5-ethyl-2-hydroxyphenylboronic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-ethyl-2-hydroxyphenylboronic acid
• 英文别名: (5-Ethyl-2-hydroxyphenyl)boronic acid
• 化学式: C₈H₁₁BO₃
• 分子量: 165.985
• InChiKey: CPGQGJFPSZFPTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.37
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-ethyl-2-hydroxyphenylboronic acid 、 2-bromo-1-methoxy-4-pentylbenzene 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 18.0h， 生成 5-ethyl-2′-methoxy-5′-pentylbiphenyl-2-ol
  参考文献：
  名称：

  Structural analogues of the natural products magnolol and honokiol as potent allosteric potentiators of GABAA receptors

  摘要：

  Biphenylic compounds related to the natural products magnolol and 4'-O-methylhonokiol were synthesized, evaluated and optimized as positive allosteric modulators (PAMs) of GABA(A) receptors. The most efficacious compounds were the magnolol analog 5-ethyl-5'-hexylbiphenyl-2,2'-diol (45) and the honokiol analogs 4'-methoxy-5-propylbiphenyl-2-ol (61), 5-butyl-4'-methoxybiphenyl-2-ol (62) and 5-hexyl-4'- methoxybiphenyl-2-ol (64), which showed a most powerful potentiation of GABA-induced currents (up to 20-fold at a GABA concentration of 3 mu M). They were found not to interfere with the allosteric sites occupied by known allosteric modulators, such as benzodiazepines and N-arachidonoylglycerol. These new PAMs will be useful as pharmacological tools and may have therapeutic potential for mono-therapy, or in combination, for example, with GABA(A) receptor agonists. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.10.027
• 作为产物：
  描述：

  4-乙基苯酚 在 正丁基锂 、 溴 、 碳酸氢钠 作用下， 以 乙醚 、 正己烷 、 氯仿 为溶剂， 反应 18.0h， 生成 5-ethyl-2-hydroxyphenylboronic acid
  参考文献：
  名称：

  Structural analogues of the natural products magnolol and honokiol as potent allosteric potentiators of GABAA receptors

  摘要：

  Biphenylic compounds related to the natural products magnolol and 4'-O-methylhonokiol were synthesized, evaluated and optimized as positive allosteric modulators (PAMs) of GABA(A) receptors. The most efficacious compounds were the magnolol analog 5-ethyl-5'-hexylbiphenyl-2,2'-diol (45) and the honokiol analogs 4'-methoxy-5-propylbiphenyl-2-ol (61), 5-butyl-4'-methoxybiphenyl-2-ol (62) and 5-hexyl-4'- methoxybiphenyl-2-ol (64), which showed a most powerful potentiation of GABA-induced currents (up to 20-fold at a GABA concentration of 3 mu M). They were found not to interfere with the allosteric sites occupied by known allosteric modulators, such as benzodiazepines and N-arachidonoylglycerol. These new PAMs will be useful as pharmacological tools and may have therapeutic potential for mono-therapy, or in combination, for example, with GABA(A) receptor agonists. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.10.027

文献信息

• Bipyridine manganese complexes
  申请人：Eukarion, Inc.

  公开号：US06177419B1

  公开（公告）日：2001-01-23

  Compounds and methods of preparing compounds represented by structural formula (I): wherein X represents any suitable counter-anion; R1 and R2 independently represent hydrogen, C1-6 alkoxy or nitro; R3, R4, R5 and R6 each independently represents hydrogen, hydroxy, halo, C1-6 alkyl, C2-6 alkenyl or C1-6 alkoxy; and R7, R8, R9 and R10 each independently represents hydrogen, hydroxy, halo, C1-6 alkyl, C2-6 alkenyl or C1-6 alkoxy. Compounds represented by structural formula (I) are useful in treating or preventing free radical-associated diseases or conditions in mammals.

  化合物和制备由结构式（I）表示的化合物的方法：其中X代表任何适当的对离子；R1和R2独立表示氢，C1-6烷氧基或硝基；R3、R4、R5和R6分别独立表示氢，羟基，卤素，C1-6烷基，C2-6烯基或C1-6烷氧基；以及R7、R8、R9和R10分别独立表示氢，羟基，卤素，C1-6烷基，C2-6烯基或C1-6烷氧基。由结构式（I）表示的化合物在治疗或预防哺乳动物中的自由基相关疾病或症状方面是有用的。
• Structural analogues of the natural products magnolol and honokiol as potent allosteric potentiators of GABAA receptors
  作者：Alexander Fuchs、Roland Baur、Clara Schoeder、Erwin Sigel、Christa E. Müller

  DOI：10.1016/j.bmc.2014.10.027

  日期：2014.12

  Biphenylic compounds related to the natural products magnolol and 4'-O-methylhonokiol were synthesized, evaluated and optimized as positive allosteric modulators (PAMs) of GABA(A) receptors. The most efficacious compounds were the magnolol analog 5-ethyl-5'-hexylbiphenyl-2,2'-diol (45) and the honokiol analogs 4'-methoxy-5-propylbiphenyl-2-ol (61), 5-butyl-4'-methoxybiphenyl-2-ol (62) and 5-hexyl-4'- methoxybiphenyl-2-ol (64), which showed a most powerful potentiation of GABA-induced currents (up to 20-fold at a GABA concentration of 3 mu M). They were found not to interfere with the allosteric sites occupied by known allosteric modulators, such as benzodiazepines and N-arachidonoylglycerol. These new PAMs will be useful as pharmacological tools and may have therapeutic potential for mono-therapy, or in combination, for example, with GABA(A) receptor agonists. (C) 2014 Elsevier Ltd. All rights reserved.