3-(2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-1H-pyrazole | 948901-13-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-1H-pyrazole
• 英文别名: 4-(4-(4-methoxyphenyl)-1H-pyrazol-3-yl)benzene-1,3-diol；4-[4-(4-methoxyphenyl)-1H-pyrazol-3-yl]benzene-1,3-diol；4-[4-(4-methoxyphenyl)-1H-pyrazol-5-yl]benzene-1,3-diol
• CAS: 948901-13-1
• 化学式: C₁₆H₁₄N₂O₃
• mdl: MFCD04196855
• 分子量: 282.299
• InChiKey: UQAAFGKMBIHHCS-UHFFFAOYSA-N

物化性质

• 熔点：
  209.2-211.0 °C(Solv: ethanol (64-17-5))
• 沸点：
  533.8±50.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)
• 溶解度：
  20.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  刺芒柄花素 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以93%的产率得到3-(2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-1H-pyrazole
  参考文献：
  名称：

  天然异黄酮和水合肼精确合成一锅3,4-二芳基-1 H-吡唑

  摘要：

  通过使水合肼与不同的天然异黄酮或其衍生物反应，已经开发了一种有效的方案，用于制备一系列新的3,4-二芳基-1 H-吡唑类，具有潜在的药理学和农业目标。在耐受各种官能团的相当温和的反应条件（80°）下，以良好至优异的收率（80-95％；表2）获得了目标化合物。完全表征了这些新化合物，并确定了3,5-二乙氧基-2- [4-（4-乙氧基苯基）-1 H-吡唑-3-基]苯酚（26）的单晶X射线结构过乙酰化的化合物2- {1-乙酰基-4- [4-乙酰氧基-3-（二乙酰氨基）苯基] -1 H-吡唑-3-基} -5-乙酰氧基苯乙酸（35）已解决（图）。

  DOI：

  10.1002/hlca.200790217

文献信息

• Synthesis, crystal structure, characterization and antifungal activity of 3,4-diaryl-1H-Pyrazoles derivatives
  作者：Jin Zhang、Da-Jin Tan、Tao Wang、Si-Si Jing、Yang Kang、Zun-Ting Zhang

  DOI：10.1016/j.molstruc.2017.07.106

  日期：2017.12

  Abstract A series of 3,4-diaryl- 1H -pyrazoles derivatives were designed and synthesized by the reaction of 3-heteroarylchromones and 3-phenylchromones with hydrazine hydrate in good yields. All of those compounds were characterized by 1 H NMR, 13 C NMR, IR, and HRMS. Moreover, 3-(2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)- 1H -pyrazole and 3-(2,4-dihydroxy phenyl)-4-(4-methoxyphenyl)- 1H -pyrazole were

  摘要 通过3-杂芳基色酮和3-苯基色酮与水合肼反应，设计并合成了一系列3,4-二芳基-1H-吡唑衍生物。所有这些化合物均通过 1 H NMR、13 C NMR、IR 和 HRMS 进行表征。此外，3-(2,4-二羟基苯基)-4-(4-羟基苯基)-1H-吡唑和3-(2,4-二羟基苯基)-4-(4-甲氧基苯基)-1H-吡唑进一步符合以下条件单晶 X 射线衍射。此外，还评估了 3,4-二芳基-1H-吡唑对五种植物病原真菌（Cytospora sp.、Colletotrichum gloeosporioides、Botrytis cinerea、Alternaria solani 和 Fusarium solani）的抗真菌活性。3-(2-Hydroxy-4-isopropoxyphenyl)-4-phenyl-1H-pyrazole对Cytospora sp., C. gloeosporioides
• Diversity-oriented synthesis of pyrazoles derivatives from flavones and isoflavones leads to the discovery of promising reversal agents of fluconazole resistance in Candida albicans
  作者：Chang-Yi Cui、Jun Liu、Hong-Bo Zheng、Xue-Yang Jin、Xiao-Yu Zhao、Wen-Qiang Chang、Bin Sun、Hong-Xiang Lou

