5-Chlor-2-phenoxy-phenol | 3489-83-6

• 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: 5-Chlor-2-phenoxy-phenol
• 英文别名: 5-Chloro-2-phenoxyphenol
• CAS: 3489-83-6
• 化学式: C₁₂H₉ClO₂
• 分子量: 220.655
• InChiKey: ZVTLRRZWZYDDLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Chlor-2-phenoxy-phenol 、 1-(6-chloropyrimidin-4-yl)-1,2,3,4-tetrahydroquinoline 在 copper(l) iodide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到
  参考文献：
  名称：

  含有嘧啶醚支架作为几丁质合酶抑制剂的新型 1,2,3,4-四氢喹啉衍生物的合成、抗真菌活性和 3D-QASR

  摘要：

  将天然产物的活性基团引入农药分子骨架是发现活性先导化合物的有效途径，因此被广泛应用于新型农用化学品的开发。在这项工作中，通过活性亚结构剪接方法设计并合成了一系列含有嘧啶醚支架的新型1,2,3,4-四氢喹啉衍生物。新化合物对几种真菌表现出良好的抗真菌活性。尤其是化合物4fh对马铃薯和核盘菌表现出优异的体外活性，EC 50值分别为0.71和2.47 μg/mL。4fh对几丁质合酶（CHS）的抑制活性（50 μM 时为 68.08%）略强于 polyoxin D（50 μM 时为 63.84%），在体内对核盘菌表现出明显的治疗和保护作用。因此，4fh可以被认为是一种新的候选杀菌剂作为几丁质合酶抑制剂。准确可靠的三维定量构效关系 (3D-QSAR) 模型为进一步开发更高活性的杀菌剂提供了有用的方向。分子对接显示，传统的氢键主要影响4fh与几丁质合酶的结合亲和力。目前的结果将为发现用于农业植物病害控制的潜在

  DOI：

  10.1021/acs.jafc.2c01348
• 作为产物：
  描述：

  4-氯-2-甲氧基苯酚 在 1-萘甲酸 copper(I) trifluoromethanesulfonate benzene 、 三溴化硼 、 caesium carbonate 、 乙酸乙酯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 5-Chlor-2-phenoxy-phenol
  参考文献：
  名称：

  Inhibition of the Bacterial Enoyl Reductase FabI by Triclosan:  A Structure−Reactivity Analysis of FabI Inhibition by Triclosan Analogues

  摘要：

  To explore the molecular basis for the picomolar affinity of triclosan for FabI, the enoyl reductase enzyme from the type II fatty acid biosynthesis pathway in Escherichia coli, an SAR study has been conducted using a series of triclosan analogues. Triclosan (1) is a slow, tight-binding inhibitor of FabI, interacting specifically with the E-NAD+ form of the enzyme with a K-1 value of 7 pM. In contrast, 2-phenoxyphenol (2) binds with equal affinity to the E.NAD+ (K-1 = 0.5 muM) and E.NADH (K-2 = 0.4 muM) forms of the enzyme and lacks the slow-binding step observed for triclosan. Thus, removal of the three triclosan chlorine atoms reduces the affinity of the inhibitor for FabI by 70 000-fold and removes the preference for the E.NAD+ FabI complex. 5-Chloro-2-phenoxyphenol (3) is a slow, tight-binding inhibitor of FabI and binds to the E.NAD+ form of the enzyme (K-1 = 1.1 pM) 7-fold more tightly than triclosan. Thus, while the two ring B chlorine atoms are not required for FabI inhibition, replacement of the ring A chlorine increases binding affinity by 450 000-fold. Given this remarkable observation, the SAR study was extended to the 5-fluoro-2-phenoxyphenol (4) and 5-methyl-2-phenoxyphenol (5) analogues to further explore the role of the ring A substituent. While both 4 and 5 are slow, tight-binding inhibitors, they bind substantially less tightly to FabI than triclosan. Compound 4 binds to both E.NAD+ and E.NADH forms of the enzyme with K-1 and K-2 values of 3.2 and 240 nM, respectively, whereas compound 5 binds exclusively to the E.NADH enzyme complex with a K-2 value of 7.2 nM. Thus, the ring A substituent is absolutely required for slow, tight-binding inhibition. In addition, pK(a) measurements coupled with simple electrostatic calculations suggest that the interaction of the ring A substituent with F203 is a major factor in governing the affinity of analogues 3-5 for the FabI complex containing the oxidized form of the cofactor.

  DOI：

  10.1021/jm030182i

文献信息

• SAEKI SEITARO; OZAWA NAOKI; YOSHIMURA HIDETOSHI, FUKUOKA IGAKU DZASSI,
  作者：SAEKI SEITARO、 OZAWA NAOKI、 YOSHIMURA HIDETOSHI

  DOI：——

  日期：——
• Verfahren zur Herstellung von 4,5-Dichlor-2-(4-chlorphenoxy)-phenol und 4,5-Dichlor-2-(4-chlorphenoxy)-anisol
  申请人：CIBA-GEIGY AG

  公开号：EP0012108B1

  公开（公告）日：1982-07-28
• Pyridone FabI Inhibitors and Uses Thereof
  申请人：The Research Foundation for the State University of New York

  公开号：US20160376235A1

  公开（公告）日：2016-12-29

  The present invention provides novel 2-pyridone compounds and 4-pyridone compounds and methods of treating a subject infected with a pathogen of Staphylococcus aureus, Mycobacterium tuberculosis, Francisella tularensis, Burkholderia pseudomallei, Yersinia pestis, Escherichia coli and Proteus mirabilisone.
• US4284828A
  申请人：——

  公开号：US4284828A

  公开（公告）日：1981-08-18
• US4410738A
  申请人：——

  公开号：US4410738A

  公开（公告）日：1983-10-18