Synthesis and in vitro antitumor activity of new series of benzothiazole and pyrimido[2,1-b]benzothiazole derivatives

New series of benzothiazole and pyrimido[2,1-b]benzothiazole derivatives were synthesized and characterized by analytical and spectrometrical methods (IR, HRMS, 1H and 13C NMR). Nineteen of the synthesized compounds were selected by the National Cancer Institute (NCI), USA, to be screened for their...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2014-10, Vol.85, p.576-592
Main Authors: Gabr, Moustafa T., El-Gohary, Nadia S., El-Bendary, Eman R., El-Kerdawy, Mohamed M.
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antitumor activity
Benzothiazoles
Benzothiazoles - chemical synthesis
Benzothiazoles - chemistry
Benzothiazoles - pharmacology
Cell Line, Tumor
Chemistry Techniques, Synthetic
Drug Screening Assays, Antitumor
Humans
Models, Molecular
Molecular Conformation
Pharmacophore study
Pyrimidobenzothiazoles
Receptor, Epidermal Growth Factor - metabolism
Structure-Activity Relationship
Synthesis
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Summary:New series of benzothiazole and pyrimido[2,1-b]benzothiazole derivatives were synthesized and characterized by analytical and spectrometrical methods (IR, HRMS, 1H and 13C NMR). Nineteen of the synthesized compounds were selected by the National Cancer Institute (NCI), USA, to be screened for their antitumor activity at a single dose (10 μM) against a panel of 60 cancer cell lines. The most active compounds, 4, 6, 10, 14, 17 and 20 were selected for further evaluation at five dose level screening. Compounds 17 (GI50 = 0.44 μM, TGI = 1.2 μM and LC50 MG-MID = 6.6 μM) and 4 (GI50 = 0.77 μM, TGI = 2.08 μM and LC50 MG-MID = 11.74 μM) were proved to be the most active members in this study. 3D and 2D pharmacophoric maps for the structural features of both compounds were studied. Compounds 4 (GI50 = 0.77 μM) and 17 (GI50 = 0.44 μM) were proved to be the most active members in this study. [Display omitted] •New series of benzothiazoles and pyrimidobenzothiazoles were synthesized.•Nineteen of the synthesized compounds were screened for antitumor activity at NCI, USA.•Compounds 4 (GI50 = 0.77 μM) and 17 (GI50 = 0.44 μM) were proved to be the most active members.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2014.07.097