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Design, Synthesis, and Molecular Docking of Paracyclophanyl-Thiazole Hybrids as Novel CDK1 Inhibitors and Apoptosis Inducing Anti-Melanoma Agents

Aly, A. A.; Bräse, Stefan; Hassan, A. A.; Mohamed, N. K.; El-Haleem, Lamiaa E. A.; Nieger, M.; Morsy, N. M.; Alshammari, M. B.; Ibrahim, M. A. A.; Abdelhafez, E. M. N.

Abstract:
Three new series of paracyclophanyl-dihydronaphtho[2,3-d]thiazoles and paracyclophanyl-thiazolium bromides were designed, synthesized, and characterized by their spectroscopic data, along with X-ray analysis. One-dose assay results of anticancer activity indicated that 3a–e had the highest ability to inhibit the proliferation of different cancer cell lines. Moreover, the hybrids 3c–e were selected for five-dose analyses to demonstrate a broad spectrum of antitumor activity without apparent selectivity. Interestingly, series I compounds (Z)-N-substituted-4,9-dihydronaphtho[2,3-d]thiazol-3(2H)-yl)-4′-[2.2]paracyclophanylamide) that are carrying 1,4-dihydronaphthoquinone were more active as antiproliferative agents than their naphthalene-containing congeners (series II: substituted 2-(4′-[2.2]paracyclophanyl)hydrazinyl)-4-(naphth-2-yl)-thiazol-3-ium bromide hybrids) and (series III: 3-(4′-[2.2]paracyclophanyl)amido-2-(cyclopropylamino)-4-(naphth-2-yl)thiazol-3-ium bromide) toward the SK-MEL-5 melanoma cell line. Further antiproliferation investigations of 3c and 3e on the healthy, normal unaffected SK-MEL-5 cell line indicated their relative safety. ... mehr

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Verlagsausgabe §
DOI: 10.5445/IR/1000128367
Veröffentlicht am 12.01.2021
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Institut für Biologische und Chemische Systeme (IBCS)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2020
Sprache Englisch
Identifikator ISSN: 1420-3049
KITopen-ID: 1000128367
Erschienen in Molecules
Verlag MDPI
Band 25
Heft 23
Seiten Art.-Nr.: 5569
Schlagwörter paracyclophane; thiazole; apoptosis; CDK1; 1,4-naphthoquinone; antitumor; melanoma; molecular docking
Nachgewiesen in Scopus
Web of Science
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