1-[3-(2,4-Dihydroxy-phenyl)-5-(2-methoxy-phenyl)-4,5-dihydro-pyrazol-1-yl]-ethanone | 686717-90-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-[3-(2,4-Dihydroxy-phenyl)-5-(2-methoxy-phenyl)-4,5-dihydro-pyrazol-1-yl]-ethanone
• 英文别名: 1-[5-(2,4-dihydroxyphenyl)-3-(2-methoxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone
• CAS: 686717-90-8
• 化学式: C₁₈H₁₈N₂O₄
• 分子量: 326.352
• InChiKey: FXEKMJTZMPNOOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[3-(2,4-Dihydroxy-phenyl)-5-(2-methoxy-phenyl)-4,5-dihydro-pyrazol-1-yl]-ethanone 生成 1-[3-(2,4-dihydroxy-phenyl)-5-(2-methoxy-phenyl)-4,5-dihydro-pyrazol-1-yl]-ethanone 、 1-[3-(2,4-dihydroxy-phenyl)-5-(2-methoxy-phenyl)-4,5-dihydro-pyrazol-1-yl]-ethanone
  参考文献：
  名称：

  Synthesis and Selective Inhibitory Activity of 1-Acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole Derivatives against Monoamine Oxidase

  摘要：

  A novel series of 1-acetyl-3-(4-hydroxy- and 2,4-dihydroxyphenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole derivatives 1 - 12 have been synthesized and investigated for the ability to selectively inhibit the activity of the A and B isoforms of monoamine oxidase (MAO). The new synthesized compounds 1-12 proved to be more reversible, potent, and selective inhibitors of MAO-A than of MAO-B. Knowing that stereochemistry may be an important modulator of biological activity, we performed the semipreparative chromatographic enantioseparation of the most potent, selective, and chiral compounds, 6 and 11. The separated enantiomers were then submitted to in vitro biological evaluation while increasing their inhibitory activity and A selectivity. The (-)-6 enantiomer shows Ki(MAO-A) 2 nM and SI = 165 000, (+)-6 shows Ki(MAO-A) = 6 nM and SI = 166 666, (-)-11 shows Ki(MAO-A) = 4 nM and SI = 80 000, and (+)-11 shows Ki(MAO-A) = 7 nM and SI = 38 571.

  DOI：

  10.1021/jm031042b
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 盐酸 、 barium dihydroxide 、 4-甲基苯磺酸吡啶 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 58.0h， 生成 1-[3-(2,4-Dihydroxy-phenyl)-5-(2-methoxy-phenyl)-4,5-dihydro-pyrazol-1-yl]-ethanone
  参考文献：
  名称：

  一些吡唑衍生物的合成及其与P-糖蛋白的亲和力结合的初步研究。

  摘要：

  合成了一系列取代的吡唑啉，并通过直接结合至包含ATP结合位点和调节剂相互作用区的纯化蛋白结构域，评估了它们的抗癌活性以及抑制P-糖蛋白介导的多药耐药性的能力。已经发现化合物2a和e以更大的亲和力与P-糖蛋白结合。

  DOI：

  10.1016/j.bmcl.2005.05.067

文献信息

• Synthesis of some pyrazole derivatives and preliminary investigation of their affinity binding to P-glycoprotein
  作者：Fedele Manna、Franco Chimenti、Rossella Fioravanti、Adriana Bolasco、Daniela Secci、Paola Chimenti、Cristiano Ferlini、Giovanni Scambia

  DOI：10.1016/j.bmcl.2005.05.067

  日期：2005.10

  A series of substituted pyrazolines were synthesized and evaluated for their anticancer activity and for their ability to inhibit P-glycoprotein-mediated multidrug resistance by direct binding to a purified protein domain containing an ATP-binding site and a modulator interacting region. Compounds 2a and e have been found to bind to P-glycoprotein with greater affinity.

  合成了一系列取代的吡唑啉，并通过直接结合至包含ATP结合位点和调节剂相互作用区的纯化蛋白结构域，评估了它们的抗癌活性以及抑制P-糖蛋白介导的多药耐药性的能力。已经发现化合物2a和e以更大的亲和力与P-糖蛋白结合。
• Synthesis and Selective Inhibitory Activity of 1-Acetyl-3,5-diphenyl-4,5-dihydro-(1<i>H</i>)-pyrazole Derivatives against Monoamine Oxidase
  作者：Franco Chimenti、Adriana Bolasco、Fedele Manna、Daniela Secci、Paola Chimenti、Olivia Befani、Paola Turini、Valentina Giovannini、Bruno Mondovì、Roberto Cirilli、Francesco La Torre

  DOI：10.1021/jm031042b

  日期：2004.4.1

  A novel series of 1-acetyl-3-(4-hydroxy- and 2,4-dihydroxyphenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole derivatives 1 - 12 have been synthesized and investigated for the ability to selectively inhibit the activity of the A and B isoforms of monoamine oxidase (MAO). The new synthesized compounds 1-12 proved to be more reversible, potent, and selective inhibitors of MAO-A than of MAO-B. Knowing that stereochemistry may be an important modulator of biological activity, we performed the semipreparative chromatographic enantioseparation of the most potent, selective, and chiral compounds, 6 and 11. The separated enantiomers were then submitted to in vitro biological evaluation while increasing their inhibitory activity and A selectivity. The (-)-6 enantiomer shows Ki(MAO-A) 2 nM and SI = 165 000, (+)-6 shows Ki(MAO-A) = 6 nM and SI = 166 666, (-)-11 shows Ki(MAO-A) = 4 nM and SI = 80 000, and (+)-11 shows Ki(MAO-A) = 7 nM and SI = 38 571.