5-amino-4'-methoxy-[1,1'-biphenyl]-2-ol | 773046-95-0

• 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-amino-4'-methoxy-[1,1'-biphenyl]-2-ol
• 英文别名: 4-Amino-2-(4-methoxyphenyl)phenol
• CAS: 773046-95-0
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: MCBDRXZGWABKCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-amino-4'-methoxy-[1,1'-biphenyl]-2-ol 在 盐酸 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 5-(7-Chloro-1-oxy-quinolin-4-ylamino)-3-diethylaminomethyl-4'-methoxy-biphenyl-2-ol
  参考文献：
  名称：

  Antimalarial drugs. 60. Synthesis, antimalarial activity, and quantitative structure-activity relationships of tebuquine and a series of related 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl][1,1'-biphenyl]-2-ols and N.omega.-oxides

  摘要：

  A series of 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl] [1,1'-biphenyl]-2-ols and N omega-oxides was prepared from the substituted 1-phenyl-2-propanones proceeding through the 5-nitro[1,1'-biphenyl]-2-ols, the corresponding amino, and acetamido derivatives to the N-[5-[(alkylamino)methyl]-6-hydroxy[1,1'-biphenyl]-3-yl]acetamides and final condensation with 4,7-dichloroquinoline or the N-oxide. In a quantitative structure-activity relationship study first run on 28 and later expanded to 40 substituted phenyl analogues and their N omega-oxides, increasing antimalarial potency vs. Plasmodium berghei in mice was found to be correlated with decreasing size (sigma MR) and electron donation (sigma sigma) of the phenyl ring substituents. A significant correlation with N omega-oxidation could not be demonstrated. Initial high activity against P. berghei infections in mice led to expanded studies that demonstrated in addition excellent activity against resistant strains of parasite, activity in primate models, and pharmacokinetic properties apparently allowing protection against infection for extended periods of time even after oral administration. Such properties encourage the clinical trial of a member of this class in man.

  DOI：

  10.1021/jm00156a009
• 作为产物：
  描述：

  对甲氧基苯基丙酮 在 镍 sodium hydroxide 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 20.0h， 生成 5-amino-4'-methoxy-[1,1'-biphenyl]-2-ol
  参考文献：
  名称：

  Antimalarial drugs. 60. Synthesis, antimalarial activity, and quantitative structure-activity relationships of tebuquine and a series of related 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl][1,1'-biphenyl]-2-ols and N.omega.-oxides

  摘要：

  A series of 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl] [1,1'-biphenyl]-2-ols and N omega-oxides was prepared from the substituted 1-phenyl-2-propanones proceeding through the 5-nitro[1,1'-biphenyl]-2-ols, the corresponding amino, and acetamido derivatives to the N-[5-[(alkylamino)methyl]-6-hydroxy[1,1'-biphenyl]-3-yl]acetamides and final condensation with 4,7-dichloroquinoline or the N-oxide. In a quantitative structure-activity relationship study first run on 28 and later expanded to 40 substituted phenyl analogues and their N omega-oxides, increasing antimalarial potency vs. Plasmodium berghei in mice was found to be correlated with decreasing size (sigma MR) and electron donation (sigma sigma) of the phenyl ring substituents. A significant correlation with N omega-oxidation could not be demonstrated. Initial high activity against P. berghei infections in mice led to expanded studies that demonstrated in addition excellent activity against resistant strains of parasite, activity in primate models, and pharmacokinetic properties apparently allowing protection against infection for extended periods of time even after oral administration. Such properties encourage the clinical trial of a member of this class in man.

  DOI：

  10.1021/jm00156a009

文献信息

• 2-hydroxy-5-amino-biphenyl-derivatives and oxidative hair colouring agents containing said compounds
  申请人：——

  公开号：US20020166180A1

  公开（公告）日：2002-11-14

  The invention relates to an oxidative coloring agent for keratin fibers, in particular hair based on a developing agent-coupling agent combination, which contains as a developing agent at least one 2-hydroxy-5-amino-biphenyl derivative of general formula (I) in addition to novel 2-hydroxy-5-amino-biphenyl derivatives.

  该发明涉及一种氧化染色剂，用于角蛋白纤维，特别是基于发展剂-偶联剂组合的头发，其中所述发展剂至少包含一种通式（I）的2-羟基-5-氨基联苯衍生物，以及新型的2-羟基-5-氨基联苯衍生物。
• Aryl Radical Selectivity in Biphasic Systems
  作者：Lisa-Marie Altmann、Michael C. D. Fürst、Eva I. Gans、Viviane Zantop、Gerald Pratsch、Markus R. Heinrich

  DOI：10.1021/acs.orglett.9b04237

  日期：2020.1.17

  Aryl radicals generated in the aqueous phase of biphasic mixtures have-regardless of a comparably low polarity- a strong preference to react with aromatic substrates in the aqueous phase and not to undergo phase-transfer into a lipophilic phase, independent from the presence of a surfactant. These results represent an important prerequisite toward future studies in biological systems, which typically

  在两相混合物的水相中产生的芳基具有相对​​低的极性，无论在何种表面活性剂的存在下，都非常希望与水相中的芳族底物反应并且不经历相转移成亲脂相。这些结果代表了未来生物学系统研究的重要前提，生物学系统通常由具有亲水性或亲脂性的各个部分组成。
• 2-HYDROXY-5-AMINO-BIPHENYL-DERIVATE SOWIE DIESE VERBINDUNGEN ENTHALTENDE OXIDATIONSHAARFÄRBEMITTEL
  申请人：Wella Aktiengesellschaft

  公开号：EP1208077A1

  公开（公告）日：2002-05-29
• US6749644B2
  申请人：——

  公开号：US6749644B2

  公开（公告）日：2004-06-15
• [DE] 2-HYDROXY-5-AMINO-BIPHENYL-DERIVATE SOWIE DIESE VERBINDUNGEN ENTHALTENDE OXIDATIONSHAARFÄRBEMITTEL<br/>[EN] 2-HYDROXY-5-AMINO-BIPHENYL-DERIVATIVES AND OXIDATIVE HAIR COLOURING AGENTS CONTAINING SAID COMPOUNDS<br/>[FR] DERIVES DE 2-HYDROXY-5-AMINO-BIPHENYLE, AINSI QUE PRODUITS COLORANTS PAR OXYDATION POUR LES CHEVEUX CONTENANT CES COMPOSES
  申请人：WELLA AG

  公开号：WO2002002507A1

  公开（公告）日：2002-01-10

  Gegenstand der vorliegenden Erfindung sind Mittel zur oxidativen Färbung von Keratinfasern, insbesondere Haaren, auf der Basis einer Entwicklersubstanz-Kupplersubstanz-Kombination, welche als Entwicklersubstanz mindestens ein 2-Hydroxy-5-amino-biphenyl-Derivat der allgemeinen Formel (I) enthalten, sowie neue 2-Hydroxy-5-amino-biphenyl-Derivate.