7-methoxy-3-(4-hydroxyphenyl)-2H-benzopyran-4-one | 206257-38-7

• 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-methoxy-3-(4-hydroxyphenyl)-2H-benzopyran-4-one
• 英文别名: 3-(4-hydroxyphenyl)-7-methoxychroman-4-one；isoformonenetin；3-(4-Hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
• CAS: 206257-38-7
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: YVVQDVPHBJABPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-methoxy-3-(4-hydroxyphenyl)-2H-benzopyran-4-one 在 盐酸 、 甲醇 、 钾硼氢 、 溶剂黄146 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 反应 0.5h， 生成 6-(7-methoxy-2H-chromen-3-yl)-3-propan-2-yl-2,4-dihydro-1,3-benzoxazine
  参考文献：
  名称：

  Synthesis and Anti-tumor Activities of Novel Oxazinyl Isoflavonoids

  摘要：

  本文介绍了一系列新型噁嗪基异黄酮的设计、合成和生物学评价。研究表明，几种类似物对 SKOV-3、DU-145 和 HL-60 人类结肠癌细胞系具有生长抑制作用，其 IC50 值在微摩尔范围内。研究发现，化合物 7e 和 12h 的体外抑制活性高于苯麝香二醇（目前正处于治疗癌症的后期临床试验阶段的母体化合物）。所显示的结果适于进一步优化先导化合物。

  DOI：

  10.1248/cpb.60.513
• 作为产物：
  描述：

  大豆甙元 在 palladium 10% on activated carbon 、 甲酸铵 、 碳酸氢钠 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 20.0h， 生成 7-methoxy-3-(4-hydroxyphenyl)-2H-benzopyran-4-one
  参考文献：
  名称：

  Synthesis and Anti-tumor Activities of Novel Oxazinyl Isoflavonoids

  摘要：

  本文介绍了一系列新型噁嗪基异黄酮的设计、合成和生物学评价。研究表明，几种类似物对 SKOV-3、DU-145 和 HL-60 人类结肠癌细胞系具有生长抑制作用，其 IC50 值在微摩尔范围内。研究发现，化合物 7e 和 12h 的体外抑制活性高于苯麝香二醇（目前正处于治疗癌症的后期临床试验阶段的母体化合物）。所显示的结果适于进一步优化先导化合物。

  DOI：

  10.1248/cpb.60.513

文献信息

• Induction of targeted osteogenesis with 3-aryl- 2H -benzopyrans and 3-aryl- 3H -benzopyrans: Novel osteogenic agents
  作者：Atul Gupta、Imran Ahmad、Jyoti Kureel、Mohammad Hasanain、Praveen Pandey、Sarita Singh、Aijaz A. John、Jayanta Sarkar、Divya Singh

  DOI：10.1016/j.jsbmb.2016.01.010

  日期：2016.4

  Development of target oriented chemotherapeutics for treatment of chronic diseases have been considered as an important approach in drug development. Following this approach, in our efforts for exploration of new osteogenic leads, substituted 3-aryl-2H-benzopyran and 3-aryl-3H-benzopyran derivatives (19, 20a-e, 21, 22a-e, 26, 27, 28a-e, 29, 31a-b, 32 and 33) have been characterized as estrogen receptor-(3 selective osteogenic (bone forming) agents. The synthesized compounds were evaluated for osteogenic activity using mouse calvarial osteoblast cells. Four compounds viz 20b, 22a, 27and 32 showed significant osteogenic activity at EC50 values 1.35, 34.5, 407 and 29.5 pM respectively. Out of these, 20b and 32 were analyzed for their bone mineralization efficacy and osteogenic gene expression by qPCR. The results showed that 20b and 32 significantly increased mineral nodule formation and the transcript levels of BMP-2, RUNX-2 and osteocalcin at 100 pM concentrations respectively. Further mechanistic studies of 20b and 32 using transiently knocked down expression of ER-alpha and beta in mouse osteoblast (MOBs) showed that 20b and 32 exerts osteogenic efficacy via activation of estrogen receptor-beta preferentially. Additionally, compounds showed significant anticancer activity in a panel of cancer cell lines within the range of (IC50) 6.54-27.79 mu M. The most active molecule, 22b inhibited proliferation of cells by inducing apoptosis and arresting cell cycle at sub-G(0) phase with concomitant decrease in cells at S phase. (C) 2016 Elsevier Ltd. All rights reserved.
• Synthesis and Anti-tumor Activities of Novel Oxazinyl Isoflavonoids
  作者：Dun Wang、Like Hou、Lirong Wu、Xin Yu

  DOI：10.1248/cpb.60.513

  日期：——

  The design, synthesis and biological evaluation of a novel series of oxazinyl isoflavonoids is described. Several analogs were shown to exhibit growth inhibitory effects against SKOV-3, DU-145 and HL-60 human colon cancer cell lines with IC50 values in the micromolar range. The cellular potency of compounds 7e and 12h were found to have greater in vitro inhibitory activities than phenoxodiol, the parental compound currently in late-stage clinical trials for the treatment of cancer. The results shown are suitable for further lead optimization.

  本文介绍了一系列新型噁嗪基异黄酮的设计、合成和生物学评价。研究表明，几种类似物对 SKOV-3、DU-145 和 HL-60 人类结肠癌细胞系具有生长抑制作用，其 IC50 值在微摩尔范围内。研究发现，化合物 7e 和 12h 的体外抑制活性高于苯麝香二醇（目前正处于治疗癌症的后期临床试验阶段的母体化合物）。所显示的结果适于进一步优化先导化合物。