Thiourea-based non-nucleoside inhibitors of HIV reverse transcriptase as bifunctional organocatalysts in the asymmetric Strecker synthesis

• Published in: Bioorganic & medicinal chemistry Vol. 13; no. 19; pp. 5680 - 5685
• Main Authors: Tsogoeva, Svetlana B., Hateley, Martin J., Yalalov, Denis A., Meindl, Kathrin, Weckbecker, Christoph, Huthmacher, Klaus
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 01.10.2005; Elsevier Science
• Subjects: Bifunctional organocatalyst; Catalysis; Chemistry; Crystallography, X-Ray; Exact sciences and technology; HIV - enzymology; HIV Reverse Transcriptase - antagonists & inhibitors; Inhibitor; Models, Molecular; Molecular Structure; NNI; Noncondensed benzenic compounds; Organic chemistry; Preparations and properties; Reverse Transcriptase Inhibitors - chemical synthesis; Reverse Transcriptase Inhibitors - chemistry; Reverse Transcriptase Inhibitors - pharmacology; Stereoisomerism; Strecker synthesis; Structure-Activity Relationship; Thiourea - chemical synthesis; Thiourea - chemistry; Thiourea - pharmacology; Thiourea derivative; NNI; Bifunctional organocatalyst; Strecker synthesis; Inhibitor; Thiourea derivative; Imidazole derivatives; Enantioselectivity; Asymmetric synthesis; Non nucleoside compound; Aminonitrile; Thioureas; Catalyst activity
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2005.05.014

The potential of novel and known pyridyl thiourea derivatives (non-nucleoside inhibitors of HIV reverse transcriptase) as bifunctional organic catalysts in the asymmetric Strecker synthesis was investigated. The potential of novel and known pyridyl thiourea derivatives (non-nucleoside inhibitors (NNI) of HIV reverse transcriptase) as bifunctional organic catalysts in the asymmetric Strecker synthesis was investigated. It was shown that incorporation of the imidazolyl moiety in place of a pyridyl group results in a new thiourea derivative that displays a much higher catalytic activity.