6-hydroxy-3-benzylideneflavanone | 132361-70-7

• 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: 6-hydroxy-3-benzylideneflavanone
• 英文别名: (+/-)-3-((E)-benzylidene)-6-hydroxy-2-phenyl-chroman-4-one；(+/-)-3-((E)-Benzyliden)-6-hydroxy-2-phenyl-chroman-4-on；(3E)-3-benzylidene-6-hydroxy-2-phenylchromen-4-one
• CAS: 132361-70-7
• 化学式: C₂₂H₁₆O₃
• 分子量: 328.367
• InChiKey: YALFFTTYNFBYQD-UYRXBGFRSA-N

物化性质

• 沸点：
  573.8±50.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-hydroxy-3-benzylideneflavanone 生成 3-benzylidene-2-phenyl-6-hydroxy-2,3-dihydro-4H-1-benzopyran-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
• 作为产物：
  描述：

  苯甲醛 、 6-羟基黄烷酮 在 哌啶 作用下， 生成 6-hydroxy-3-benzylideneflavanone
  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

• Mallik; Saha; Mallik, Journal of the Indian Chemical Society, 1990, vol. 67, # 6, p. 478 - 481
  作者：Mallik、Saha、Mallik

  DOI：——

  日期：——
• Vyas; Shah, Journal of the Indian Chemical Society, 1949, vol. 26, p. 273,274
  作者：Vyas、Shah

  DOI：——

  日期：——
• Structure–cytotoxic activity relationship of 3-arylideneflavanone and chromanone (E,Z isomers) and 3-arylflavones
  作者：Bogumiła Kupcewicz、Grażyna Balcerowska-Czerniak、Magdalena Małecka、Piotr Paneth、Urszula Krajewska、Marek Rozalski

  DOI：10.1016/j.bmcl.2013.05.044

  日期：2013.7

  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.