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 language | English |
|---|---|
| Pages (from-to) | 631-633 |
| Number of pages | 3 |
| Journal | Journal of Chemical Education |
| Volume | 87 |
| Issue number | 6 |
| DOIs | |
| State | Published - 2010 |
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All Science Journal Classification (ASJC) codes
- Chemistry(all)
- Education
Cite this
Benzodiazepine synthesis and rapid toxicity assay. / Fletcher, James T.; Boriraj, Grit.
In: Journal of Chemical Education, Vol. 87, No. 6, 2010, p. 631-633.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Benzodiazepine synthesis and rapid toxicity assay
AU - Fletcher, James T.
AU - Boriraj, Grit
PY - 2010
Y1 - 2010
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=77955882710&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=77955882710&partnerID=8YFLogxK
U2 - 10.1021/ed100185n
DO - 10.1021/ed100185n
M3 - Article
AN - SCOPUS:77955882710
VL - 87
SP - 631
EP - 633
JO - Journal of Chemical Education
JF - Journal of Chemical Education
SN - 0021-9584
IS - 6
ER -