠道细菌，对抗抗菌剂抗性菌株具有抗菌作用，并且对胃酸分泌具有抑制作用的化合物；以及包含该化合物的制药组合物。具体揭示了一种由通式（I）表示的化合物或其盐；以及包含该化合物或其盐的制药组合物：其中R表示具有4至8个碳原子的线性烷基，优选5至7个碳原子。
• US8778975B2
  申请人：——

  公开号：US8778975B2

  公开（公告）日：2014-07-15
• Structure-Activity Relationship of Omeprazole and Analogs as Helicobacter pylori Urease Inhibitors
  作者：Thomas C. Kuehler、Jan Fryklund、Nils-ke Bergman、Jessica Weilitz、Adrian Lee、Haakan Larsson

  DOI：10.1021/jm00025a008

  日期：1995.12

  Helicobacter pylori urease belongs to a family of highly conserved urea-hydrolyzing enzymes. A common feature of these enzymes is the presence of two Lewis acid nickel ions and a reactive cysteine residue in the active site. The H+/K(+)-ATPase inhibitor omeprazole is a prodrug of a sulfenamide which covalently modifies cysteine residues on the luminal side of the H+/K(+)-ATPase of gastric parietal cells. Omeprazole and eight analogues were selected based on their chemical, electronic, and kinetic properties, and each was incubated with viable H. pylori in phosphate-buffered saline at pH 7.4 for 30 min, after which 100 mM urea was added and the amount of ammonia formed analyzed after a further 10 min. Inhibition between 0% and 100% at a 0.1 mM concentration was observed for the different analogues and could be expressed as a function of the pKa-value of the pyridine, the pKa-value of the benzimidazole, the overall lipophilicity, and, most importantly, the rate of sulfenamide formation, in a quantitative structure-activity relationship. The inhibition was potentiated by a lower pH (favoring the formation of the sulfenamide) but abolished in the presence of beta-mercaptoethanol (a scavenger of the sulfenamide). Structural analogues incapable of yielding the sulfenamide did not inhibit ammonia production. Treatment of Helicobacter felis-infected mice with 230 mumol/kg flurofamide b.i.d. for 4 weeks, known to potently inhibit urease activity in vivo, as a means of eradicating the infection, was tested and compared with the effect of 125 mumol/kg omeprazole b.i.d. for 4 weeks. Neither treatment proved efficacious.
• HELICOBACTER PYLORI ERADICATING AGENT HAVING INHIBITORY ACTIVITY ON GASTRIC ACID SECRETION
  申请人：Arigen Pharmaceuticals, Inc.

  公开号：EP2103608B1

  公开（公告）日：2012-08-29