2-溴-1-[(4-氟苯基)甲基]苯并咪唑 | 111782-98-0

• 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: 2-溴-1-[(4-氟苯基)甲基]苯并咪唑
• 英文名称: 2-bromo-1-(4-fluorophenylmethyl)-1H-benzimidazole
• 英文别名: 2-Bromo-1-[(4-fluorophenyl)methyl]-1H-benzimidazole；2-bromo-1-[(4-fluorophenyl)methyl]benzimidazole
• CAS: 111782-98-0
• 化学式: C₁₄H₁₀BrFN₂
• 分子量: 305.149
• InChiKey: WDDROCRSDDOJNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-溴-1-[(4-氟苯基)甲基]苯并咪唑 在 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 、 乙腈 为溶剂， 反应 25.0h， 生成 7-chloro-N-[3-[4-[1-[(4-fluorophenyl)methyl]benzimidazol-2-yl]piperazin-1-yl]propyl]quinolin-4-amine
  参考文献：
  名称：

  Chloroquine–astemizole hybrids with potent in vitro and in vivo antiplasmodial activity

  摘要：

  A dual activity, conjugated approach has been taken to form hybrid molecules of two known antimalarial drugs, chloroquine (CQ) and the non-sedating H1 antagonist astemizole. A variety of linkers were investigated to conjugate the two agents into one molecule. Compounds 5-8 possessed improved in vitro activity against a CQ-resistant strain of Plasmodium falciparum, and examples 7 and 8 were active in vivo in mouse models of malaria. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.047
• 作为产物：
  描述：

  2-氯苯并咪唑 、 4-氟溴苄 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以94%的产率得到2-溴-1-[(4-氟苯基)甲基]苯并咪唑
  参考文献：
  名称：

  Chloroquine–astemizole hybrids with potent in vitro and in vivo antiplasmodial activity

  摘要：

  A dual activity, conjugated approach has been taken to form hybrid molecules of two known antimalarial drugs, chloroquine (CQ) and the non-sedating H1 antagonist astemizole. A variety of linkers were investigated to conjugate the two agents into one molecule. Compounds 5-8 possessed improved in vitro activity against a CQ-resistant strain of Plasmodium falciparum, and examples 7 and 8 were active in vivo in mouse models of malaria. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.047

文献信息

• 1-(2-benzimidazolyl)-1,5-diazacyclooctane compounds
  申请人：Kissei Pharmaceutical Co., Ltd.

  公开号：US05624948A1

  公开（公告）日：1997-04-29

  1-(2-benzimidazolyl)-1,5-diazacyclooctane compounds represented by the formula: ##STR1## wherein X represents a hydrogen atom or a halogen atom; Y represents a covalent bond, a straight- or branched-chain alkylene group having 1 to 6 carbon atoms, or a straight- or branched-chain alkenylene group having 2 to 6 carbon atoms; R represents a hydrogen atom, or a straight- or branched-chain alkyl group having 1 to 6 carbon atoms; and pharmaceutically acceptable salts thereof. The compounds represented above are novel potent and long-lasting histamine HI-receptor antagonist with less-topical irritation, and can be topically administered by inhalation for the treatment of bronchial asthma.

  1-(2-苯并咪唑基)-1,5-二氮杂环辛烷化合物的化学式如下：其中X代表氢原子或卤原子；Y代表共价键，具有1至6个碳原子的直链或支链烷基基团，或具有2至6个碳原子的直链或支链烯烃基团；R代表氢原子，或具有1至6个碳原子的直链或支链烷基基团；以及其药学上可接受的盐。上述化合物是新颖的高效长效组胺H1受体拮抗剂，具有较少局部刺激性，可通过吸入经皮途径治疗支气管哮喘。
• Second-Generation AUTACs for Targeted Autophagic Degradation
  作者：Daiki Takahashi、Taiichi Ora、Shigekazu Sasaki、Naoki Ishii、Toshio Tanaka、Takumi Matsuda、Mutsuki Ikeda、Jun Moriyama、Nobuo Cho、Hiroshi Nara、Hironobu Maezaki、Masahiro Kamaura、Kenichiro Shimokawa、Hirokazu Arimoto

  DOI：10.1021/acs.jmedchem.3c00861

  日期：2023.9.14

  Targeted protein degradation via the ubiquitin-proteasome system has emerged as one of the most promising drug discovery modalities. Autophagy, another intracellular degradation system, can target a wide range of nonproteinous substrates as well as proteins, but its application to targeted degradation is still in its infancy. Our previous work revealed a relationship between guanine modification of

  通过泛素-蛋白酶体系统进行的靶向蛋白质降解已成为最有前途的药物发现方式之一。自噬是另一种细胞内降解系统，可以靶向多种非蛋白质底物以及蛋白质，但其在靶向降解中的应用仍处于起步阶段。我们之前的工作揭示了细胞内蛋白质上半胱氨酸残基的鸟嘌呤修饰与选择性自噬之间的关系，从而产生了第一个基于自噬的降解剂，即自噬靶向嵌合体（AUTAC）。基于研究背景，所有报道的AUTACs化合物都含有半胱氨酸作为子结构。在这里，我们通过进行 SAR 研究来检查该子结构的重要性，并报告通过用其他部分替换半胱氨酸来显着改善降解剂的活性。几种衍生物表现出亚μM范围的降解活性，证明了AUTAC增加的实用价值。
• 1-(2-BENZIMIDAZOLYL)-1,5-DIAZACYCLOOCTANE DERIVATIVE
  申请人：Kissei Pharmaceutical Co., Ltd.

  公开号：EP0699668A1

  公开（公告）日：1996-03-06

  A 1-(2-benzimidazolyl)-1,5-diazacyclooctane derivative represented by general formula (I) (wherein X represents hydrogen or halogen; Y represents a single bond, C₁-C₆ linear or branched alkylene or C₂-C₆ linear or branched alkenylene; and R represents hydrogen or C₁-C₆ linear or branched alkyl) and a pharmacologically acceptable salt thereof. This compound is a histamine H¹ receptor antagonist which can be topically administered via inhalation as a remedy for bronchial asthma.

  一种由通式（I）代表的 1-（2-苯并咪唑基）-1,5-二氮杂环辛烷衍生物（其中 X 代表氢或卤素；Y 代表单键、C₁-C₆ 直链或支链亚烷基或 C₂-C₆ 直链或支链烯基；R 代表氢或 C₁-C₆ 直链或支链烷基）及其药理学上可接受的盐。该化合物是一种组胺 H¹ 受体拮抗剂，可通过吸入局部给药，作为治疗支气管哮喘的药物。
• US5624948A
  申请人：——

  公开号：US5624948A

  公开（公告）日：1997-04-29
• Chloroquine–astemizole hybrids with potent in vitro and in vivo antiplasmodial activity
  作者：Chitalu C. Musonda、Gavin A. Whitlock、Michael J. Witty、Reto Brun、Marcel Kaiser

  DOI：10.1016/j.bmcl.2008.11.047

  日期：2009.1

  A dual activity, conjugated approach has been taken to form hybrid molecules of two known antimalarial drugs, chloroquine (CQ) and the non-sedating H1 antagonist astemizole. A variety of linkers were investigated to conjugate the two agents into one molecule. Compounds 5-8 possessed improved in vitro activity against a CQ-resistant strain of Plasmodium falciparum, and examples 7 and 8 were active in vivo in mouse models of malaria. (C) 2008 Elsevier Ltd. All rights reserved.