2-(5-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)phenol | 421573-08-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(5-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)phenol
• 英文别名: Cambridge id 6605013；2-[5-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]phenol
• CAS: 421573-08-2
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: RMOCLYAXEFWGCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  64.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(5-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)phenol 在 羟胺 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 N-hydroxy-3-(2-hydroxyphenyl)-5-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide
  参考文献：
  名称：

  Chemical scaffolds with structural similarities to siderophores of nonribosomal peptide–polyketide origin as novel antimicrobials against Mycobacterium tuberculosis and Yersinia pestis

  摘要：

  Mycobacterium tuberculosis (Mtb) and Yersinia pestis (Yp) produce siderophores with scaffolds of nonribosomal peptide-polyketide origin. Compounds with structural similarities to these siderophores were synthesized and evaluated as antimicrobials against Mtb and Yp under iron-limiting conditions mimicking the iron scarcity these pathogens encounter in the host and under standard iron-rich conditions. Several new antimicrobials were identified, including some with increased potency in the iron-limiting condition. Our study illustrates the possibility of screening compound libraries in both iron-rich and iron-limiting conditions to identify antimicrobials that may selectively target iron scarcity-adapted bacteria and highlights the usefulness of building combinatorial libraries of compounds having scaffolds with structural similarities to siderophores to feed into antimicrobial screening programs. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.08.052
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 一水合肼 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 2-(5-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)phenol
  参考文献：
  名称：

  功能取代的查耳酮及其衍生物的合成，结构和抗炎活性

  摘要：

  已经合成了功能取代的查耳酮，吡唑啉和黄酮。通过1 H和13 C NMR光谱研究了它们的结构，包括COZY和HMQC实验。已评估了合成的查耳酮，吡唑啉和黄酮的抗炎活性。

  DOI：

  10.1134/s1070363219070028

文献信息

• Synthesis, Structure, and Anti-Inflammatory Activity of Functionally Substituted Chalcones and Their Derivatives
  作者：O. A. Nurkenov、M. K. Ibraev、I. A. Schepetkin、A. I. Khlebnikov、T. M. Seilkhanov、A. E. Arinova、M. B. Isabaeva

  DOI：10.1134/s1070363219070028

  日期：2019.7

  Functionally substituted chalcones, pyrazolines, and flavonones have been synthesized. Their structure has been studied by means of 1H and 13C NMR spectroscopy, including COSY and HMQC experiments. Anti-inflammatory activity of the synthesized chalcones, pyrazolines, and flavonones has been evaluated.

  已经合成了功能取代的查耳酮，吡唑啉和黄酮。通过1 H和13 C NMR光谱研究了它们的结构，包括COZY和HMQC实验。已评估了合成的查耳酮，吡唑啉和黄酮的抗炎活性。
• Facile One-Pot Synthesis Methodology for Nitrogen-Containing Heterocyclic Derivatives of 3,5-Disubstituted 4,5-Dihydro-1H-Pyrazole, Their Biological Evaluation and Molecular Docking Studies
  作者：Savita Upadhyay、Avinash C. Tripathi、Sarvesh Paliwal、Shailendra K. Saraf

  DOI：10.1007/s11094-017-1655-7

  日期：2017.10

  A series of 2-pyrazoline derivatives (PS-1 to PS-16) were synthesized by reacting different aromatic/heteroaromatic aldehydes and ketones, in a two-step reaction through Claisen – Schmidt condensation, followed by cyclization of the resulting chalcones with hydrazine hydrate in the presence of a base using conventional and microwave approaches. The synthesized derivatives were characterized by various

  一系列 2-吡唑啉衍生物（PS-1 到 PS-16）是通过不同的芳香/杂芳香醛和酮反应合成的，在两步反应中通过克莱森-施密特缩合反应，然后将所得查尔酮与水合肼环化使用常规方法和微波方法在碱存在的情况下。合成的衍生物通过各种物理化学方法进行表征，包括 IR、1H-NMR、13C-NMR、质谱数据和元素分析。使用合适的动物模型评估抗抑郁和抗焦虑活性。化合物 PS-3 和 PS-14 显示出显着的抗抑郁活性，通过在两个测试中减少不动的持续时间，同时发现化合物 PS-9 和 PS-12 在测试剂量（50 和 100 毫克/千克体重）下与标准药物丙咪嗪和丙咪嗪相比具有良好的抗焦虑活性（通过增加手臂进入次数和开放手臂探索时间）地西泮，分别。为了阐明合成衍生物与 MAO-A 靶蛋白的结合相互作用，采用了分子对接，证明了与结合位点处的氨基酸残基 Phe208、Asn181 和 Tyr407 的关键相互作用。此外，预测合成衍生物的
• 10.17179/excli2017-250
  作者：Upadhyay, Savita、Tripathi, Avinash C.、Paliwal, Sarvesh、Saraf, Shailendra K.

  DOI：10.17179/excli2017-250

  日期：——
• Small molecules with structural similarities to siderophores as novel antimicrobials against Mycobacterium tuberculosis and Yersinia pestis
  作者：Karen L. Stirrett、Julian A. Ferreras、Venkatesan Jayaprakash、Barij N. Sinha、Tao Ren、Luis E.N. Quadri

  DOI：10.1016/j.bmcl.2008.03.025

  日期：2008.4

  Drugs inhibiting the iron scarcity-induced, siderophore-mediated iron-scavenging systems of Mycobacterium tuberculosis (Mtb) and Yersinia pestis (Yp) may provide new therapeutic lines of defense. Compounds with structural similarities to siderophores were synthesized and evaluated as antimicrobials against Mtb and Yp under iron-limiting conditions, which mimic the iron scarcity these pathogens encounter and must adapt to in the host, and under standard iron-rich conditions for comparison. New antimicrobials were identified, some of which warrant exploration as initial leads against potentially novel targets and small-molecule tools to assist in the elucidation of targets specific to iron-scarcity adapted Mtb and Yp. (C) 2008 Elsevier Ltd. All rights reserved.
• Pyrazoline-based mycobactin analogues as MAO-inhibitors
  作者：Venkatesan Jayaprakash、Barij N. Sinha、Gulberk Ucar、Ayse Ercan

  DOI：10.1016/j.bmcl.2008.10.084

  日期：2008.12

  3,5-Diaryl carbothioamide pyrazolines designed as mycobactin analogs (mycobacterial siderophore) were reported to be potent antitubercular agents under iron limiting condition in our earlier study. Clinical complications of newly introduced antibiotic Linezolid, due its MAO inhibitory activity, prompted us to evaluate our compounds for their MAO-inhibitory activity against rat liver MAO-A and MAO-B as pyrazolines were reported to be antidepressants and MAO inhibitors. The present study carried out with this pilot library of 32 compounds will provide us with necessary information for designing antitubercular molecules with reduced MAO-inhibitory activity and also help us in identifying a selective MAO-B inhibitor which has potential clinical utility in neurodegenerative disorders. Thirty-two compounds analyzed has shown spectrum of activity from selective to nonselective against two isoforms of rat liver MAO-A and MAO-B and also as competitive, reversible to non-competitive, irreversible. It is also interesting to note that anti-tubercular compound 11, 14 and 16 were also found to be selective inhibitors of rat liver MAO-B. Docking studies with human MAO shows that compound 11 interacts with the catalytic site of both the isoforms, suggesting compound 11 as nonselective inhibitor of human MAO isoforms. (C) 2008 Elsevier Ltd. All rights reserved.