Synonyms:dihydropyrrole;pyrroline
99% *data from raw suppliers
The research aims to explore the thermal conversion of 1-azidohepta-3,4,6-trienes into cyclopentennelated dihydropyrroles, a process that holds promise for the efficient synthesis of cognate alkaloids. The study provides detailed mechanistic insights into this multistep reaction sequence, utilizing density functional theory calculations to support the intervention of unexpected mechanistic subtleties, such as the planarity of an azatrimethylenemethane diyl intermediate and an apparent Woodward-Hoffmann-type electrocyclization of a five-atom diyl array. The research concludes that the thermally initiated cascade cyclization of 1-azido-hepta-3,4,6-trienes is an effective methodology for the efficient assembly of cyclopentennelated dihydropyrroles with complete regiochemical and stereochemical control.
The research focuses on the synthesis and application of pyrrolidine and pyrroline derivatives of fullerenes C60 and C70 through [2+3] cycloaddition reactions using azomethine and nitrile ylides generated from picolylamine and benzylamine derivatives. The study explores the use of catalysts and microwave radiation to enhance the formation of ylides and their addition to fullerenes, resulting in higher yields (80-85%) compared to the classical Prato reaction. The synthesized compounds exhibit high regio- and stereoselectivity, forming cis-2′,5′-disubstituted and trans-1′,2′,5′-trisubstituted pyrrolidinofullerenes. These derivatives are of interest for their potential use in light-converting systems, such as solar cells, due to their ability to form self-ordered coordination complexes with metalloporphyrins and phthalocyanines, which can mimic natural photosynthetic antenna systems through photoinduced charge separation. The research also highlights the development of efficient methods for synthesizing these derivatives on a macroscale, addressing challenges related to scalability, energy consumption, and product separation.
The research focuses on the discovery and optimization of 2-propylamino-2,4-diaryl-2,5-dihydropyrroles as potent, water-soluble inhibitors of kinesin spindle protein (KSP), a target for cancer therapy. The study highlights the challenge of overcoming cellular efflux by P-glycoprotein (Pgp), which reduces the efficacy of these inhibitors in multidrug-resistant (MDR) cancer cells. Key chemicals involved in this research include dihydropyrazole 1, dihydropyrrole 2, and their derivatives such as dihydropyrazole 3 and dihydropyrrole 4, which were synthesized and evaluated for their potency against KSP and their solubility. The researchers introduced a C2-aminopropyl side chain to enhance potency and solubility but found that this modification made the compounds susceptible to Pgp-mediated efflux. To address this, they employed β-fluorination to modulate the basicity of the amino group, resulting in compounds like 15c and 18, which retained KSP inhibitory activity while significantly reducing Pgp-mediated efflux. The study demonstrates that careful modulation of the pKa of the amino group can balance KSP potency with resistance to Pgp efflux, potentially improving the efficacy of these inhibitors in cancer treatment.
Total 8 Pictures about this product
