7-hydroxy-2-hydroxymethyl-3-phenyl-chromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-hydroxy-2-hydroxymethyl-3-phenyl-chromen-4-one
• 英文别名: 7-Hydroxy-2-hydroxymethyl-3-phenyl-chromen-4-on；7-Hydroxy-2-(hydroxymethyl)-3-phenylchromen-4-one
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: BWYVIKXMTLFQFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-acetoxy-2-bromomethyl-3-phenyl-chromen-4-one 在 silver(I) acetate 、 乙酸酐 作用下， 生成 7-hydroxy-2-hydroxymethyl-3-phenyl-chromen-4-one
  参考文献：
  名称：

  Sehgal; Seshadri, Journal Of Scientific and Industrial Research, 1953, vol. 12 B, p. 231,233

  摘要：

  DOI：

文献信息

• One step synthesis of 2-hydroxymethylisoflavone and their osteogenic activity
  作者：Manmeet Kumar、Preeti Rawat、Jyoti Kureel、Anuj Kumar Singh、Divya Singh、Rakesh Maurya

  DOI：10.1016/j.bmcl.2011.01.095

  日期：2011.3

  An efficient one step synthesis of new 2-hydroxymethylisoflavone is reported. A series of deoxybenzoin was subjected to cyclization with glyoxal in the presence of basic condition (KOH/EtOH) to afford the 2-hydroxymethyl isoflavone. The structures of compounds 5a-g were confirmed by NMR experiments including H-1, C-13, HMBC, HSQC and COSY. These compounds were assessed for stimulation of osteoblast function using primary culture of rat calvarial osteoblasts in vitro. Compounds 5a, 5d, 5f and 5g were potent in stimulating differentiation of osteoblasts as assessed by measuring alkaline phosphatase (ALP) activity. Besides, effect of these analogs was also seen on the transcript levels of osteogenic genes like Runx-2, osteocalcin and Bone morphogenetic protein-2 (BMP-2), involved in osteoblast differentiation and mineralization. Based on quantitative PCR data, compound 5f was found to be the potent followed by 5d. Compound 5f robustly increased the mRNA levels of Runx-2 (8.0 fold), BMP-2 (similar to 2 fold) and osteocalcin (similar to 2.0 fold) in osteoblasts. Collectively, we demonstrate osteogenic activity of the novel 2-hydroxymethyl isoflavones with 5f having the most potent activity. (C) 2011 Elsevier Ltd. All rights reserved.
• Sehgal; Seshadri, Journal Of Scientific and Industrial Research, 1953, vol. 12 B, p. 231,233
  作者：Sehgal、Seshadri

  DOI：——

  日期：——