1-(2,4,6-triisopropylphenylsulfonyl)-1H-benzo[d]imidazole | 294874-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2,4,6-triisopropylphenylsulfonyl)-1H-benzo[d]imidazole
• 英文别名: 1-[2,4,6-Tri(propan-2-yl)phenyl]sulfonylbenzimidazole
• CAS: 294874-59-2
• 化学式: C₂₂H₂₈N₂O₂S
• 分子量: 384.543
• InChiKey: AYXOZMQPSXGAPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2,4,6-triisopropylphenylsulfonyl)-1H-benzo[d]imidazole 、 二环己基氯化膦 在 正丁基锂 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.25h， 以77%的产率得到2-(dicyclohexylphosphino)-1-(2,4,6-triisopropylphenylsulfonyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  [EN] NOVEL PHOSPHINES, SYNTHESIS THEREOF AND THEIR USE IN CATALYSIS
  [FR] NOUVELLES PHOSPHINES, LEUR SYNTHÈSE ET LEUR UTILISATION DANS LA CATALYSE

  摘要：

  本发明涉及一种新型的苯并咪唑基/咪唑基膦配体，通过简单的一锅法制备这种配体的方法，以及这些配体在催化反应中的应用。

  公开号：

  WO2015039606A1
• 作为产物：
  描述：

  苯并咪唑 、 2,4,6-三异丙基苯磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.5h， 以82%的产率得到1-(2,4,6-triisopropylphenylsulfonyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Novel fatty acid binding protein 4 (FABP4) inhibitors: Virtual screening, synthesis and crystal structure determination

  摘要：

  Fatty acid binding protein 4 (FABP4) is a potential drug target for diabetes and atherosclerosis. For discovering new chemical entities as FABP4 inhibitors, structure-based virtual screening (VS) was performed, bioassay demonstrated that 16 of 251 tested compounds are FABP4 inhibitors, among which compound m1 are more active than endogenous ligand linoleic acid (LA). Based on the structure of m1, new derivatives were designed and prepared, leading to the discovery of two more potent inhibitors, compounds 9 and 10. To further explore the binding mechanisms of these new inhibitors, we determined the X-ray structures of the complexes of FABP4-9 and FABP4-10, which revealed similar binding conformations of the two compounds. Residue Ser53 and Arg126 formed direct hydrogen bonding with the ligands. We also found that 10 could significantly reduce the levels of lipolysis on mouse 3T3-L1 adipocytes. Taken together, in silico, in vitro and crystallographic data provide useful hints for future development of novel inhibitors against FABP4. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.020

文献信息

• [EN] NOVEL PHOSPHINES, SYNTHESIS THEREOF AND THEIR USE IN CATALYSIS<br/>[FR] NOUVELLES PHOSPHINES, LEUR SYNTHÈSE ET LEUR UTILISATION DANS LA CATALYSE
  申请人：UNIV HONG KONG POLYTECHNIC

  公开号：WO2015039606A1

  公开（公告）日：2015-03-26

  The present invention relates to a novel class of benzimidazolyl/imidazolyl phosphine ligands, methods of preparing such ligands via a simple one-pot protocol, and applications of the ligands in catalytic reactions.

  本发明涉及一种新型的苯并咪唑基/咪唑基膦配体，通过简单的一锅法制备这种配体的方法，以及这些配体在催化反应中的应用。
• NOVEL PHOSPHINES, SYNTHESIS THEREOF AND THEIR USE IN CATALYSIS
  申请人：THE HONG KONG POLYTECHNIC UNIVERSITY

  公开号：US20160222042A1

  公开（公告）日：2016-08-04

  The present invention relates to a novel class of benzimidazolyl/imidazolyl phosphine ligands, methods of preparing such ligands via a simple one-pot protocol, and applications of the ligands in catalytic reactions.

  本发明涉及一种新型的苯并咪唑基/咪唑基膦配体类，通过简单的一锅法制备此类配体的方法，以及在催化反应中应用该配体的应用。
• Phosphines, synthesis thereof and their use in catalysis
  申请人：The Hong Kong Polytechnic University

  公开号：US10093692B2

  公开（公告）日：2018-10-09

  The present invention relates to a novel class of benzimidazolyl/imidazolyl phosphine ligands, methods of preparing such ligands via a simple one-pot protocol, and applications of the ligands in catalytic reactions.

  本发明涉及一类新型苯并咪唑基/咪唑基膦配体、通过简单的一锅法制备这类配体的方法，以及这类配体在催化反应中的应用。
• Novel fatty acid binding protein 4 (FABP4) inhibitors: Virtual screening, synthesis and crystal structure determination
  作者：Haiyan Cai、Qiufeng Liu、Dingding Gao、Ting Wang、Tiantian Chen、Guirui Yan、Kaixian Chen、Yechun Xu、Heyao Wang、Yingxia Li、Weiliang Zhu

  DOI：10.1016/j.ejmech.2014.11.020

  日期：2015.1

  Fatty acid binding protein 4 (FABP4) is a potential drug target for diabetes and atherosclerosis. For discovering new chemical entities as FABP4 inhibitors, structure-based virtual screening (VS) was performed, bioassay demonstrated that 16 of 251 tested compounds are FABP4 inhibitors, among which compound m1 are more active than endogenous ligand linoleic acid (LA). Based on the structure of m1, new derivatives were designed and prepared, leading to the discovery of two more potent inhibitors, compounds 9 and 10. To further explore the binding mechanisms of these new inhibitors, we determined the X-ray structures of the complexes of FABP4-9 and FABP4-10, which revealed similar binding conformations of the two compounds. Residue Ser53 and Arg126 formed direct hydrogen bonding with the ligands. We also found that 10 could significantly reduce the levels of lipolysis on mouse 3T3-L1 adipocytes. Taken together, in silico, in vitro and crystallographic data provide useful hints for future development of novel inhibitors against FABP4. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Design of Benzimidazolyl Phosphines Bearing Alterable <i>P</i>,<i>O</i> or <i>P</i>,<i>N</i>-Coordination: Synthesis, Characterization, and Insights into Their Reactivity
  作者：Shun Man Wong、Pui Ying Choy、Qingyang Zhao、On Ying Yuen、Chung Chiu Yeung、Chau Ming So、Fuk Yee Kwong

  DOI：10.1021/acs.organomet.0c00816

  日期：2021.7.26