4-氨基丙泊酚盐酸盐 | 100251-91-0

• 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: 4-氨基丙泊酚盐酸盐
• 英文名称: 4-Amino-2,6-diisopropylphenol hydrochloride
• 英文别名: 4-amino-2,6-diisopropyl-phenol; hydrochloride；4-Amino-2,6-diisopropyl-phenol; Hydrochlorid；4-amino-propofol hydrochloride；4-Amino Propofol Hydrochloride；4-amino-2,6-di(propan-2-yl)phenol;hydrochloride
• CAS: 100251-91-0
• 化学式: C₁₂H₁₉NO*ClH
• 分子量: 229.75
• InChiKey: TZJBRMGVYGSBDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  255-258 °C
• 溶解度：
  甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -0.48
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氨基丙泊酚盐酸盐 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 3,5-Diisopropylparacetamol
  参考文献：
  名称：

  Propofol Analogues. Synthesis, Relationships between Structure and Affinity at GABA_A Receptor in Rat Brain, and Differential Electrophysiological Profile at Recombinant Human GABA_A Receptors

  摘要：

  A number of propofol (2,6-diisopropylphenol) congeners and derivatives were synthesized and their in vitro capability to affect GABA(A) receptors determined by the inhibition of the specific [S-35]-tert-butylbicyclophosphorothionate ([S-35]TBPS) binding to rat whole brain membranes. Introduction of halogen (Cl, Br, and I) and benzoyl substituents in the para position of the phenyl group resulted in ligands with higher potency at inhibiting [S-35]TBPS binding. A quantitative structure-affinity relationship (QSAR) study demonstrated that affinity is enhanced by increases in lipophilicity of the ligand whereas affinity is adversely affected by increases in size of the substituent para to the phenolic hydroxyl group. Consistent with the displacement of [S-35]TBPS and with the activation of GABA(A) receptors, we demonstrate that ligands displaying high affinity (i.e., 2-4, and 8) are able to increase GABA-stimulated chloride currents in oocytes expressing human GABA(A) receptors and to directly activate chloride currents in an electrophysiological assay. Among them, compound 4 showed a rather peculiar profile in the electrophysiological examination with cloned alpha(1) beta(2) gamma(2) GABA(A) receptors. Indeed, compared to propofol, it displayed a much greater efficacy at potentiating GABA-elicited chloride currents, but a much lower efficacy at producing a direct activation of the chloride channel in the absence of GABA. This behavior may give to compound 4 pharmacological properties that are more similar to anxiolytic and anticonvulsant drugs than to those of general anesthetics.

  DOI：

  10.1021/jm970681h
• 作为产物：
  描述：

  丙泊酚 在 盐酸 、 tin 、 硫酸 、 硝酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 4-氨基丙泊酚盐酸盐
  参考文献：
  名称：

  Propofol Analogues. Synthesis, Relationships between Structure and Affinity at GABA_A Receptor in Rat Brain, and Differential Electrophysiological Profile at Recombinant Human GABA_A Receptors

  摘要：

  A number of propofol (2,6-diisopropylphenol) congeners and derivatives were synthesized and their in vitro capability to affect GABA(A) receptors determined by the inhibition of the specific [S-35]-tert-butylbicyclophosphorothionate ([S-35]TBPS) binding to rat whole brain membranes. Introduction of halogen (Cl, Br, and I) and benzoyl substituents in the para position of the phenyl group resulted in ligands with higher potency at inhibiting [S-35]TBPS binding. A quantitative structure-affinity relationship (QSAR) study demonstrated that affinity is enhanced by increases in lipophilicity of the ligand whereas affinity is adversely affected by increases in size of the substituent para to the phenolic hydroxyl group. Consistent with the displacement of [S-35]TBPS and with the activation of GABA(A) receptors, we demonstrate that ligands displaying high affinity (i.e., 2-4, and 8) are able to increase GABA-stimulated chloride currents in oocytes expressing human GABA(A) receptors and to directly activate chloride currents in an electrophysiological assay. Among them, compound 4 showed a rather peculiar profile in the electrophysiological examination with cloned alpha(1) beta(2) gamma(2) GABA(A) receptors. Indeed, compared to propofol, it displayed a much greater efficacy at potentiating GABA-elicited chloride currents, but a much lower efficacy at producing a direct activation of the chloride channel in the absence of GABA. This behavior may give to compound 4 pharmacological properties that are more similar to anxiolytic and anticonvulsant drugs than to those of general anesthetics.

