2',3,5-trichloro-4-hydroxybiphenyl | 72490-71-2

• 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: 2',3,5-trichloro-4-hydroxybiphenyl
• 英文别名: 4-hydroxy-2',3,5-trichlorobiphenyl；4-OH PCB 34；4-OHPCB 34；2',3,5-Trichlor-4-hydroxy-biphenyl；2,6-dichloro-4-(2-chlorophenyl)phenol
• CAS: 72490-71-2
• 化学式: C₁₂H₇Cl₃O
• 分子量: 273.546
• InChiKey: XLRWQPVYQISORN-UHFFFAOYSA-N

物化性质

• 沸点：
  340.9±37.0 °C(Predicted)
• 密度：
  1.447±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

代谢

4-羟基-2',3',5'-三氯联苯已知的人类代谢物包括2',3',5'-三氯联苯和4'-硫酸盐。

4-hydroxy-2p,3,5-trichlorobiphenyl has known human metabolites that include 2p,3,5-trichlorobiphenyl, 4-sulfate.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  2',3,5-trichloro-4-hydroxybiphenyl 、 6-氨基-9-[3-羟基-5-[(羟基-磺基氧基-磷酰)氧基甲基]-4-膦酰氧基-四氢呋喃-2-基]-嘌呤 在 potassium phosphate 、 human hydroxysteroid sulfotransferase 2A₁ 、 2-巯基乙醇 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 [2,6-Dichloro-4-(2-chlorophenyl)phenyl] hydrogen sulfate 、 腺苷 3',5'-二磷酸酯; 3',5'-二磷酸腺苷
  参考文献：
  名称：

  Structure–Activity Relationships for Hydroxylated Polychlorinated Biphenyls As Inhibitors of the Sulfation of Dehydroepiandrosterone Catalyzed by Human Hydroxysteroid Sulfotransferase SULT2A1

  摘要：

  Polychlorinated biphenyls (PCBs) are persistent worldwide pollutants that are of concern due to their bioaccumulation and health effects. Metabolic oxidation of PCBs results in the formation of hydroxylated metabolites (OHPCBs). Among their biological effects, OHPCBs have been shown to alter the metabolism of endocrine hormones, including inhibition of mammalian cytosolic sulfotransferases (SULTs) that are responsible for the inactivation of thyroid hormones and phenolic steroids (i.e., hSULT1A1, hSULT1B1, and hSULT1E1). OHPCBs also interact with a human hydroxysteroid sulfotransferase that plays a role in the sulfation of endogenous alcohol-containing steroid hormones and bile acids (i.e., hSULT2A1). The objectives of our current study were to examine the effects of a series of OHPCB congeners on the activity of hSULT2A1 and to develop a three-dimensional quantitative structure activity relationship (3D-QSAR) model for OHPCBs as inhibitors of the enzyme. A total of 15 OHPCBs were examined, and the sulfation of 1 mu M [H-3] dehydroepiandrosterone (DHEA) was utilized as a model reaction catalyzed by the enzyme. All 15 OHPCBs inhibited the sulfation of DHEA, with IC50 values ranging from 0.6 mu M to 96 mu M, and eight of these OHPCBs were also substrates for the enzyme. Comparative molecular field analysis (CoMFA) provided a predictive 3D-QSAR model with a q(2) value of 0.697 and an r(2) value of 0.949. The OHPCBs that had the highest potency as inhibitors of DHEA sulfation were those with a 3, 5-dichloro-4-hydroxy substitution pattern on the biphenyl ring system, and these congeners were also substrates for sulfation catalyzed by hSULT2A1.

  DOI：

  10.1021/tx200260h
• 作为产物：
  描述：

  2,6-二氯苯酚 在 四(三苯基膦)钯 sodium hydroxide 、 氢溴酸 、 三溴化硼 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 36.5h， 生成 2',3,5-trichloro-4-hydroxybiphenyl
  参考文献：
  名称：

  Synthesis of hydroxylated PCB metabolites with the Suzuki-coupling

  摘要：

  An improved synthesis of hydroxylated polychlorinated biphenyls (PCBs) which are structurally related to the major hydroxy PCB, congeners identified in human plasma is described. The coupling of (chlorinated) aryl boronic acids with bromochloro anisoles using the standard conditions of the Suzuki coupling gave the desired hydroxylated PCB metabolites in good to excellent yields. The approach offers the advantage of high selectivity and good yields compared to conventional methods such as the Cadogan reaction and allows the use of less toxic starting materials. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0045-6535(01)00052-2

文献信息

• Synthesis of hydroxylated PCB metabolites with the Suzuki-coupling
  作者：Hans-Joachim Lehmler、Larry W. Robertson

  DOI：10.1016/s0045-6535(01)00052-2

  日期：2001.12

  An improved synthesis of hydroxylated polychlorinated biphenyls (PCBs) which are structurally related to the major hydroxy PCB, congeners identified in human plasma is described. The coupling of (chlorinated) aryl boronic acids with bromochloro anisoles using the standard conditions of the Suzuki coupling gave the desired hydroxylated PCB metabolites in good to excellent yields. The approach offers the advantage of high selectivity and good yields compared to conventional methods such as the Cadogan reaction and allows the use of less toxic starting materials. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Structure–Activity Relationships for Hydroxylated Polychlorinated Biphenyls As Inhibitors of the Sulfation of Dehydroepiandrosterone Catalyzed by Human Hydroxysteroid Sulfotransferase SULT2A1
  作者：Edugie J. Ekuase、Yungang Liu、Hans-Joachim Lehmler、Larry W. Robertson、Michael W. Duffel

  DOI：10.1021/tx200260h

  日期：2011.10.17

  Polychlorinated biphenyls (PCBs) are persistent worldwide pollutants that are of concern due to their bioaccumulation and health effects. Metabolic oxidation of PCBs results in the formation of hydroxylated metabolites (OHPCBs). Among their biological effects, OHPCBs have been shown to alter the metabolism of endocrine hormones, including inhibition of mammalian cytosolic sulfotransferases (SULTs) that are responsible for the inactivation of thyroid hormones and phenolic steroids (i.e., hSULT1A1, hSULT1B1, and hSULT1E1). OHPCBs also interact with a human hydroxysteroid sulfotransferase that plays a role in the sulfation of endogenous alcohol-containing steroid hormones and bile acids (i.e., hSULT2A1). The objectives of our current study were to examine the effects of a series of OHPCB congeners on the activity of hSULT2A1 and to develop a three-dimensional quantitative structure activity relationship (3D-QSAR) model for OHPCBs as inhibitors of the enzyme. A total of 15 OHPCBs were examined, and the sulfation of 1 mu M [H-3] dehydroepiandrosterone (DHEA) was utilized as a model reaction catalyzed by the enzyme. All 15 OHPCBs inhibited the sulfation of DHEA, with IC50 values ranging from 0.6 mu M to 96 mu M, and eight of these OHPCBs were also substrates for the enzyme. Comparative molecular field analysis (CoMFA) provided a predictive 3D-QSAR model with a q(2) value of 0.697 and an r(2) value of 0.949. The OHPCBs that had the highest potency as inhibitors of DHEA sulfation were those with a 3, 5-dichloro-4-hydroxy substitution pattern on the biphenyl ring system, and these congeners were also substrates for sulfation catalyzed by hSULT2A1.