(3,5-dichloro-4-hydroxyphenyl)acetic acid | 89894-49-5

• 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: (3,5-dichloro-4-hydroxyphenyl)acetic acid
• 英文别名: 4-hydroxy-3,5-dichlorophenylacetic acid；3,5-Dichlor-4-hydroxyphenylessigsaeure；2-(3,5-dichloro-4-hydroxyphenyl)acetic acid
• CAS: 89894-49-5
• 化学式: C₈H₆Cl₂O₃
• 分子量: 221.04
• InChiKey: WKGVWIDAQMUITK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3,5-dichloro-4-hydroxyphenyl)acetic acid 在 硫酸 、 氰化钠 、 氨 作用下， 以 甲醇 、 苯 为溶剂， 生成 4-hydroxy-3,5-dichlorophenylacetamide
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1012799002863
• 作为产物：
  描述：

  对羟基苯乙酸 在 氯化亚砜 作用下， 生成 (3,5-dichloro-4-hydroxyphenyl)acetic acid
  参考文献：
  名称：

  Synthesis of verongiaquinol and related compounds and study of their inhibiting action on rat brain Na+,K+-ATPase

  摘要：

  DOI：

  10.1007/bf00629820

文献信息

• Novel, racemic or nearly-racemic antibacterial bromo- and chloroquinols and ?-lactams of the verongiaquinol and the cavernicolin type from the marine spongeAplysina (=Verongia)cavernicola
  作者：Michele D'Ambrosio、Antonio Guerriero、Francesco Pietra

  DOI：10.1002/hlca.19840670610

  日期：1984.9.26

  Both 1 and 1c proved to be racemic from NMR examination of their esterification products with (–)-methyl-oxyacetic acid, whilst 6 had a ca. 6% enantiomeric purity as shown by a 1H-NMR study of its monoacetate 6′ in the presence of a chiral shift reagent. These chiroptical data of the first chiral quinols from the Verongida and of 6 suggest phenol oxidative routes from tyrosine precursors for their formation

  地中海海绵的丁醇提取物Aplysina（= Verongia）cavernicola给，通过反相HPLC，抗菌quinols（±）-3- bromoverongiaquinol（=（±）-3-溴-1-羟基-4-氧代-2- ，5-环己基-1-乙酰胺；1d）和（±）-3-溴-5-氯verongiaquinol（=（±）-3-溴-5-氯-1-羟基-4-氧代-2,5-环己氨酸-1-乙酰胺；1c）除其正式环化的产物5-氯己二烯-1-乙酰胺外；1c）除了其正式环化的产物5-氯曲霉素（= 5-cloro-3,3a，7,7aβ-tetrahydro-3aβ-hydroxy-2,6（1 H）-indoledione; 6），C（7）-致敏的7β-溴-5-氯卡维尼可林（= 7β-溴-5-氯-3,3a，7,7aβ-四氢-3aβ-羟基-2,6（1H）-吲哚二酮; 4a和7α-bromo-5- chlorocavernicolin
• WO2006/92268
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] BICYLONONENE DERIVATIVES<br/>[FR] DERIVES DE BICYCLONONENE
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2006021401A3

  公开（公告）日：2006-04-13
• 518. The synthesis of thyroxine and related compounds. Part XV. The preparation of thyronines from iodonium salts and derivatives of 3,5-disubstituted tyrosines
  作者：A. Dibbo、L. Stephenson、T. Walker、W. K. Warburton

  DOI：10.1039/jr9610002645

  日期：——
• Halogenation of 4-hydroxy/amino-3-methoxyphenyl acetamide TRPV1 agonists showed enhanced antagonism to capsaicin
  作者：Dong Wook Kang、Yong Soo Kim、Kwang Su Lim、Myeong Seop Kim、Larry V. Pearce、Vladimir A. Pavlyukovets、Andy K. Tao、Krystle A. Lang-Kuhs、Peter M. Blumberg、Jeewoo Lee

  DOI：10.1016/j.bmc.2010.09.001

  日期：2010.11.15

  As an extension of our analysis of the effect of halogenation on thiourea TRPV1 agonists, we have now modified selected 4-hydroxy(or 4-amino)-3-methoxyphenyl acetamide TRPV1 agonists by 5- or 6-halogenation on the aromatic A-region and evaluated them for potency for TRPV1 binding and regulation and for their pattern of agonism/antagonism (efficacy). Halogenation shifted the functional activity at TRPV1 toward antagonism with a greater extent of antagonism as the size of the halogen increased (I > Br > Cl), as previously observed for the thiourea series. The extent of antagonism was greater for halogenation at the 5-position than at the 6-position, in contrast to SAR for the thiourea series. In this series, compounds 55 and 75 showed the most potent antagonism, with K-i (ant) = 2.77 and 2.19 nM, respectively, on rTRPV1 expressed in Chinese hamster ovary cells. The compounds were thus ca. 40-60-fold more potent than 6'-iodononivamide. (C) 2010 Elsevier Ltd. All rights reserved.