Environmentally Responsible and Cost-Effective Synthesis of the Antimalarial Drug Pyronaridine
Joseph R. A. Kincaid, Rahul D. Kavthe, Juan C. Caravez, Balaram S. Takale, Ruchita R. Thakore, Bruce H. Lipshutz
Abstract
Two routes to the antimalarial drug Pyronaridine are described. The first is a linear sequence that includes a two-step, one-pot transformation in an aqueous surfactant medium, leading to an overall yield of 87%. Alternatively, a convergent route utilizes a telescoped three-step sequence involving an initial neat reaction, followed by two steps performed under aqueous micellar catalysis conditions affording Pyronaridine in 95% overall yield. Comparisons to existing literature performed exclusively in organic solvents reveal a 5-fold decrease in environmental impact as measured by E Factors.
Topics & Concepts
ChemistryYield (engineering)Sequence (biology)Aqueous solutionPulmonary surfactantCombinatorial chemistryDrugAqueous mediumCatalysisOrganic chemistryStereochemistryPharmacologyBiochemistryMaterials scienceMedicineMetallurgyChemistry and Chemical EngineeringPharmaceutical and Antibiotic Environmental ImpactsInnovative Microfluidic and Catalytic Techniques Innovation