水相光解药物甾体的生物活性重排产物。
Bioactive Rearrangement Products from Aqueous Photolysis of Pharmaceutical Steroids.
出版信息
Org Lett. 2019 May 17;21(10):3568-3571. doi: 10.1021/acs.orglett.9b00972. Epub 2019 Apr 25.
Abstract
In an ongoing effort to study the environmental fate of endocrine-active steroid hormones, we report the formation of phenolic rearrangement products (3 and 4) with a novel 6,5,8,5-ring system following aqueous photolysis of dienogest (1) and methyldienolone (2). The structures were established by analysis of 2D NMR and HRMS data, and that of 3 was confirmed by X-ray diffraction analysis. These photoproducts exhibit progestogenic and androgenic activity, albeit with less potency than their parent compounds.
摘要
为了研究具有内分泌活性的甾体激素在环境中的归宿，我们报告了在水中光解双羟孕酮（1）和甲羟孕素（2）后形成具有新型 6,5,8,5 环系的酚重排产物（3 和 4）。结构通过二维 NMR 和高分辨质谱数据分析得到确立，3 的结构通过 X 射线衍射分析得到确证。这些光产物表现出孕激素和雄激素活性，但效力低于其母体化合物。
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2
Dioxygen: What Makes This Triplet Diradical Kinetically Persistent?氧气：是什么使这个三重自由基动力学稳定？
J Am Chem Soc. 2017 Jul 5;139(26):9010-9018. doi: 10.1021/jacs.7b04232. Epub 2017 Jun 14.
3
Reversible Photohydration of Trenbolone Acetate Metabolites: Mechanistic Understanding of Product-to-Parent Reversion through Complementary Experimental and Theoretical Approaches.反相光水合作用：通过互补的实验和理论方法对产物到母体的反转进行机制理解。
Environ Sci Technol. 2016 Jul 5;50(13):6753-61. doi: 10.1021/acs.est.5b03905. Epub 2016 Feb 4.
4
Sex in troubled waters: Widespread agricultural contaminant disrupts reproductive behaviour in fish.性在困境中：广泛存在的农业污染物扰乱鱼类的生殖行为。
Horm Behav. 2015 Apr;70:85-91. doi: 10.1016/j.yhbeh.2015.03.002. Epub 2015 Mar 19.
5
Environmental designer drugs: when transformation may not eliminate risk.环境设计药物：当转化可能无法消除风险时。
Environ Sci Technol. 2014 Oct 21;48(20):11737-45. doi: 10.1021/es503425w. Epub 2014 Oct 2.
6
Sources, concentrations, and exposure effects of environmental gestagens on fish and other aquatic wildlife, with an emphasis on reproduction.环境中孕体激素对鱼类及其他水生野生动物的来源、浓度和暴露影响，重点关注生殖方面。
Gen Comp Endocrinol. 2014 Jul 1;203:241-9. doi: 10.1016/j.ygcen.2014.03.038. Epub 2014 Apr 20.
7
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8
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Photochem Photobiol Sci. 2012 Jan;11(1):38-53. doi: 10.1039/c1pp05164d. Epub 2011 Aug 22.
9
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