2-溴-1-[4-[(4-氯苯基)甲氧基]苯基]乙酮 | 79615-84-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-溴-1-[4-[(4-氯苯基)甲氧基]苯基]乙酮
• 英文名称: ω-bromo-4(4-chlorobenzoyloxy)acetophenone
• 英文别名: 2-Bromo-1-{4-[(4-chlorophenyl)methoxy]phenyl}ethan-1-one；2-bromo-1-[4-[(4-chlorophenyl)methoxy]phenyl]ethanone
• CAS: 79615-84-2
• 化学式: C₁₅H₁₂BrClO₂
• 分子量: 339.616
• InChiKey: JULJEGIULUZUIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 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-[(4-氯苯基)甲氧基]苯基]乙酮 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 1-{4-[(4-chlorobenzyl)oxy]phenyl}-2-(1H-imidazol-1-yl)ethanol
  参考文献：
  名称：

  Potholing of the hydrophobic heme oxygenase-1 western region for the search of potent and selective imidazole-based inhibitors

  摘要：

  Here we report the design, synthesis, and molecular modeling of new potent and selective imidazolebased HO-1 inhibitors in which the imidazole nucleus and the hydrophobic groups are linked by a phenylethanolic spacer. Most of the tested compounds showed a good inhibitor activity with IC50 values in the low micromolar range, with two of them (lb and 1j) exhibiting also high selectivity toward HO-2. These results were obtained by the idea of potholing the entire volume of the principal hydrophobic western region with an appropriate ligand volume. Molecular modeling studies showed that these molecules bind to the HO-1 in the consolidated fashion where the imidazolyl moiety coordinates the heme iron while the aromatic groups are stabilized by hydrophobic interaction in the western region of the binding pocket. Finally, the synthesized compounds were analyzed for in silico ADME-Tox properties to establish oral drug-like behavior and showed satisfactory results. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.007
• 作为产物：
  描述：

  1-[4-[(4-氯苯基)甲氧基]苯基]乙酮 在 pyridinium hydrobromide perbromide 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以68%的产率得到2-溴-1-[4-[(4-氯苯基)甲氧基]苯基]乙酮
  参考文献：
  名称：

  Kawamatsu; Sohda; Iami, European Journal of Medicinal Chemistry, 1981, vol. 16, # 4, p. 355 - 362

  摘要：

  DOI：

文献信息

• [EN] THIAZOLE OR IMIDAZOLE DERIVATIVES AS MAILLARD REACTION INHIBITORS<br/>[FR] DERIVES DE THIAZOLE OU D'IMIDAZOLE INHIBANT LA REACTION DE MAILLARD
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：WO1994019335A1

  公开（公告）日：1994-09-01

  (EN) A compound represented by formula (I) is disclosed, wherein the all symbols are defined in the disclosure. A process for producing the compound, and a method for treating diseases caused by a Maillard reaction in living body using the compound are also disclosed.(FR) On décrit un composé représenté par la formule (I), où tous les symboles correspondent aux définitions de la description. On décrit aussi un procédé permettant de produire ce composé et un procédé permettant de traiter des maladies provoquées par une réaction de Maillard chez un être vivant, grâce à ce composé.

  (EN) 揭示了一种由式(I)表示的化合物，其中所有符号均在说明中定义。还揭示了一种生产该化合物的方法，以及一种使用该化合物治疗由Maillard反应引起的疾病的方法。(FR) 描述了一种由式(I)表示的化合物，其中所有符号均符合说明中的定义。还描述了一种制备该化合物的方法和一种使用该化合物治疗生物体中由Maillard反应引起的疾病的方法。
• THIAZOLE OR IMIDAZOLE DERIVATIVES AS MAILLARD REACTION INHIBITORS
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0638075A1

  公开（公告）日：1995-02-15
• US5677322A
  申请人：——

  公开号：US5677322A

  公开（公告）日：1997-10-14
• Potholing of the hydrophobic heme oxygenase-1 western region for the search of potent and selective imidazole-based inhibitors
  作者：Loredana Salerno、Emanuele Amata、Giuseppe Romeo、Agostino Marrazzo、Orazio Prezzavento、Giuseppe Floresta、Valeria Sorrenti、Ignazio Barbagallo、Antonio Rescifina、Valeria Pittalà

  DOI：10.1016/j.ejmech.2018.02.007

  日期：2018.3

  Here we report the design, synthesis, and molecular modeling of new potent and selective imidazolebased HO-1 inhibitors in which the imidazole nucleus and the hydrophobic groups are linked by a phenylethanolic spacer. Most of the tested compounds showed a good inhibitor activity with IC50 values in the low micromolar range, with two of them (lb and 1j) exhibiting also high selectivity toward HO-2. These results were obtained by the idea of potholing the entire volume of the principal hydrophobic western region with an appropriate ligand volume. Molecular modeling studies showed that these molecules bind to the HO-1 in the consolidated fashion where the imidazolyl moiety coordinates the heme iron while the aromatic groups are stabilized by hydrophobic interaction in the western region of the binding pocket. Finally, the synthesized compounds were analyzed for in silico ADME-Tox properties to establish oral drug-like behavior and showed satisfactory results. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Kawamatsu; Sohda; Iami, European Journal of Medicinal Chemistry, 1981, vol. 16, # 4, p. 355 - 362
  作者：Kawamatsu、Sohda、Iami

  DOI：——

  日期：——