Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs

被引：31
|
作者：
Ramírez, JA [1 ]
Gros, EG [1 ]
Galagovsky, LR [1 ]
机构：
[1] Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, RA-1428 Buenos Aires, DF, Argentina
来源：
TETRAHEDRON | 2000年 / 56卷 / 34期
关键词：
brassinosteroids; bioactivity; C-5 fluorinated analogs; C-5 hydroxylated analogs;
D O I：
10.1016/S0040-4020(00)00582-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Five new 28-humobrassinosteroids have been synthesized, namely, (22R,23R)-5-fluoro-3 alpha,22,23-trihydroxy-5 alpha-stigmastan-6-one, (22R,23R)-5-fluoro-3 beta,22,23-trihydroxy-5 alpha-stigmastan-6-one (22R,23 R)-5-fluoro-2 alpha,3 alpha,22, 23-tetrahydroxy-5 alpha-stigmastan-6-one, (22R,23R)-3 alpha,5,21,23-tetrahydroxy-5 alpha-stigmastan-6-one and (22R,23R)-3 beta,5,22,23-tetrahydroxy-5 alpha-stigmastan-6-one. Their bioactivities were evaluated by the rice lamina inclination test. C-5 alpha Fluorinated analogs showed excellent in vitro bioactivity, also revealed at low doses, while C-5 alpha hydroxylated analogs resulted in an important decrease in bioactivity. Previously given explanations to justify the decreasing effect due to C-5 alpha electronegative groups should be revised. (C) 2000 Elsevier Science Ltd. All rights reserved.
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页码：6171 / 6180
页数：10
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