2-((4-methoxybenzyl)thio)-1H-benzo[d]imidazole

• 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-methoxybenzyl)thio)-1H-benzo[d]imidazole
• 英文别名: 2-(4-Methoxy-benzylsulfanyl)-1H-benzoimidazole；2-[(4-methoxyphenyl)methylsulfanyl]-1H-benzimidazole
• 化学式: C₁₅H₁₄N₂OS
• mdl: MFCD00520507
• 分子量: 270.355
• InChiKey: SFNVMKKUISRNFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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-((4-methoxybenzyl)thio)-1H-benzo[d]imidazole 、 alkaline earth salt of/the/ methylsulfuric acid 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以63 %的产率得到1-ethyl-2-((4-methoxybenzyl)thio)-1H-benzo[d]imidazole
  参考文献：
  名称：

  天然产物中的基序作为有用的支架来获得新型苯并[d]咪唑基大麻素 2 型 (CB2) 受体激动剂。

  摘要：

  内源性大麻素系统（ECS）是哺乳动物体内稳态的广谱调节剂，为多种病理学提供治疗机会。它的两个主要受体，1 型大麻素 (CB1) 和 2 型大麻素 (CB2) 受体，介导抗炎反应；然而，它们不同的表达模式使得 CB2 选择性配体的开发在治疗上更具吸引力。苯并[d]咪唑环被认为是药物发现中的特殊支架，并已证明其在开发具有不同药理学特性的分子中的多功能性。另一方面，大麻的主要精神活性成分，δ-9-四氢大麻酚（THC），在结构上可以描述为与芳香族多酚（间苯二酚）结构融合的脂肪族萜类基序。受这种植物大麻素结构的启发，我们将不同的天然产物基序与苯并[d]咪唑支架结合起来，获得了针对 CB2 受体的新化合物库。在这里，我们合成了 26 种新化合物，其中 15 种具有 CB2 结合作用，3 种显示出有效的激动剂活性。SAR分析表明，由带负电的原子连接的苯并[d]咪唑环的2位上存在大体积的脂肪族或芳香族天然

  DOI：

  10.3390/ijms241310918
• 作为产物：
  描述：

  1H-苯并咪唑-2-硫醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以37%的产率得到2-((4-methoxybenzyl)thio)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Synthesis and preliminary evaluation of benzimidazole derivatives as antimicrobial agents

  摘要：

  A series of 2-alkylsulphanylbenzimidazoles was synthesised and the compounds were evaluated for their in vitro antimicrobial activity. The structures of the compounds were confirmed by H-1-NMR and IR data, and their purity by elemental analysis. Antimycobacterial activities against Mycobacterium tuberculosis and non-tuberculous mycobacteria as well as antifungal activities against Candida albicans, Candida tropicalis, Candida krusei, Candida glabrata, Trichosporon beigelii, Trichophyton mentagrophytes and Aspergillus fumigatus were expressed as the corresponding MIC values. The substances exhibited appreciable antimycobacterial activity, in particular, against non-tuberculous mycobacteria. The activity of the most active compound in the set, 3,5-dinitro derivative 4t, exceeded that of the standard isoniazide against M. kansasii and M. avium. The antifungal activities of the compounds were relatively low. A weak antifungal effect was observed against the dermatophyte Trichophyton mentagrophytes. None of the compounds showed significant inhibitory activity against yeasts. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01342-9

文献信息

• Three‐Component Synthesis of 2‐Substituted Thiobenzoazoles Using Tetramethyl Thiuram Monosulfide (TMTM) as Thiocarbonyl Surrogate
  作者：Xi Wang、Chun‐Yan Wu、Yue‐Sheng Li、Zhi‐Bing Dong

  DOI：10.1002/ejoc.202001214

  日期：2020.11.22

  A metal‐free synthesis of 2‐benzyl/allyl‐substituted thiobenzoazoles was developed starting from tetramethyl thiuram monosulfide (TMTM) which served as thiocarbonyl surrogate. By using 2‐aminophenols (or 2‐aminothiophenols, or 1,2‐phenylenediamines) and TMTM as starting materials, 2‐mercaptobenzoazoles could be synthesized efficiently, and the subsequent C–S bond formation with allyl/benzyl halides

  从用作硫代羰基替代物的四甲基秋兰姆单硫化物（TMTM）出发，开发了2-苄基/烯丙基取代的硫代苯并恶唑的无金属合成方法。通过使用2-氨基苯酚（或2-氨基硫酚或1,2-苯二胺）和TMTM作为起始原料，可以高效合成2-巯基苯并恶唑，随后与烯丙基/苄基卤化物的CS键形成最终产物（ 2-烯丙基/苄基取代的硫代苯并唑），具有良好或优异的收率。
• TREATMENT OF DUCHENNE MUSCULAR DYSTROPHY
  申请人：Wynne Graham Michael

