Benzodiazepine synthesis and rapid toxicity assay

James T. Fletcher, Grit Boriraj

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

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 a1,5-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.

Original languageEnglish (US)
Pages (from-to)631-633
Number of pages3
JournalJournal of chemical education
Volume87
Issue number6
DOIs
StatePublished - Aug 27 2010

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Education

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