Acetic acid 3-[3-(3-acetoxy-phenyl)-2,3-dipropyl-oxiranyl]-phenyl ester | 80149-90-2

• 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-[3-(3-acetoxy-phenyl)-2,3-dipropyl-oxiranyl]-phenyl ester
• 英文别名: [3-[3-(3-Acetyloxyphenyl)-2,3-dipropyloxiran-2-yl]phenyl] acetate
• CAS: 80149-90-2
• 化学式: C₂₄H₂₈O₅
• 分子量: 396.483
• InChiKey: NZYXSJGGVFBLBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-[(E)-5-(3-hydroxyphenyl)oct-4-en-4-yl]phenol 在 吡啶 、 间氯过氧苯甲酸 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 Acetic acid 3-[3-(3-acetoxy-phenyl)-2,3-dipropyl-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

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.