Novel Cyano-and Amidinobenzothiazole Derivatives : Synthesis, Antitumor Evaluation, and X-ray and Quantitative Structure-Activity Relationship (QSAR) Analysis

CALETA, Irena ; KRALJ, Marijeta ; et al.

In: Journal of medicinal chemistry (Print), Jg. 52 (2009), Heft 6, S. 1744-1756

academicJournal - print, 39 ref

Synthesis of a series of novel cyano- and amidinobenzothiazole 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 because of 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 the 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 physicochemical descriptors and on the measured biological activities, indicated the relevance of molecular polarizability and particular distribution of pharmacophores on the molecular surface for activity. In conclusion, benzothiazoles containing either isopropylamidino or imidazolyl groups will be considered as starting compounds for further investigation on lead identification.

Titel:	Novel Cyano-and Amidinobenzothiazole Derivatives : Synthesis, Antitumor Evaluation, and X-ray and Quantitative Structure-Activity Relationship (QSAR) Analysis
Autor/in / Beteiligte Person:	CALETA, Irena ; KRALJ, Marijeta ; MARJANOVIC, Marko ; BERTOSA, Branimir ; TOMIC, Sanja ; PAVLOVIC, Gordana ; PAVELIC, Kresimir ; KARMINSKI-ZAMOLA, Grace
Link:	E-Journal im Bestand der UB Hagen? View record from PASCAL Archive
Zeitschrift:	Journal of medicinal chemistry (Print), Jg. 52 (2009), Heft 6, S. 1744-1756
Veröffentlichung:	Columbus, OH: American Chemical Society, 2009
Medientyp:	academicJournal
Umfang:	print, 39 ref
ISSN:	0022-2623 (print)
Schlagwort:	Pharmacology drugs Pharmacologie, galénique Sciences biologiques et medicales Biological and medical sciences Sciences medicales Medical sciences Pharmacologie. Traitements medicamenteux Pharmacology. Drug treatments Anticancéreux Antineoplastic agents Généralités General aspects Amidine Amidina Analyse composante principale Principal component analysis Análisis componente principal Antineoplastic agent Anticanceroso Apoptose Apoptosis Cellule tumorale Tumor cell Célula tumoral Chimiométrie Chemometrics Quimiometría Col utérus Uterine cervix Cuello útero Cycle cellulaire Cell cycle Ciclo celular Côlon Colon Colón Dérivé de l'imidazole Imidazole derivatives Imidazol derivado Dérivé de la pyridine Pyridine derivatives Piridina derivado Dérivé du benzothiazole Benzothiazole derivatives Benzotiazol derivado Fibroblaste Fibroblast Fibroblasto Glande mammaire Mammary gland Glándula mamaria Homme Human Hombre Hydrosolubilité Water solubility Hidrosolubilidad Imidazoline dérivé Imidazoline derivatives Imidazolina derivado In vitro Larynx Laringe Lignée HeLa Hela cell line Célula HeLa Lignée cellulaire Cell line Línea celular Mort cellulaire Cell death Muerte celular Nitrile Nitrilo Pancréas Pancreas Páncreas Propriété physicochimique Physicochemical properties Propiedad fisicoquímica Prédiction Prediction Predicción Relation structure activité Structure activity relation Relación estructura actividad Synthèse chimique Chemical synthesis Síntesis química Benzothiazole-6-carboxamidine(N1-isopropyl-2-[6-méthyl-2-pyridylamino]) Lignée HEP2 Lignée MCF7 Lignée Miapaca2 Lignée SW620 Lignée WI38 QSAR
Sonstiges:	Nachgewiesen in: PASCAL Archive Sprachen: English Original Material: INIST-CNRS Document Type: Article File Description: text Language: English Author Affiliations: Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulicev trg 20, P.O. Box 177, 10000 Zagreb, Croatia ; Division of Molecular Medicine, Ruder BoškoviĆ Institute, Bijenička cesta 54, P.O. Box 1016, 10000 Zagreb, Croatia ; Division of Physical Chemistry, Ruder BoškoviĆ Institute, Bijenička cesta 54, P.O. Box 1016, 10000 Zagreb, Croatia ; Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovica 28a, 10000, Zagreb, Croatia Rights: Copyright 2009 INIST-CNRS ; CC BY 4.0 ; Sauf mention contraire ci-dessus, le contenu de cette notice bibliographique peut être utilisé dans le cadre d’une licence CC BY 4.0 Inist-CNRS / Unless otherwise stated above, the content of this bibliographic record may be used under a CC BY 4.0 licence by Inist-CNRS / A menos que se haya señalado antes, el contenido de este registro bibliográfico puede ser utilizado al amparo de una licencia CC BY 4.0 Inist-CNRS Notes: Pharmacological treatments

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