3-溴-5-苯基水杨酸 | 4906-68-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-溴-5-苯基水杨酸
• 英文名称: 3-bromo-5-phenylsalicylic acid
• 英文别名: 5-Bromo-4-hydroxy-[1,1'-biphenyl]-3-carboxylic acid；3-bromo-2-hydroxy-5-phenylbenzoic acid
• CAS: 4906-68-7
• 化学式: C₁₃H₉BrO₃
• 分子量: 293.117
• InChiKey: XVZSXNULHSIRCQ-UHFFFAOYSA-N

物化性质

• 熔点：
  212-214 °C
• 沸点：
  401.2±45.0 °C(Predicted)
• 密度：
  1.611±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：15mg/mL； DMF:PBS (pH 7.2) (1:9)：0.1 mg/mL； DMSO：12.5mg/mL；乙醇：0.1mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

生物活性

AKR1C1-IN-1 是一种高效、选择性的 AKR1C1 抑制剂，其 Ki 值为 4 nM。具体来说：

• AKR1C1: 4 nM
• AKR1C2: 87 nM
• AKR1C3: 4.2 μM
• AKR1C4: 18.2 μM

体外研究

AKR1C1-IN-1 显著抑制了过表达 AKR1C1 的BAECs中孕酮的代谢，其 IC₅₀ 值为 460 nM。

反应信息

• 作为反应物：
  描述：

  3-溴-5-苯基水杨酸 在 sodium hydroxide 、 sodium carbonate 、 sodium hydrogensulfite 作用下， 生成 5-phenyl-2,3-dihydroxy-benzoic acid
  参考文献：
  名称：

  Phenyl dihydroxybenzoic acids

  摘要：

  公开号：

  US02756256A1
• 作为产物：
  描述：

  2-羟基-5-苯基苯甲酸 在 溴 、 溶剂黄146 作用下， 生成 3-溴-5-苯基水杨酸
  参考文献：
  名称：

  Halogenated phenyl-salicylic acids

  摘要：

  公开号：

  US02779785A1

文献信息

• Mono- and disalicylic acid derivatives: PTP1B inhibitors as potential anti-obesity drugs
  作者：Suja Shrestha、Bharat Raj Bhattarai、Keun-Hyeung Lee、Hyeongjin Cho

  DOI：10.1016/j.bmc.2007.07.010

  日期：2007.10

  A series of compounds containing one or two salicylic acid moieties were synthesized, and their efficacy to inhibit the phosphohydrolase activity of PTP1B examined. Some of the methylenedisalicylic acid derivatives were potent inhibitors of PTP1B. Of those derivatives, 3c exhibited about a 14-fold selectivity against TC-PTP, and this compound was tested in a mouse model for its efficacy to prevent

  合成了一系列包含一个或两个水杨酸部分的化合物，并研究了其抑制PTP1B磷酸水解酶活性的功效。一些亚甲基二水杨酸衍生物是PTP1B的有效抑制剂。在这些衍生物中，3c对TC-PTP表现出约14倍的选择性，并在小鼠模型中测试了该化合物预防饮食引起的肥胖的功效。它有效地抑制了体重和脂肪的增加，而没有任何明显的毒性作用。该化合物还可以防止血浆甘油三酸酯，胆固醇和非酯化脂肪酸浓度的增加。因此，将其治疗潜力扩展到其他相关的代谢性疾病，例如高脂血症和高胆固醇血症。
• Devices and methods of treating methamphetamine addiction and medical and behavioral consequences of methamphetamine use and of HIV infection
  申请人：Goeders Nicholas E.

  公开号：US10022383B2

  公开（公告）日：2018-07-17

  A method of treating a condition of in a human patient comprising pharmacologically activating a translocator protein of 18 kDa (TSPO), wherein the condition is one of a chronic methamphetamine addiction, a medical consequence of methamphetamine use; a behavioral consequence of methamphetamine use, an HIV associated cognitive motor disorder, an HIV-associated neurodegenerative disorder, and a neuroinflammatory response.

  一种治疗人类患者病症的方法，包括药理激活 18 kDa 转运体蛋白（TSPO），其中所述病症为慢性甲基苯丙胺成瘾、使用甲基苯丙胺的医疗后果、使用甲基苯丙胺的行为后果、HIV 相关认知运动障碍、HIV 相关神经退行性障碍和神经炎症反应中的一种。
• Structure-Guided Design, Synthesis, and Evaluation of Salicylic Acid-Based Inhibitors Targeting a Selectivity Pocket in the Active Site of Human 20α-Hydroxysteroid Dehydrogenase (AKR1C1)
  作者：Ossama El-Kabbani、Peter J. Scammells、Joshua Gosling、Urmi Dhagat、Satoshi Endo、Toshiyuki Matsunaga、Midori Soda、Akira Hara

  DOI：10.1021/jm9001633

  日期：2009.5.28

  The first design, synthesis, and evaluation of human 20(x-hydroxysteroid dehydrogenase (AKR1C1) inhibitors based on the recently published crystal structure of its ternary complex with inhibitor are reported. While the enzyme-inhibitor interactions observed in the crystal structure remain conserved with the newly designed inhibitors, the additional phenyl group of the most potent compound, 3-bromo-5-phenylsalicylic acid, targets a nonconserved hydrophobic pocket in the active site of AKR1C1 resulting in 21-fold improved potency (K(i) = 4 nM) over the structurally similar 3 alpha-hydroxysteroid dehydrogenase isoform (AKR1C2). The compound is hydrogen bonded to Tyr55, His 117, and His222, and the phenyl ring forms additional van der Waals interactions with residues Leu308, Phe311, and the nonconserved Leu54 (Val in AKR1C2). Additionally, the metabolism of progesterone in AKR1C1-overexpressed cells was potently inhibited by 3-bromo-5-phenylsalicylic acid, which was effective from 10 nM with an IC(50) value equal to 460 nM.
• DEVICES AND METHODS OF TREATING METHAMPHETAMINE ADDICTION AND MEDICAL AND BEHAVIORAL CONSEQUENCES OF METHAMPHETAMINE USE AND OF HIV INFECTION
  申请人：GOEDERS Nicholas E.

  公开号：US20160367565A1

  公开（公告）日：2016-12-22

  A method of treating a condition of in a human patient comprising pharmacologically activating a translocator protein of 18 kDa (TSPO), wherein the condition is one of a chronic methamphetamine addiction, a medical consequence of methamphetamine use; a behavioral consequence of methamphetamine use, an HIV associated cognitive motor disorder, an HIV-associated neurodegenerative disorder, and a neuroinflammatory response.
• Halogenated phenyl-salicylic acids
  申请人：DOW CHEMICAL CO

  公开号：US02779785A1

  公开（公告）日：1957-01-29