Facile and Adaptable Synthesis of a Prazosin Analogue Library: Bringing Medicinal Chemistry into the Undergraduate Curriculum

Jozafina Milicaj, Vasudeva R. Dodda, Kaelan R. Patel, Ingrid Rodriguez Aragon, Timothy O'connell, Ramaiah Muthyala, Erika A. Taylor, Yuk Y. Sham

Research output: Contribution to journalArticlepeer-review

2 Scopus citations


Research has shown that the use of practical examples in undergraduate education promotes the retention of historically underrepresented students in STEM majors and lowers achievement gaps within courses. Since many students of color and women aspire toward careers in healthcare and the pharmaceutical industry, efforts to incorporate medicinal chemistry into the organic chemistry and advanced chemistry lab curriculum could potentially help enhance diversity and retention. There is currently a dearth of laboratory experiments that are medically relevant and technically accessible for incorporation into the undergraduate organic chemistry lab curriculum. The theoretical framework for optimization of drug leads and design of chemical libraries used in the exploration of structure-activity relationships is typically introduced in senior-level courses without hands-on laboratory training. In response to this, we have designed a laboratory experiment that translates the typical medicinal chemistry synthesis of a chemical analogue library into a method that can readily be deployed within an undergraduate laboratory setting through the synthesis of the clinically important antihypertensive drug prazosin and its analogues. By the use of commercially available starting materials, a small library of prazosin analogues can be synthesized utilizing nucleophilic aromatic substitution and amide-bond-forming condensation reactions. The experiment introduces a variety of concepts, including (1) retrosynthetic analysis in the design of chemical libraries, (2) methods in extraction and purification, and (3) instrumental analyses via 1H and 13C NMR spectroscopy, mass spectrometry, and melting point determination.

Original languageEnglish (US)
Pages (from-to)1428-1434
Number of pages7
JournalJournal of Chemical Education
Issue number3
StatePublished - Mar 8 2022

Bibliographical note

Publisher Copyright:
© 2022 American Chemical Society and Division of Chemical Education, Inc.


  • Applications of Chemistry
  • Carboxylic Acids
  • Combinatorial Chemistry
  • Drugs/Pharmaceuticals
  • Heterocycles
  • Laboratory Instruction
  • Medicinal Chemistry
  • Organic Chemistry
  • Second-Year Undergraduate
  • Upper-Division Undergraduate


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