2-(5-(2-chlorophenyl)-4,5-dihydro-1H-pyrazol-3-yl)phenol | 610277-48-0

• 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: 2-(5-(2-chlorophenyl)-4,5-dihydro-1H-pyrazol-3-yl)phenol
• 英文别名: 2-[5-(2-chlorophenyl)-4,5-dihydro-1H-pyrazol-3-yl]phenol
• CAS: 610277-48-0
• 化学式: C₁₅H₁₃ClN₂O
• 分子量: 272.734
• InChiKey: LZNZESSYBZBIPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  44.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-(2-chlorophenyl)-4,5-dihydro-1H-pyrazol-3-yl)phenol 、 硫代异氰酸苯酯 反应 0.5h， 以79%的产率得到5-(2-chlorophenyl)-3-(2-hydroxyphenyl)-N-phenyl-4,5-dihydro-1H-pyrazole-1-carbothioamide
  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
• 作为产物：
  描述：

  2-氯苯甲醛 在 hydrazine hydrate 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 54.0h， 生成 2-(5-(2-chlorophenyl)-4,5-dihydro-1H-pyrazol-3-yl)phenol
  参考文献：
  名称：

  Mycobactin Analogues with Excellent Pharmacokinetic Profile Demonstrate Potent Antitubercular Specific Activity and Exceptional Efflux Pump Inhibition

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c01349

文献信息

• 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.