(E)-3-(4-chlorophenyl)-1-[2-hydroxy-4-(oxan-2-yloxy)phenyl]prop-2-en-1-one | 1027244-50-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(4-chlorophenyl)-1-[2-hydroxy-4-(oxan-2-yloxy)phenyl]prop-2-en-1-one
• CAS: 1027244-50-3
• 化学式: C₂₀H₁₉ClO₄
• 分子量: 358.821
• InChiKey: PCXYBGFCOXZLND-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-chlorophenyl)-1-[2-hydroxy-4-(oxan-2-yloxy)phenyl]prop-2-en-1-one 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 (E)-3-(4-chlorophenyl)-1-(2',4'-dihydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  吡唑啉衍生物的合成及其体外选择性抗幽门螺杆菌活性。

  摘要：

  为了开发新的抗幽门螺杆菌药物，制备了一系列N1取代的3,5-二苯基吡唑啉P1-P13，并对其抗菌活性进行了评估。所有合成的化合物对具有临床相关性的不同种类的革兰氏阳性细菌和革兰氏阴性细菌以及各种病原真菌菌株都几乎没有或没有活性。相同的衍生物对一系列幽门螺杆菌菌株（包括对参考化合物甲硝唑有抗性的菌株）表现出显着的活性。在所制备的化合物中，在5-苯环中具有N1-乙酰基和4-甲氧基取代基的化合物在1-4 microg / mL MIC范围内显示出对幽门螺杆菌甲硝唑耐药菌株的最佳活性。

  DOI：

  10.1016/j.bmcl.2004.11.042
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 barium dihydroxide 、 4-甲基苯磺酸吡啶 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 (E)-3-(4-chlorophenyl)-1-[2-hydroxy-4-(oxan-2-yloxy)phenyl]prop-2-en-1-one
  参考文献：
  名称：

  吡唑啉衍生物的合成及其体外选择性抗幽门螺杆菌活性。

  摘要：

  为了开发新的抗幽门螺杆菌药物，制备了一系列N1取代的3,5-二苯基吡唑啉P1-P13，并对其抗菌活性进行了评估。所有合成的化合物对具有临床相关性的不同种类的革兰氏阳性细菌和革兰氏阴性细菌以及各种病原真菌菌株都几乎没有或没有活性。相同的衍生物对一系列幽门螺杆菌菌株（包括对参考化合物甲硝唑有抗性的菌株）表现出显着的活性。在所制备的化合物中，在5-苯环中具有N1-乙酰基和4-甲氧基取代基的化合物在1-4 microg / mL MIC范围内显示出对幽门螺杆菌甲硝唑耐药菌株的最佳活性。

  DOI：

  10.1016/j.bmcl.2004.11.042

文献信息

• Chalcones: A Valid Scaffold for Monoamine Oxidases Inhibitors
  作者：Franco Chimenti、Rossella Fioravanti、Adriana Bolasco、Paola Chimenti、Daniela Secci、Francesca Rossi、Matilde Yáñez、Francisco Orallo、Francesco Ortuso、Stefano Alcaro

  DOI：10.1021/jm801590u

  日期：2009.5.14

  A large series of substituted chalcones have been synthesized and tested in vitro for their ability to inhibit human monoamine oxidases A and B (hMAO-A and hMAO-B). While all the compounds showed hMAO-B selective activity in the micro- and nanomolar ranges, the best results were obtained in the presence of chlorine and hydroxyl or methoxyl substituents. To better understand the enzyme-inhibitor interaction and to explain the selectivity of the most active compounds toward hMAO-B, molecular modeling studies were carried out on new, high resolution, hMAO-B crystallographic structures. For the only compound that also showed activity against hMAO-A as well as low selectivity, the molecular modeling study was also performed on the hMAO-A crystallographic structure. The docking technique provided new insight on the inhibition mechanism and the rational drug design of more potent/selective hMAO inhibitors based on the chalcone scaffold.
• 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.
• Synthesis and activity of a new series of chalcones as aldose reductase inhibitors
  作者：Fabio Severi、Stefania Benvenuti、Luca Costantino、Gabriella Vampa、Michele Melegari、Luciano Antolini

  DOI：10.1016/s0223-5234(99)80010-5

  日期：1998.11

  A new series of chalcone derivatives has been synthesized and tested in vitro in order to assess their ability to inhibit aldose reductase enzyme (ALR2) and their specificity towards the target enzyme with respect to other oxidoreductases, such as aldehyde reductase, sorbitol dehydrogenase, and glutathione reductase. All the compounds display affinity for ALR2. The X-ray crystal structure of 1-(2,4-dihydroxyphenyl)-3-(2-methoxyphenyl)propen-1-one was determined. (C) Elsevier, Paris.