5-methoxy-2-[(4-methylbenzyl)sulfanyl]-1H-benzimidazole | 309735-05-5

• 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: 5-methoxy-2-[(4-methylbenzyl)sulfanyl]-1H-benzimidazole
• 英文别名: 6-methoxy-2-[(4-methylphenyl)methylsulfanyl]-1H-benzimidazole
• CAS: 309735-05-5
• 化学式: C₁₆H₁₆N₂OS
• mdl: MFCD01953222
• 分子量: 284.382
• InChiKey: HRUYBRGMRSNLNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-巯基-5-甲氧基苯并咪唑 、 4-甲基苄溴 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以92%的产率得到5-methoxy-2-[(4-methylbenzyl)sulfanyl]-1H-benzimidazole
  参考文献：
  名称：

  BENZIMIDAZOLE INHIBITION OF BIOFILM FORMATION

  摘要：

  各种实施例涉及一种化合物，包括：其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11和R12各自独立地为氢、烷基、烯基、炔基、芳基、杂芳基、杂环基、烷氧基、芳氧基、杂芳氧基、烷氧羰基、芳氧羰基、杂芳氧羰基、烷基磺酰基、芳基磺酰基、氨基磺酰基、烷基羰基、芳基羰基、杂芳基羰基、酰基、酰胺基、氨基、烷基氨基、二烷基氨基、芳基氨基、羧酸盐（-CO2H）、氰基、硝基、-CONH2、杂芳基氨基、肟、烷氧肟、芳氧肟、氨基肟或卤素，当A、B、C、D、E、F、G、H、I、J、K、L、M、N、O、P和Q为碳时，X为O、NR（其中R为氢、烷基、芳基或酰基）、S、SO（亚砜）、SO2（砜）或C（R）2（其中R=H、烷基、芳基、烯基、炔基或酰基）；或者当A、B、C、D、E、F、G、H、I、J、K、L、M、N、O、P和Q各自独立地为氮时，R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11和R12各自独立地为氢或羟基，以及其药学上可接受的盐、酯和前药组合物。本发明还涉及使用这种化合物和组合物的方法。

  公开号：

  US20130345261A1

文献信息

• Benzimidazole inhibition of biofilm formation
  申请人：Waters Christopher

  公开号：US08710082B2

  公开（公告）日：2014-04-29

  The various embodiments relate to a compound comprising: wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, and R12 are each independently hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocyclyl, alkoxy, aryloxy, heteroaryloxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, amino, alkylamino, dialkylamino, arylamino, carboxylate (—CO2H), cyano, nitro, —CONH2, heteroarylamino, oxime, alkyloxime, aryloxime, amino-oxime or halogen when A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, P, and Q are carbon, and X is O, NR (where R is hydrogen, alkyl, aryl or acyl), S, SO (sulfoxide), SO2 (sulfone), or C(R)2 (where R=H, alkyl, aryl, alkenyl, alkynyl, or acyl); or wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, and R12 are each independently hydrogen or hydroxyl when A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, P, and Q are each independently nitrogen, and compositions, combinations, pharmaceutically acceptable salts, esters, and prodrugs thereof. The invention also relates to methods of using such compounds and compositions.

  各种实施方式涉及一种化合物，其包括：其中R1，R2，R3，R4，R5，R6，R7，R8，R9，R10，R11和R12各自独立地为氢，烷基，烯基，炔基，芳基，杂芳基，杂环基，烷氧基，芳氧基，杂芳氧基，烷氧羰基，芳氧羰基，杂芳氧羰基，烷基磺酰基，芳基磺酰基，氨基磺酰基，烷基羰基，芳基羰基，杂芳基羰基，酰基，酰胺基，氨基，烷基氨基，二烷基氨基，芳基氨基，羧酸盐（-CO2H），氰基，硝基，-CONH2，杂芳基氨基，肟，烷氧肟，芳氧肟，氨基肟或卤素，当A，B，C，D，E，F，G，H，I，J，K，L，M，N，O，P和Q为碳时，X为O，NR（其中R为氢，烷基，芳基或酰基），S，SO（亚砜），SO2（砜）或C（R）2（其中R = H，烷基，芳基，烯基，炔基或酰基）; 或其中R1，R2，R3，R4，R5，R6，R7，R8，R9，R10，R11和R12各自独立地为氢或羟基，当A，B，C，D，E，F，G，H，I，J，K，L，M，N，O，P和Q各自独立地为氮时，以及其组合物，组合物，药学上可接受的盐，酯和前药。本发明还涉及使用此类化合物和组合物的方法。
• 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.
• BENZIMIDAZOLE INHIBITION OF BIOFILM FORMATION
  申请人：Waters Christopher

  公开号：US20130345261A1

  公开（公告）日：2013-12-26

  The various embodiments relate to a compound comprising: wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 are each independently hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocyclyl, alkoxy, aryloxy, heteroaryloxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, amino, alkylamino, dialkylamino, arylamino, carboxylate (—CO 2 H), cyano, nitro, —CONH 2 , heteroarylamino, oxime, alkyloxime, aryloxime, amino-oxime or halogen when A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, P, and Q are carbon, and X is O, NR (where R is hydrogen, alkyl, aryl or acyl), S, SO (sulfoxide), SO 2 (sulfone), or C(R) 2 (where R═H, alkyl, aryl, alkenyl, alkynyl, or acyl); or wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 are each independently hydrogen or hydroxyl when A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, P, and Q are each independently nitrogen, and compositions, combinations, pharmaceutically acceptable salts, esters, and prodrugs thereof. The invention also relates to methods of using such compounds and compositions.

  各种实施例涉及一种化合物，包括：其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11和R12各自独立地为氢、烷基、烯基、炔基、芳基、杂芳基、杂环基、烷氧基、芳氧基、杂芳氧基、烷氧羰基、芳氧羰基、杂芳氧羰基、烷基磺酰基、芳基磺酰基、氨基磺酰基、烷基羰基、芳基羰基、杂芳基羰基、酰基、酰胺基、氨基、烷基氨基、二烷基氨基、芳基氨基、羧酸盐（-CO2H）、氰基、硝基、-CONH2、杂芳基氨基、肟、烷氧肟、芳氧肟、氨基肟或卤素，当A、B、C、D、E、F、G、H、I、J、K、L、M、N、O、P和Q为碳时，X为O、NR（其中R为氢、烷基、芳基或酰基）、S、SO（亚砜）、SO2（砜）或C（R）2（其中R=H、烷基、芳基、烯基、炔基或酰基）；或者当A、B、C、D、E、F、G、H、I、J、K、L、M、N、O、P和Q各自独立地为氮时，R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11和R12各自独立地为氢或羟基，以及其药学上可接受的盐、酯和前药组合物。本发明还涉及使用这种化合物和组合物的方法。