2-<(4-methoxy-6,7,8,9-tetrahydro-5H-cycloheptapyridin-9-yl)thio>-1H-benzimidazole | 136176-91-5

• 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-methoxy-6,7,8,9-tetrahydro-5H-cycloheptapyridin-9-yl)thio>-1H-benzimidazole
• 英文别名: 2-(4-methoxy-6,7,8,9-tetrahydro-5H-cycloheptapyridin-9-ylthio)-1H-benzimidazole；9-(1H-benzimidazol-2-ylsulfanyl)-4-methoxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine
• CAS: 136176-91-5
• 化学式: C₁₈H₁₉N₃OS
• 分子量: 325.434
• InChiKey: KDBQPLMPBDHVEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 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-methoxy-6,7,8,9-tetrahydro-5H-cycloheptapyridin-9-yl)thio>-1H-benzimidazole 以89%的产率得到
  参考文献：
  名称：

  Yamada Shin-ichi, Goto Takao, Shimanuki Eiji, Narita Sen-ichi, Chem. and Pharm. Bull, 42 (1994) N 3, S 718-720

  摘要：

  DOI：
• 作为产物：
  描述：

  4-methoxy-6,7,8,9-tetrahydro-5H-cycloheptapyridine N-oxide 在 sodium hydroxide 、 氯化亚砜 、 乙酸酐 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 生成 2-<(4-methoxy-6,7,8,9-tetrahydro-5H-cycloheptapyridin-9-yl)thio>-1H-benzimidazole
  参考文献：
  名称：

  Syntheses and Antiulcer Activities of Novel 2-((6,7,8,9-Tetrahydro-5H-cyclohepta(b)pyridin-9-yl)sulfin-yl)-1H-benzimidazole Analogues.

  摘要：

  一项关于一系列含有环烯丙[b]吡啶基团的苯并咪唑衍生物的合成研究已完成。在这些合成的化合物中，发现一种具有6, 7, 8, 9-四氢-5H-环七烯[b]吡啶基团的新型抗胃酸剂（TY-11345）在(H++K+)-ATP酶抑制活性和抗分泌能力方面优于奥美拉唑。

  DOI：

  10.1248/cpb.42.718

文献信息

• Synthetic Study of 2-((6,7,8,9-Tetrahydro-5H-cyclohepta(b)pyridin-9-yl)-sulfinyl)-1H-benzimidazole Analogs and Their Biological Properties as Novel Proton Pump Inhibitors.
  作者：Shin-ichi YAMADA、Takao GOTO、Takaji YAMAGUCHI、Kazuyuki AIHIARA、Kentaro KOGI、Sen-ichi NARITA

  DOI：10.1248/cpb.43.421

  日期：——

  series of 2-[(cycloalka[b]pyridinyl)sulfinyl]-1H-benzimidazoles (11) was synthesized and tested for antisecretory activity against pentagastrin-induced gastric acid secretion in rats. A novel benzimidazole derivative containing a cyclohepta[b]pyridine moiety was found to be the most potent among the congeners, which included five- to eight-membered cycloalka[b]pyridine ring systems. Some 2-[(6,7,8,9

  合成了一系列的2-[（（环烷基[b]吡啶基）亚磺酰基] -1H-苯并咪唑）（11），并测试了其对五肽胃泌素诱导的胃酸分泌的抗分泌活性。发现一种新的含有环庚[b]吡啶部分的苯并咪唑衍生物在同类物中最有效，其包括五至八元环烷基[b]吡啶环系统。某些在芳香环上带有各种取代基的2-[（6,7,8,9-四氢-5H-环庚[b]吡啶-9-基）亚磺酰基] -1H-苯并咪唑类似物（14）比奥美拉唑（ 1）在体内进行生物检查。选择非对映异构体TY-11345（28Ba）作为有前途的试剂进行进一步评估。
• Biological Activities of Four Stereoisomers of 2-(4-Methoxy-6,7,8,9-tetrahydro-5H-cyclohepta(b)pyridin-9-ylsulfinyl)-1H-benzimidazole Sodium Salt and Acid-Induced Transformations: Novel Proton Pump Inhibitor.
  作者：Shin-ichi YAMADA、Takaji YAMAGUCHI、Kazuyuki AIHARA、Akihiko NAGAI、Kentaro KOGI、Sen-ichi NARITA

