trans-3-phenyl-5(4-hydroxyphenyl)-2-pyrazoline

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: trans-3-phenyl-5(4-hydroxyphenyl)-2-pyrazoline
• 英文别名: 4-(3-phenyl-4,5-dihydro-1H-pyrazol-5-yl)phenol
• 化学式: C₁₅H₁₄N₂O
• 分子量: 238.289
• InChiKey: GXVJVHSJVJLBTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 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：
  44.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-3-phenyl-5(4-hydroxyphenyl)-2-pyrazoline 在 sodium hydroxide 作用下， 反应 0.5h， 生成 trans-1-(4-hydroxyphenyl)-2-(phenyl)cyclopropane
  参考文献：
  名称：

  一种合成羟基取代的1,2-二苯基环丙烷的简单新方法

  摘要：

  摘要 通过碱催化分解羟基查尔酮与一水合肼反应产物羟基取代的3,5-二苯基-2-吡唑啉，合成了单羟基和二羟基取代的-1,2-二苯基环丙烷。

  DOI：

  10.1080/00397919508015434
• 作为产物：
  描述：

  (E)-3-(4-羟基苯基)-1-苯基丙-2-烯-1-酮 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 trans-3-phenyl-5(4-hydroxyphenyl)-2-pyrazoline
  参考文献：
  名称：

  Small molecules with structural similarities to siderophores as novel antimicrobials against Mycobacterium tuberculosis and Yersinia pestis

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.03.025

文献信息

• Pyrazoline based MAO inhibitors: Synthesis, biological evaluation and SAR studies
  作者：Monika Jagrat、Jagannath Behera、Samiye Yabanoglu、Ayse Ercan、Gulberk Ucar、Barij Nayan Sinha、Vadivelan Sankaran、Arijit Basu、Venkatesan Jayaprakash

  DOI：10.1016/j.bmcl.2011.05.057

  日期：2011.7

  Twenty-two pyrazoline derivatives were synthesized and tested for their human MAO (hMAO) inhibitory activity. Twelve molecules with unsubstituted ring A and substituted ring C (5–16) were found to be potent inhibitors of hMAO-A isoform with SIMAO-A in the order 103 and 104. Ten molecules with unsubstituted ring A and without ring C (21–30), in which eight molecules (21, 23–26, and 28–30) were selective

  合成了22种吡唑啉衍生物，并测试了其对人MAO（hMAO）的抑制活性。未取代的环A和取代的环C（十二分子5 - 16）被发现与SI hMAO-A同种型的强效抑制剂，MAO-A的顺序10 3和10 4。十个分子与未取代的环A和无环C（21 - 30），其中8个分子（21，23 - 26，和28 - 30）是选择性的hMAO-A，一个用于hMAO-B（22），另一1个非选择性（27）。环C的存在增加了针对hMAO-A的效力以及SI。然而，它的缺乏降低了针对hMAO-A和hMAO-B的效力和SI。
• 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.
• US5444147A
  申请人：——

  公开号：US5444147A

  公开（公告）日：1995-08-22
• 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.
• A New Simple Method for the Synthesis of Hydroxy Substituted 1,2-Diphenylcyclopropanes
  作者：Chunping Gao、Allan S. Hay

  DOI：10.1080/00397919508015434

  日期：1995.6

  Abstract Mono and dihydroxysubstituted-1,2-diphenylcyclopropanes were synthesized by base catalyzed decomposition of the corresponding hydroxy substituted 3,5-diphenyl-2-pyrazolines which were the products of the reaction between hydroxychalcones and hydrazine monohydrate.

  摘要 通过碱催化分解羟基查尔酮与一水合肼反应产物羟基取代的3,5-二苯基-2-吡唑啉，合成了单羟基和二羟基取代的-1,2-二苯基环丙烷。