3-(4-chlorophenoxy)benzoate | 129764-91-6

• 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-(4-chlorophenoxy)benzoate
• 英文别名: 3-(4-Chlorophenoxy)benzoic acid
• CAS: 129764-91-6
• 化学式: C₁₃H₉ClO₃
• mdl: MFCD06203217
• 分子量: 248.666
• InChiKey: ICBGRQBEFICVLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 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-(4-chlorophenoxy)benzoate 在 硫酸 、 一水合肼 作用下， 反应 2.0h， 生成 3-(4-Chloro-phenoxy)-benzoic acid hydrazide
  参考文献：
  名称：

  Nagarapu, Lingaiah; Ravirala, Narender; Akkewar, Dattatray M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 12, p. 1254 - 1257

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(4-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-(4-chlorophenoxy)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

• Arylamidoalkyl-N-hydroxyurea compounds having lipoxygenase inhibitory
  申请人：Abbott Laboratories

  公开号：US05514702A1

  公开（公告）日：1996-05-07

  The present invention provides certain (substituted carbocyclic aryl)amidoalkyl- and (substituted heterocyclic aryl)amidoalkyl-N-Hydroxy urea compounds which inhibit lipoxygenase enzyme activity and are thus useful in the treatment of allergic and inflammatory disease states.

  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。
• Rhodium(III)-catalyzed Intramolecular Ar–H/Ar–H Coupling Directed by Carboxylic Group to Produce Dibenzofuran Carboxylic Acids
  作者：Takeshi Okada、Yuto Unoh、Tetsuya Satoh、Masahiro Miura

  DOI：10.1246/cl.150739

  日期：2015.11.5

  The rhodium-catalyzed intramolecular Ar–H/Ar–H coupling of 3-phenoxybenzoic acids proceeds smoothly, accompanied by double C–H bond cleavage at the 2- and 2′-positions, to produce dibenzofuran-1-carboxylic acid derivatives. Related tetra- and pentacyclic molecules can also be readily constructed by the present procedure. A reaction mechanism involving 1,4-rhodium(III) migration is proposed.

  在铑催化下，3-苯氧基苯甲酸的分子内 Ar-H/Ar-H 偶联顺利进行，同时在 2- 和 2′-位发生双 C-H 键裂解，生成二苯并呋喃-1-羧酸衍生物。相关的四环和五环分子也很容易通过本程序生成。提出了一种涉及 1,4-铑(III)迁移的反应机理。
• Chemical Proteomics Reveals Antibiotic Targets of Oxadiazolones in MRSA
  作者：Alexander T. Bakker、Ioli Kotsogianni、Liza Mirenda、Verena M. Straub、Mariana Avalos、Richard J. B. H. N. van den Berg、Bogdan I. Florea、Gilles P. van Wezel、Antonius P. A. Janssen、Nathaniel I. Martin、Mario van der Stelt

  DOI：10.1021/jacs.2c10819

  日期：2023.1.18

  antibacterial potency against multidrug-resistant Staphylococcus aureus. In situ competitive and comparative chemical proteomics with a tailor-made activity-based probe, in combination with transposon and resistance studies, revealed several cysteine and serine hydrolases as relevant targets. Our data showcase oxadiazolones as a novel antibacterial chemotype with a polypharmacological mode of action, in

  表型筛选是鉴定新型抗生素的有效方法，但对于具有多药理学作用模式的化合物，阐明负责抗菌活性的靶点通常具有挑战性。在这里，我们展示了基于活性的蛋白质分析绘制了一系列 1,3,4-oxadiazole-3-ones 的靶标相互作用图谱，这些 1,3,4-oxadiazole-3-ones 在表型筛选中被鉴定为对多重耐药金黄色葡萄球菌具有高抗菌效力. 原位竞争和比较化学蛋白质组学与定制的基于活性的探针，结合转座子和抗性研究，揭示了几种半胱氨酸和丝氨酸水解酶作为相关目标。我们的数据显示恶二唑酮是一种新型抗菌化学型，具有多药理学作用模式，其中 FabH、FphC 和 AdhE 起着核心作用。
• 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