35950-55-1Relevant academic research and scientific papers
Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity
Scholz, Therese,Heyl, Carina L.,Bernardi, Dan,Zimmermann, Stefan,Kattner, Lars,Klein, Christian D.
, p. 795 - 804 (2013)
A di-bromo substituted nitrovinylfuran with reported broad-spectrum antibacterial activity was found to be a potent inhibitor of MurA, a key enzyme in peptidoglycan biosynthesis. Further characterization of the compound was carried out to assess its reactivity towards thiol nucleophiles, its stability and degradation under aqueous conditions, inhibitory potential at other enzymes, and antibacterial and cytotoxic activity. Our results indicate that the nitrovinylfuran derivative is reactive towards cysteine residues in proteins, as demonstrated by the irreversible inhibition of MurA and bacterial methionine aminopeptidase. Experiments with proteins and model thiols indicate that the compound forms covalent adducts with SH groups and induces intermolecular disulfide bonds, with the intermediate formation of a monobromide derivative. The parent molecule as well as most of its breakdown products are potent antibiotics with MIC values below 4 μg/mL and are active against multiresistant strains such as methicillin-resistant Staphylococcus aureus (MRSA). Further development of the bromonitrovinyl scaffold towards antibiotics with clinical relevance, however, requires optimization of the antibiotic-cytotoxic selectivity profile.
Synthesis of 2-(2-arylethenyl)-5-arylfurans by regioselective palladium(0)-catalyzed coupling reactions of 2-(2-bromo-2-nitroethenyl)-5- bromofuran
Tuan, Dang Thanh,Tung, Dang Thanh,Langer, Peter
, p. 2812 - 2814 (2006)
The Suzuki reaction of 2-(2-bromo-2-nitroethenyl)-5-bromofuran, readily available from furfural, resulted in regioselective attack onto the furan moiety. The alkenyl moiety could be functionalized in a second Suzuki reaction. Georg Thieme Verlag Stuttgart.
Furan-containing gem-bromonitroethenes: Synthesis and reaction with morpholine
Eliseenko,Makarenko,Berestovitskaya
, p. 1424 - 1430 (2015)
The first time the representative of furan-containing gem-bromonitroethenes 5-nitro-2-(2-bromo-2-nitro-ethenyl)furan was synthesized by bromination of 5-nitro-2-(2-nitroethenyl)furan followed by dehydrohalogenation of the dibromide. Morpholine adducts of the synthesized β-substituted gem-bromonitroethene and its analog with a 5-bromo-2-furyl substituent were obtained. The structures of the gem-bromonitroethenes and aza adducts were characterized by spectral methods (IR, UV, 1H, and 13C-{1H} NMR, including 1H-13C HMQC and HMBC).
An improved, fully heterogeneous, diastereoselective synthesis of (Z)-α-bromonitroalkenes
Ballini, Roberto,Gabrielli, Serena,Palmieri, Alessandro
, p. 114 - 116,3 (2013/02/23)
α-Bromonitroalkenes are both key starting materials for the preparation of complex structures and possess antimicrobial activity. In this context, we disclose a simple, fully heterogeneous synthetic approach for their preparation in good overall yields. Georg Thieme Verlag Stuttgart · New York.
