2-(3-phenyl-5-(4-bromophenyl)-2-pyrazolin-1-yl)-3-methyl-4(3H)-quinazolinone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(3-phenyl-5-(4-bromophenyl)-2-pyrazolin-1-yl)-3-methyl-4(3H)-quinazolinone
• 英文别名: 2-[3-(4-Bromophenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-3-methylquinazolin-4-one
• 化学式: C₂₄H₁₉BrN₄O
• 分子量: 459.345
• InChiKey: BDJWWNSBQCHNKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-肼基-3-甲基喹唑啉-4(3h)-酮 在 溶剂黄146 作用下， 以 丙醇 为溶剂， 反应 72.0h， 生成 2-(3-phenyl-5-(4-bromophenyl)-2-pyrazolin-1-yl)-3-methyl-4(3H)-quinazolinone
  参考文献：
  名称：

  合成、抗炎镇痛合成、抗炎镇痛新4（3H）-喹唑啉酮衍生物

  摘要：

  4 (3H)-喹唑啉酮和吡唑衍生物已被证明具有镇痛和抗炎特性。本研究中，14个新的3-甲基-4(3H)喹唑啉酮衍生物带有2-[1'-苯基-3'-(取代-苯基)-2'-亚丙烯]肼基或2[5'-(取代苯基) -3'-苯基-2'-吡唑啉-1'-基]基团已被合成，目的是获得新的镇痛和抗炎线索。通过UV、IR、1H-NMR、13C-NMR、质谱和元素分析数据对其结构进行了阐明。通过角叉菜胶诱导的小鼠后爪水肿试验测定合成化合物的抗炎活性。所有化合物均显示出统计学上显着的效果。对于镇痛活性评估，对苯醌诱导的扭体试验应用于小鼠。

  DOI：

  10.1002/ardp.200200752

文献信息

• New pyrazoline bearing 4(3H)-quinazolinone inhibitors of monoamine oxidase: Synthesis, biological evaluation, and structural determinants of MAO-A and MAO-B selectivity
  作者：Nesrin Gökhan-Kelekçi、Semra Koyunoğlu、Samiye Yabanoğlu、Kemal Yelekçi、Özen Özgen、Gülberk Uçar、Kevser Erol、Engin Kendi、Akgül Yeşilada

  DOI：10.1016/j.bmc.2008.11.068

  日期：2009.1

  A new series of pyrazoline derivatives were prepared starting from a quinazolinone ring and evaluated for antidepressant, anxiogenic and MAO-A and -B inhibitory activities by in vivo and in vitro tests, respectively. Most of the synthesized compounds showed high activity against both the MAO-A (compounds 4a-4h, 4j-4n, and 5g-5l) and the MAO-B (compounds 4i and 5a-5f) isoforms. However, none of the novel compounds showed antidepressant activity except for 4b. The reason for such biological properties was investigated by computational methods using recently published crystallographic models of MAO-A and MAO-B. The differences in the intermolecular hydrophobic and H-bonding of ligands to the active site of each MAO isoform were correlated to their biological data. Compounds 4i, 4k, 5e, 5i, and 5l were chosen for their ability to reversibly inhibit MAO-B and MAO-A and the availability of experimental inhibition data. Observation of the docked positions of these ligands revealed interactions with many residues previously reported to have an effect on the inhibition of the enzyme. Among the pyrazoline derivatives, it appears that the binding interactions for this class of compounds are mostly hydrophobic. All have potential edge-to-face hydrophobic interactions with F343, as well as pi-pi stacking with Y398 and other hydrophobic interactions with L171. Strong hydrophobic and H-bonding interactions in the MAO recognition of 4i could be the reason why this compound shows selectivity toward the MAO-B isoform. The very high MAO-B selectivity for 4i can be also explained in terms of the distance between the FAD and the compound, which was greater in the complex of MAO-A-4i as compared to the corresponding MAO-B complex. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis, Anti-inflammatory and Analgesic Synthesis, Anti-inflammatory and Analgesic New 4(3H)-Quinazolinone Derivatives
  作者：Akgül Yeşilada、Semra Koyunoğlu、Nezire Saygılıa、Esra Kupeli、Erdem Yeşilada、Erdal Bedir、Ikhlas Khanc

  DOI：10.1002/ardp.200200752

  日期：2004.2

  derivatives have been shown to have analgesic and anti‐inflammatory properties. In this study, 14 new 3‐methyl‐4(3H)quinazolinone derivatives bearing 2‐[1′‐phenyl‐3′‐(substituted‐phenyl)‐2′‐propenylidene]hydrazino or 2[5′‐(substituted phenyl)‐3′‐phenyl‐2′‐pyrazolin‐1′‐yl] groups have been synthesized with the aim of obtaining new analgesic and anti‐inflam matory leads. The structures were elucidated

  4 (3H)-喹唑啉酮和吡唑衍生物已被证明具有镇痛和抗炎特性。本研究中，14个新的3-甲基-4(3H)喹唑啉酮衍生物带有2-[1'-苯基-3'-(取代-苯基)-2'-亚丙烯]肼基或2[5'-(取代苯基) -3'-苯基-2'-吡唑啉-1'-基]基团已被合成，目的是获得新的镇痛和抗炎线索。通过UV、IR、1H-NMR、13C-NMR、质谱和元素分析数据对其结构进行了阐明。通过角叉菜胶诱导的小鼠后爪水肿试验测定合成化合物的抗炎活性。所有化合物均显示出统计学上显着的效果。对于镇痛活性评估，对苯醌诱导的扭体试验应用于小鼠。