Synthesis and bioactivity of C-29 brassinosteroid analogues with different functional groups at C-6
In this paper, we report the synthesis and bioactivity of four synthetic analogues of 28-homobrassinosteroids, in order to evaluate the influence in bioactivity when the C-6 keto group is replaced by different functional groups. The synthetic analogues are 6-deoxo-28-homocastasterone [(22R,23R)-stig...
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todo:paper_00319422_v66_n5_p581_Ramirez2023-10-03T14:44:27Z Synthesis and bioactivity of C-29 brassinosteroid analogues with different functional groups at C-6 Ramírez, J.A. Brosa, C. Galagovsky, L.R. Bioactivity Brassinosteroids Gramineae Oryza sativa Synthesis of fluorinated analogues 6 deoxo 28 homocastasterone stigmasta 2alpha,3alpha,22,23 tetraol 6alpha fluorostigmasta 2alpha,3alpha,22,23 tetraol 6alpha hydroxy 28 homocastasterone stigmasta 2alpha,3alpha,6alpha,22,23 pentaol 6beta hydroxy 28 homocastasterone stigmasta 2alpha,3alpha,6beta,22,23 pentaol brassinosteroid functional group hexamethonium bromide hydroxyl group phytohormone unclassified drug article drug activity hormone action Poaceae rice synthesis synthesis Oryza sativa Poaceae In this paper, we report the synthesis and bioactivity of four synthetic analogues of 28-homobrassinosteroids, in order to evaluate the influence in bioactivity when the C-6 keto group is replaced by different functional groups. The synthetic analogues are 6-deoxo-28-homocastasterone [(22R,23R)-stigmasta- 2α,3α,22,23-tetraol], 6α-hydroxy-28-homocastasterone [(22R,23R)-stigmasta-2α,3α,6α,22,23-pentaol], 6β-hydroxy-28-homocastasterone [(22R,23R)-stigmasta-2α,3α, 6β,22,23-pentaol], and [(22R,23R)-6α-fluorostigmasta-2α, 3α,22,23-tetraol]. Results indicate that replacement of the 6-keto moiety by an β or α hydroxyl group led to a decrease in activity, whereas the 6-deoxo analogue showed a very low activity, confirming the importance of an electronegative moiety at C-6 to observe hormonal potency. The 6α-fluorinated analogue elicited a low activity, similar to that of the 6-deoxo analogue. © 2005 Elsevier Ltd. All rights reserved. Fil:Ramírez, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00319422_v66_n5_p581_Ramirez |
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Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Bioactivity Brassinosteroids Gramineae Oryza sativa Synthesis of fluorinated analogues 6 deoxo 28 homocastasterone stigmasta 2alpha,3alpha,22,23 tetraol 6alpha fluorostigmasta 2alpha,3alpha,22,23 tetraol 6alpha hydroxy 28 homocastasterone stigmasta 2alpha,3alpha,6alpha,22,23 pentaol 6beta hydroxy 28 homocastasterone stigmasta 2alpha,3alpha,6beta,22,23 pentaol brassinosteroid functional group hexamethonium bromide hydroxyl group phytohormone unclassified drug article drug activity hormone action Poaceae rice synthesis synthesis Oryza sativa Poaceae |
| spellingShingle |
Bioactivity Brassinosteroids Gramineae Oryza sativa Synthesis of fluorinated analogues 6 deoxo 28 homocastasterone stigmasta 2alpha,3alpha,22,23 tetraol 6alpha fluorostigmasta 2alpha,3alpha,22,23 tetraol 6alpha hydroxy 28 homocastasterone stigmasta 2alpha,3alpha,6alpha,22,23 pentaol 6beta hydroxy 28 homocastasterone stigmasta 2alpha,3alpha,6beta,22,23 pentaol brassinosteroid functional group hexamethonium bromide hydroxyl group phytohormone unclassified drug article drug activity hormone action Poaceae rice synthesis synthesis Oryza sativa Poaceae Ramírez, J.A. Brosa, C. Galagovsky, L.R. Synthesis and bioactivity of C-29 brassinosteroid analogues with different functional groups at C-6 |
| topic_facet |
Bioactivity Brassinosteroids Gramineae Oryza sativa Synthesis of fluorinated analogues 6 deoxo 28 homocastasterone stigmasta 2alpha,3alpha,22,23 tetraol 6alpha fluorostigmasta 2alpha,3alpha,22,23 tetraol 6alpha hydroxy 28 homocastasterone stigmasta 2alpha,3alpha,6alpha,22,23 pentaol 6beta hydroxy 28 homocastasterone stigmasta 2alpha,3alpha,6beta,22,23 pentaol brassinosteroid functional group hexamethonium bromide hydroxyl group phytohormone unclassified drug article drug activity hormone action Poaceae rice synthesis synthesis Oryza sativa Poaceae |
| description |
In this paper, we report the synthesis and bioactivity of four synthetic analogues of 28-homobrassinosteroids, in order to evaluate the influence in bioactivity when the C-6 keto group is replaced by different functional groups. The synthetic analogues are 6-deoxo-28-homocastasterone [(22R,23R)-stigmasta- 2α,3α,22,23-tetraol], 6α-hydroxy-28-homocastasterone [(22R,23R)-stigmasta-2α,3α,6α,22,23-pentaol], 6β-hydroxy-28-homocastasterone [(22R,23R)-stigmasta-2α,3α, 6β,22,23-pentaol], and [(22R,23R)-6α-fluorostigmasta-2α, 3α,22,23-tetraol]. Results indicate that replacement of the 6-keto moiety by an β or α hydroxyl group led to a decrease in activity, whereas the 6-deoxo analogue showed a very low activity, confirming the importance of an electronegative moiety at C-6 to observe hormonal potency. The 6α-fluorinated analogue elicited a low activity, similar to that of the 6-deoxo analogue. © 2005 Elsevier Ltd. All rights reserved. |
| format |
JOUR |
| author |
Ramírez, J.A. Brosa, C. Galagovsky, L.R. |
| author_facet |
Ramírez, J.A. Brosa, C. Galagovsky, L.R. |
| author_sort |
Ramírez, J.A. |
| title |
Synthesis and bioactivity of C-29 brassinosteroid analogues with different functional groups at C-6 |
| title_short |
Synthesis and bioactivity of C-29 brassinosteroid analogues with different functional groups at C-6 |
| title_full |
Synthesis and bioactivity of C-29 brassinosteroid analogues with different functional groups at C-6 |
| title_fullStr |
Synthesis and bioactivity of C-29 brassinosteroid analogues with different functional groups at C-6 |
| title_full_unstemmed |
Synthesis and bioactivity of C-29 brassinosteroid analogues with different functional groups at C-6 |
| title_sort |
synthesis and bioactivity of c-29 brassinosteroid analogues with different functional groups at c-6 |
| url |
http://hdl.handle.net/20.500.12110/paper_00319422_v66_n5_p581_Ramirez |
| work_keys_str_mv |
AT ramirezja synthesisandbioactivityofc29brassinosteroidanalogueswithdifferentfunctionalgroupsatc6 AT brosac synthesisandbioactivityofc29brassinosteroidanalogueswithdifferentfunctionalgroupsatc6 AT galagovskylr synthesisandbioactivityofc29brassinosteroidanalogueswithdifferentfunctionalgroupsatc6 |
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