7-(allyloxy)-4-phenyl-2H-chromen-2-one | 16024-13-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 7-(allyloxy)-4-phenyl-2H-chromen-2-one
• 英文别名: 7-O-allyl-4-phenylcoumarin；7-allyloxy-4-phenyl-chromen-2-one；7-Allyloxy-4-phenyl-chromen-2-on；7-Allyloxy-4-phenyl-cumarin；4-phenyl-7-prop-2-enoxychromen-2-one
• CAS: 16024-13-8
• 化学式: C₁₈H₁₄O₃
• 分子量: 278.307
• InChiKey: JUYUQNXHIYUYER-UHFFFAOYSA-N

物化性质

• 熔点：
  183-184 °C
• 沸点：
  457.0±45.0 °C(predicted)
• 密度：
  1.202±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  4
• 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：

  7-(allyloxy)-4-phenyl-2H-chromen-2-one 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 64.0h， 生成 4-phenyl-8,11-dihydro-2H-oxepino[2,3-h]chromen-2-one
  参考文献：
  名称：

  新型oxepin环化香豆素的合成及抗增殖活性

  摘要：

  分别通过烯丙基化、克莱森重排、烯丙基化和闭环复分解 (RCM) 合成了一系列稠合的二氢氧杂[h] 和二氢氧杂[g] 香豆素（7 和 8）。通过适当的光谱分析表征所有合成的化合物。使用以下方法评估了化合物 5a-c、6a、6c、7a-c 和 8a-c 对人结肠癌 (Caco-2)、肝癌 (HepG2) 和乳腺癌 (SKBR-3) 细胞系的抗增殖活性他莫昔芬 (TAM) 作为阳性对照。与所有其他香豆素衍生物相比，化合物 7b 对抗性 Caco-2 和 SKBR-3 细胞系显示出显着的抗增殖活性。有趣的是，化合物 8b 比 TAM 更有效地对抗敏感的 HepG2 细胞系。

  DOI：

  10.24820/ark.5550190.p010.547
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 在 高氯酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.5h， 生成 7-(allyloxy)-4-phenyl-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and in vitro evaluation of leishmanicidal activity of 7-hydroxy-4-phenylcoumarin derivatives

  摘要：

  Eight coumarin derivatives (2-8) were synthesized from 7-hydroxy-4-phenylcoumarin 1 and were evaluated for their in vitro leishmanicidal activity against promastigote and amastigote forms of Leishmania amazonensis, as well their toxicity in murine macrophages. Compounds 4 and 7 showed the most significant results against promastigote forms of L. amazonensis. They were at least three-fold more active than 1 and Compound 4 was as effective as Amphotericin B. Compound 4, a 7-O-prenylated derivative, and 7, a tetra- O -acetyl-beta- D -glucopyranosyl derivative, presented IC50 values of 21.35 and 10.03 A mu M against promastigote and IC50 values of 58.10 and 34.93 A mu M, respectively against amastigote forms. Furthermore, they do not cause toxicity in mammalian or Leishmania cells in vitro. This study shows that these coumarin derivatives are potential prototypes for the development of novel drugs with leishmanicidal activity.

  DOI：

  10.1007/s00044-016-1729-1

文献信息

• AHUJA M.; BANDOPADHYAY M.; SESHADRI T. R., INDIAN J. CHEM. <IJOC-AP>, 1974 12, NO 3, 292-294
  作者：AHUJA M.、 BANDOPADHYAY M.、 SESHADRI T. R.

  DOI：——

  日期：——
• US6143766A
  申请人：——

  公开号：US6143766A

  公开（公告）日：2000-11-07
• Synthesis and anti-proliferative activity of novel oxepin-annulated coumarins
  作者：Saisuree Prateeptongkum、Wiratchanee Mahavorasirikul、Nongnaphat Duangdee

  DOI：10.24820/ark.5550190.p010.547

  日期：——

  A series of fused dihydrooxepino[h]and dihydrooxepino[g]coumarins (7 and 8) were synthesized through allylation, Claisen rearrangement, allylation and ring-closing metathesis (RCM), respectively. All the synthesized compounds were characterized by appropriate spectral analysis. The anti-proliferative activities of compound 5a-c, 6a, 6c, 7a-c and 8a-c were evaluated against human colon cancer (Caco-2)

  分别通过烯丙基化、克莱森重排、烯丙基化和闭环复分解 (RCM) 合成了一系列稠合的二氢氧杂[h] 和二氢氧杂[g] 香豆素（7 和 8）。通过适当的光谱分析表征所有合成的化合物。使用以下方法评估了化合物 5a-c、6a、6c、7a-c 和 8a-c 对人结肠癌 (Caco-2)、肝癌 (HepG2) 和乳腺癌 (SKBR-3) 细胞系的抗增殖活性他莫昔芬 (TAM) 作为阳性对照。与所有其他香豆素衍生物相比，化合物 7b 对抗性 Caco-2 和 SKBR-3 细胞系显示出显着的抗增殖活性。有趣的是，化合物 8b 比 TAM 更有效地对抗敏感的 HepG2 细胞系。
• Synthesis and in vitro evaluation of leishmanicidal activity of 7-hydroxy-4-phenylcoumarin derivatives
  作者：Isael A. Rosa、Letícia de Almeida、Karina F. Alves、Marcos J. Marques、Antônio M. Fregnan、Claudinei A. Silva、Juliana O. S. Giacoppo、Teodorico C. Ramalho、Diogo T. Carvalho、Marcelo H. dos Santos

  DOI：10.1007/s00044-016-1729-1

  日期：2017.1

  Eight coumarin derivatives (2-8) were synthesized from 7-hydroxy-4-phenylcoumarin 1 and were evaluated for their in vitro leishmanicidal activity against promastigote and amastigote forms of Leishmania amazonensis, as well their toxicity in murine macrophages. Compounds 4 and 7 showed the most significant results against promastigote forms of L. amazonensis. They were at least three-fold more active than 1 and Compound 4 was as effective as Amphotericin B. Compound 4, a 7-O-prenylated derivative, and 7, a tetra- O -acetyl-beta- D -glucopyranosyl derivative, presented IC50 values of 21.35 and 10.03 A mu M against promastigote and IC50 values of 58.10 and 34.93 A mu M, respectively against amastigote forms. Furthermore, they do not cause toxicity in mammalian or Leishmania cells in vitro. This study shows that these coumarin derivatives are potential prototypes for the development of novel drugs with leishmanicidal activity.