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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Detalles Bibliográficos
Autores principales: Ramírez, J.A., Gros, E.G., Galagovsky, L.R.
Formato: JOUR
Materias:
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
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00404020_v56_n34_p6171_Ramirez
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
Descripción
Sumario: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.

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