2-(4-氯苯基)-4-[(7-氯喹啉-4-基)氨基]-6-(二乙基氨基甲基)苯酚 | 79286-94-5

• 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: 2-(4-氯苯基)-4-[(7-氯喹啉-4-基)氨基]-6-(二乙基氨基甲基)苯酚
• 英文名称: 5'-(4-chlorophenyl)amodiaquine
• 英文别名: 6-(4-chlorophenyl)-4-(7-chloroquinolin-4-ylamino)-2-diethylaminomethylphenol；2-(4-Chlorophenyl)-4-[(7-chloroquinolin-4-yl)amino]-6-(diethylaminomethyl)phenol
• CAS: 79286-94-5
• 化学式: C₂₆H₂₅Cl₂N₃O
• 分子量: 466.41
• InChiKey: ZXODOMROLXVJNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  48.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-氨基-4'-氯[1,1'-联苯基]-2-醇 在 盐酸 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 2-(4-氯苯基)-4-[(7-氯喹啉-4-基)氨基]-6-(二乙基氨基甲基)苯酚
  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

• [EN] NOVEL AMODIAQUINE ANALOGS AND METHODS OF USES THEREOF<br/>[FR] NOUVEAUX ANALOGUES D'AMODIAQUINE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：TEXAS BIOMEDICAL RES INSTITUTE

  公开号：WO2018191642A1

  公开（公告）日：2018-10-18

  Described herein are pharmaceutical compositions capable of blocking entry of a virus into a host cell and containing one or more compounds of the general formula I or a pharmaceutically acceptable derivative thereof and methods of treatment or prophylactic administration of these pharmaceutical compositions to treat viral infections.

  本文描述了一种能够阻止病毒进入宿主细胞的药物组合物，其中包含一种或多种通用式I的化合物或其药用可接受的衍生物，并提供了使用这些药物组合物进行治疗或预防的方法，以治疗病毒感染。
• Substituted-5-((7-chloro-4-quinolinyl)amino)-3-(amino-methyl)-(1,1'-biphenyl)-2-ol compounds; processes for their production; and pharmaceutical compositions containing the compounds
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0027679A2

  公开（公告）日：1981-04-29

  Substituted-5-[(7-chloro-4-quinohny))amino]-3-(aminomethyl)-[(1,1'-biphenyl]-2-ol compounds and salts thereof; and processes for their production are disclosed. In addition, antimalarial pharmaceutical compositions including such compounds and methods of treatment employing the compositions are taught. Also disclosed are intermediates for use in producing the substituted compounds. The substituted compounds are those of the formula:- wherein X is a hydrogen, fluorine, bromine or chlorine atom or a lower alkyl radical; Y is a chlorine, fluorine or bromine atom or a trifluoromethyl, lower alkoxy, cyano, hydroxy, nitro, lower alkylthio, amino, lower alkyl amino, di(lower alkyl) amino, pyrrolidino or piperidino radical; R'and R2, which are the same or different, are each a hydrogen atom or a lower alkyl radical, or R1R2N taken together is a pyrrolidino, piperidino or homopiperidino radical of which the heterocyclic ring is unsubstituted or substituted by from one to four lower alkyl radicals; Z is zero or one.

  公开了取代的-5-[(7-氯-4-喹啉))氨基]-3-(氨基甲基)-[(1,1'-联苯]-2-醇化合物及其盐类；以及生产它们的工艺。此外，还教导了包括此类化合物的抗疟药物组合物和使用该组合物的治疗方法。还公开了用于生产取代化合物的中间体。取代的化合物是那些式如下的化合物 其中 X 是氢、氟、溴或氯原子或低级烷基自由基；Y 是氯、氟或溴原子或三氟甲基、低级烷氧基、氰基、羟基、硝基、低级烷硫基、氨基、低级烷基氨基、二（低级烷基）氨基、吡咯烷基或哌啶基自由基；R'和 R2（相同或不同）各自为氢原子或低级烷基，或 R1R2N 合在一起为吡咯烷基、哌啶基或均哌啶基，其中杂环未被取代或被 1 至 4 个低级烷基取代；Z 为 0 或 1。
• WERBEL L. M.; COOK P. D.; ELSLAGER E. F.; HUNG J. H.; JOHNSON J. L.; KEST+, J. MED. CHEM., 29,(1986) N 6, 924-939
  作者：WERBEL L. M.、 COOK P. D.、 ELSLAGER E. F.、 HUNG J. H.、 JOHNSON J. L.、 KEST+

  DOI：——

  日期：——
• NOVEL AMODIAQUINE ANALOGS AND METHODS OF USES THEREOF
  申请人：TEXAS BIOMEDICAL RESEARCH INSTITUTE

  公开号：US20200113891A1

  公开（公告）日：2020-04-16

  Described herein are pharmaceutical compositions capable of blocking entry of a virus into a host cell and containing one or more compounds of the general formula I or a pharmaceutically acceptable derivative thereof and methods of treatment or prophylactic administration of these pharmaceutical compositions to treat viral infections.
• 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
  作者：Leslie M. Werbel、P. Dan Cook、Edward F. Elslager、Jocelyn H. Hung、Judith L. Johnson、Stephen J. Kesten、Dennis J. McNamara、Daniel F. Ortwine、Donald F. Worth

  DOI：10.1021/jm00156a009

  日期：1986.6

  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.