3-(4-methoxyphenyl)-2,3-dihydro-1H-benzo[f]chromen-1-one | 28656-21-5

• 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: 3-(4-methoxyphenyl)-2,3-dihydro-1H-benzo[f]chromen-1-one
• 英文别名: 3-(4-Methoxyphenyl)-2,3-dihydro-1H-naphtho[2,1-b]pyran-1-one；3-(4-methoxyphenyl)-2,3-dihydrobenzo[f]chromen-1-one
• CAS: 28656-21-5
• 化学式: C₂₀H₁₆O₃
• 分子量: 304.345
• InChiKey: MHOXVVONZXOBEG-UHFFFAOYSA-N

物化性质

• 熔点：
  143 °C
• 沸点：
  509.5±50.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-2,3-dihydro-1H-benzo[f]chromen-1-one 在 五氯化磷 、 苯 作用下， 生成 4-甲氧基-5,6-苯并黄酮
  参考文献：
  名称：

  CCCLXI：色酮组中的合成实验。第四部分1：4-βα-萘并吡喃酮

  摘要：

  DOI：

  10.1039/jr9310002591
• 作为产物：
  描述：

  2'-hydroxy-4-methoxy-5',6'-benzochalcone 在 正丁胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 3-(4-methoxyphenyl)-2,3-dihydro-1H-benzo[f]chromen-1-one
  参考文献：
  名称：

  Sathe, S. W.; Wadodkar, K. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 2, p. 153 - 154

  摘要：

  DOI：

文献信息

• Synthetic Naphthoflavonoids Showing Inhibitory Effects on Clonogenicity against Cisplatin-Resistant A2780/Cis Human Ovarian Cancer Cells
  作者：Yearam Jung、Soon Young Shin、Yeonjoong Yong、Hyuk Yoon、Seunghyun Ahn、Hyeryoung Jung、Dongsoo Koh、Young Han Lee、Yoongho Lim

  DOI：10.2174/1570180812666150213230949

  日期：2015.7.30

  Detecting early-stage ovarian cancer, the fourth leading cause of cancerrelated deaths in women, is difficult, and the development of novel chemotherapeutic agents is required. Since several flavonoids show anticancer activities against ovarian cancer, 35 naphthylated flavonoids including 3’,4’-naphthochalcones, 5’,6’-naphthochalcone, 7,8-nap-hthoflavones, 5,6-naphthoflavanones, 5,6-naphthoflavones, 2,3-naphthochalcone, N-phenylpyrazolyl-5’,6’-naphthocha-lcones, carbothioamidepyrazolyl-5’,6’-naphthochalcones, pyrazolyl-3’,4’-naphthochalcone, and carbothioamidepyrazolyl-3’,4’-naphthochalcone were designed and synthesized. To explore the anticancer effects of these compounds, clonogenic long-term survival assays were applied on human cisplatin-resistant A2780/Cis ovarian cancer cells. Relationships between the structural properties of 35 naphthylated flavonoids and their clonogenicities were explored using comparative molecular field analysis and hologram quantitative structure– activity relationships. As a result, several structural features that increased cell growth inhibitory activity were identified, and a compound satisfying these conditions, 5-(2,3-dimethoxyphenyl)-3-(1-hydroxynaphthalen-2-yl)-N-phenyl-4,5-dihydro-1Hpyrazole- 1-carbothioamide, was designed and synthesized. This novel compound´s half-maximal cell growth inhibitory concentration was lower than those of the 35 flavonoid derivatives tested here. Therefore, the structural features observed in this report can be used to design and develop potent chemotherapeutic agents to treat ovarian cancer cells.

  早期卵巢癌的检测难度较大，而卵巢癌是女性癌症相关死亡的第四大原因，因此需要开发新型化疗药物。由于几种类黄酮显示出对卵巢癌的抗癌活性，本研究设计并合成了35种萘基类黄酮，包括3',4'-萘酮酮、5',6'-萘酮、7,8-萘黄酮、5,6-萘黄烷酮、5,6-萘黄酮、2,3-萘酮、N-苯基吡唑基-5',6'-萘酮、碳硫酰胺吡唑基-5',6'-萘酮、吡唑基-3',4'-萘酮及碳硫酰胺吡唑基-3',4'-萘酮。为了探索这些化합物的抗癌效果，采用了克隆形成长期存活实验，对人类顺铂耐药的A2780/Cis卵巢癌细胞进行实验。使用比较分子场分析和全息量化结构-活性关系探讨了35种萘基类黄酮的结构特性与它们的克隆形成能力之间的关系。结果表明，识别出几种可以增强细胞生长抑制活性的结构特征，进一步设计并合成了满足这些条件的化合物5-(2,3-二甲氧基苯基)-3-(1-羟基萘-2-基)-N-苯基-4,5-二氢-1H-吡唑-1-碳硫酰胺。该新型化合物的半最大细胞生长抑制浓度低于本文测试的35种类黄酮衍生物。因此，本报告中观察到的结构特征可用于设计和开发有效的化疗药物以治疗卵巢癌细胞。
• Athappan, P. R.; Shanthi, P.; Natarajan, C., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1995, vol. 34, # 8, p. 648 - 651
  作者：Athappan, P. R.、Shanthi, P.、Natarajan, C.

  DOI：——

  日期：——
• SYNTHESIS OF DIHYDROFLAVONOLS AND FLAVONOLS
  作者：M. G. MARATHEY

  DOI：10.1021/jo01123a003

  日期：1955.5
• Athappan, P.; Shanthi, P.; Murugesan, R., Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1993, vol. 23, p. 1445 - 1468
  作者：Athappan, P.、Shanthi, P.、Murugesan, R.、Natarajan, C.

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• Fujise; Suzuki, Nippon Kagaku Zasshi, 1951, vol. 72, p. 1073
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