2017
DOI: 10.1016/j.steroids.2017.05.006
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Synthesis of 16α-amino-pregnenolone derivatives via ionic liquid-catalyzed aza-Michael addition and their evaluation as C 17,20 -lyase inhibitors

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Cited by 11 publications
(13 citation statements)
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“…As part of our ongoing interest in using sustainable methods for the synthesis of steroid derivatives, our goal was the synthesis of 16‐substituted androstane and estrane derivatives including promising 17β‐HSD1 inhibitors mentioned above through a green approach, replacing traditionally used inorganic bases to a switchable polarity solvent mixture as catalyst and reaction medium.…”
Section: Introductionmentioning
confidence: 99%
“…As part of our ongoing interest in using sustainable methods for the synthesis of steroid derivatives, our goal was the synthesis of 16‐substituted androstane and estrane derivatives including promising 17β‐HSD1 inhibitors mentioned above through a green approach, replacing traditionally used inorganic bases to a switchable polarity solvent mixture as catalyst and reaction medium.…”
Section: Introductionmentioning
confidence: 99%
“…This clearly shows the catalytic activity of [HDBU][OAc] and the necessity of using a catalyst in these reactions. It should be mentioned that in contrast to the aza‐Michael reaction of steroids carried out in the same ionic liquid, [40] no hydrolysis of the ester functionality of substrate 1 was observed. Addition of other thiols ( 3 b‐3 d ) to 16‐dehydropregnenolone acetate ( 1 ) (entries 5, 7, 10) and reactions of 16‐dehydropregnenolone ( 2 ) (entries 4, 6, 9, 12) led to the corresponding thioether derivatives with similar results.…”
Section: Resultsmentioning
confidence: 83%
“…As a comparison, the application of other ILs such as 2hydroxyethylammonium formate [36] and [HDBU][Lac] (Lac: lactate) [40] was also considered. As our previous studies on ILcatalyzed reactions [28,40,[44][45][46] of steroidal substrates have shown that a temperature higher than 60 °C is necessary to dissolve the substrates in IL solvents, the use of imidazolium ILs, susceptible to decomposition and leading to side reactions in the presence of basic anions [37] was excluded.…”
Section: Thiol-michael Addition Reactionsmentioning
confidence: 99%
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“…[16][17][18][19][20][21][22] Notably, 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU)-based ILs has exhibited a high catalytic activity in the aza-Michael reactions compared to conventional catalysts and with imidazole-based ILs. 1,[23][24][25][26][27] However, the effective role of catalysis by DBU-based ILs has not been completely investigated and to know the catalytic model is very important for designing and developing ionic liquids with excellent catalytic properties.…”
Section: Introductionmentioning
confidence: 99%