2-Phenyl-3-pyridin-4-ylmethylene-chroman-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-Phenyl-3-pyridin-4-ylmethylene-chroman-4-one
• 英文别名: (3Z)-2-phenyl-3-(pyridin-4-ylmethylidene)chromen-4-one
• 化学式: C₂₁H₁₅NO₂
• 分子量: 313.356
• InChiKey: YQBABXZFWNTIHJ-NBVRZTHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  E-3-(4-pyridinylmethylene)flavanone 生成 2-Phenyl-3-pyridin-4-ylmethylene-chroman-4-one
  参考文献：
  名称：

  Structure–cytotoxic activity relationship of 3-arylideneflavanone and chromanone (E,Z isomers) and 3-arylflavones

  摘要：

  The E,Z-isomers of 3-arylidene substituted flavanone, chromanone and 3-aryl substituted flavone derivatives were tested in vitro for their cytotoxic activity against three cancer cell lines (HL-60, NALM-6, WM-115) and normal cell line (HUVEC). It was observed that substitution at C-3 position led to significant enhance in cytotoxicity. Isomeric configuration of 3-arylideneflavanones had an influence on the cytotoxic potential. Multiple regression analysis combined with variable selection by genetic algorithm was used to model relationships between molecular descriptors and the cytotoxic activity. The most accurate QSAR models were based on a combination between energy of LUMO, experimental value of logP and partial charge on carbonyl oxygen (delta O-2). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.044

文献信息

• New aromatase inhibitors. Synthesis and inhibitory activity of pyridinyl-Substituted flavanone derivatives
  作者：Christelle Pouget、Catherine Fagnere、Jean-Philippe Basly、Gerard Habrioux、Albert-José Chulia

  DOI：10.1016/s0960-894x(02)00072-0

  日期：2002.4

  Two (L)-pyridinyl-substituted flavanone derivatives were synthesized and UV irradiation of these compounds afforded a Z-enriched mixture. These products were tested for their ability to inhibit the cytochrome P450 aromatase. It was observed that the introduction of a pyridinylmethylene group at carbon 3 on flavanone nucleus led to a significant increase of aromatase inhibitory effect. Moreover, configuration had a substantial influence on the aromatase inhibitory activity since (E)-isomers were found to be more active than (Z)-isomers. (C), 2002 Elsevier Science Ltd. All rights reserved.