Synthesis and photophysical characterization of quasi push–pull dicyanodibenzodioxins and their anti-tumor activity against glioma cell line C6

[Display omitted] Dibenzodioxins bearing multiple electron withdrawing groups were synthesized using a simple one-step methodology including examples of molecules possessing electron acceptor groups in both ends. As a consequence internal charge delocalization occurs and the optical spectra are foun...

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Bibliographic Details
Published in:	Bioorganic & medicinal chemistry letters Vol. 25; no. 4; pp. 753 - 757
Main Authors:	Banerjee, Subhadeep, Chattopadhyay, Anjan, Banerjee, Arnab, Haridas, Meera, Saini, Praveen, Das, Moitreyi, Majik, Mahesh S., Maurya, Yogesh Kr
Format:	Journal Article
Language:	English
Published:	England Elsevier Ltd 15-02-2015
Subjects:	Animals Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Cell Line, Tumor Cell Survival - drug effects Cell viability Dibenzodioxins Dioxins - chemical synthesis Dioxins - chemistry Dioxins - pharmacology Glioma - drug therapy Glioma - pathology Internal charge transfer Nitriles - chemical synthesis Nitriles - chemistry Nitriles - pharmacology Photochemical Processes Propanolamines - chemical synthesis Propanolamines - chemistry Propanolamines - pharmacology Quasi push–pull Rats Solvatochromism Solvatochromism Cell viability Internal charge transfer Dibenzodioxins Quasi push–pull
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Summary:	[Display omitted] Dibenzodioxins bearing multiple electron withdrawing groups were synthesized using a simple one-step methodology including examples of molecules possessing electron acceptor groups in both ends. As a consequence internal charge delocalization occurs and the optical spectra are found to be bathochromically shifted compared to similar examples known thus far. A theoretical analysis of the molecular orbitals reveals the origin of the peaks in the dibenzodioxin optical spectra. Select examples exhibit in vitro neuro-cytotoxicity against glioma cell line C6, a finding which enhances existing knowledge about the pharmacologically relevant structural motifs in dibenzodioxins.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0960-894X 1464-3405
DOI:	10.1016/j.bmcl.2015.01.006