Syntheses of immunomodulating androstanes and stigmastanes: Comparison of their TNF-α inhibitory activity
In a previous work our group showed that some synthetic stigmastanes may play a role in immune-mediated inflammation. In this paper we report the syntheses of a series of new steroidal compounds derived from dehydroepiandrosterone and stigmasterol, and the evaluation of their in vitro inhibitory act...
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2007
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v15_n24_p7538_Ramirez http://hdl.handle.net/20.500.12110/paper_09680896_v15_n24_p7538_Ramirez |
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paper:paper_09680896_v15_n24_p7538_Ramirez2023-06-08T15:58:50Z Syntheses of immunomodulating androstanes and stigmastanes: Comparison of their TNF-α inhibitory activity Ramirez, Javier Alberto Bruttomesso, Andrea Claudia Michelini, Flavia Mariana Acebedo, Sofìa Lorena Alche, Laura Edith Androstane DHEA Immune regulation Steroids Stigmastane Tumor necrosis factor-α 3beta bromo 5 hydroxy 5alpha androstane 6,17 dione 3beta bromo 5 hydroxy dextro homo 17alpha oxa 5alpha androstane 6,17 dione 3beta bromo 5alpha,6alpha epoxy dextro homo 17alpha oxaandrostan 17 one 3beta bromo 5alpha,6alpha epoxyandrostan 17 one 3beta bromostigmast 5 ene 22,23 diol 3beta chlorostigmast 5 ene 22,23 diol 3beta fluoro 5 hydroxy 5alpha stigmast 22 en 6 one 3beta fluoro 5,22,23 trihydroxy 5alpha stigmastan 6 one 3beta fluorostigmast 5 ene 22,23 diol 3beta,5 dihydroxy 5alpha androstane 6,17 dione androstane derivative prasterone steroid stigmast 5 ene 3beta,22,23 triol stigmasterol tumor necrosis factor alpha unclassified drug animal cell article controlled study drug activity drug inhibition in vitro study macrophage nonhuman structure activity relation Androstanes Animals Cell Line Cholestanes Dehydroepiandrosterone Drug Evaluation, Preclinical Immunologic Factors Mice Molecular Structure Stigmasterol Structure-Activity Relationship Tumor Necrosis Factor-alpha In a previous work our group showed that some synthetic stigmastanes may play a role in immune-mediated inflammation. In this paper we report the syntheses of a series of new steroidal compounds derived from dehydroepiandrosterone and stigmasterol, and the evaluation of their in vitro inhibitory activity of the TNF-α production by macrophages. A preliminary qualitative structure-activity relationship was established. © 2007 Elsevier Ltd. All rights reserved. Fil:Ramírez, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Bruttomesso, A.C. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Michelini, F.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Acebedo, S.L. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Alché, L.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2007 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v15_n24_p7538_Ramirez http://hdl.handle.net/20.500.12110/paper_09680896_v15_n24_p7538_Ramirez |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Androstane DHEA Immune regulation Steroids Stigmastane Tumor necrosis factor-α 3beta bromo 5 hydroxy 5alpha androstane 6,17 dione 3beta bromo 5 hydroxy dextro homo 17alpha oxa 5alpha androstane 6,17 dione 3beta bromo 5alpha,6alpha epoxy dextro homo 17alpha oxaandrostan 17 one 3beta bromo 5alpha,6alpha epoxyandrostan 17 one 3beta bromostigmast 5 ene 22,23 diol 3beta chlorostigmast 5 ene 22,23 diol 3beta fluoro 5 hydroxy 5alpha stigmast 22 en 6 one 3beta fluoro 5,22,23 trihydroxy 5alpha stigmastan 6 one 3beta fluorostigmast 5 ene 22,23 diol 3beta,5 dihydroxy 5alpha androstane 6,17 dione androstane derivative prasterone steroid stigmast 5 ene 3beta,22,23 triol stigmasterol tumor necrosis factor alpha unclassified drug animal cell article controlled study drug activity drug inhibition in vitro study macrophage nonhuman structure activity relation Androstanes Animals Cell Line Cholestanes Dehydroepiandrosterone Drug Evaluation, Preclinical Immunologic Factors Mice Molecular Structure Stigmasterol Structure-Activity Relationship Tumor Necrosis Factor-alpha |
| spellingShingle |
