4-(p-acetoxyphenyl)-7-methoxy-3-phenylcoumarin | 33257-84-0

• 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: 4-(p-acetoxyphenyl)-7-methoxy-3-phenylcoumarin
• 英文别名: 3-Phenyl-4-(4-acetoxyphenyl)-7-methoxycumarin；4-(4-Acetoxyphenyl)-7-methoxy-3-phenyl-coumarin；[4-(7-methoxy-2-oxo-3-phenylchromen-4-yl)phenyl] acetate
• CAS: 33257-84-0
• 化学式: C₂₄H₁₈O₅
• 分子量: 386.404
• InChiKey: RXZUFHHBPSHYOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  562.6±50.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(p-acetoxyphenyl)-7-methoxy-3-phenylcoumarin 在 盐酸 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 1.0h， 生成 7-(2-(piperidin-1-yl)ethoxy)-4-(4-hydroxyphenyl)-3-phenyl-2H-chromen-2-one
  参考文献：
  名称：

  Design, synthesis, and anti-tumor activities of novel triphenylethylene–coumarin hybrids, and their interactions with Ct-DNA

  摘要：

  Novel triphenylethylene-coumarin hybrid derivatives containing different amounts of amino side chains Were designed and synthesized in good yields under microwave radiation. The derivatives 5b-d which possessed two amino side chains (except morpholinyl) showed a broad-spectrum and good anti-proliferative activity against five tumor cells and low cytotoxicity in osteoblast. UV-vis, fluorescence, and circular dichroism (CD) spectroscopies and thermal denaturation exhibited that compounds 10c, 5c, and 13c bearing amino side chain (except morpholinyl) on 4-phenyl had significant interactions with Ct-DNA by the intercalative mode of binding. Structure-activity relationships (SARs) analysis suggested that the amino alkyl chain would play an important role both in the compounds against tumor cells proliferation and their interactions with DNA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.009
• 作为产物：
  描述：

  对羟基苯甲酸 在 三乙胺 、 zinc(II) chloride 、 三氯氧磷 作用下， 以 环丁砜 为溶剂， 反应 2.5h， 生成 4-(p-acetoxyphenyl)-7-methoxy-3-phenylcoumarin
  参考文献：
  名称：

  Design, synthesis, and anti-tumor activities of novel triphenylethylene–coumarin hybrids, and their interactions with Ct-DNA

  摘要：

  Novel triphenylethylene-coumarin hybrid derivatives containing different amounts of amino side chains Were designed and synthesized in good yields under microwave radiation. The derivatives 5b-d which possessed two amino side chains (except morpholinyl) showed a broad-spectrum and good anti-proliferative activity against five tumor cells and low cytotoxicity in osteoblast. UV-vis, fluorescence, and circular dichroism (CD) spectroscopies and thermal denaturation exhibited that compounds 10c, 5c, and 13c bearing amino side chain (except morpholinyl) on 4-phenyl had significant interactions with Ct-DNA by the intercalative mode of binding. Structure-activity relationships (SARs) analysis suggested that the amino alkyl chain would play an important role both in the compounds against tumor cells proliferation and their interactions with DNA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.009

文献信息

• [EN] NOVEL (-)-ENANTIOMERS OF CIS-3,4-CHROMAN DERIVATIVES USEFUL IN THE PREVENTION OR TREATMENT OF ESTROGEN RELATED DISEASES OR SYNDROMES<br/>[FR] NOUVEAUX (-)-ENANTIOMERES DE DERIVES DE CIS-3,4-CHROMANE UTILES POUR LA PREVENTION OU LE TRAITEMENT DE MALADIES OU DE SYNDROMES ASSOCIES AUX OESTROGENES
  申请人：NOVO NORDISK A/S

  公开号：WO1998018771A1

  公开（公告）日：1998-05-07

  (EN) The present invention relates to therapeutically active compounds of formula (I), a method of preparing the same and to pharmaceutical compositions comprising the compounds. The novel compounds are useful in the prevention or treatment of estrogen related diseases or syndromes.(FR) L'invention concerne des composés actifs sur le plan thérapeutique représentés par la formule (I), un procédé servant à les préparer et des compositions pharmaceutiques contenant ces composés. Ces nouveaux composés sont utiles pour la prévention et le traitement de maladies ou de syndromes associés aux oestrogènes.

  本发明涉及公式（I）的治疗活性化合物，其制备方法以及包含该化合物的制药组合物。这些新型化合物可用于预防或治疗与雌激素相关的疾病或综合症。
• [EN] NOVEL CIS-3,4-CHROMAN DERIVATIVES USEFUL IN THE PREVENTION OR TREATMENT OF ESTROGEN RELATED DISEASES OR SYNDROMES<br/>[FR] NOUVEAUX DERIVES DE CIS-3,4-CHROMANE UTILES POUR LA PREVENTION OU LE TRAITEMENT DE MALADIES OU DE SYNDROMES RELATIFS AUX OESTROGENES
  申请人：NOVO NORDISK A/S

  公开号：WO1998018776A1

  公开（公告）日：1998-05-07

  (EN) The present invention relates to therapeutically active compounds of formula (I), a method of preparing the same and to pharmaceutical compositions comprising the compounds. The novel compounds are useful in the prevention or treatment of estrogen related diseases or syndromes.(FR) L'invention concerne des composés actifs sur le plan thérapeutique représentés par la formule (I) un procédé servant à préparer ces composés et des compositions pharmaceutiques contenant ces composés. Ces nouveaux composés sont utiles pour la prévention ou le traitement de maladies ou de syndromes relatifs aux oestrogènes.

  本发明涉及公式（I）的治疗活性化合物，其制备方法以及包含这些化合物的制药组合物。这些新型化合物可用于预防或治疗与雌激素相关的疾病或综合症。
• Trans-3,4-chroman derivatives useful in the prevention or treatment of
  申请人：Novo Nordisk

  公开号：US05994390A1

  公开（公告）日：1999-11-30

  The present invention relates to therapeutically active compounds of formula I ##STR1## a method of preparing the same and to pharmaceutical compositions comprising the compounds. The novel compounds are useful in the prevention or treatment of estrogen related diseases or syndromes.

  本发明涉及式I的治疗活性化合物，其公式为：##STR1##以及制备该化合物的方法和包含该化合物的制药组合物。这些新化合物可用于预防或治疗与雌激素相关的疾病或综合症。
• cis-3,4-chroman derivatives useful in the prevention or treatment of
  申请人：Novo Nordisk A/S

  公开号：US06043269A1

  公开（公告）日：2000-03-28

  The present invention relates to therapeutically active compounds of formula I ##STR1## a method of preparing the same and to pharmaceutical compositions comprising the compounds. The novel compounds are useful in the prevention or treatment of estrogen related diseases or syndromes.

  本发明涉及公式I的治疗活性化合物，其制备方法，以及包含该化合物的药物组合物。这些新型化合物在预防或治疗与雌激素相关的疾病或综合症方面具有用途。
• cis3, 4-chroman derivatives useful in the prevention or treatment of estrogen related diseases or syndromes
  申请人：Novo Nordisk A/S

  公开号：US06316494B1

  公开（公告）日：2001-11-13

  The present invention relates to therapeutically active compounds of formula I a method of preparing the same and to pharmaceutical compositions comprising the compounds. The novel compounds are useful in the prevention or treatment of estrogen related diseases or syndromes.

  本发明涉及公式I的治疗活性化合物、其制备方法以及包含该化合物的药物组合物。这些新型化合物可用于预防或治疗与雌激素相关的疾病或综合征。