4H-嘧啶并[2,1-b]喹唑啉-4-酮,6,11-二氢-11-甲基- | 97148-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 4H-嘧啶并[2,1-b]喹唑啉-4-酮,6,11-二氢-11-甲基-
• 英文名称: 2-(Ethylsulfanyl)-6-methoxy-1h-benzimidazole
• 英文别名: 2-ethylsulfanyl-6-methoxy-1H-benzimidazole
• CAS: 97148-48-6
• 化学式: C₁₀H₁₂N₂OS
• mdl: MFCD04307717
• 分子量: 208.284
• InChiKey: CZSQXDMMIUJHSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2-巯基-5-甲氧基苯并咪唑	2-Mercapto-5-methoxybenzimidazole	37052-78-1	C8H8N2OS	180.23

反应信息

• 作为反应物：
  描述：

  3-[4-(2-氯乙基)-1-哌啶基]-6-甲基哒嗪 、 碘甲烷 、 4H-嘧啶并[2,1-b]喹唑啉-4-酮,6,11-二氢-11-甲基- 在 sodium hydride 、 三溴化硼 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-Ethylsulfanyl-1-methyl-6-[2-[1-(6-methylpyridazin-3-yl)piperidin-4-yl]ethoxy]benzimidazole 、 2-Ethylsulfanyl-1-methyl-5-[2-[1-(6-methylpyridazin-3-yl)piperidin-4-yl]ethoxy]benzimidazole
  参考文献：
  名称：

  2-Ethoxybenzoxazole as a bioisosteric replacement of an ethyl benzoate group in a human rhinovirus (HRV) capsid binder

  摘要：

  A series of pyridazinylpiperidinyl capsid-binding compounds with novel bicyclic substituents were synthesized and screened against human rhinovirus (HRV). Several 2-alkoxy- and 2-alkylthio-benzoxazole and benzothiazole derivatives showed excellent anti-HRV activity. When tested against a panel of 16 representative HRV types the 2-ethoxybenzoxazole derivative 13 was found to have superior HRV activity (median EC50 3.88 ng/mL) to known capsid-binders Pleconaril and Pirodavir. Compound 13 illustrates that a 2-alkoxybenzoxazole group can be an effective bioisostere for a benzoate ester or benzaldehyde oxime ether functionality. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.054
• 作为产物：
  描述：

  2-巯基-5-甲氧基苯并咪唑 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以47.4%的产率得到4H-嘧啶并[2,1-b]喹唑啉-4-酮,6,11-二氢-11-甲基-
  参考文献：
  名称：

  Ligand-Based Design of a Potent and Selective Inhibitor of Cytochrome P450 2C19

  摘要：

  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.

  DOI：

  10.1021/jm201346g

文献信息

• New Compounds Useful for the Synthesis of S- and R-Omeprazole and a Process for Their Preparation
  申请人：von Unge Sverker

  公开号：US20090253911A1

  公开（公告）日：2009-10-08

  The present invention relates to an improved method for the synthesis of the (S)- or (R)-enantiomer of omeprazole, characterized in that 2-[[(4-X-3,5-dimethylpyridin-2-yl)methyl]thio]-5-methoxy-1H-benzimidazole or 2-[[(4-X-3,5-dimethyl-1-oxidopyridin-2-yl)methyl]thio]-5-methoxy-1H-benzimidazole, wherein X is a leaving group, is oxidized into the corresponding sulphoxide which is obtained as a crystalline compound. Recrystallisation of the thus obtained sulphoxide results in a compound of enhanced chemical and optical purity, which is subsequently transformed into the (S)- or (R)-enantiomer of omeprazole.