Androstane DHEA Immune regulation Steroids Stigmastane Tumor necrosis factor-α 3beta bromo 5 hydroxy 5alpha androstane 6,17 dione 3beta bromo 5 hydroxy dextro homo 17alpha oxa 5alpha androstane 6,17 dione 3beta bromo 5alpha,6alpha epoxy dextro homo 17alpha oxaandrostan 17 one 3beta bromo 5alpha,6alpha epoxyandrostan 17 one 3beta bromostigmast 5 ene 22,23 diol 3beta chlorostigmast 5 ene 22,23 diol 3beta fluoro 5 hydroxy 5alpha stigmast 22 en 6 one 3beta fluoro 5,22,23 trihydroxy 5alpha stigmastan 6 one 3beta fluorostigmast 5 ene 22,23 diol 3beta,5 dihydroxy 5alpha androstane 6,17 dione androstane derivative prasterone steroid stigmast 5 ene 3beta,22,23 triol stigmasterol tumor necrosis factor alpha unclassified drug animal cell article controlled study drug activity drug inhibition in vitro study macrophage nonhuman structure activity relation Androstanes Animals Cell Line Cholestanes Dehydroepiandrosterone Drug Evaluation, Preclinical Immunologic Factors Mice Molecular Structure Stigmasterol Structure-Activity Relationship Tumor Necrosis Factor-alpha Ramirez, Javier Alberto Bruttomesso, Andrea Claudia Michelini, Flavia Mariana Acebedo, Sofìa Lorena Alche, Laura Edith Syntheses of immunomodulating androstanes and stigmastanes: Comparison of their TNF-α inhibitory activity |
| topic_facet |
Androstane DHEA Immune regulation Steroids Stigmastane Tumor necrosis factor-α 3beta bromo 5 hydroxy 5alpha androstane 6,17 dione 3beta bromo 5 hydroxy dextro homo 17alpha oxa 5alpha androstane 6,17 dione 3beta bromo 5alpha,6alpha epoxy dextro homo 17alpha oxaandrostan 17 one 3beta bromo 5alpha,6alpha epoxyandrostan 17 one 3beta bromostigmast 5 ene 22,23 diol 3beta chlorostigmast 5 ene 22,23 diol 3beta fluoro 5 hydroxy 5alpha stigmast 22 en 6 one 3beta fluoro 5,22,23 trihydroxy 5alpha stigmastan 6 one 3beta fluorostigmast 5 ene 22,23 diol 3beta,5 dihydroxy 5alpha androstane 6,17 dione androstane derivative prasterone steroid stigmast 5 ene 3beta,22,23 triol stigmasterol tumor necrosis factor alpha unclassified drug animal cell article controlled study drug activity drug inhibition in vitro study macrophage nonhuman structure activity relation Androstanes Animals Cell Line Cholestanes Dehydroepiandrosterone Drug Evaluation, Preclinical Immunologic Factors Mice Molecular Structure Stigmasterol Structure-Activity Relationship Tumor Necrosis Factor-alpha |
| description |
In a previous work our group showed that some synthetic stigmastanes may play a role in immune-mediated inflammation. In this paper we report the syntheses of a series of new steroidal compounds derived from dehydroepiandrosterone and stigmasterol, and the evaluation of their in vitro inhibitory activity of the TNF-α production by macrophages. A preliminary qualitative structure-activity relationship was established. © 2007 Elsevier Ltd. All rights reserved. |
| author |
Ramirez, Javier Alberto Bruttomesso, Andrea Claudia Michelini, Flavia Mariana Acebedo, Sofìa Lorena Alche, Laura Edith |
| author_facet |
Ramirez, Javier Alberto Bruttomesso, Andrea Claudia Michelini, Flavia Mariana Acebedo, Sofìa Lorena Alche, Laura Edith |
| author_sort |
Ramirez, Javier Alberto |
| title |
Syntheses of immunomodulating androstanes and stigmastanes: Comparison of their TNF-α inhibitory activity |
| title_short |
Syntheses of immunomodulating androstanes and stigmastanes: Comparison of their TNF-α inhibitory activity |
| title_full |
Syntheses of immunomodulating androstanes and stigmastanes: Comparison of their TNF-α inhibitory activity |
| title_fullStr |
Syntheses of immunomodulating androstanes and stigmastanes: Comparison of their TNF-α inhibitory activity |
| title_full_unstemmed |
Syntheses of immunomodulating androstanes and stigmastanes: Comparison of their TNF-α inhibitory activity |
| title_sort |
syntheses of immunomodulating androstanes and stigmastanes: comparison of their tnf-α inhibitory activity |
| publishDate |
2007 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v15_n24_p7538_Ramirez http://hdl.handle.net/20.500.12110/paper_09680896_v15_n24_p7538_Ramirez |
| work_keys_str_mv |
AT ramirezjavieralberto synthesesofimmunomodulatingandrostanesandstigmastanescomparisonoftheirtnfainhibitoryactivity AT bruttomessoandreaclaudia synthesesofimmunomodulatingandrostanesandstigmastanescomparisonoftheirtnfainhibitoryactivity AT micheliniflaviamariana synthesesofimmunomodulatingandrostanesandstigmastanescomparisonoftheirtnfainhibitoryactivity AT acebedosofialorena synthesesofimmunomodulatingandrostanesandstigmastanescomparisonoftheirtnfainhibitoryactivity AT alchelauraedith synthesesofimmunomodulatingandrostanesandstigmastanescomparisonoftheirtnfainhibitoryactivity |
| _version_ |
1768546031803301888 |