  DOI：10.1016/j.bmcl.2018.03.066

  日期：2018.5

  Diversity-oriented synthesis of derivatives of natural products is an important approach for the discovery of novel drugs. In this paper, a series of novel 3,4-diaryl-1H-pyrazoles and 3,5-diaryl-1H-pyrazoles derivatives were synthesized through the one-pot reaction of flavones and isoflavones with the hydrazine hydrate and substituted hydrazine hydrate. Some of these novel compounds exhibited antifungal

  天然产物衍生物的多样性导向合成是发现新药的重要途径。本文通过黄酮和异黄酮与水合肼和取代水合肼的一锅反应合成了一系列新型3,4-二芳基-1 H-吡唑和3,5-二芳基-1 H-吡唑衍生物。这些新颖的化合物中的一些对白色念珠菌SC5314表现出抗真菌作用，对外排泵不足菌株DSY654表现出更强的抑制活性。另外，化合物25，28和32A显示对临床唑电阻的出色逆转活性吡咯类抗白色念珠菌与氟康唑（FLC）组合，FICI值在0.012至0.141之间。还讨论了这些化合物的初步结构-活性关系（SAR）。总之，这项研究提供了几种新颖的药物，它们单独或与氟康唑一起显示有效的抗真菌活性，这为抗真菌药物的开发取得了进展。
• Synthesis, antimycobacterial evaluation and pharmacophore modeling of analogues of the natural product formononetin
  作者：Peggoty Mutai、Elumalai Pavadai、Ian Wiid、Andile Ngwane、Bienyameen Baker、Kelly Chibale

  DOI：10.1016/j.bmcl.2015.04.064

  日期：2015.6

  The synthesis and antimycobacterial activity of formononetin analogues is hereby reported. Formononetin and its analogue 11E showed 88% and 95% growth inhibition, respectively, against the H37Rv strain of Mycobacterium tuberculosis. Pharmacophore modeling studies indicated that the presence of a hydroxyl group in formononetin and its analogues, is crucial for maintaining activity. (C) 2015 Elsevier Ltd. All rights reserved.
• Repurposing Hsp90 inhibitors as antibiotics targeting histidine kinases
  作者：Chau D. Vo、Hanna L. Shebert、Shannon Zikovich、Rebecca A. Dryer、Tony P. Huang、Lindsey J. Moran、Juno Cho、Douglas R. Wassarman、Bryn E. Falahee、Peter D. Young、Garrick H. Gu、James F. Heinl、John W. Hammond、Taylor N. Jackvony、Thomas E. Frederick、Jimmy A. Blair

  DOI：10.1016/j.bmcl.2017.10.036

  日期：2017.12

  To address the growing need for new antimicrobial agents, we explored whether inhibition of bacterial signaling machinery could inhibit bacterial growth. Because bacteria rely on two-component signaling systems to respond to environmental changes, and because these systems are both highly conserved and mediated by histidine kinases, inhibiting histidine kinases may provide broad spectrum antimicrobial activity. The histidine kinase ATP binding domain is conserved with the ATPase domain of eukaryotic Hsp90 molecular chaperones. To find a chemical scaffold for compounds that target histidine kinases, we leveraged this conservation. We screened ATP competitive Hsp90 inhibitors against CckA, an essential histidine kinase in Caulobacter crescentus that controls cell growth, and showed that the diaryl pyrazole is a promising scaffold for histidine kinase inhibition. We synthesized a panel of derivatives and found that they inhibit the histidine kinases C. crescentus CckA and Salmonella PhoQ but not C. crescentus DivJ; and they inhibit bacterial growth in both Gram-negative and Gram-positive bacterial strains. (C) 2017 The Authors. Published by Elsevier Ltd.
• [EN] SMALL MOLECULE INHIBITORS OF VIRAL REPLICATION<br/>[FR] INHIBITEURS À PETITES MOLÉCULES DE RÉPLICATION VIRALE
  申请人：UNIV PRINCETON

  公开号：WO2020231979A1

  公开（公告）日：2020-11-19

  Provided herein are methods involving a compound of the following structural formula: (I) or a pharmaceutically acceptable salt thereof, wherein values for the variables are as described herein. For example, methods for inhibiting replication of a virus, treating a viral infection, inhibiting heat shock protein 90 and treating a heat shock protein 90-mediated disease or condition using a compound of Structural Formula I are provided.