caa a22 4500 445875704 CHVBK 20180317145527.0 cr unu---uuuuu 170323e20110901xx s 000 0 eng 10.1007/s10593-011-0832-y doi (NATIONALLICENCE)springer-10.1007/s10593-011-0832-y Synthesis and biological activity of alkylidene-substituted cephems and penams [Elektronische Daten] [I. Potorocina, M. Vorona, I. Shestakova, I. Domracheva, E. Liepinsh, G. Veinberg] The condensation of tert-butyl esters of 3-methyl-7-oxoceph-3-em-4-carboxylic and 6-oxopenicillanic acids with a series of 2-oxoalkylidene(triphenyl)phosphoranes gave tert-butyl esters of new cephalosporin and penicillin analogs with an alkylidene substituent in the β-lactam ring. Most of these products were oxidized by meta-chloroperbenzoic acid to the corresponding sulfones. The cephemes and penams synthesized including the oxidized products displayed high cytotoxicity relative to cancer cells in vitro. Some of the alkylidene-substituted cephems as the free acids, similar to Tazobactam, inhibit the catalytic activity of Enterobacter cloacae penicillinase. Springer Science+Business Media, Inc., 2011 tert -butyl esters of (6 Z )-alkylidene-1,1-dioxopenicillanic acids nationallicence tert -butyl esters of (7 Z )-alkylidene-3-methyl-1,1-dioxoceph-3-em-4-carboxylic acids nationallicence (6 Z )-(N-methyl-N-methoxycarbamoylmethylidene)-1,1-dioxopenicillanic acid nationallicence 3-methyl-(7 Z )-(N-methyl-N-methoxycarbamoylmethylidene)-1,1-dioxoceph-3-em-4-carboxylic acid nationallicence cyclic sulfones nationallicence condensation nationallicence oxidation by m -chloroperbenzoic acid nationallicence Potorocina I. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., LV-1006, Riga, Latvia aut Vorona M. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., LV-1006, Riga, Latvia aut Shestakova I. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., LV-1006, Riga, Latvia aut Domracheva I. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., LV-1006, Riga, Latvia aut Liepinsh E. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., LV-1006, Riga, Latvia aut Veinberg G. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., LV-1006, Riga, Latvia aut Chemistry of Heterocyclic Compounds Springer US; http://www.springer-ny.com 47/6(2011-09-01), 767-775 0009-3122 47:6<767 2011 47 10593 https://doi.org/10.1007/s10593-011-0832-y text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10593-011-0832-y text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Potorocina I. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., LV-1006, Riga, Latvia aut NATIONALLICENCE 700 1- Vorona M. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., LV-1006, Riga, Latvia aut NATIONALLICENCE 700 1- Shestakova I. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., LV-1006, Riga, Latvia aut NATIONALLICENCE 700 1- Domracheva I. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., LV-1006, Riga, Latvia aut NATIONALLICENCE 700 1- Liepinsh E. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., LV-1006, Riga, Latvia aut NATIONALLICENCE 700 1- Veinberg G. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., LV-1006, Riga, Latvia aut NATIONALLICENCE 773 0- Chemistry of Heterocyclic Compounds Springer US; http://www.springer-ny.com 47/6(2011-09-01), 767-775 0009-3122 47:6<767 2011 47 10593 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer