1239-31-2Relevant articles and documents
Elemental fluorine. Part 22. Fluorination of 3β-acetoxy-5α-androstan-17-one using fluorine and Selectfluor
Chambers, Richard D.,Nakano, Takashi,Parsons, Mandy,Sandford, Graham,Batsanov, Andrei S.,Howard, Judith A.K.
, p. 811 - 816 (2008)
Reactions of 3β-acetoxy-5α-androstan-17-one with elemental fluorine and Selectfluor are reported and give contrasting results. Fluorine gives a mixture of mono-fluorinated steroids in which fluorine atoms are attached to tertiary carbon sites whereas Selectfluor gives fluoro-steroid systems arising from electrophilic aliphatic substitution of the most sterically accessible secondary saturated positions. The identities of the fluoro-steroid products were determined by NMR analysis and X-ray crystallography.
Diastereoselective synthesis of C60/steroid conjugates
Ruiz, Alberto,Coro, Julieta,Almagro, Luis,Ruiz, Jose A.,Molero, Dolores,Maroto, Enrique E.,Filippone, Salvatore,Herranz, Maria Angeles,Martinez-Alvarez, Roberto,Sancho-Garcia, Juan Carlos,Di Meo, Florent,Suarez, Margarita,Martin, Nazario
, p. 2819 - 2826 (2013)
The design and synthesis of fullerene-steroid hybrids by using Prato's protocol has afforded new fullerene derivatives endowed with epiandrosterone, an important naturally occurring steroid hormone. Since the formation of the pyrrolidine ring resulting from the 1,3-dipolar cyloaddition reaction takes place with generation of a new stereogenic center on the C2 of the five-membered ring, the reaction proceeds with formation of a diastereomeric mixture [compounds 6 and 7 in 70:30 ratio, 8 and 9 in 26:74 ratio (HPLC)] in which the formation of the major diasteroisomers 6 and 9 is consistent with an electrophilic attack of [60]fullerene on the Re face of the azomethine ylide directed by the steroidic unit. The chiroptical properties of these conjugates reveal typical Cotton effects in CD spectra that have been used to assign the absolute configuration of the new fulleropyrrolidines. The electrochemical study of the new compounds reveals the presence of four quasi-reversible reduction waves which are cathodically shifted in comparison with the parent C 60, thus ascertaining the proposed structures.
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Steiger,Reichstein
, p. 546,550, 558 (1938)
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Ruzicka,Goldberg,Bruengger
, p. 1389,1392 (1934)
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Steroid–Fullerene Hybrids from Epiandrosterone: Synthesis, Characterization and Theoretical Study
Almagro, Luis,Hernández-Castillo, David,Ortiz, Orlando,Alonso, Dayana,Ruiz, Alberto,Coro, Julieta,Herranz, María ángeles,Molero, Dolores,Martínez-álvarez, Roberto,Suárez, Margarita,Martín, Nazario
, p. 4512 - 4522 (2018)
New hybrid fullerene–steroid derivatives were prepared by using the Bingel–Hirsch protocol, by treatment of [60]fullerene with malonates bearing the appropriate steroid moieties obtained, in turn, from the functionalization of epiandrosterone, an important naturally occurring steroid hormone. Monocycloadduct C60-steroid conjugates were obtained by functionalization of ring A or ring D of the steroid moiety. We have also described the multistep preparation of a [60]fullerene hybrid dumbbell endowed with two fullerene units connected through an epiandrosterone molecule by a cyclopropanation reaction. The new compounds have been spectroscopically characterized and their redox potentials, determined by cyclic voltammetry, reveal three reversible reduction waves for monocycloadducts (8, 9 and 11, 12), whereas dumbbell-type derivative 10 exhibits the best electron-accepting abilities of the Bingel-type fullerene–steroid series. Theoretical calculations at semiempirical (AM1) and single point B3LYP-D3/6-31G+(d,p) levels have predicted the most stable conformations for the hybrid compounds and allow explaining the observed regioselectivity in the cyclopropanation reaction with dimalonate 7 during the synthesis of the dumbbell derivative.
Development of Selective Steroid Inhibitors for the Glucose-6-phosphate Dehydrogenase from Trypanosoma cruzi
Fredo Naciuk, Fabrício,Do Nascimento Faria, Jéssica,Gonc?lves Eufrásio, Amanda,Torres Cordeiro, Artur,Bruder, Marjorie
supporting information, p. 1250 - 1256 (2020/07/27)
Chagas disease is a parasitic infection affecting millions of people across Latin America, imposing a dramatic socioeconomic burden. Despite the availability of drugs, nifurtimox and benznidazole, lack of efficacy and incidence of side-effects prompt the identification of novel, efficient, and affordable drug candidates. To address this issue, one strategy could be probing the susceptibility of Trypanosoma parasites toward NADP-dependent enzyme inhibitors. Recently, steroids of the androstane group have been described as highly potent but nonselective inhibitors of parasitic glucose-6-phosphate dehydrogenase (G6PDH). In order to promote selectivity, we have synthesized and evaluated 26 steroid derivatives of epiandrosterone in enzymatic assays, whereby 17 compounds were shown to display moderate to high selectivity for T. cruzi over the human G6PDH. In addition, three compounds were effective in killing intracellular T. cruzi forms infecting rat cardiomyocytes. Altogether, this study provides new SAR data around G6PDH and further supports this target for treating Chagas disease.
