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Insights on the Chemical Behavior of Ethyl Cyanoformate: Dipolarophile, Cyano or Ethoxycarbonyl Source
Author(s) -
Dascălu AncaElena,
Bîcu Elena,
Shova Segiu,
Lipka Emmanuelle,
Rigo Benoît,
Billamboz Muriel,
Ghinet Alina
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201903114
Subject(s) - candida albicans , cryptococcus neoformans , microbiology and biotechnology , acinetobacter baumannii , chemistry , staphylococcus aureus , pyridinium , cycloaddition , klebsiella pneumoniae , escherichia coli , bacteria , biology , pseudomonas aeruginosa , organic chemistry , biochemistry , genetics , gene , catalysis
Imidazo[1,2‐ a ]pyridines (azaindolizines) 1a‐k have been designed and easily synthesized by the [3+2] cycloaddition reaction between cycloimmonium salts and ethyl cyanoformate used as dipolarophile. The behavior of the latter in cycloaddition reactions has been studied using different pyridinium, ( iso )quinolinium or benzimidazolium salts and demonstrated the substrate‐dependent reactivity, and the observation in many cases of its reaction as a cyano or an ethoxycarbonyl donor reagent. New chemical platforms have been identified thanks to the different reactivity of ethyl cyanoformate. Final molecules were subjected to a biological evaluation on ESKAPE pathogens (five bacteria: Escherichia coli , Klebsiella pneumoniae (MDR), Acinetobacter baumannii , Pseudomonas aeruginosa , Staphylococcus aureus (MRSA) and two fungi: Cryptococcus neoformans (H99) and Candida albicans ). Azaindolizines 1b and 1e displayed antifungal activity on Candida albicans and ylide 11 inhibited both fungi Candida albicans and Cryptococcus neoformans . These results open the way for the development of analogues with improved antifungal activity.