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Pregled bibliografske jedinice broj: 479386

6-Alkylquinolone-3-carboxylic acid tethered to macrolides synthesis and antimicrobial profile


Kapić, Samra; Čipčić Paljetak, Hana; Alihodžić, Sulejman; Antolović, Roberto; Eraković Haber, Vesna; Jarvest, Richard L.; Holmes, David J.; Broskey, John P.; Hunt, Eric
6-Alkylquinolone-3-carboxylic acid tethered to macrolides synthesis and antimicrobial profile // Bioorganic & medicinal chemistry, 18 (2010), 17; 6569-6577 doi:10.1016/j.bmc.2010.06.048 (međunarodna recenzija, članak, znanstveni)


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Naslov
6-Alkylquinolone-3-carboxylic acid tethered to macrolides synthesis and antimicrobial profile

Autori
Kapić, Samra ; Čipčić Paljetak, Hana ; Alihodžić, Sulejman ; Antolović, Roberto ; Eraković Haber, Vesna ; Jarvest, Richard L. ; Holmes, David J. ; Broskey, John P. ; Hunt, Eric

Izvornik
Bioorganic & medicinal chemistry (0968-0896) 18 (2010), 17; 6569-6577

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
tethered macrolides; 6-(x-carboxy)-alkyl-N(1)-ethyl-3- carboxylquinolones; aAntimicrobial activity; structure–activity relationship

Sažetak
Two series of clarithromycin and azithromycin derivatives with terminal 6-alkylquinolone-3-carboxylic unit with central ether bond in the linker were prepared and tested for antimicrobial activity. Quinolonelinker intermediates were prepared by Sonogashira-type C(6)-alkynylation of 6-iodo-quinolone precursors. In the last step, 400 site-selective acylation of 20-protected macrolides was completed with the EDC reagent, which selectively activated a terminal, aliphatic carboxylic group in dicarboxylic intermediates. Antimicrobial activity of the new series of macrolones is discussed. The most potent compound, 400-O-{; ; 6-[3-(3-carboxy-1-ethyl-4-oxo-1, 4-dihydroquinolin-6-yl)-propoxy]-hexanoyl}; ; -azithromycin (10), is highly active against bacterial respiratory pathogens resistant to macrolide antibiotics and represents a promising lead for further investigation.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Ustanove:
Fidelta d.o.o.

Citiraj ovu publikaciju

Kapić, Samra; Čipčić Paljetak, Hana; Alihodžić, Sulejman; Antolović, Roberto; Eraković Haber, Vesna; Jarvest, Richard L.; Holmes, David J.; Broskey, John P.; Hunt, Eric
6-Alkylquinolone-3-carboxylic acid tethered to macrolides synthesis and antimicrobial profile // Bioorganic & medicinal chemistry, 18 (2010), 17; 6569-6577 doi:10.1016/j.bmc.2010.06.048 (međunarodna recenzija, članak, znanstveni)
Kapić, S., Čipčić Paljetak, H., Alihodžić, S., Antolović, R., Eraković Haber, V., Jarvest, R., Holmes, D., Broskey, J. & Hunt, E. (2010) 6-Alkylquinolone-3-carboxylic acid tethered to macrolides synthesis and antimicrobial profile. Bioorganic & medicinal chemistry, 18 (17), 6569-6577 doi:10.1016/j.bmc.2010.06.048.
@article{article, year = {2010}, pages = {6569-6577}, DOI = {10.1016/j.bmc.2010.06.048}, keywords = {tethered macrolides, 6-(x-carboxy)-alkyl-N(1)-ethyl-3- carboxylquinolones, aAntimicrobial activity, structure–activity relationship}, journal = {Bioorganic and medicinal chemistry}, doi = {10.1016/j.bmc.2010.06.048}, volume = {18}, number = {17}, issn = {0968-0896}, title = {6-Alkylquinolone-3-carboxylic acid tethered to macrolides synthesis and antimicrobial profile}, keyword = {tethered macrolides, 6-(x-carboxy)-alkyl-N(1)-ethyl-3- carboxylquinolones, aAntimicrobial activity, structure–activity relationship} }
@article{article, year = {2010}, pages = {6569-6577}, DOI = {10.1016/j.bmc.2010.06.048}, keywords = {tethered macrolides, 6-(x-carboxy)-alkyl-N(1)-ethyl-3- carboxylquinolones, aAntimicrobial activity, structure–activity relationship}, journal = {Bioorganic and medicinal chemistry}, doi = {10.1016/j.bmc.2010.06.048}, volume = {18}, number = {17}, issn = {0968-0896}, title = {6-Alkylquinolone-3-carboxylic acid tethered to macrolides synthesis and antimicrobial profile}, keyword = {tethered macrolides, 6-(x-carboxy)-alkyl-N(1)-ethyl-3- carboxylquinolones, aAntimicrobial activity, structure–activity relationship} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


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