Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs
Five new 28-homobrassinosteroids have been synthesized, namely, (22R,23R)-5-fluoro-3α,22,23-trihydroxy-5α-stigmastan-6-one, (22R,23R)-5-fluoro-3β,22,23-trihydroxy-5α-stigmastan-6-one, (22R,23R)-5-fluoro-2α,3α,22,23-tetrahydroxy-5α-stigmastan-6-one, (22R,23R)-3α,5,22,23-tetrahydroxy-5α-stigmastan-6-o...
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2000
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v56_n34_p6171_Ramirez http://hdl.handle.net/20.500.12110/paper_00404020_v56_n34_p6171_Ramirez |
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paper:paper_00404020_v56_n34_p6171_Ramirez2023-06-08T15:04:13Z Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs Ramirez, Javier Alberto Gros, Eduardo Gervasio Bioactivity Brassinosteroids C-5 fluorinated analogs C-5 hydroxylated analogs brassinolide brassinosteroid phytohormone article chemical structure hydrogen bond molecular model nonhuman nuclear magnetic resonance priority journal reaction analysis structure activity relation structure analysis synthesis Five new 28-homobrassinosteroids have been synthesized, namely, (22R,23R)-5-fluoro-3α,22,23-trihydroxy-5α-stigmastan-6-one, (22R,23R)-5-fluoro-3β,22,23-trihydroxy-5α-stigmastan-6-one, (22R,23R)-5-fluoro-2α,3α,22,23-tetrahydroxy-5α-stigmastan-6-one, (22R,23R)-3α,5,22,23-tetrahydroxy-5α-stigmastan-6-one and (22R,23R)-3β,5,22,23-tetrahydroxy-5α-stigmastan-6-one. Their bioactivities were evaluated by the rice lamina inclination test. C-5α Fluorinated analogs showed excellent in vitro bioactivity, also revealed at low doses, while C-5α hydroxylated analogs resulted in an important decrease in bioactivity. Previously given explanations to justify the decreasing effect due to C-5α electronegative groups should be revised. (C) 2000 Elsevier Science Ltd. Fil:Ramírez, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Gros, E.G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2000 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v56_n34_p6171_Ramirez http://hdl.handle.net/20.500.12110/paper_00404020_v56_n34_p6171_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 |
Bioactivity Brassinosteroids C-5 fluorinated analogs C-5 hydroxylated analogs brassinolide brassinosteroid phytohormone article chemical structure hydrogen bond molecular model nonhuman nuclear magnetic resonance priority journal reaction analysis structure activity relation structure analysis synthesis |
| spellingShingle |
Bioactivity Brassinosteroids C-5 fluorinated analogs C-5 hydroxylated analogs brassinolide brassinosteroid phytohormone article chemical structure hydrogen bond molecular model nonhuman nuclear magnetic resonance priority journal reaction analysis structure activity relation structure analysis synthesis Ramirez, Javier Alberto Gros, Eduardo Gervasio Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs |
| topic_facet |
Bioactivity Brassinosteroids C-5 fluorinated analogs C-5 hydroxylated analogs brassinolide brassinosteroid phytohormone article chemical structure hydrogen bond molecular model nonhuman nuclear magnetic resonance priority journal reaction analysis structure activity relation structure analysis synthesis |
| description |
Five new 28-homobrassinosteroids have been synthesized, namely, (22R,23R)-5-fluoro-3α,22,23-trihydroxy-5α-stigmastan-6-one, (22R,23R)-5-fluoro-3β,22,23-trihydroxy-5α-stigmastan-6-one, (22R,23R)-5-fluoro-2α,3α,22,23-tetrahydroxy-5α-stigmastan-6-one, (22R,23R)-3α,5,22,23-tetrahydroxy-5α-stigmastan-6-one and (22R,23R)-3β,5,22,23-tetrahydroxy-5α-stigmastan-6-one. Their bioactivities were evaluated by the rice lamina inclination test. C-5α Fluorinated analogs showed excellent in vitro bioactivity, also revealed at low doses, while C-5α hydroxylated analogs resulted in an important decrease in bioactivity. Previously given explanations to justify the decreasing effect due to C-5α electronegative groups should be revised. (C) 2000 Elsevier Science Ltd. |
| author |
Ramirez, Javier Alberto Gros, Eduardo Gervasio |
| author_facet |
Ramirez, Javier Alberto Gros, Eduardo Gervasio |
| author_sort |
Ramirez, Javier Alberto |
| title |
Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs |
| title_short |
Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs |
| title_full |
Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs |
| title_fullStr |
Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs |
| title_full_unstemmed |
Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs |
| title_sort |
effects on bioactivity due to c-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs |
| publishDate |
2000 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v56_n34_p6171_Ramirez http://hdl.handle.net/20.500.12110/paper_00404020_v56_n34_p6171_Ramirez |
| work_keys_str_mv |
AT ramirezjavieralberto effectsonbioactivityduetoc5heteroatomsubstituentsonsynthetic28homobrassinosteroidanalogs AT groseduardogervasio effectsonbioactivityduetoc5heteroatomsubstituentsonsynthetic28homobrassinosteroidanalogs |
| _version_ |
1768542637671841792 |