2,4-dichloroestradiol | 25940-39-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 2,4-dichloroestradiol
• 英文别名: (8R,9S,13S,14S,17S)-2,4-dichloro-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 25940-39-0
• 化学式: C₁₈H₂₂Cl₂O₂
• 分子量: 341.277
• InChiKey: GYWMGWUSHSLJEW-ZICKVNAASA-N

物化性质

• 沸点：
  452.1±45.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  雌二醇 在 chloroperoxidase from Caldariomyces fumago 、 双氧水 、 氯 作用下， 生成 2,4-dichloroestradiol
  参考文献：
  名称：

  真菌氯过氧化物酶催化的雌激素卤化

  摘要：

  摘要 氯过氧化物酶 (CPO) 是一种血红素硫醇盐酶，能够催化多种有机底物的卤化和氧化。在这项工作中，表征了天然雌激素的 CPO 催化的氯化和溴化反应。在氯化物或溴化物和过氧化氢的存在下，雌二醇、雌酮和马林可以有效地转化为卤代化合物。该反应中 CPO 的催化效率与其他芳烃底物的催化效率相似；正如预期的那样，溴化反应比氯化反应进行得更有效。检测出三种主要的雌二醇氯化产物；其中两种是单卤代化合物，而第三种产物是芳环 A 的 2 位和 4 位的二卤代化合物。氯化化合物不是酪氨酸酶的底物，邻醌。

  DOI：

  10.1080/14786419.2021.1925269

文献信息

• Mukawa, Fumikazu, Journal of the Chemical Society. Perkin transactions I, 1988, p. 457 - 460
  作者：Mukawa, Fumikazu

  DOI：——

  日期：——
• Products of Aqueous Chlorination of 17β-Estradiol and Their Estrogenic Activities
  作者：Jianying Hu、Shuijie Cheng、Takako Aizawa、Yoshiyasu Terao、Shoichi Kunikane

  DOI：10.1021/es034324+

  日期：2003.12.1

  To assess the estrogenic activity potentially stemming from 17beta-estradiol (E2) in drinking water, ESI-LC-MS was used to identify the products of its aqueous chlorination under the following conditions: 50 mug/L E2, 1.46 mg/L sodium hypochlorite, pH 7.5, 25 degreesC. Seven products, including 2,4-dichloro-17beta-estradiol, monochloroestrone, 2,4-dichloroestrone, and the four byproducts such as 4-[2-(2,6-dichloro-3-hydroxyphenyl)ethyl]-7alpha-methyloctahydroinden-5-one (product C in the text) were identified in chlorinated E2 solution. The estrogenic activities of the aqueous chlorinated E2 solution at 10, 30, 60, 120, and 180 min contact time were assessed by a yeast two-hybrid system based on the ligand-dependent interaction of two proteins, a human estrogen receptor (ER) and a coactivator. All five solutions elicited transcriptional activation induction. The maximal beta-galactosidase activities induced by the chlorinated solution at 10, 30, and 60 min were similar and slightly lower than those before chlorination, while the activities of the chlorinated solution at 120 and 180 min were about 40% of those before chlorination. Finally, 4-chloro-17beta-estradiol (4-chloro-E2) (we failed to synthesize the 2-chloroestrone (2-chloro-E1)), 2,4-dichloro-17beta-estradiol (2,4-dichloro-E2), and 2,4-dichloroestrone (2,4-dichloro-E1) were synthesized, and product C was fractionated by HPLC. It was found that 4-chloro-E2 elicited strong estrogenic activity, at almost the same level as that of estrone (EC50 = 10(2) nM), while 2,4-dichloro-E2 elicited weaker beta-galactosidase activity compared with that of 4-chloro-E2. The EC50 was ca. 10(3) nM. The maximal beta-galactosidase activity for 2,4-dichloro-E1 was lower than that of 2,4-dichloro-E2, while its EC50 was similar to that of 2,4-dichloro-E2. In addition, product C, 4-[2-(2,6-dichloro-3-hydroxyphenyl)ethyl]-7alpha-methyloctahydroinden-5-one, induced high beta-galactosidase activity at the relatively higher concentration of 3.5 x 10(5) nM. On the basis of the dose-response curve of a single byproduct of chlorinated E2, the estrogenic activity 120 and 180 min appears to be induced mainly by 2,4-dichloro-E2 and 2,4-dichloro-E1.