Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids
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 ana...
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2012
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paper:paper_00404020_v68_n19_p3685_Acebedo2023-06-08T15:04:19Z Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids Acebedo, Sofìa Lorena Ramirez, Javier Alberto 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 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. Fil:Acebedo, S.L. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ramírez, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2012 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v68_n19_p3685_Acebedo http://hdl.handle.net/20.500.12110/paper_00404020_v68_n19_p3685_Acebedo |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 Acebedo, Sofìa Lorena Ramirez, Javier Alberto Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids |
| topic_facet |
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 |
| description |
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. |
| author |
Acebedo, Sofìa Lorena Ramirez, Javier Alberto |
| author_facet |
Acebedo, Sofìa Lorena Ramirez, Javier Alberto |
| author_sort |
Acebedo, Sofìa Lorena |
| title |
Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids |
| title_short |
Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids |
| title_full |
Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids |
| title_fullStr |
Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids |
| title_full_unstemmed |
Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids |
| title_sort |
synthesis of aromatic stigmastanes: application to the synthesis of aromatic analogs of brassinosteroids |
| publishDate |
2012 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v68_n19_p3685_Acebedo http://hdl.handle.net/20.500.12110/paper_00404020_v68_n19_p3685_Acebedo |
| work_keys_str_mv |
AT acebedosofialorena synthesisofaromaticstigmastanesapplicationtothesynthesisofaromaticanalogsofbrassinosteroids AT ramirezjavieralberto synthesisofaromaticstigmastanesapplicationtothesynthesisofaromaticanalogsofbrassinosteroids |
| _version_ |
1768546200805441536 |