2,2'-(4,5-dihydro-1H-pyrazol-3,5-diyl)diphenol | 55370-67-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,2'-(4,5-dihydro-1H-pyrazol-3,5-diyl)diphenol
• 英文别名: 2,2'-(4,5-dihydro-1H-pyrazole-3,5-diyl)diphenol；3,5-bis-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazole；2-[3-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-5-yl]phenol
• CAS: 55370-67-7
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: INFGLUYMRONKHY-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：

  2,2'-(4,5-dihydro-1H-pyrazol-3,5-diyl)diphenol 在 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  新型异烟肼-螺环吲哚衍生物：设计、合成、生物学评价、计算机 ADMET 预测和计算研究

  摘要：

  摘要 在目前的情况下，合成新的和理想的抗分枝杆菌药物对抵抗结核分枝杆菌 (MTB) 有着永恒的需求。设计和鉴定用于治疗结核病的新分子是有机和药物化学研究中的一项重要任务。在本研究中，我们报告了使用两种通用且重要的部分、异烟肼和螺吲哚衍生物组合所需化合物。一系列新型异烟肼-螺环吲哚杂化分子 (6a-6ao) 被设计、合成并通过各种光谱方法充分表征。我们已经评估了它们对结核分枝杆菌 H37Rv (MTB) 菌株和耐多药结核病的体外抗分枝杆菌活性。其中，与其他化合物相比，化合物 6ab 被发现是最有效的。将计算所有化合物的 ADMET 相关描述符，以预测用于选择有效和生物可利用化合物的药代动力学特性。此外，分子对接和分子动力学研究表明，所有化合物在耐异烟肼烯酰-ACP(COA)还原酶活性位点的结合模式，有助于建立抑制结核分枝杆菌的结构基础。

  DOI：

  10.1016/j.molstruc.2020.128881
• 作为产物：
  描述：

  trans-2,2'-dihydroxychalcone 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以72%的产率得到2,2'-(4,5-dihydro-1H-pyrazol-3,5-diyl)diphenol
  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

• Enantioseparation and antioxidant activity of novel diarylpyrazoline derivatives
  作者：Messaouda Ameur、Khaled Sekkoum、Francisco Gonazles、Jorge Comez‐Carpintero、Carlos Menendez、Nasser Belboukhari、Hassan Y. Aboul‐Enein

  DOI：10.1002/chir.23493

  日期：2022.10

  Three chiral pyrazoline derivatives were synthesized by a flavanone ring-opening reaction followed by cyclocondensation with hydrazine hydrate to give better yields. Their enantiomeric resolution was achieved using polysaccharide chiral stationary phase columns consisting of cellulose (Chiralcel®OD-RH, Chiralcel®OZ-3) and amylose (Chiralpak®IA) by high-performance liquid chromatography. The separation

  通过黄烷酮开环反应合成了三种手性吡唑啉衍生物，然后与水合肼进行环缩合，以得到更好的收率。通过高效液相色谱法，使用由纤维素（Chiralcel®OD-RH、Chiralcel®OZ-3）和直链淀粉（Chiralpak®IA）组成的多糖手性固定相柱实现了它们的对映体分离。分离受到流动相中醇改性剂的性质和浓度的影响。以 5-methoxy-2-(3-phenyl-4,5-dihydro-1H-pyrazol-5-yl)phenol ( 3a ) 为例，使用 Chiralpak®IA 色谱柱获得最佳分离度，分离度在 <30 分钟的分析时间内，因子 α = 1.24 和 Rs = 5.66。DPPH法研究表明二芳基吡唑啉具有良好的抗氧化活性。
• Mycobactin Analogues with Excellent Pharmacokinetic Profile Demonstrate Potent Antitubercular Specific Activity and Exceptional Efflux Pump Inhibition
  作者：Mousumi Shyam、Harshita Verma、Gourab Bhattacharje、Piyali Mukherjee、Samsher Singh、Sujit Kamilya、Pushpendu Jalani、Swetarka Das、Arunava Dasgupta、Abhishake Mondal、Amit Kumar Das、Amit Singh、Federico Brucoli、Claire Bagnéris、Rachael Dickman、Vinay N. Basavanakatti、Patibandla Naresh Babu、Vadivelan Sankaran、Abhimanyu Dev、Barij Nayan Sinha、Sanjib Bhakta、Venkatesan Jayaprakash

  DOI：10.1021/acs.jmedchem.1c01349

  日期：2022.1.13
• Chemical scaffolds with structural similarities to siderophores of nonribosomal peptide–polyketide origin as novel antimicrobials against Mycobacterium tuberculosis and Yersinia pestis
  作者：Julian A. Ferreras、Akash Gupta、Neal D. Amin、Arijit Basu、Barij N. Sinha、Stefan Worgall、Venkatesan Jayaprakash、Luis E.N. Quadri

  DOI：10.1016/j.bmcl.2011.08.052

  日期：2011.11

  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.
• 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.