  公开号：US20090075938A1

  公开（公告）日：2009-03-19

  There are disclosed compound of Formula (1): A 1 , A 2 , A 3 and A 4 which may be the same or different, represent N or CR 1 , X is a divalent group selected from O, S(O) n , C═W, NR 4 , NC(═O)R 5 and CR 6 R 7 , W is O, S, NR 20 , Y is N or CR 8 , one of R 4 , R 5 , R 6 , R 8 , R 9 and NR 20 represents -L-R 3 , in which L is a single bond or a linker group, additionally, R 1 , R 3 -R 9 , which may be the same or different, independently represent hydrogen or a substituent and R 20 represents hydrogen, hydroxyl, alkyl optionally substituted by aryl, alkoxy optionally substituted by aryl, aryl, CN, optionally substituted alkoxy, optionally substituted aryloxy, optionally substitute alkanoyl, optionally substituted aroyl, NO 2 , NR 30 R 31 , in which R 30 and R 31 , which may be the same or different, represent hydrogen, optionally substituted alkyl or optionally substituted aryl; additionally, one of R 30 and R 31 may represent optionally substituted alkanoyl or optionally substituted aroyl, n represents an integer from 0 to 2, in addition, when an adjacent pair of A 1 -A 4 each represent CR 1 , then the adjacent carbon atoms, together with their substituents may form a ring B, when X is CR 6 R 7 , R 6 and R 7 , together with the carbon atom to which they are attached may form a ring C, or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the therapeutic and/or prophylactic treatment of Duchenne muscular dystrophy, Becker muscular dystrophy or cachexia.

  公式（1）的化合物被揭示：A1，A2，A3和A4，它们可以相同或不同，代表N或CR1，X是从O，S（O）n，C═W，NR4，NC（═O）R5和CR6R7中选择的二价基团，W是O，S，NR20，Y是N或CR8，R4，R5，R6，R8，R9和NR20中的一个表示-L-R3，在其中L是单键或连接基团，此外，R1，R3-R9可以相同或不同，独立地表示氢或取代基，R20表示氢，羟基，可以用芳基取代的烷基，可以用芳基取代的烷氧基，芳基，CN，可以用芳基取代的烷氧基，可以用芳基取代的芳氧基，可以用取代基取代的烷酰基，可以用取代基取代的芳酰基，NO2，NR30R31，在其中R30和R31可以相同或不同，表示氢，可选地取代的烷基或可选地取代的芳基；此外，R30和R31中的一个可以表示可选地取代的烷酰基或可选地取代的芳酰基，n表示从0到2的整数，另外，当相邻的A1-A4中的一对表示CR1时，那么相邻的碳原子及其取代基可以形成环B，当X为CR6R7时，R6和R7与它们附着的碳原子一起可以形成环C，或其药学上可接受的盐，在制造用于治疗和/或预防杜氏肌萎缩症，贝克肌萎缩症或消瘦症的药物时使用。
• Drug Combinations for the Treatment of Duchenne Muscular Dystrophy
  申请人：Wynne Graham Michael

  公开号：US20110195932A1

  公开（公告）日：2011-08-11

  Combinations comprising (or consisting essentially of) one or more compounds of formula (1) with one or more ancillary agents, to processes for preparing the combinations, and to various therapeutic uses of the combinations. Also provided are pharmaceutical compositions containing the combinations as well as a method of treatment of Duchenne muscular dystrophy, Becker muscular dystrophy or cachexia using the combinations.

  本发明涉及与一种或多种化合物（1）的一个或多个辅助剂组合的组合物，以制备这些组合物的过程，以及这些组合物的各种治疗用途。还提供了包含这些组合物的制药组合物，以及使用这些组合物治疗杜氏肌营养不良症、贝克肌营养不良症或消瘦的方法。
• DRUG COMBINATIONS FOR THE TREATMENT OF DUCHENNE MUSCULAR DYSTROPHY
  申请人：Summit Corporation PLC

  公开号：US20140011782A1

  公开（公告）日：2014-01-09

  Combinations comprising (or consisting essentially of) one or more compounds of formula (1) with one or more ancillary agents, to processes for preparing the combinations, and to various therapeutic uses of the combinations. Also provided are pharmaceutical compositions containing the combinations as well as a method of treatment of Duchenne muscular dystrophy, Becker muscular dystrophy or cachexia using the combinations.

  该专利涉及包含（或基本上由）一个或多个式（1）化合物和一个或多个辅助剂的组合物，以及制备这些组合物的方法，以及这些组合物的各种治疗用途。此外，还提供了包含这些组合物的药物组合物以及使用这些组合物治疗杜兴肌肉萎缩症，贝克肌肉萎缩症或消瘦症的方法。
• N-LINKED GLYCAN BIOSYNTHESIS MODULATORS
  申请人：Crawford Brett E.

  公开号：US20120100609A1

  公开（公告）日：2012-04-26

  Provided herein are N-linked glycan inhibitors, including modulators of N-linked glycan glycosylation, mannosidase, an N-linked glycan N-acetylglucosaminyl transferase, an N-linked glycan fucosyl transferase, an N-linked glycan galactosyl transferase, an N-linked glycan sialyl transferase, an N-linked glycan sulfotransferase, N-linked glycan glycophosphotransferase or a combination thereof.