Benzodiazepine Synthesis and Rapid Toxicity Assay
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James T. Fletcher [1] ; Grit Boriraj [1]
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[1] Creighton University
Creighton University
City of Omaha, Estados Unidos
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- Localización: Journal of chemical education, ISSN 0021-9584, Vol. 87, Nº 6 (June), 2010, págs. 631-633
- Idioma: inglés
- Texto completo no disponible (Saber más ...)
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Resumen
A second-year organic chemistry laboratory experiment to introduce students to general concepts of medicinal chemistry is described. Within a single three-hour time window, students experience the synthesis of a biologically active small molecule and the assaying of its biological toxicity. Benzodiazepine rings are commonly found in antidepressant therapeutics, including Valium and Xanax. This experiment involves the one-step synthesis of a 1,5-benzodiazepine derivative via the condensation−cyclization of ortho-phenylenediamine with two equivalents of acetone. Following its isolation, the toxicity of the benzodiazepine product is evaluated via a brine shrimp assay, which allows students to rapidly observe differences in biological activity among varying benzodiazepine concentrations.
