Rational design of 2-pyrrolinones as inhibitors of HIV-1 integrase

A Brønsted Acid-Catalyzed Multicomponent Reaction for the Synthesis of Highly Functionalized γ-Lactam Derivatives

“…Based on our previous experience in MCRs for the synthesis of 3-amino 1,5-dihydro-2 H -pyrrol-2-ones [11,14], we firstly used BINOL-derived phosphoric acid 9 as a Brønsted acid catalyst in the three-component reaction of benzaldehyde 2 , p -toluidine 3 (R = p -MeC 6 H 4 ), and diethyl acetylenedicarboxylate 8 using refluxing dichloromethane as solvent (Scheme 2). However, only the enamine and/or imine intermediates that result from the reaction of amine substrate 3 with benzaldehyde 2 or alkyne 8 were observed in the crude (Table 1, Entry 1).…”

“…Considering the relevance of the γ-lactam ring I (Figure 1) [7] and the increasing demand of potentially active compounds in medicinal sciences, MCR protocols were extensively used during the last decades for the synthesis of a wide number of densely functionalized γ-lactam derivatives [8,9]. In particular, 1,5-dihydro-2 H -pyrrol-2-ones II (Figure 1) are conjugated unsaturated γ-lactam substrates with huge potential as intermediates in synthetic chemistry that also show assorted pharmacological activities [10,11,12,13].…”

Microwave-assisted synthesis of pyrrolidinone derivatives using 1,1’-butylenebis(3-sulfo-3H-imidazol-1-ium) chloride in ethylene glycol

“…2-Pyrrolidinone derivatives substituted in position-4 were able to reduce the extracellular glutamate level, therefore effective for the prophylaxis and treatment of a large number of disorders such as stroke [19]. This fascinating scaffold has diverse pharmacological activities including antibacterial, antifungal, anticancer and anticonvulsant [20][21][22][23]; therefore, many procedures for the preparation of substituted pyrrolidinone have been reported and also their various reactions offer great scope in the field of medicinal chemistry [24][25][26][27][28][29][30].…”

One‐pot synthesis of polysubstituted pyrrolidinones using novel magnetic nanoparticles as an efficient and reusable catalyst

“…Five‐membered nitrogen‐containing heterocyclic polysubstituted 3‐hydroxy‐2‐pyrrolidinones are major structural units found in pharmacological agents and natural products . These compounds have significant biological activities such as antibacterial, antimicrobial, anti‐inflammatory and anticancer activities . For example, two pyrrolidinone epicatechins, 6‐(2‐pyrrolidinone‐5‐yl)‐(−)‐epicatechin ( 1 , Figure ) and 8‐(2‐pyrrolidinone‐5‐yl)‐(−)‐epicatechin ( 2 , Figure ), displayed significant in vivo inhibitory activity against advanced glycation end‐product formation .…”