  DOI：10.1248/cpb.44.215

  日期：——

  The sodium salts (5) of four stereoisomeric benzimidazolylsulfoxides, (Ss, 9R)-(-)-4, (Rs, 9S)-(+)-4, (Ss, 9S)-(-)-4 and (Rs, 9R)-(+)-4, were prepared from optically pure sulfides, (+)-8 and (-)-8. The sulfoxides (4) were transformed into sulfenamides (6) and symmetric disulfides (9) under acidic conditions, without any change of stererochemical configuration at the α-carbon bearing the sulfinyl group. No significant difference was observed among the four stereoisomers in inhibitory activity towards (H++K+)-ATPase in vitro. However, (Ss, 9R)-(-)-5 showed more long-lasting antisecretion activity in vivo than that of another enantiomer, (Rs, 9S)-(+)-5.

  四种立体异构体苯并咪唑基亚砜（Ss，9R）-（-）-4、（Rs，9S）-（+）-4、（Ss，9S）-（-）-4和（Rs，9R）-（+）-4的钠盐（5）由光学纯硫化物（+）-8和（-）-8制备而成。在酸性条件下，亚砜（4）转化为亚磺酰胺（6）和对称二硫醚（9），但带有亚磺酰基的α-碳的立体化学结构没有任何变化。体外实验中，四种立体异构体对（H++K+）-ATP酶的抑制活性没有显著差异。然而，（Ss，9R）-（-）-5在体内表现出比另一种对映异构体（Rs，9S）-（+）-5更持久的抗分泌活性。
• Synthesis and Isomerization of Optical Active 2-((6,7,8,9-Tetrahydro-5H-cyclohepta(b)pyridin-9-yl)-sul-finyl) - 1H-benzimidazole Analogs.
  作者：Shin-ichi YAMADA、Sen-ichi NARITA

  DOI：10.1248/cpb.42.1679

  日期：——

  Four stereoisomers, (Rs, 9R)-(+)-5, (Ss, 9R)-(-)-5, (Ss, 9S)-(-)-5 and (Rs, 9S)-(+)-5, were prepared from optically active (R)-(+)-3 and (S)-(-)-3, and their absolute structures were unambiguously determined by X-ray crystallographic analysis of (Ss, 9R)-(-)-5. Epimerization of the carbon bearing the sulfinyl group of 5 could be carried out with NaOCH3. At the same time, it found that the stereochemistries of the sulfinyl group of (Rs, 9R)-(+)-5 and (Ss, 9S)-(-)-5 were spontaneously inverted in MeOH solution at room temperature.

  通过对 (Ss，9R)-(-)-5 进行 X 射线晶体分析，明确确定了它们的绝对结构。5 中带有亚磺酰基的碳可以用 NaOCH3 进行外聚。同时还发现，在室温下的 MeOH 溶液中，(Rs, 9R)-(+)-5 和 (Ss, 9S)-(-)-5 的亚磺酰基的立体化学结构自发颠倒。
• PROCESS FOR SYNTHESIS OF SUBSTITUTED SULPHOXIDES
  申请人：AstraZeneca AB

  公开号：EP0773940B1

  公开（公告）日：2003-06-04
• SYNTHESIS OF PRAZOLE COMPOUNDS
  申请人：CODEXIS, INC.

  公开号：US20160076008A1

  公开（公告）日：2016-03-17

  The present disclosure relates to non-naturally occurring monooxygenase polypeptides useful for preparing prazole compounds, polynucleotides encoding the polypeptides, and methods of using the polypeptides.