Synthesis and properties of macrolones characterized by two ether bonds in the linker

Jakopović, Ivana Palej; Kragol, Goran; Forrest, Andrew K.; Frydrych, Catherine S.V.; Štimac, Vlado; Kapić, Samra; Škugor, Maja Matanović; Ilijaš, Marina; Paljetak, Hana Čipčić; Jelić, Dubravko; Holmes, David; Hickey, Deirdre M. B.; Verbanac, Donatella; Haber, Vesna Eraković; Alihodžić, Sulejman

doi:10.1016/j.bmc.2010.07.007

Cited by 24 publications

(15 citation statements)

References 63 publications

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“…32 Interestingly, we have successfully applied Pd-catalyzed O-alkylation of complex macrocyclic alcohols by allyl-tert-butylcarbonate. 33,34 Diaryl ethers, 9,35 aryl alkyl ethers 36 and enol ethers 37 can be synthesized by means of a palladium-catalyzed Buchwald-Hartwig reaction. Broad application of this metal-catalyzed coupling reaction has mainly been achieved by developing ever more effective ligands for the catalytic complexes, starting from dinitrogen ligands to mono-and bidentate phosphines, and -donor alkenes, dba (dibenzylideneacetone) in particular.…”

Section: Overview Of Traditional and Less Known Methodsmentioning

confidence: 99%

Ethers from esters; from exceptional transformation to synthetic method

Jakopović¹,

Kapić²,

Alihodžić³

et al. 2015

Arkivoc

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Most ether-bond forming reactions based on traditional methods or modifications thereof require strongly acidic or basic conditions and often harsh reaction conditions. Reduction of esters to ethers has been regarded as an impracticable method, generally affording alcohols as the principal products. Only recently, original, mostly catalytic methods for reduction of esters to ethers have been reported, which proceed under mild conditions and are compatible with many functional groups present in the substrate ester molecule. These reactions are considered as a valuable alternative to traditional methods, and specific protocols have been reported. An account of the progress in this synthetic methodology is given.

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Section: Overview Of Traditional and Less Known Methodsmentioning

confidence: 99%

Ethers from esters; from exceptional transformation to synthetic method

Jakopović¹,

Kapić²,

Alihodžić³

et al. 2015

Arkivoc

Self Cite

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“…15 The 15-membered ring macrolide antibiotics-for example, azithromycin 16 -are an important series within the macrolide class of antibiotics, since they offer some advantages over 14-membered macrolides derived from erythromycin A. These advantages include better gastrointestinal tolerance, safety profile, and pharmacokinetics coupled with activity against Gramnegative pathogens.…”

Section: à14mentioning

confidence: 99%

Discovery of 4′′-Ether Linked Azithromycin-Quinolone Hybrid Series: Influence of the Central Linker on the Antibacterial Activity

Pavlović

Mutak

2011

ACS Med. Chem. Lett.

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A series of novel C-4′′-substituted azithromycins was synthesized and evaluated for in vitro antibacterial activity against a panel of representative erythromycin-susceptible and macrolide-lincosamide-streptogramin (MLS) resistant pathogens. In summary, azithromycin and quinolone substructures merged in a mutually SAR-compatible design gave rise to a new class of antimicrobials with an improved spectrum and potency over azithromycin. Prototypical analogues 7f and 8f display an improved potency versus azithromycin against Gram-positive and fastidious Gram-negative pathogens. In particular, these new leads maintain activity against MLS-resistant strains of Streptococcus pneumoniae and Streptococcus pyogenes. In addition, they represent an improvement over telithromycin (1) and cethromycin (2) against the fastidious Gram-negative pathogen Haemophilus influenzae.

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“…al, 2011a;Kapić et. al., 2011b;Marušić Ištuk et al, 2011;Matanović Škugor et al, 2010;Palej Jakopović et al, 2010;Pavlović et al, 2010;Pavlović & Mutak, 2011;Štimac et al, 2010).…”

Section: Introductionmentioning

confidence: 99%