ISSN:
0947-3440
Keywords:
Antibiotics
;
Soraphen
;
Macrolide antibiotics
;
Structure-activity relationship
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The present paper describes the chemical modification of the antifungal macrolide soraphen A1α (1) by selective removal of oxygen substituents in the south-east ring segment. In the course of this investigation two key derivatives were prepared: 4-demethyl-5-O-(4-methoxybenzyl)-4-episoraphen (6) and 3,5-dideoxy-4-oxosoraphen (22). 6 served as precursor for 4-demethoxysoraphen (19) and 4-demethoxy-5-deoxysoraphen (20). 22 was used for the deoxygenation in positions C-3, C-4 and C-5 and for the synthesis of 3,5-didesoxysoraphen (24) as well as 4-demethoxy-3,5-dideoxysoraphen (27). The comparison of the antifungicidal activity of these derivatives showed that the OH group in position C-3 is essential for the biological activity of the soraphens.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970135
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