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Abstract:

In this paper, we report the first synthesis of aromatic analogs of brassinosteroids. In order to accomplish this task, we explored two different synthetic approaches, which involved demethylation of the C-19 of stigmasterol to yield A-ring aromatic 3-hydroxystigmastanes. One of the new aromatic analogs showed a reduced but significant bioactivity when compared to the natural hormones. © 2012 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids
Autor:Acebedo, S.L.; Alonso, F.; Ramírez, J.A.; Galagovsky, L.R.
Filiación:Departamento de Química Orgánica, UMYMFOR (CONICET - Facultad de Ciencias Exactas y Naturales), Universidad de Buenos Aires, Pabellón 2, Piso 3, C1428EGA Buenos Aires, Argentina
Palabras clave:A-ring; Aromatic stigmastanes; Bioactivity; Brassinosteroids; 19 acetoxystigmasta 4,22 dien 3,6 dione; 19 nor 3,22,23 trihydroxystigmasta 1,3,5(10) triene 6 one; 19 norstigmasta 1(10),5,22 trien 3b ol; 19 norstigmasta 1,3,5(10) triene 3,22,23 triol; 19 norstigmasta 1,3,5(10),22 tetraen 3 ol; 3 hydroxystigmastane; 3beta acetoxy 19 norstigmasta 1(10),5,22 triene; 3beta acetoxy 5alpha bromo 6,19 epoxystigmast 22 ene; 3beta acetoxy 5alpha bromostigmast 22 en 6beta ol; 3beta acetoxy 5beta,6beta epoxystigmast 22 ene; 3beta acetoxystigmasta 5,22 dien 19 ol; 3beta,19 diacetoxystigmasta 5,22 diene; 9 acetoxystigmasta 5,22 dien 3beta ol; 9 nor 3 hydroxystigmasta 1,3,5(10),22 tetraen 6 one; aromatic compound; brassinosteroid; stigmasta 1,4,22 trien 3 one; stigmasta 3beta,22,23 triol (6 deoxo 28 homoteasterone); stigmasterol; unclassified drug; aromatization; article; demethylation; drug activity; hydrolysis; oxidation; priority journal; proton nuclear magnetic resonance; stereochemistry; synthesis
Año:2012
Volumen:68
Número:19
Página de inicio:3685
Página de fin:3691
DOI: http://dx.doi.org/10.1016/j.tet.2012.03.082
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
CODEN:TETRA
CAS:stigmasterol, 83-48-7
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v68_n19_p3685_Acebedo

Referencias:

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Citas:

---------- APA ----------
Acebedo, S.L., Alonso, F., Ramírez, J.A. & Galagovsky, L.R. (2012) . Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids. Tetrahedron, 68(19), 3685-3691.
http://dx.doi.org/10.1016/j.tet.2012.03.082
---------- CHICAGO ----------
Acebedo, S.L., Alonso, F., Ramírez, J.A., Galagovsky, L.R. "Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids" . Tetrahedron 68, no. 19 (2012) : 3685-3691.
http://dx.doi.org/10.1016/j.tet.2012.03.082
---------- MLA ----------
Acebedo, S.L., Alonso, F., Ramírez, J.A., Galagovsky, L.R. "Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids" . Tetrahedron, vol. 68, no. 19, 2012, pp. 3685-3691.
http://dx.doi.org/10.1016/j.tet.2012.03.082
---------- VANCOUVER ----------
Acebedo, S.L., Alonso, F., Ramírez, J.A., Galagovsky, L.R. Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids. Tetrahedron. 2012;68(19):3685-3691.
http://dx.doi.org/10.1016/j.tet.2012.03.082