3-(4-hydroxyphenyl)-1-(5-propylpyrazin-2-yl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(4-hydroxyphenyl)-1-(5-propylpyrazin-2-yl)prop-2-en-1-one
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: TWWXJHDCUAAWEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  63.08
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  对羟基苯甲醛 、 1-(5-丙基-2-吡嗪基)乙酮 生成 3-(4-hydroxyphenyl)-1-(5-propylpyrazin-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Study of hydrophobic properties of biologically active open analogues of flavonoids

  摘要：

  Hydrophobicity can either be determined experimentally or predicted by means of commercially available programs. In the studies concerning biological activities of pyrazine analogues of chalcones, 3-(2-hydroxyphenyl)-1-(pyrazin-2-yl)prop-2-en-1-ones were more potent than the corresponding 3(4-hydroxyphenyl)-1-(pyrazin-2-yl)prop-2-en-1-ones. As the difference in lipophilicity may be a factor responsible for the difference in the potency, R-M values of the compounds were determined by RP-TLC and compared with log P values calculated by various commercially available programs. Important discrepancies were found between experimental and computational lipophilicity data. Therefore, we have tried to find a reliable method for calculating R-M values from in silico derived molecular parameters. The R-M values obtained with the chromatographic system consisting of Silufol UV 254 plates impregnated with silicon oil as the stationary phase and acetone-citrate buffer ( pH = 3)50:50 (v/v) as the mobile phase correlated well with van der Waals volumes (V-W) and hydration energies (Delta G(H2O)) derived of molecular models calculated on RHF/AM1 level. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jmgm.2012.07.009

文献信息

• Study of hydrophobic properties of biologically active open analogues of flavonoids
  作者：Veronika Opletalová、Petr Kastner、Marta Kučerová-Chlupáčová、Karel Palát

  DOI：10.1016/j.jmgm.2012.07.009

  日期：2013.2

  Hydrophobicity can either be determined experimentally or predicted by means of commercially available programs. In the studies concerning biological activities of pyrazine analogues of chalcones, 3-(2-hydroxyphenyl)-1-(pyrazin-2-yl)prop-2-en-1-ones were more potent than the corresponding 3(4-hydroxyphenyl)-1-(pyrazin-2-yl)prop-2-en-1-ones. As the difference in lipophilicity may be a factor responsible for the difference in the potency, R-M values of the compounds were determined by RP-TLC and compared with log P values calculated by various commercially available programs. Important discrepancies were found between experimental and computational lipophilicity data. Therefore, we have tried to find a reliable method for calculating R-M values from in silico derived molecular parameters. The R-M values obtained with the chromatographic system consisting of Silufol UV 254 plates impregnated with silicon oil as the stationary phase and acetone-citrate buffer ( pH = 3)50:50 (v/v) as the mobile phase correlated well with van der Waals volumes (V-W) and hydration energies (Delta G(H2O)) derived of molecular models calculated on RHF/AM1 level. (C) 2012 Elsevier Inc. All rights reserved.