1-(3-hydroxy-4-phenoxyphenyl)ethanone | 600173-41-9

• 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: 1-(3-hydroxy-4-phenoxyphenyl)ethanone
• 英文别名: 1-(3-Hydroxy-4-phenoxyphenyl)ethan-1-one
• CAS: 600173-41-9
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: SFPQMGYVVZPRRM-UHFFFAOYSA-N

物化性质

• 熔点：
  84-85 °C
• 沸点：
  371.6±37.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  1-(3-hydroxy-4-phenoxyphenyl)ethanone 在 正丁基锂 、 对甲苯磺酸 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.08h， 生成 (2E)-1-(3'-hydroxy-4'-phenoxyphenyl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  A route to the structure proposed for puetuberosanol and approaches to the natural products marshrin and phebalosin

  摘要：

  Synthesis of the structure claimed for puetuberosanol 1 (using the Julia-Colonna oxidation in a key step) showed that the natural product was a different material. The isomeric epoxy alcohols 16-18 can be discounted from the alternatives. An analogue 19 of marshrin 2 was prepared but the synthesis of the natural product was thwarted by failure of a Julia-Colonna oxidation in the key step. The epoxy ketone 29 was prepared by Darzens condensation and was converted into (+/-)-phebalosin 3. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00624-0
• 作为产物：
  描述：

  香草乙酮 在 吡啶 、 copper diacetate 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 75.0h， 生成 1-(3-hydroxy-4-phenoxyphenyl)ethanone
  参考文献：
  名称：

  针对结核分枝杆菌药物敏感和耐药菌株的新型二苯醚衍生物的设计，合成和评估

  摘要：

  在我们努力开发可药用的二苯醚作为潜在的抗结核药的努力中，设计并合成了一系列新型的二苯醚衍生物（5a - f，6a - f）。代表性化合物显示出对结核分枝杆菌的药物敏感，异烟肼耐药和多药耐药菌株的体外活性，其MIC值为1.56μg/ ml（6b），6.25μg/ ml（6a–d）和3.125μg / ml（6b–c）分别。所有合成的化合物均显示出令人满意的安全性（CC 50 > 300μg/ ml）对抗Vero和HepG2细胞。反相高效液相色谱法用于探测合成化合物的理化性质。该系列化合物显示出较低的logP值。代表性化合物的p K a值表明它们是弱酸。另外，体外人肝微粒体稳定性测定证实了合成的化合物在研究条件下具有可接受的稳定性。因此，本研究确立了化合物6b为具有可接受的药物样似性的最有希望的抗结核药。

  DOI：

  10.1111/cbdd.13379

文献信息

• Synthesis, Biological Evaluation and Molecular Dynamics Simulation Studies of Novel Diphenyl Ethers
  作者：Amol B. Khade、Sidhartha S. Kar、Cinu T. Alummoottil、Ashutosh Tiwari、Mradul Tiwari、Vandana K. Eshwara、Pritesh Bhat、Varadaraj B. Giliyar、Gurupur G. Shenoy

  DOI：10.2174/1573406415666190306152907

  日期：2020.2.20

  design a superior molecule that might have more inhibitory potential. This unveils tons of potential interaction space to take advantage of future inhibitor design. OBJECTIVES Synthesis of TCL mimicking novel diphenyl ether derivatives, biological evaluation as potential antiproliferative agents and molecular docking and molecular dynamics simulation studies. METHODS A series of novel N-(1-(3-hydr

  背景技术已经描述了靶向细菌的烯醇二酰基蛋白还原酶的众所周知的抗菌剂三氯生（TCL），其通过烯醇二酰基还原酶结构域抑制人脂肪酸合酶（FASN）。文献调查表明，TCL对癌细胞具有选择性毒性，此外，确实可能降低体内癌症的发生率。最近的一项研究发现，TCL通过充当变构蛋白-蛋白界面（PPI）抑制剂来抑制FASN。它诱导二聚体方向变化，从而影响NADPH结合位点中催化残基的下游重新定向，从而提出将TCL用作可行的支架来设计可能具有更大抑制潜力的优良分子。这揭示了大量潜在的相互作用空间，以利用未来抑制剂的设计优势。目的模仿新的二苯醚衍生物的TCL的合成，作为潜在的抗增殖剂的生物学评估以及分子对接和分子动力学模拟研究。方法一系列新型的N-（1-（3-羟基-4-苯氧基苯基）-3-氧代-3-苯基丙基）乙酰胺（3a-n​​）和N-（3（3-羟基-4苯氧基苯基）-3-氧代针对HepG2，A-549，MCF-7和
• Design, synthesis, in silico and in vitro evaluation of novel diphenyl ether derivatives as potential antitubercular agents
  作者：Ashutosh Prasad Tiwari、B. Sridhar、Helena I. Boshoff、Kriti Arora、G. Gautham Shenoy、K. E. Vandana、G. Varadaraj Bhat

