A Concise Synthesis of Pyrrole-Based Drug Candidates from α-Hydroxyketones, 3-Oxobutanenitrile, and Anilines
Mengxin Xia,
Mardi Santoso,
Ziad Moussa,
Zaher M. A. Judeh
Affiliations
Mengxin Xia
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 62 Nanyang Drive, N1.2-B1-14, Singapore 637459, Singapore
Mardi Santoso
Department of Chemistry, Faculty of Science, Institut Teknologi Sepuluh Nopember, Sukolilo, Surabaya 60111, Indonesia
Ziad Moussa
Department of Chemistry, College of Science, United Arab Emirates University, Al-Ain P.O. Box 15551, United Arab Emirates
Zaher M. A. Judeh
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 62 Nanyang Drive, N1.2-B1-14, Singapore 637459, Singapore
A simple and concise three-component synthesis of a key pyrrole framework was developed from the reaction between α-hydroxyketones, oxoacetonitriles, and anilines. The synthesis was used to obtain several pyrrole-based drug candidates, including COX-2 selective NSAID, antituberculosis lead candidates BM212, BM521, and BM533, as well as several analogues. This route has potential to obtain diverse libraries of these pyrrole candidates in a concise manner to develop optimum lead compounds.
