Acetic acid 3-[(E)-2-(3-acetoxy-phenyl)-1-butyl-hex-1-enyl]-phenyl ester | 80149-86-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: Acetic acid 3-[(E)-2-(3-acetoxy-phenyl)-1-butyl-hex-1-enyl]-phenyl ester
• 英文别名: [3-[(E)-6-(3-acetyloxyphenyl)dec-5-en-5-yl]phenyl] acetate
• CAS: 80149-86-6
• 化学式: C₂₆H₃₂O₄
• 分子量: 408.538
• InChiKey: CQJPSIPPRMTHEE-OCEACIFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Acetic acid 3-[(E)-2-(3-acetoxy-phenyl)-1-butyl-hex-1-enyl]-phenyl ester 在 间氯过氧苯甲酸 作用下， 以 乙醚 为溶剂， 生成 Acetic acid 3-[3-(3-acetoxy-phenyl)-2,3-dibutyl-oxiranyl]-phenyl ester
  参考文献：
  名称：

  Mammary tumor inhibiting effect of 3,3'-diacetoxy-.alpha.,.beta.-dialkylstilbenes and of related stilbene oxides

  摘要：

  3,3'-Diacetoxy-alpha, beta-dialkylstilbenes (alkyl = CH3 to C4H9, 1-4) 3,3'-dihydroxy-alpha, beta-diethylstilbene (5), and their corresponding stilbene oxides (6-10) were synthesized. Compounds 1-10 competitively antagonized in vitro the interaction of [3H]estradiol with its receptor. 3,3'-Diacetoxy-alpha, beta-diethylstilbene (2), 3,3'-diacetoxy-alpha, beta-diethylstilbene oxide (7), and their phenolic analogues (5 and 10) were most effective. Shortening or lengthening the alkyl side chains led to a decrease in receptor affinity. Among the stilbenes and epoxides, those with C2H5 and C3H7 groups (2, 3, 5 and 7, 8, 10) caused the strongest inhibition of the growth of a hormone-dependent postmenopausal human mammary carcinoma serially implanted in nude mice. The strong antitumor activity of 5 and 10 was confirmed by experiments on the 9,10-dimethyl-1,2-benzanthracene-induced, hormone-dependent mammary carcinoma of the Sprague-Dawley rat.

  DOI：

  10.1021/jm00344a010
• 作为产物：
  描述：

  乙酸酐 、 3-[(E)-6-(3-hydroxyphenyl)dec-5-en-5-yl]phenol 在 吡啶 作用下， 反应 0.5h， 生成 Acetic acid 3-[(E)-2-(3-acetoxy-phenyl)-1-butyl-hex-1-enyl]-phenyl ester
  参考文献：
  名称：

  Mammary tumor inhibiting effect of 3,3'-diacetoxy-.alpha.,.beta.-dialkylstilbenes and of related stilbene oxides

  摘要：

  3,3'-Diacetoxy-alpha, beta-dialkylstilbenes (alkyl = CH3 to C4H9, 1-4) 3,3'-dihydroxy-alpha, beta-diethylstilbene (5), and their corresponding stilbene oxides (6-10) were synthesized. Compounds 1-10 competitively antagonized in vitro the interaction of [3H]estradiol with its receptor. 3,3'-Diacetoxy-alpha, beta-diethylstilbene (2), 3,3'-diacetoxy-alpha, beta-diethylstilbene oxide (7), and their phenolic analogues (5 and 10) were most effective. Shortening or lengthening the alkyl side chains led to a decrease in receptor affinity. Among the stilbenes and epoxides, those with C2H5 and C3H7 groups (2, 3, 5 and 7, 8, 10) caused the strongest inhibition of the growth of a hormone-dependent postmenopausal human mammary carcinoma serially implanted in nude mice. The strong antitumor activity of 5 and 10 was confirmed by experiments on the 9,10-dimethyl-1,2-benzanthracene-induced, hormone-dependent mammary carcinoma of the Sprague-Dawley rat.

  DOI：

  10.1021/jm00344a010

文献信息

• Mammary tumor inhibiting effect of 3,3'-diacetoxy-.alpha.,.beta.-dialkylstilbenes and of related stilbene oxides
  作者：Martin R. Schneider、Helmut Schoenenberger、Ralf T. Michel、H. P. Fortmeyer

  DOI：10.1021/jm00344a010

  日期：1982.2

  3,3'-Diacetoxy-alpha, beta-dialkylstilbenes (alkyl = CH3 to C4H9, 1-4) 3,3'-dihydroxy-alpha, beta-diethylstilbene (5), and their corresponding stilbene oxides (6-10) were synthesized. Compounds 1-10 competitively antagonized in vitro the interaction of [3H]estradiol with its receptor. 3,3'-Diacetoxy-alpha, beta-diethylstilbene (2), 3,3'-diacetoxy-alpha, beta-diethylstilbene oxide (7), and their phenolic analogues (5 and 10) were most effective. Shortening or lengthening the alkyl side chains led to a decrease in receptor affinity. Among the stilbenes and epoxides, those with C2H5 and C3H7 groups (2, 3, 5 and 7, 8, 10) caused the strongest inhibition of the growth of a hormone-dependent postmenopausal human mammary carcinoma serially implanted in nude mice. The strong antitumor activity of 5 and 10 was confirmed by experiments on the 9,10-dimethyl-1,2-benzanthracene-induced, hormone-dependent mammary carcinoma of the Sprague-Dawley rat.