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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


Verlagsausgabe §
DOI: 10.5445/IR/1000128367
Veröffentlicht am 12.01.2021
Originalveröffentlichung
DOI: 10.3390/molecules25235569
Scopus
Zitationen: 5
Web of Science
Zitationen: 4
Dimensions
Zitationen: 5
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
HGF-Programm 47.01.01 (POF III, LK 01) Biol.Netzwerke u.Synth.Regulat. ITG+ITC
Erschienen in Molecules
Verlag MDPI
Band 25
Heft 23
Seiten Art.-Nr.: 5569
Bemerkung zur Veröffentlichung Gefördert durch den KIT-Publikationsfonds
Vorab online veröffentlicht am 27.11.2020
Schlagwörter paracyclophane; thiazole; apoptosis; CDK1; 1,4-naphthoquinone; antitumor; melanoma; molecular docking
Nachgewiesen in Web of Science
Scopus
Dimensions
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