顺式己烯雌酚 | 22610-99-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 顺式己烯雌酚
• 中文别名: (Z)-4,4'-(1,2-二乙基-1,2-亚乙烯基)双苯酚；尼龙6/9
• 英文名称: cis-3,4-Bis(p-hydroxyphenyl)-3-hexene
• 英文别名: (Z)-3,4-Bis(4-hydroxyphenyl)-3-hexen；cis-diethylstilbesterol；cis-diethylstilbestrol；diethylstilbestrol；4.4'-dihydroxy-α.α'-diethyl-cis-stilbene；4.4'-Dihydroxy-α.α'-diaethyl-cis-stilben；4-[(Z)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol
• CAS: 22610-99-7
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: RGLYKWWBQGJZGM-ZCXUNETKSA-N

物化性质

• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2907299090

反应信息

• 作为反应物：
  描述：

  顺式己烯雌酚 生成 己烯雌酚
  参考文献：
  名称：

  �ber k�rperfremde synthetische �strogene

  摘要：

  DOI：

  10.1007/bf00898697
• 作为产物：
  描述：

  己烯雌酚频哪醇酮 在 盐酸 、 sodium tetrahydroborate 、 calcium chloride 作用下， 以 异丙醇 为溶剂， 反应 16.0h， 生成 顺式己烯雌酚
  参考文献：
  名称：

  Improved method for the preparation of diethylstilbestrol from 4,4-bis(p-acetoxyphenyl)-3-hexanone

  摘要：

  DOI：

  10.1007/bf00780182

文献信息

• Design of drugs involving receptor-ligand-DNA interactions
  申请人：——

  公开号：US20020064790A1

  公开（公告）日：2002-05-30

  It has been discovered that the degree of hormonal activity of candidate ligands correlates better with degree of fit into DNA than with the strength of receptor binding, and that the receptors in the steroid/thyroid hormone/vitamin A and D family alter the physiochemical properties of DNA and in concert with other transcription factors facilitate insertion of the ligand into DNA. As a result, the magnitude of the response is a function of the structure of the ligand as it related to insertion and fit into the DNA and the specificity of the response is a function of the stereochemistry of the receptor through binding to both the ligand and to the DNA. Based on these discoveries, a method is described herein for identifying drugs having increased activity as compared with the natural ligand for receptors such as the estrogenic receptors.

  人们发现，候选配体的荷尔蒙活性程度与 DNA 的匹配程度的相关性比与受体结合强度的相关性要好，类固醇/甲状腺激素/维生素 A 和 D 家族中的受体会改变 DNA 的理化性质，并与其他转录因子一起促进配体插入 DNA。因此，反应的大小是配体结构的函数，因为它与插入和适合 DNA 有关，而反应的特异性则是受体通过与配体和 DNA 结合的立体化学的函数。基于这些发现，本文介绍了一种方法，用于鉴定与雌激素受体等受体的天然配体相比活性更强的药物。
• Leimner, Juergen; Weyerstahl, Peter, Chemische Berichte, 1982, vol. 115, # 12, p. 3697 - 3705
  作者：Leimner, Juergen、Weyerstahl, Peter

  DOI：——

  日期：——
• Non-estrogenic metabolites of diethylstilbestrol produced by prostaglandin synthase mediated metabolism
  作者：Gisela H. Degen、John A. McLachlan

  DOI：10.1016/0039-128x(83)90038-7

  日期：1983.9

  Incubation of trans-diethylstilbestrol (E-DES) with prostaglandin synthase (PGS) in vitro leads to the formation of the metabolites cis, cis-dienestrol (Z,Z-DIES) and cis-diethylstilbestrol (Z-DES) which have considerably decreased estrogenic activity compared to their parent compound. Incubations of (14C)-E-DES with PGS in the presence of arachidonic acid (AA) predominantly catalyze formation of the oxidative metabolite Z,Z-DIES, accompanied by the formation of protein bound radioactivity. Inhibition of peroxidative metabolism through addition of indomethacin or absence of AA favors isomerization of E-DES to Z-DES without concomitant formation of protein bound radioactivity. Isomerization is inhibited by phenidone (1-phenyl-3-pyrazolidone). Since PGS activity is present in uterine tissue, these pathways may play a role in the metabolism of DES in its target tissue.
• BAGNATI, RENZO;GRAZIA, CASTELLI MARIA;AIROLDI, LUISA;PALEOLOGO, ORIUNDI M+, J. CHROMATOGR. BIOMED. APPL., 527,(1990) N, C. 267-278
  作者：BAGNATI, RENZO、GRAZIA, CASTELLI MARIA、AIROLDI, LUISA、PALEOLOGO, ORIUNDI M+

  DOI：——

  日期：——
• LEIMNER, J.;WEYERSTAHL, P., CHEM. BER., 1982, 115, N 12, 3697-3705
  作者：LEIMNER, J.、WEYERSTAHL, P.

  DOI：——

  日期：——