  本发明涉及一种改进的奥美拉唑（omeprazole）（S）或（R）对映体合成方法，其特征在于将2-[[(4-X-3,5-二甲基吡啶-2-基)甲基]硫基]-5-甲氧基-1H-苯并咪唑或2-[[(4-X-3,5-二甲基-1-氧代吡啶-2-基)甲基]硫基]-5-甲氧基-1H-苯并咪唑，其中X是一个离去基团，氧化为相应的磺酸氧化物，该磺酸氧化物以晶体化合物的形式获得。因此获得的磺酸氧化物再结晶，可得到化学和光学纯度更高的化合物，随后转化为奥美拉唑（S）或（R）对映体。
• Compounds Useful for the Synthesis of S- and R-Omeprazole and a Process for Their Preparation
  申请人：Fregler Christina

  公开号：US20080255199A1

  公开（公告）日：2008-10-16

  The present invention relates to an improved method for the synthesis of the (S)- or (R)-enantiomer of omeprazole, characterized in that 2-[[(4-X-3,5-dimethylpyridin-2-yl)methyl]thio]-5-methoxy-1H-benzimidazole or 2-[[(4-X-3,5-dimethyl-1-ox-idopyridin-2-yl) methyl]thio]-5-methoxy-1H-benzimidazole, wherein X is a leaving group, is oxidized into the corresponding sulphoxide which is obtained as a crystalline compound. Recrystallisation of the thus obtained sulphoxide results in a compound of enhanced chemical and optical purity, which is subsequently transformed into the (S)- or (R)-enantiomer of omeprazole.

  本发明涉及一种改进的奥美拉唑（omeprazole）（S）或（R）对映体合成方法，其特征在于将2-[[(4-X-3,5-二甲基吡啶-2-基)甲基]硫基]-5-甲氧基-1H-苯并咪唑或2-[[(4-X-3,5-二甲基-1-氧代吡啶-2-基)甲基]硫基]-5-甲氧基-1H-苯并咪唑（其中X是一个离去基团）氧化成相应的亚砜，该亚砜以结晶化合物的形式得到。因此获得的亚砜再结晶可得到化学和光学纯度提高的化合物，随后将其转化为（S）或（R）对映体的奥美拉唑。
• Compounds Useful for the Synthesis of S- and R-Omeprazole and a Process for their Preparation
  申请人：Unge Von Sverker

  公开号：US20070161682A1

  公开（公告）日：2007-07-12

  The present invention relates to an improved method for the synthesis of the (S)- or (R)-enantiomer of omeprazole, characterized in that 2-[[(4-X-3,5-dimethylpyridin-2-yl)methyl]thio]-5-methoxy-1H-benzimidazole or 2-[[(4-X-3,5-dimethyl-1-oxidopyridin-2-yl)methyl]thio]-5-methoxy-1H-benzimidazole, wherein X is a leaving group, is oxidized into the corresponding sulphoxide which is obtained as a crystalline compound. Recrystallisation of the thus obtained sulphoxide results in a compound of enhanced chemical and optical purity, which is subsequently transformed into the (S)- or (R)-enantiomer of omeprazole.

  本发明涉及一种改进的奥美拉唑（omeprazole）的(S)-或(R)-对映体合成方法，其特征在于将2-[[(4-X-3,5-二甲基吡啶-2-基)甲基]硫基]-5-甲氧基-1H-苯并咪唑或2-[[(4-X-3,5-二甲基-1-氧代吡啶-2-基)甲基]硫基]-5-甲氧基-1H-苯并咪唑（其中X为离去基）氧化为相应的亚砜，所得的亚砜为结晶化合物。因此得到的亚砜经再结晶后，可得到化学和光学纯度更高的化合物，随后转化为(S)-或(R)-奥美拉唑的对映体。
• Substituted benzimidazole derivatives as D-amino acid oxidase (DAAO) inhibitors
  申请人：NATIONAL TAIWAN UNIVERSITY

  公开号：US11370775B2

  公开（公告）日：2022-06-28

  The present invention provides novel substituted benzimidazole derivatives of formula (I) used as DAAO inhibitors and for treatment and/or prevention of neurological disorders.

  本发明提供了新型取代的式 (I) 苯并咪唑衍生物，可用作 DAAO 抑制剂，用于治疗和/或预防神经系统疾病。
• NOVEL SUBSTITUTED BENZIMIDAZOLE DERIVATIVES AS D-AMINO ACID OXIDASE (DAAO) INHIBITORS
  申请人：TSENG Yufeng Jane

  公开号：US20200361894A1

  公开（公告）日：2020-11-19

  The present invention provides novel substituted benzimidazole derivatives used as DAAO inhibitors and for treatment and/or prevention of neurological disorders.