(+/-)-2-benzo[1,3]dioxol-5-yl-5,7-dihydroxy-chroman-4-one | 115782-43-9

• 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-benzo[1,3]dioxol-5-yl-5,7-dihydroxy-chroman-4-one
• 英文别名: 2-benzo[1,3]dioxol-5-yl-5,7-dihydroxy-chroman-4-one；(+/-)-2-Benzo[1,3]dioxol-5-yl-5,7-dihydroxy-chroman-4-on；2-Benzo[1,3]dioxol-5-yl-5,7-dihydroxy-chroman-4-on；5.7-Dihydroxy-3'.4'-methylendioxy-flavanon；2-(1,3-Benzodioxol-5-yl)-5,7-dihydroxy-2,3-dihydrochromen-4-one
• CAS: 115782-43-9
• 化学式: C₁₆H₁₂O₆
• 分子量: 300.268
• InChiKey: SCYVPEQZLVCGHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  sodium acetate 、 乙酸酐 、 (+/-)-2-benzo[1,3]dioxol-5-yl-5,7-dihydroxy-chroman-4-one 生成 1-benzo[1,3]dioxol-5-yl-3-(2,4,6-triacetoxy-phenyl)-propenone
  参考文献：
  名称：

  Shinoda; Ueda; Sato, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1930, vol. 50, p. 65

  摘要：

  DOI：
• 作为产物：
  描述：

  (+/-)-5,7-dimethoxymethoxy-3',4'-methylenedioxy-flavanone 在 盐酸 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.75h， 以82%的产率得到(+/-)-2-benzo[1,3]dioxol-5-yl-5,7-dihydroxy-chroman-4-one
  参考文献：
  名称：

  Synthesis, biological evaluation and quantitative structure-activities relationship of flavonoids as vasorelaxant agents

  摘要：

  A series of flavonoid derivatives were designed, synthesized. Their vasorelaxant activities were evaluated experimentally against rat aorta rings pretreated with phenylephrine (PE). Among them, 6-hydroxy-8-allyl- 4'-chloro-flavanone 8q exhibited the highest vasodilatory activity (EC50 = 4.6 mu M, E-max = 95.1%). The 3D-QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method, and a statistically reliable model with good predictive power (r(2) = 0.872 and q(cv)(2) = 0.496) was established. The contour plots of CoMFA model provide a good insight into the structure-activity relationships of these compounds and may be used to design more potent flavonoids derivatives as vasorelaxant agents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.052

文献信息

• Hishida, Nippon Kagaku Zasshi, 1955, vol. 76, p. 204,206
  作者：Hishida

  DOI：——

  日期：——
• Shinoda; Sato, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1928, vol. 48, p. 109
  作者：Shinoda、Sato

  DOI：——

  日期：——
• CHEN, JUNJIE;YANG, WEIWEN;PAN, XINFU;LI, YULIN;TAN, ZHEN, CHEM. J. CHIN. UNIV., 8,(1987) N 10, 914-916
  作者：CHEN, JUNJIE、YANG, WEIWEN、PAN, XINFU、LI, YULIN、TAN, ZHEN

  DOI：——

  日期：——
• Shinoda; Ueda; Sato, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1930, vol. 50, p. 65
  作者：Shinoda、Ueda、Sato

  DOI：——

  日期：——
• Synthesis, biological evaluation and quantitative structure-activities relationship of flavonoids as vasorelaxant agents
  作者：Xiaowu Dong、Tao Liu、Jingying Yan、Peng Wu、Jing Chen、Yongzhou Hu

  DOI：10.1016/j.bmc.2008.11.052

  日期：2009.1

  A series of flavonoid derivatives were designed, synthesized. Their vasorelaxant activities were evaluated experimentally against rat aorta rings pretreated with phenylephrine (PE). Among them, 6-hydroxy-8-allyl- 4'-chloro-flavanone 8q exhibited the highest vasodilatory activity (EC50 = 4.6 mu M, E-max = 95.1%). The 3D-QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method, and a statistically reliable model with good predictive power (r(2) = 0.872 and q(cv)(2) = 0.496) was established. The contour plots of CoMFA model provide a good insight into the structure-activity relationships of these compounds and may be used to design more potent flavonoids derivatives as vasorelaxant agents. (C) 2008 Elsevier Ltd. All rights reserved.