1996
DOI: 10.1021/jm950539l
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Structure−Activity Relationships of a New Family of Steroidal Aromatase Inhibitors. 1. Synthesis and Evaluation of a Series of Analogs Related to 19-[(Methylthio)methyl]androstenedione (RU54115)

Abstract: During the course of a study aimed at the search for new potent aromatase inhibitors, several new androstenedione analogs were synthesized and evaluated. This study led to the discovery of 19-[(methylthio)methyl]androsta-4,9(11)-diene-3,17-dione (7; RU54115) already described by our laboratory. The object of the present series of papers is to disclose the result of the structure-activity relationship studies that gave rise to this compound. This first part deals mainly with the substitution in the 19-position … Show more

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Cited by 17 publications
(10 citation statements)
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“…One of recent papers devoted to 19-functionalised androstanes presents the results of extensive studies on the synthesis and structure ± aromatase affinity relationships of several series of androstane-4,9(11)-diene-3,17-diones carrying a sulfur-containing group, [(CH 2 ) n SR], at the C(10) atom, where n = 0 ± 3 and R stands for various alkyl, acyl and aryl substituents. 46 19-Ethoxycarbonylandrosta-4,9(11)-diene-3,17-dione 37 obtained from the allylic alcohol 36 by the [3.3]-Claisen rearrangement was used as the starting compound in these syntheses (Scheme 2). Thus the reaction of steroid 36 with triethyl orthoacetate in the presence of propionic acid gave the ethoxycarbonyl derivative 37 in > 80% yield.…”
Section: Methods For the Synthesis Of Aromatase Inhibitors Of The And...mentioning
confidence: 99%
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“…One of recent papers devoted to 19-functionalised androstanes presents the results of extensive studies on the synthesis and structure ± aromatase affinity relationships of several series of androstane-4,9(11)-diene-3,17-diones carrying a sulfur-containing group, [(CH 2 ) n SR], at the C(10) atom, where n = 0 ± 3 and R stands for various alkyl, acyl and aryl substituents. 46 19-Ethoxycarbonylandrosta-4,9(11)-diene-3,17-dione 37 obtained from the allylic alcohol 36 by the [3.3]-Claisen rearrangement was used as the starting compound in these syntheses (Scheme 2). Thus the reaction of steroid 36 with triethyl orthoacetate in the presence of propionic acid gave the ethoxycarbonyl derivative 37 in > 80% yield.…”
Section: Methods For the Synthesis Of Aromatase Inhibitors Of The And...mentioning
confidence: 99%
“…Methylthiovinyl steroids 48 and 50 have also been described. 46 The acetoxy derivative 47 was deacetylated into the corresponding 3,17-diol which was introduced into the reaction with diethyl methylthiomethylphosphonate and butyllithium. The thus prepared (10E)-methylthiovinyl derivative was further oxidised into steroid 48.…”
Section: Methods For the Synthesis Of Aromatase Inhibitors Of The And...mentioning
confidence: 99%
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“…There are several examples of such facially selective addition of thiols to substituted sp 2 carbon atoms, including intramolecular conjugate addition in steroidal systems [3839] and intermolecular addition directed by substrate stereochemistry [4041] or a chiral auxiliary [4243]. Despite these examples, there are very few general procedures for the preparation of chiral tertiary thiols and thioethers by this method.…”
Section: Reviewmentioning
confidence: 99%