Synthesis and activity of polyacetylene substituted 2-hydroxy acids, esters, and amides against microbes of clinical importance.
A series of novel polyacetylene substituted 2-hydroxy acids and derivatives were prepared and characterized. Alkylation of butane-2,3-diacetal (BDA) protected glycolic acid with iodoalkyl substituted polyacetylene compounds gave the corresponding diacetal protected polyacetylene substituted 2-hydroxy acids. Diacetal deprotection through acid mediated hydrolysis, transesterification or aminolysis afforded the 2-hydroxy-polyacetylenic acid, ester or amide derivatives. Twenty one of these novel compounds were tested against 10 microbes of clinical importance and several of them showed good antimicrobial activity, in particular against Pseudomonas aeruginosa.
Kyi
Stella
S
CSIRO, Molecular and Health Technologies, Clayton South, Vic. 3169, Australia.
Wongkattiya
Nalin
N
Warden
Andrew C
AC
O'Shea
Michael S
MS
Deighton
Margaret
M
Macreadie
Ian
I
Graichen
Florian H M
FH
D000577:Amides / Q000737:chemistry*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D004952:Esters; D006880:Hydroxy Acids / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D053279:Polyynes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D013329:Structure-Activity Relationship
D000577:Amides; D000935:Antifungal Agents; D004952:Esters; D006880:Hydroxy Acids; D053279:Polyynes