(E)-2-(3-甲氧基苯乙烯基)-4H-色烯-4-酮 | 80212-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: (E)-2-(3-甲氧基苯乙烯基)-4H-色烯-4-酮
• 英文名称: (E)-2-(3-methoxystyryl)-4H-chromen-4-one
• 英文别名: 2-[(E)-2-(3-methoxyphenyl)ethenyl]chromen-4-one
• CAS: 80212-22-2
• 化学式: C₁₈H₁₄O₃
• 分子量: 278.307
• InChiKey: JCKVPKCDIHLNJA-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (E)-2-(3-甲氧基苯乙烯基)-4H-色烯-4-酮 在 air 作用下， 以 苯 为溶剂， 以15%的产率得到3-Methoxy-benzo[a]xanthen-12-one
  参考文献：
  名称：

  Photochemistry of Flavonoids. V. Photocyclization of 2-Styryl-4H-chromen-4-ones

  摘要：

  在室温空气中用高压汞灯辐照 2-苯乙烯基-4H-苯并吡喃-4-酮 (1)，可得到苯并 [α]黄酮 (2)。甲氧基取代的苯乙烯基色酮的环化发生在苯乙烯基环上相对于 OMe 基团的对位，而 2-[β-（2-萘基）乙烯基]色酮（3）则在萘环的 α 位发生环化。

  DOI：

  10.1248/cpb.29.2670
• 作为产物：
  描述：

  2-甲基色原酮 、 3-甲氧基苯甲醛 在 sodium 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以43%的产率得到(E)-2-(3-甲氧基苯乙烯基)-4H-色烯-4-酮
  参考文献：
  名称：

  Photochemistry of Flavonoids. V. Photocyclization of 2-Styryl-4H-chromen-4-ones

  摘要：

  在室温空气中用高压汞灯辐照 2-苯乙烯基-4H-苯并吡喃-4-酮 (1)，可得到苯并 [α]黄酮 (2)。甲氧基取代的苯乙烯基色酮的环化发生在苯乙烯基环上相对于 OMe 基团的对位，而 2-[β-（2-萘基）乙烯基]色酮（3）则在萘环的 α 位发生环化。

  DOI：

  10.1248/cpb.29.2670

文献信息

• DNA METHYLATION INHIBITORS
  申请人：Chen Ching-Shih

  公开号：US20120157465A1

  公开（公告）日：2012-06-21

  A number of DNA methylation inhibitors are described. The DNA methylation inhibitors were identified using a two-component enhanced green fluorescent protein reporter system to screen a compound library containing procainamide derivatives. The DNA methylation inhibitors can be used for cancer therapy and prevention.
• US8546397B2
  申请人：——

  公开号：US8546397B2

  公开（公告）日：2013-10-01
• [EN] DNA METHYLATION INHIBITORS<br/>[FR] INHIBITEURS DE MÉTHYLATION DE L'ADN
  申请人：UNIV OHIO STATE RES FOUND

  公开号：WO2012087889A2

  公开（公告）日：2012-06-28

  A number of DNA methylation inhibitors are described. The DNA methylation inhibitors were identified using a two-component enhanced green fluorescent protein reporter system to screen a compound library containing procainamide derivatives. The DNA methylation inhibitors can be used for cancer therapy and prevention.
• Structure–activity relationship study of growth inhibitory 2-styrylchromones against carcinoma cells
  作者：Chen Lin、Pei-Jung Lu、Chia-Ning Yang、Christopher Hulme、Arthur Y. Shaw

  DOI：10.1007/s00044-012-0232-6

  日期：2013.5

  The structure-activity relationship study of 2-styrylchromones against carcinoma cell growth is discussed in the present report. Taking advantage of 2-styrylchromone as a molecular template, a series of structural modifications was carried out and examined on several carcinoma cell lines. Interestingly, AGS cells exhibited more sensitivity in response to methoxy-bearing compounds, of which compound 23 (3,4,5-trimethoxy group on ring B) showed the most potent activity with a GI(50) value of 1.3 mu M. Surprisingly, as methoxy groups in 12 and 24-27 were demethylated to generate their hydroxyl counterparts 28-32, none of them displayed appreciable activity against all carcinoma cells. We further confirmed the pivotal role of rigidity for growth inhibitory activity between the rigid 12 and its flexible counterpart 33. Taken together, in the present report, we have clearly demonstrated the structure-activity relationship study of 2-styrylchromones targeting carcinoma cell growth.
• Photochemistry of Flavonoids. V. Photocyclization of 2-Styryl-4H-chromen-4-ones
  作者：ICHIRO YOKOE、KYOKO HIGUCHI、YOSHIAKI SHIRATAKI、MANKI KOMATSU

  DOI：10.1248/cpb.29.2670

  日期：——

  Irradiation of 2-styryl-4H-chromen-4-ones (1) with a high pressure Hg lamp at room temperature under air gave benzo [α] xanthones (2). The cyclization of methoxy-substituted styrylchromones occurred at the para position relative to the OMe group on the styryl ring, whereas 2-[β-(2-naphthyl) vinyl] chromone (3) cyclized at the α-position of the naphthalene ring.

  在室温空气中用高压汞灯辐照 2-苯乙烯基-4H-苯并吡喃-4-酮 (1)，可得到苯并 [α]黄酮 (2)。甲氧基取代的苯乙烯基色酮的环化发生在苯乙烯基环上相对于 OMe 基团的对位，而 2-[β-（2-萘基）乙烯基]色酮（3）则在萘环的 α 位发生环化。