Pregled bibliografske jedinice broj: 581420
Novel Substituted Benzothiophene- and Thienothiophene-carboxanilides and quinolones : Synthesis, Photochemical Synthesis, DNA–binding Properties, Antitumor evaluation and 3D-derived QSAR analysis
Novel Substituted Benzothiophene- and Thienothiophene-carboxanilides and quinolones : Synthesis, Photochemical Synthesis, DNA–binding Properties, Antitumor evaluation and 3D-derived QSAR analysis // Journal of medicinal chemistry, 55 (2012), 11; 5044-5060 doi:10.1021/jm300505h (međunarodna recenzija, članak, znanstveni)
CROSBI ID: 581420 Za ispravke kontaktirajte CROSBI podršku putem web obrasca
Naslov
Novel Substituted Benzothiophene- and Thienothiophene-carboxanilides and quinolones : Synthesis, Photochemical Synthesis, DNA–binding Properties, Antitumor evaluation and 3D-derived QSAR analysis
Autori
Aleksić, Maja ; Bertoša, Branimir ; Nhili, Raja ; Uzelac, Lidija ; Jarak, Ivana ; Depauw, Sabine ; David-Cordonnier, Marie-Hélène ; Kralj, Marijeta ; Tomić, Sanja ; Karminski-Zamola, Grace
Izvornik
Journal of medicinal chemistry (0022-2623) 55
(2012), 11;
5044-5060
Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni
Ključne riječi
substituted benzothiophene-; thienothiophene-carboxanilides; quinolones; antitumor evluation; QSAR analysis; DNA-binding
Sažetak
A series of new N, N-dimethylaminopropyl- and 2-imidazolinyl-substituted derivatives of benzo[b]thienyl- and thieno[2, 3-b]thienyl-carboxanilides and benzo[b]thieno[2, 3-c]- and thieno[3’, 2’:4, 5]thieno[2, 3-c]quinolones were prepared. Quinolones were prepared by the reaction of photochemical dehydrohalogenation of corresponding anilides. Carboxanilides and quinolones were tested for the antiproliferative activity. 2-Imidazolinyl-substituted derivatives showed very prominent activity. Using the experimentally obtained antitumor measurements, 3D-derived QSAR analysis was performed for the set of compounds. Higly predicitive 3D-derived QSAR models were obtained and molecular properties that have the highest impact on antitumor activity were identified. Carboxanilides 6a-c and quinolones 9a-c and 11a were evaluated for DNA binding propensities and topoisomerases I and II inhibition as part of their mechanism of action assessment. The evaluated differences in the mode of action nicely correlate with the results of the 3D- QSAR analysis. Taken together the results indicate which modifications of the compounds from the series should further improve their anticancer properties.
Izvorni jezik
Engleski
Znanstvena područja
Kemija, Biologija, Temeljne medicinske znanosti
Napomena
Na radu su radili i suradnici u okviru bilateralne suradnje Hubert Curien između Hrvatske i Francuske institucije u okviru Cogito programa kao Egide project N°24765PH. M-H.D.-C.
POVEZANOST RADA
Projekti:
098-0982464-2514 - Uloga različitih mehanizama odgovora stanica na terapiju oštećenjem DNA (Kralj, Marijeta, MZOS ) ( CroRIS)
098-1191344-2860 - Proučavanje biomakromolekula računalnim metodama i razvoj novih algoritama (Tomić, Sanja, MZOS ) ( CroRIS)
125-0982464-1356 - Novi heterocikli kao antitumorski i antivirusni (pametni) lijekovi (Hranjec, Marijana, MZOS ) ( CroRIS)
Ustanove:
Institut "Ruđer Bošković", Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb
Profili:
Maja Cindrić (autor)
Ivana Jarak (autor)
Sanja Tomić (autor)
Lidija Uzelac (autor)
Branimir Bertoša (autor)
Grace Karminski-Zamola (autor)
Marijeta Kralj (autor)
Citiraj ovu publikaciju:
Časopis indeksira:
- Current Contents Connect (CCC)
- Web of Science Core Collection (WoSCC)
- Science Citation Index Expanded (SCI-EXP)
- SCI-EXP, SSCI i/ili A&HCI
- Scopus
- MEDLINE