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Novel Cyano- and Amidino- Benzothiazole Derivatives: Synthesis, Antitumor Evaluation, X-ray and QSAR Analysis


Ćaleta, Irena; Kralj, Marijeta; Marjanović, Marko; Bertoša, Branimir; Tomić, Sanja; Pavlović, Gordana; Pavelić, Krešimir; Karminski-Zamola, Grace
Novel Cyano- and Amidino- Benzothiazole Derivatives: Synthesis, Antitumor Evaluation, X-ray and QSAR Analysis // Journal of Medicinal Chemistry, 52 (2009), 6; 1744-1756 doi:10.1021/jm801566q (međunarodna recenzija, članak, znanstveni)


Naslov
Novel Cyano- and Amidino- Benzothiazole Derivatives: Synthesis, Antitumor Evaluation, X-ray and QSAR Analysis

Autori
Ćaleta, Irena ; Kralj, Marijeta ; Marjanović, Marko ; Bertoša, Branimir ; Tomić, Sanja ; Pavlović, Gordana ; Pavelić, Krešimir ; Karminski-Zamola, Grace

Izvornik
Journal of Medicinal Chemistry (0022-2623) 52 (2009), 6; 1744-1756

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

Ključne riječi
Novel benzothiazoles; synthesis; amidines; antitumor evaluation; X-ray; QSAR analysis

Sažetak
Synthesis of a series of novel cyano- and amidino- benzothiazole derivatives (3-31) is described. All studied amidino derivatives showed noticeable antiproliferative effect on several tumor cell lines. Cyano derivatives (11-17) showed considerably less pronounced activity due to their poor solubility in aqueous cell culture medium, which was confirmed by the principal components (PC) analysis. Compounds 21, 22, 28 and 29 were tested for their effects on the cell cycle and apoptosis, whereby 22 and 29, having methyl group at C-6 position in pyridine ring showed drastic cell cycle perturbations that were both concentration- and time-dependent and induced apoptosis. The QSAR modeling, based on the physico-chemical descriptors and on the measured biological activities, indicated the relevance of molecular polarizability and particular distribution of pharmacophores on molecular surface for the activity. In conclusion, benzothiazoles containing either isopropylamidino- or imidazolyl- groups will be considered as starting compounds for further investigation on lead identification

Izvorni jezik
Engleski

Znanstvena područja
Fizika, Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekt / tema
098-0982464-2393 - Molekularna obilježja miofibroblasta Dupuytrenove bolesti (Krešimir Pavelić, )
098-0982464-2514 - Uloga različitih mehanizama odgovora stanica na terapiju oštećenjem DNA (Marijeta Kralj, )
098-1191344-2860 - Proučavanje biomakromolekula računalnim metodama i razvoj novih algoritama (Sanja Tomić, )
119-119307-1332
125-0982464-1356 - Novi heterocikli kao antitumorski i antivirusni ("pametni") lijekovi (Marijana Hranjec, )

Ustanove
Institut "Ruđer Bošković", Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb

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


Uključenost u ostale bibliografske baze podataka:


  • CAS
  • EBSCOhost
  • British Library
  • PubMed
  • CABI
  • SwetsWise


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