title: Synthesis and antimicrobial activity of novel structural hybrids of benzofuroxan and benzothiazole derivatives.
abstract: New compounds containing both benzofuroxan and benzothiazole scaffolds were synthesized through electrophile/nucleophile combination of nitrobenzofuroxan derivatives and 2-mercapto- or 2-aminobenzothiazole derivatives and their biological effect on the natural strain Vibrio genus and different bacterial lux-biosensors was studied. Among all the compounds synthesized, that obtained from 2-mercaptobenzothiazole and 7-chloro-4,6-dinitrobenzofuroxan was toxic for bacterial cells, and also able to activated the 1st type Quorum Sensing system. The reaction between 7-chloro-4,6-dinitrobenzofuroxan and 2-aminobenzothiazole derivatives gave two products, one bearing the benzofuroxan moiety linked to the exocyclic amino nitrogen, and the second derived from the attack of two molecules of electrophile to both the nitrogen atoms of the benzothiazole reagent. Their relative ratio is modifiable by tuning the reagents ratio and the reaction time.
authors.affiliation: A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov st. 8, Kazan, Tatarstan 420088 Russia. Electronic address: chugunova.e.a@gmail.com.
authors.forename: Elena
authors.initials: E
authors.lastname: Chugunova
authors.affiliation: Department of Industrial Chemistry "Toso Montanari", Alma Mater Studiorum-University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy. Electronic address: carla.boga@unibo.it.
authors.forename: Carla
authors.initials: C
authors.lastname: Boga
authors.affiliation: The Research Institute of Biology, Southern Federal University (SFedU), 194/1 Stachki Ave., 344090 Rostov-on-Don, Russia.
authors.forename: Ivan
authors.initials: I
authors.lastname: Sazykin
authors.affiliation: Department of Industrial Chemistry "Toso Montanari", Alma Mater Studiorum-University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy.
authors.forename: Silvia
authors.initials: S
authors.lastname: Cino
authors.affiliation: Department of Industrial Chemistry "Toso Montanari", Alma Mater Studiorum-University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy.
authors.forename: Gabriele
authors.initials: G
authors.lastname: Micheletti
authors.affiliation: Department of Industrial Chemistry "Toso Montanari", Alma Mater Studiorum-University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy.
authors.forename: Andrea
authors.initials: A
authors.lastname: Mazzanti
authors.affiliation: The Research Institute of Biology, Southern Federal University (SFedU), 194/1 Stachki Ave., 344090 Rostov-on-Don, Russia.
authors.forename: Marina
authors.initials: M
authors.lastname: Sazykina
authors.affiliation: A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov st. 8, Kazan, Tatarstan 420088 Russia.
authors.forename: Alexander
authors.initials: A
authors.lastname: Burilov
authors.affiliation: The Research Institute of Biology, Southern Federal University (SFedU), 194/1 Stachki Ave., 344090 Rostov-on-Don, Russia.
authors.forename: Ludmila
authors.initials: L
authors.lastname: Khmelevtsova
authors.affiliation: The Research Institute of Biology, Southern Federal University (SFedU), 194/1 Stachki Ave., 344090 Rostov-on-Don, Russia.
authors.forename: Natalia
authors.initials: N
authors.lastname: Kostina
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001583:Benzoxazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D060326:Chemistry Techniques, Synthetic; D004926:Escherichia coli / Q000187:drug effects / Q000235:genetics; D005798:Genes, Bacterial / Q000235:genetics; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship; D014733:Vibrio / Q000187:drug effects / Q000235:genetics; D010069:Oxadiazoles
chemical_list: D000900:Anti-Bacterial Agents; D052160:Benzothiazoles; D001583:Benzoxazoles; C014354:benzofuroxan; D010069:Oxadiazoles; C005465:benzothiazole
keywords: Ambident nitrogen reactivity; Benzofuroxan; Benzothiazole; Lux-biosensors