  DOI：10.1007/s11030-019-09990-z

  日期：2020.11

  Abstract Diphenyl ether derivatives inhibit mycobacterial cell wall synthesis by inhibiting an enzyme, enoyl-acyl carrier protein reductase (InhA), which catalyses the last step in the fatty acid synthesis cycle of genus Mycobacterium. To select and validate a protein crystal structure of enoyl-acyl carrier protein reductase of Mycobacterium tuberculosis for designing inhibitors using molecular modelling

  摘要 二苯醚衍生物通过抑制烯醇酰基载体蛋白还原酶（InhA）来抑制分枝杆菌细胞壁的合成，该酶催化分枝杆菌属脂肪酸合成周期的最后一步。为了选择和验证结核分枝杆菌的烯酰基-酰基载体蛋白还原酶的蛋白质晶体结构，以使用分子模型设计抑制剂，进行了对接和相关研究。从该模型合成了一系列新型的1-（3-（3-羟基-4-苯氧基苯基）-5-苯基-4,5-二氢-1H-吡唑-1-基）乙烷-1-酮并进行了筛选其抗结核分枝杆菌H37Rv的抗结核活性。化合物PYN-8表现出良好的抗结核活性结核分枝杆菌H37Rv（MIC = 4-7 µM）和牛分枝杆菌（10 µM时的抑制百分比= 95.91％）。使用各种细胞系评估了所有合成衍生物的细胞毒性，发现它们是安全的。通过单晶X射线衍射也证实了PYN-8的结构。分子建模研究还证实了化合物的生物活性。此外，计算机分析发现，所有这些测试的化合物均表现出良好的ADME性质和药物相似性，
• Rational design and synthesis of novel diphenyl ether derivatives as antitubercular agents
  作者：G Gautham、Sidhartha Sankar Kar、Varadaraj Bhat、Praveen Rao P N、Vishnu P Shenoy、Indira Bairy

  DOI：10.2147/dddt.s104037

  日期：——

  A series of triclosan mimic diphenyl ether derivatives have been synthesized and evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv. The binding mode of the compounds at the active site of enoyl-acyl carrier protein reductase of M. tuberculosis has been explored. Among them, compound 10b was found to possess antitubercular activity (minimum inhibitory concentration = 12.5 mu g/mL) comparable to triclosan. All the synthesized compounds exhibited low levels of cytotoxicity against Vero and HepG2 cell lines, and three compounds 10a, 10b, and 10c had a selectivity index more than 10. Compound 10b was also evaluated for log P, pKa, human liver microsomal stability, and % protein binding, in order to probe its druglikeness. Based on the antitubercular activity and druglikeness profile, it may be concluded that compound 10b could be a lead for future development of antitubercular drugs.
• Carboxy-Substituted Cinnamides:  A Novel Series of Potent, Orally Active LTB₄ Receptor Antagonists
  作者：Paul D. Greenspan、Roger A. Fujimoto、Paul J. Marshall、Anil Raychaudhuri、Kenneth E. Lipson、Huanghai Zhou、Robert A. Doti、David E. Coppa、Lijuan Zhu、Roberta Pelletier、Susan Uziel-Fusi、Robert H. Jackson、Michael H. Chin、Bernard L. Kotyuk、John J. Fitt

  DOI：10.1021/jm980540v

  日期：1999.1.1

  A series of carboxy-substituted cinnamides were investigated as antagonists of the human cell surface leukotriene B-4 (LTB4) receptor. Binding was determined through measurement of [H-3]-LTB4 displacement from human neutrophils. Receptor antagonism was confirmed through a functional assay, which measures inhibition of Ca2+ release in human neutrophils. Potent antagonists were discovered through optimization of a random screening hit, a p-(alpha-methylbenzyloxy)cinnamide, having low-micromolar activity. Substantial improvement of in vitro potency was realized by the attachment of a carboxylic acid moiety to the cinnamide phenyl ring through a flexible tether, leading to identification of compounds with low-nanomolar potency. Modification of the benzyloxy substituent, either through ortho-substitution on the benzyloxy phenyl group or through replacement of the ether oxygen with a methylene or sulfur atom, produced achiral antagonists of equal or greater potency. The most potent compounds in vitro were assayed for oral activity using the arachidonic acid-induced mouse ear edema model of inflammation. Several compounds in this series were found to significantly inhibit edema formation and myeloperoxidase activity in this model up to 17 h after oral administration. Representatives of this series have been shown to be potent and long-acting orally active inhibitors of the LTB4 receptor.