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Int. J. Mol. Sci. 2017, 18(7), 1365; doi:10.3390/ijms18071365

Novel Thiazolo[5,4-b]phenothiazine Derivatives: Synthesis, Structural Characterization, and In Vitro Evaluation of Antiproliferative Activity against Human Leukaemia

1
Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, 400028 Cluj-Napoca, Romania
2
Tumor Biology Department, Ion Chiricuta Oncology Institute, 400015 Cluj-Napoca, Romania
3
Medfuture Research Center, Iuliu Hatieganu University of Medicine and Pharmacy, 400012 Cluj-Napoca, Romania
4
Research Center for Functional Genomics and Translational Medicine, Iuliu Hatieganu University of Medicine and Pharmacy, 400012 Cluj-Napoca, Romania
5
Faculty of Pharmacy, Iuliu Hatieganu University of Medicine and Pharmacy, 400012 Cluj-Napoca, Romania
*
Authors to whom correspondence should be addressed.
Received: 17 May 2017 / Revised: 10 June 2017 / Accepted: 16 June 2017 / Published: 26 June 2017
(This article belongs to the Section Bioactives and Nutraceuticals)
View Full-Text   |   Download PDF [1976 KB, uploaded 29 June 2017]   |  

Abstract

The molecular frame of the reported series of new polyheterocyclic compounds was intended to combine the potent phenothiazine and benzothiazole pharmacophoric units. The synthetic strategy applied was based on oxidative cyclization of N-(phenothiazin-3-yl)-thioamides and it was validated by the preparation of new 2-alkyl- and 2-aryl-thiazolo[5,4-b]phenothiazine derivatives. Optical properties of the series were experimentally emphasized by UV-Vis absorption/emission spectroscopy and structural features were theoretically modelled using density functional theory (DFT). In vitro activity as antileukemic agents of thiazolo[5,4-b]phenothiazine and N-(phenothiazine-3-yl)-thioamides were comparatively evaluated using cultivated HL-60 human promyelocytic and THP-1 human monocytic leukaemia cell lines. Some representatives proved selectivity against tumour cell lines, cytotoxicity, apoptosis induction, and cellular metabolism impairment capacity. 2-Naphthyl-thiazolo[5,4-b]phenothiazine was identified as the most effective of the series by displaying against THP-1 cell lines a cytotoxicity close to cytarabine antineoplastic agent. View Full-Text
Keywords: phenothiazine; thiazole; antiproliferative activity; structure-activity relationship phenothiazine; thiazole; antiproliferative activity; structure-activity relationship
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Brem, B.; Gal, E.; Găină, L.; Silaghi-Dumitrescu, L.; Fischer-Fodor, E.; Tomuleasa, C.I.; Grozav, A.; Zaharia, V.; Filip, L.; Cristea, C. Novel Thiazolo[5,4-b]phenothiazine Derivatives: Synthesis, Structural Characterization, and In Vitro Evaluation of Antiproliferative Activity against Human Leukaemia. Int. J. Mol. Sci. 2017, 18, 1365.

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