  DOI：

  10.1021/jm970681h

文献信息

• 4-aminophenol derivatives and processes for preparing the same
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US05047555A1

  公开（公告）日：1991-09-10

  There are disclosed a 4-aminophenol derivative of the formula: ##STR1## (wherein R.sup.1 and R.sup.2 each represent a lower alkyl group, Y represents a single bonding arm, a lower alkylene group or a lower alkenylene group, R.sup.3 represents a thienyl group or pyrrolyl group which may be also substituted with a lower alkyl group; benzothienyl group, indolyl group; or a phenol group which is substituted with 1 to 2 groups selected from a lower alkoxy group and a lower alkanoyloxy group; or Y-R.sup.3 represents integrally an alkyl group with 6 to 9 carbon atoms; or a hydrocarbon group with 5 to 14 carbon atoms having 2 or 3 double bonds) or a pharmacologically acceptable salt thereof, and processes for preparing the same.

  揭示了一种公式为：##STR1##（其中R.sup.1和R.sup.2分别代表较低的烷基基团，Y代表单键合臂，较低的烷基烯基团或较低的烯基烯基团，R.sup.3代表一硫代吡咯基团或吡咯基团，也可以用较低烷基基团取代；苯并噻吩基团，吲哚基团；或被1至2个从较低烷氧基和较低烷酰氧基中选择的基团取代的苯酚基团；或Y-R.sup.3代表整体地具有6至9个碳原子的烷基基团；或具有2或3个双键的5至14个碳原子的烃基团）或其药理学上可接受的盐，以及其制备方法。
• [EN] COMPOUNDS FOR USE IN THE TREATMENT OF PAIN<br/>[FR] COMPOSÉS POUR UTILISATION DANS LE TRAITEMENT DE LA DOULEUR
  申请人：UNIV LIVERPOOL

  公开号：WO2010067069A1

  公开（公告）日：2010-06-17

  The present invention concerns compounds derived from the anaethetic propofol. The compounds may be useful in the treatment of pain, particularly, but not exclusively, chronic pain and central pain sensitisation.

  本发明涉及从麻醉药丙泊酚衍生的化合物。这些化合物可能在治疗疼痛方面有用，尤其是慢性疼痛和中枢疼痛敏化，但不仅限于此。
• 4-Aminophenol derivatives and processes for preparing the same
  申请人：TANABE SEIYAKU CO., LTD.

  公开号：EP0374048A1

  公开（公告）日：1990-06-20

  There are disclosed a 4-aminophenol derivative of the formula: (wherein R¹ and R² each represent a lower alkyl group, Y represents a single bonding arm, a lower alkylene group or a lower alkenylene group, R³ represents a thienyl group or pyrrolyl group which may be also substituted with a lower alkyl group; benzothienyl group, indolyl group; or a phenyl group which is substituted with 1 to 2 groups selected from a lower alkoxy group and a lower alkanoyloxy group; or Y-R³ represents integrally an alkyl group with 6 to 9 carbon atoms; or a hydrocarbon group with 5 to 14 carbon atoms having 2 or 3 double bonds) or a pharmacologically acceptable salt thereof, and pro­cesses for preparing the same.

  公开了一种4-氨基苯酚衍生物，其式如下 (其中R¹和R²各代表一个低级烷基，Y代表一个单键臂、一个低级亚烷基或一个低级亚烯基，R³代表一个噻吩基或吡咯基，它们也可被一个低级烷基取代；苯并噻吩基、吲哚基；或被 1 至 2 个选自低级烷氧基和低级烷酰氧基的基团取代的苯基；或 Y-R³ 整体代表 6 至 9 个碳原子的烷基；或具有 2 或 3 个双键的 5 至 14 个碳原子的烃基）或其药理学上可接受的盐，以及制备这些盐的工艺。
• The Effect of Alkyl Groups on 4-Nitro- and 4-Nitroso-phenols
  作者：WYMAN R. VAUGHAN、G. KIRKWOOD FINCH

  DOI：10.1021/jo01117a001

  日期：1956.11
• Isotopic Effect Study of Propofol Deuteration on the Metabolism, Activity, and Toxicity of the Anesthetic
  作者：J. Helfenbein、C. Lartigue、E. Noirault、E. Azim、J. Legailliard、M. J. Galmier、J. C. Madelmont

  DOI：10.1021/jm020864q

  日期：2002.12.1

  The use of isotopic substitution to delay the oxidative metabolism of the anesthetic prbpofol I was studied. The aromatic hydrogens of propofol 1 were replaced by deuterium to produce the mono- and trideuterated derivatives 4 and 5. In vitro metabolic studies on human hepatic microsomes showed no isotopic effect in the para hydroxylation of propofol, and 1, 4, and 5 display similar hypnotic activity and toxicity in mice.