1-Pyrrolines (3,4-Dihydro-2H-pyrroles) as a Template for New Drugs

Recent Development in Preparation Reactivity and Biological Activity of Enaminoketones and Enaminothiones and Their Utilization to Prepare Heterocyclic Compounds

“…One-pot transformations of pyrrolidine enaminones 93 into 5-(3-aminopropyl)isoxazoles and the corresponding pyrazoles were achieved with hydroxylamine in an a c e t a t e -b u ffered solution and with hydrazine sulfate, respectively ( Figure 37). The ring transformation sequence allowed simple access to heterocycles which are histamine analogues and both enaminones and heterocycles possess histaminergic activity [77,78].…”

Synthesis, anti-inflammatory evaluation and docking studies of some new fluorinated fused quinazolines

“…COX-2 isoenzyme is evident to be over-expressed during inflammatory conditions and was also found to exhibit a protective role in asthma [3]. Literature reports reveal that COX isoenzymes are the attractive molecular targets for the development of NSAIDs [4]. Thus, inhibition of these enzymes leads to a decreased production of prostaglandins and thromboxanes which in turn accounts for the beneficial effects of NSAIDs (e.g.…”

Synthesis of 5-hydroxy-Δ1-pyrrolines from aryl isoalkyl ketoximes and acetylene in a tuned superbase medium

“…Although it was reported 17 that 3,3-dimethyl-2-phenyl-5-hydroxypyrroline reacted with acetylene to give 3H-pyrrole, this transformation was mainly related to the mechanism of 3H-pyrrole formation. Another example is the formation of 2-phenyl-3,3-dimethylpyrroline 18a and 4,4-dimethyl-5-phenyl-1-vinyl- [3,3] 2-pyrrolidinone 18b which was proposed to originate from the intermediate 3,3-dimethyl-2-phenyl-5-hydroxypyrroline without robust evidence.…”

“…2 Furthermore, a number of unnatural D 1 -pyrrolines have been used as synthons for new drugs 3 and intermediates in the synthesis of biologically active compounds, 4 light-driven switches, 5 and boranil fluorophores. 6 Despite the advances in methods to synthesize the D 1 -pyrroline scaffold (e.g., by intramolecular cyclizations of bifunctional compounds and multi-component cyclizations, 7 1,3-dipolar cycloadditions, 8 photo-and thermo-induced 9,10 reactions), the synthesis of hydroxy-substituted pyrrolines, particularly 5-hydroxy-D 1 -pyrrolines (3,4-dihydro-2H-pyrrol-2-ols) with aromatic substituents, is much less developed.…”