Novel amidino substituted 2-phenylbenzothiazoles : Synthesis, antitumor evaluation in vitro and acute toxicity testing in vivo

Racané, Livio; Kralj, Marijeta; Šuman, Lidija; Stojković, Ranko; Tralić-Kulenović, Vesna; Karminski-Zamola, Grace

doi:10.1016/j.bmc.2009.12.054

Pregled bibliografske jedinice broj: 438258

Novel amidino substituted 2-phenylbenzothiazoles : Synthesis, antitumor evaluation in vitro and acute toxicity testing in vivo

Racané, Livio; Kralj, Marijeta; Šuman, Lidija; Stojković, Ranko; Tralić-Kulenović, Vesna; Karminski-Zamola, Grace

Novel amidino substituted 2-phenylbenzothiazoles : Synthesis, antitumor evaluation in vitro and acute toxicity testing in vivo // Bioorganic & medicinal chemistry, 18 (2010), 3; 1038-1044 doi:10.1016/j.bmc.2009.12.054 (međunarodna recenzija, članak, znanstveni)

CROSBI ID: 438258 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Novel amidino substituted 2-phenylbenzothiazoles : Synthesis, antitumor evaluation in vitro and acute toxicity testing in vivo

Autori
Racané, Livio ; Kralj, Marijeta ; Šuman, Lidija ; Stojković, Ranko ; Tralić-Kulenović, Vesna ; Karminski-Zamola, Grace

Izvornik
Bioorganic & medicinal chemistry (0968-0896) 18 (2010), 3; 1038-1044

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

Ključne riječi
nitro-amidino- ; amino-amidino- and diamidino-substituted

Sažetak
The efficient synthesis of new bis-substituted nitro-amidino, amino-amidino (10a, 10b - 13a, 13b) and previously prepared diamidino 2-phenyl-benzothiazoles (9a, 9b) is described. The compounds 11a and 11b were prepared by recently developed methodology of the key precursors in zwitterionic form 8a and 8b with 4-nitrobenzoylchloride in a very good yield (70 %). All compounds except diamidino-substituted 2-phenylbenzothiazole 9a show exceptionally prominent tumor cell-growth inhibitory activity and cytotoxicity, whereby the special selectivity of amino-amidine 2-phenylbenzothiazole 12a towards MCF-7 and H 460 cells makes this compound a prospective lead compound that should be further evaluated in animal models. All in vivo tested compounds (12a, 12b, 13a and 13b) are absorbed from mice gastrointestinal system. LD50 are between 67.33 and 696.2 mg/kg body weight (OECD/EPA toxicity categories 2-3).

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija, Temeljne medicinske znanosti

POVEZANOST RADA

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