{"title":"一个新的和简单的协议,以获得6-烷氧基-Δ4,6-二烯-3- 1衍生物从现有的甾醇","authors":"Roxana Martínez-Pascual , Lidia Gabriela Felipe-Zaragoza , Miguel Ángel Peña-Rico , Alain Cruz-Nolasco , Lemuel Pérez-Picaso , Samuel Núñez-López , Adolfo López-Torres , Omar Viñas-Bravo","doi":"10.1016/j.steroids.2023.109323","DOIUrl":null,"url":null,"abstract":"<div><p>Herein we report an unprecedented and efficient methodology for accessing 6-alkoxy-Δ<sup>4,6</sup>-diene-3-one derivatives. Such scaffolds were serendipitously obtained in the course of the study of the reaction of Δ<sup>4</sup>-3-keto steroids with catalytic amounts of iodine in refluxing methanol. A series of 6-methoxy and 6-ethoxy- Δ<sup>4,6</sup>-diene-3-ones were prepared from easily-available sterols in a two-step sequence; first, oxidation of sterols furnished the Δ<sup>4</sup>-3-keto steroids, which were then refluxed with ethanol or methanol with I<sub>2</sub> as catalyst to obtain a series of ten derivatives. Furthermore, this protocol was also effective for the introduction of a larger carbon chain at C-6. Druglikeliness properties of synthesized compounds were predicted using the SwissADME tool.</p></div>","PeriodicalId":21997,"journal":{"name":"Steroids","volume":null,"pages":null},"PeriodicalIF":2.1000,"publicationDate":"2023-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"A novel and easy protocol to obtain 6-alkoxy-Δ4,6-diene-3-one derivatives from available sterols\",\"authors\":\"Roxana Martínez-Pascual , Lidia Gabriela Felipe-Zaragoza , Miguel Ángel Peña-Rico , Alain Cruz-Nolasco , Lemuel Pérez-Picaso , Samuel Núñez-López , Adolfo López-Torres , Omar Viñas-Bravo\",\"doi\":\"10.1016/j.steroids.2023.109323\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Herein we report an unprecedented and efficient methodology for accessing 6-alkoxy-Δ<sup>4,6</sup>-diene-3-one derivatives. Such scaffolds were serendipitously obtained in the course of the study of the reaction of Δ<sup>4</sup>-3-keto steroids with catalytic amounts of iodine in refluxing methanol. A series of 6-methoxy and 6-ethoxy- Δ<sup>4,6</sup>-diene-3-ones were prepared from easily-available sterols in a two-step sequence; first, oxidation of sterols furnished the Δ<sup>4</sup>-3-keto steroids, which were then refluxed with ethanol or methanol with I<sub>2</sub> as catalyst to obtain a series of ten derivatives. Furthermore, this protocol was also effective for the introduction of a larger carbon chain at C-6. Druglikeliness properties of synthesized compounds were predicted using the SwissADME tool.</p></div>\",\"PeriodicalId\":21997,\"journal\":{\"name\":\"Steroids\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2023-10-07\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Steroids\",\"FirstCategoryId\":\"3\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0039128X23001514\",\"RegionNum\":4,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Steroids","FirstCategoryId":"3","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0039128X23001514","RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
A novel and easy protocol to obtain 6-alkoxy-Δ4,6-diene-3-one derivatives from available sterols
Herein we report an unprecedented and efficient methodology for accessing 6-alkoxy-Δ4,6-diene-3-one derivatives. Such scaffolds were serendipitously obtained in the course of the study of the reaction of Δ4-3-keto steroids with catalytic amounts of iodine in refluxing methanol. A series of 6-methoxy and 6-ethoxy- Δ4,6-diene-3-ones were prepared from easily-available sterols in a two-step sequence; first, oxidation of sterols furnished the Δ4-3-keto steroids, which were then refluxed with ethanol or methanol with I2 as catalyst to obtain a series of ten derivatives. Furthermore, this protocol was also effective for the introduction of a larger carbon chain at C-6. Druglikeliness properties of synthesized compounds were predicted using the SwissADME tool.
期刊介绍:
STEROIDS is an international research journal devoted to studies on all chemical and biological aspects of steroidal moieties. The journal focuses on both experimental and theoretical studies on the biology, chemistry, biosynthesis, metabolism, molecular biology, physiology and pharmacology of steroids and other molecules that target or regulate steroid receptors. Manuscripts presenting clinical research related to steroids, steroid drug development, comparative endocrinology of steroid hormones, investigations on the mechanism of steroid action and steroid chemistry are all appropriate for submission for peer review. STEROIDS publishes both original research and timely reviews. For details concerning the preparation of manuscripts see Instructions to Authors, which is published in each issue of the journal.