5,2′-dibromo-2,4′,5′-trihydroxydiphenylmethanone | 1239703-18-4

• 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: 5,2′-dibromo-2,4′,5′-trihydroxydiphenylmethanone
• 英文别名: 2,5'-Dibromo-4,5,2'-trihydroxyl diphenylmethanone；(2-bromo-4,5-dihydroxyphenyl)-(5-bromo-2-hydroxyphenyl)methanone
• CAS: 1239703-18-4
• 化学式: C₁₃H₈Br₂O₄
• 分子量: 388.012
• InChiKey: GKGFCIICHDPASP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻苯二甲醚 在 aluminum (III) chloride 、 N-溴代丁二酰亚胺(NBS) 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 5,2′-dibromo-2,4′,5′-trihydroxydiphenylmethanone
  参考文献：
  名称：

  5,2'-二溴-2,4',5'-三羟基二苯甲酮作为急性肾盂肾炎新候选药物的高效放大制备的工艺开发和工艺相关杂质的合成

  摘要：

  基于上述克级实验室工艺，开发了急性肾盂肾炎新候选药物5,2'-二溴-2,4',5'-三羟基二苯甲酮（LM49-API）的高效放大制备工艺，并进行了生产。经验证旨在减少副产物并获得更好的杂质分布。同时，还对LM49-API的多晶型和工艺相关杂质进行了研究。最终，通过评估合成过程中的杂质分布及其形成来验证最佳反应条件。合成并鉴定了六种与工艺相关的杂质，可用于 LM49-API 的质量控制。其最终的制备工艺在329-410 g放大生产中得到了进一步验证，总产率为53.4-57.1%，高效液相色谱（HPLC）纯度为99.95-99.98%，目前可用于商业生产。经鉴定，LM49-API中主要单一杂质为LM49-API-imC和LM49-API-imX，含量控制在0.03%以下。

  DOI：

  10.3390/molecules25030468

文献信息

• [EN] USE OF BENZOPHENONE COMPOUND IN PHARMACEUTICALS<br/>[FR] UTILISATION D'UN COMPOSÉ DE BENZOPHÉNONE DANS DES PRODUITS PHARMACEUTIQUES<br/>[ZH] 二苯甲酮类化合物在制药中的应用
  申请人：UNIV SHANXI MEDICAL

  公开号：WO2017186141A1

  公开（公告）日：2017-11-02

  本发明公开了两种二苯甲酮类化合物4,5,2'-三羟基-2,5'-二溴二苯甲酮和4,5,2'-三(4-吗啉甲酰氧基)-2,5'-二氯二苯甲酮的医药新用途，具体为在制备抗Ⅱ型糖尿病肾病、治疗急性肾盂肾炎和慢性肾炎药物中的应用，同时本发明也公开了以上述两种化合物为活性成分的抗Ⅱ型糖尿病肾病药物及治疗急性肾盂肾炎和慢性肾炎的药物。这两种化合物均能有效改善Ⅱ型糖尿病肾病模型大鼠、急性肾盂肾炎模型大鼠和慢性肾炎模型大鼠的的肾功能，显示了在抗糖尿病肾病、治疗急性肾盂肾炎和慢性肾炎方面重要的应用前景。
• Synthesis and biological activity of halophenols as potent antioxidant and cytoprotective agents
  作者：Wanyi Zhao、Xiue Feng、Shurong Ban、Wenhan Lin、Qingshan Li

  DOI：10.1016/j.bmcl.2010.05.068

  日期：2010.7

  A series of new bromophenols and chlorophenols were prepared by a practical route. The in vitro antioxidative activity of the halophenols was evaluated by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assay, and their cytoprotective activity was also tested on hydrogen peroxide (H2O2)-induced injury in human umbilical vein endothelial cells (HUVEC). All halophenols tested displayed moderate to good DPPH radical-scavenging activity, and two bromophenols, 2,3'-dibromo-4,5,6'-trihydroxydiphenyl-methanone (16c) and 2,3-dibromo-4,5-dihydroxydiphenylmethanone (17c) exhibited high protective activity against H2O2-induced injury in HUVEC with EC50 values of 0.4 and 0.8 mu M, respectively. The preliminary structure-activity relationships of these compounds were also investigated in order to determine the essential structures required for their bioactivities. (C) 2010 Elsevier Ltd. All rights reserved.
• Applications of benzophenones in preparation of drug
  申请人：SHANXI MEDICAL UNIVERSITY

  公开号：US20190133968A1

  公开（公告）日：2019-05-09

  Medical applications of 2,5′-dibromo-4,5,2′-trihydroxyldiphenylmethanone and 4,5,2′-tris(4-morpholinemethanoyl)-2,5′-dichlorobenzophenone are provided, particularly applications in preparation of drugs respectively for resisting type II diabetic nephropathy and for treating acute pyelonephritis and chronic nephritis. Moreover, two drugs respectively with the above two compounds as the active ingredient are provided, respectively for resisting the type II diabetic nephropathy and for treating the acute pyelonephritis and the chronic nephritis. Both of the two compounds are able to effectively improve renal functions of model rats suffered from the type II diabetic nephropathy, the acute pyelonephritis, and the chronic nephritis, showing an important application prospect in resisting the diabetic nephropathy and treating the acute pyelonephritis and the chronic nephritis.
• Process Development and Synthesis of Process-Related Impurities of an Efficient Scale-Up Preparation of 5,2′-Dibromo-2,4′,5′-Trihydroxy Diphenylmethanone as a New Acute Pyelonephritis Candidate Drug
  作者：Xiu E Feng、Ke Meng Cui、Qing Shan Li、Zi Cheng Wu、Fei Lei

  DOI：10.3390/molecules25030468

  日期：——

  (LM49-API), a new acute pyelonephritis candidate drug, was developed and validated aiming to reduce by-products and achieve better impurity profiles. Meanwhile, the polymorph of LM49-API and process-related impurities were also investigated. Ultimately, the optimal reaction conditions were verified by evaluating the impurity profiles and their formation during the synthesis. Six process-related impurities

  基于上述克级实验室工艺，开发了急性肾盂肾炎新候选药物5,2'-二溴-2,4',5'-三羟基二苯甲酮（LM49-API）的高效放大制备工艺，并进行了生产。经验证旨在减少副产物并获得更好的杂质分布。同时，还对LM49-API的多晶型和工艺相关杂质进行了研究。最终，通过评估合成过程中的杂质分布及其形成来验证最佳反应条件。合成并鉴定了六种与工艺相关的杂质，可用于 LM49-API 的质量控制。其最终的制备工艺在329-410 g放大生产中得到了进一步验证，总产率为53.4-57.1%，高效液相色谱（HPLC）纯度为99.95-99.98%，目前可用于商业生产。经鉴定，LM49-API中主要单一杂质为LM49-API-imC和LM49-API-imX，含量控制在0.03%以下。