Synthesis of 5-Substituted Phthalimide Analogs of Biological Significance
Additional Funding Sources
This project is supported by a 2018-2019 STEM Undergraduate Research Grant from the Higher Education Research Council.
Abstract
Phthalimide has druggable properties and applications in several drug discovery efforts. Cyclic imides, such as succinimide, maleimide, and phthalimide possess structural features of pharmacological relevance and pharmaceutical use. Phthalimide motif is used in synthesis of polymers, new materials, and agrochemicals. Biologically, several phthalimide derivatives possess anticancer, antibacterial, antifungal, and analgesic properties. The imide functionality [-CO-N(R)-CO-] in phthalimide makes it hydrophobic and neutral to cross different biological membranes in vivo. In this current study, we plan to develop 5-substituted-phthalimide based analogs towards targeting sphingosine (Sph) metabolizing enzymes. A Sonogashira coupling strategy was employed towards synthesis of the new C-C bond involving sp2-sp3 hybridization. Several alkyl, aryl substitued Pthalimide analogs were synthesized with an optimum yields of 40 % - 70%. The reaction mechanism, electronic effects, and reaction methodology will be discussed.
Synthesis of 5-Substituted Phthalimide Analogs of Biological Significance
Phthalimide has druggable properties and applications in several drug discovery efforts. Cyclic imides, such as succinimide, maleimide, and phthalimide possess structural features of pharmacological relevance and pharmaceutical use. Phthalimide motif is used in synthesis of polymers, new materials, and agrochemicals. Biologically, several phthalimide derivatives possess anticancer, antibacterial, antifungal, and analgesic properties. The imide functionality [-CO-N(R)-CO-] in phthalimide makes it hydrophobic and neutral to cross different biological membranes in vivo. In this current study, we plan to develop 5-substituted-phthalimide based analogs towards targeting sphingosine (Sph) metabolizing enzymes. A Sonogashira coupling strategy was employed towards synthesis of the new C-C bond involving sp2-sp3 hybridization. Several alkyl, aryl substitued Pthalimide analogs were synthesized with an optimum yields of 40 % - 70%. The reaction mechanism, electronic effects, and reaction methodology will be discussed.
Comments
W21