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Bioorg Med Chem ; 25(19): 5068-5076, 2017 10 01.
Article in English | MEDLINE | ID: mdl-28864149

ABSTRACT

Diazinane and aryl moieties with vinylamine linkers were synthesized to investigate the importance of their structural variations as potential anti-glioblastoma agents. Structural variations incorporated on to the diazinane moiety included oxa and thio derivatives, each with a variety of nitrogen-bound substituents. The size and shape of the aromatic moiety was varied, with the final variation introducing two carbonyl groups, yielding a substituted anthraquinone. Readily available diazinanes and aryl amines were used asan advantageous foundation. Several parameters were calculated whilst engineering these compounds, including: ClogP, molecular polarizability, polar surface area, minimal molecular projected area, and pKa. In addition, a simple and efficient procedure was developed to synthesize these compounds. It was demonstrated that a vinylamine with 1,3-diazinane-2,4,6-trione and 1-anthraquinone moiety is the most promising drug candidate causing almost 70% of LN229 tumor cell death at 1µg/ml. In addition, its molecular polarizability, polar surface area and minimal molecular projected area indicate a possible potential of this molecule for crossing BBB.


Subject(s)
Anthraquinones/chemistry , Anthraquinones/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Barbiturates/chemistry , Barbiturates/pharmacology , Glioblastoma/drug therapy , Amination , Anthraquinones/chemical synthesis , Antineoplastic Agents/chemical synthesis , Barbiturates/chemical synthesis , Cell Death/drug effects , Cell Line, Tumor , Drug Screening Assays, Antitumor , Humans
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