3-(3,4-dichlorophenoxy)benzoate | 149609-33-6

• 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-(3,4-dichlorophenoxy)benzoate
• 英文别名: 3(3,4-Dichloro-phenoxy)-benzoic acid；3-(3,4-dichlorophenoxy)benzoic acid
• CAS: 149609-33-6
• 化学式: C₁₃H₈Cl₂O₃
• mdl: MFCD06203272
• 分子量: 283.111
• InChiKey: OEMPBYVYCDVPOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3,4-dichlorophenoxy)benzoate 生成 N-hydroxy-N-[2-((3-(3,4-dichlorophenoxy)benzoyl)amino)ethyl]urea
  参考文献：
  名称：

  Arylamidoalkyl-N-hydroxyurea compounds having lipoxygenase inhibitory

  摘要：

  这项发明提供了一些抑制脂氧合酶酶活性的（取代的碳环芳基）氨基烷基-和（取代的杂环芳基）氨基烷基-N-羟基脲化合物，因此在治疗过敏和炎症性疾病状态中具有用处。

  公开号：

  US05514702A1
• 作为产物：
  描述：

  3-(3,4-二氯苯氧基)苯甲醛 在 rat hepatic microsomal aldehyde dehydrogenase 、 β-烟酰胺腺嘌呤二核苷酸 作用下， 以 phosphate buffer 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(3,4-dichlorophenoxy)benzoate
  参考文献：
  名称：

  Rat Hepatic Microsomal Aldehyde Dehydrogenase. Identification of 3- and 4-Substituted Aromatic Aldehydes as Substrates of the Enzyme

  摘要：

  The rat hepatic microsomal aldehyde dehydrogenase (mALDH) metabolizes aliphatic and aromatic aldehydes to the corresponding acids with NAD as the optimal cofactor. However, dehydrogenation of the aliphatic compounds is substantially more efficient. In the present study, a series of aromatic aldehydes was evaluated as substrates of the purified mALDH so that the physicochemical factors that contribute to substrate affinity could be evaluated. Substitution of the aromatic system in the 3- and 4-positions produced relatively good substrates, but 2-substituted congeners did not undergo dehydrogenation. However, aldehydes with hydrophilic substituents in the 3- or 4-positions and those with extremely bulky substituents at both positions (e.g., 3,4-dibenzyloxy) were also poor substrates for the enzyme and dehydrogenation was undetectable. A quantitative structure-activity relationship was determined that related the logarithm of the Michaelis constants for 27 substituted aromatic aldehydes with the zero-order connectivity function of the molecule ((0) chi), the shapes of the 3- and 4-substituents (kappa), and the electronic nature of the 4-substituent (sigma). In this equation, 81% of the data variance was explained. From a consideration of the dimensions of 3-phenoxybenzaldehyde, which was a relatively good substrate, the mALDH possesses a narrow cleft within the active site that is at least 7.5 Angstrom wide and extends at least 12 Angstrom from the the catalytic residue (probably cysteine). Previously established relationships between connectivity functions and molecular polarizability suggest that dipolar interactions within the active site, as well as dispersion forces, may play a role in substrate specificity. Although optimal shapes for carbocyclic substituents were not provided by the analysis, the unfavorable effect on dehydrogenation from hydrophilic and large substituents suggests that the active site of the mALDH is relatively rigid and that the orientation of the substrate in relation to the catalytic cysteine and the cofactor binding site is critical.

  DOI：

  10.1021/tx950106l

文献信息

• Discovery of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid diamides that increase CFTR mediated chloride transport
  作者：Bradford H. Hirth、Shuang Qiao、Lisa M. Cuff、Brian M. Cochran、Marko J. Pregel、Jill S. Gregory、Scott F. Sneddon、John L. Kane

  DOI：10.1016/j.bmcl.2005.02.041

  日期：2005.4

  A series of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid diamides that increase chloride transport in cells expressing mutant cystic fibrosis transmembrane conductance regulator (CFTR) protein has been identified from our compound library. Analoging efforts and the resulting structure-activity relationships uncovered are detailed. Compound potency was improved over 30-fold from the original lead, yielding several analogs with EC50 values below 10 nM in our cellular chloride transport assay. (c) 2005 Elsevier Ltd. All rights reserved.
• ARYLAMIDOALKYL-N-HYDROXYUREA COMPOUNDS HAVING LIPOXYGENASE INHIBITORY ACTIVITY
  申请人：ABBOTT LABORATORIES

  公开号：EP0595995A1

  公开（公告）日：1994-05-11
• EP0595995A4
  申请人：——

  公开号：EP0595995A4

  公开（公告）日：1994-08-24
• ARYLAMIDOALKYL- AND ARYLAMINOALKYL-N-HYDROXYUREA COMPOUNDS AND -N-HYDROXYFORMAMIDE DERIVATIVES HAVING LIPOXYGENASE INHIBITORY ACTIVITY
  申请人：ABBOTT LABORATORIES

  公开号：EP0595995B1

  公开（公告）日：1997-01-15
• US5214204A
  申请人：——

  公开号：US5214204A

  公开（公告）日：1993-05-25