2-butylsulfanyl-6-methoxy-1H-benzimidazole | 933910-44-2

• 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-butylsulfanyl-6-methoxy-1H-benzimidazole
• CAS: 933910-44-2
• 化学式: C₁₂H₁₆N₂OS
• 分子量: 236.338
• InChiKey: SUMJDTVJSTZJFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-butylsulfanyl-6-methoxy-1H-benzimidazole 、 6-氯-3-(2-溴乙酰基)-2-色烯酮 在 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以65%的产率得到3-(2-(2-(butylthio)-5-methoxy-1H-benzo[d]imidazol-1-yl)acetyl)-6-chloro-2H-chromen-2-one
  参考文献：
  名称：

  Preparation of Benzimidazole Based Coumarin Derivatives as Antimicrobial and Antioxidant Agents

  摘要：

  本研究旨在提供苯并咪唑基香豆素作为抗微生物和抗氧化剂。化合物3a-3j通过将化合物1a-1b与化合物2a-2e在丙酮中反应而制备。通过光谱分析证明了3a-3j的化学结构。通过连续稀释程序记录了3a-3j的最小抑制浓度。抗氧化潜力通过1,1-二苯基-2-苯硝基肼法进行评估。化合物1a和3g被确定为有前途的抗微生物剂。大多数化合物显示出中等抗氧化活性。结论是，用2-戊硫基或2-己硫基取代2-丁硫基基团，以及用另一种接近的类黄酮结构替换香豆素结构可能会提供更好的双重抗微生物/抗氧化剂化合物。

  DOI：

  10.13005/ojc/350420
• 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70.4%的产率得到2-butylsulfanyl-6-methoxy-1H-benzimidazole
  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

• Preparation of Benzimidazole Based Coumarin Derivatives as Antimicrobial and Antioxidant Agents
  作者：Mohd. Imran

  DOI：10.13005/ojc/350420

  日期：2019.8.31

  The aim of the present work was to afford benzimidazole-based coumarins as antimicrobial and antioxidant agents. The compounds 3a-3j were prepared by reaction the compounds 1a-1b with the compounds 2a-2e in acetone. Chemical structures of 3a-3j were proven by their spectral analysis. Minimum inhibitory concentrations of 3a-3j were recorded by serial dilution procedure. Antioxidant potential was assessed by the 1,1-diphenyl-2-picrylhydrazyl method. Compounds 1a and 3g were identified as promising antimicrobial agents. Most of the compounds displayed moderate antioxidant activity. It has been concluded that the replacement of the 2-butylthio group with 2-pentylthio or 2-hexylthio substituents and the coumarin structure with another close flavonoid structure may provide better dual antimicrobial/antioxidant compounds.

  本研究旨在提供苯并咪唑基香豆素作为抗微生物和抗氧化剂。化合物3a-3j通过将化合物1a-1b与化合物2a-2e在丙酮中反应而制备。通过光谱分析证明了3a-3j的化学结构。通过连续稀释程序记录了3a-3j的最小抑制浓度。抗氧化潜力通过1,1-二苯基-2-苯硝基肼法进行评估。化合物1a和3g被确定为有前途的抗微生物剂。大多数化合物显示出中等抗氧化活性。结论是，用2-戊硫基或2-己硫基取代2-丁硫基基团，以及用另一种接近的类黄酮结构替换香豆素结构可能会提供更好的双重抗微生物/抗氧化剂化合物。
• 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.