Pyrrolidine-2,3,4-tricarboxylic anhydrides: I. Organocatalytic synthesis and fusion of pyrrole ring by the action of p-fluorobenzylamine (original) (raw)
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HETEROCYCLES, 1995
A synthesis of 1,4d1deoxy-1,4-imino-D-lyxitol and N-benzyI-4-epr-(-)-anison1yc!n was described Polyhydroxylated pyrrolid~nes and piperidines provide an extensive class of powerful and specific glycostdase inhibitors I 1.4-Didcoxy-1.4-min noD -lyx~tol (I) was reported as a potent competitive inhibitor of a-galactodase (-)-Swainsonine (2) has potentlal actwlty for the prevention of metastasis of cancer (-)-Anisomycin (3) possesses strong and selective acttvities against pathogenic protozoa and fungi. and has been used successfully m the clmc for the treatment of atneb~c dysenetry and trichomonas vagmitts.4 1 2 3 A survey of literature suggested that polyhydroxylated pyrrolidines and piperidines, such as compounds (1-3) were mostly synthesized from natural sugars5 although a number of chtral synthesis of l 6 and 37 have been reported by using different approachs. The formallon of the pyrrolidine ring has been achieved by many ways, such as an intramolecular nucleophtlic displacen~ent with a m n e nitrogen.5h-J.51 anodic cycl~zat~on of 6-alkmylamine,'a or a D~eckrnann cyclizat~ot~ of arn~nodiester.~"' Being tnterested in the remarkable physlologlcal effects of these compounds, and as a contmuation of our work on the utility of optically actwe 1.2-epoxy-4-penten-3-01 (5) for the asymmetric synthcs~s of natural p d u c t s , 8 we 278
Pyrrolidines: Priveleged Structure in Bioactive Molecules and Synthesis
International Journal for Research in Applied Science and Engineering Technology, 2017
Pyrrolidines constitute an important structural motif in natural and designed biologically active molecules. In addition, these heterocycles can be used for pharmaceutical purposesand ligands of transition metal catalysts.Pyrrolidines are also used as an effective chiral controller in various organic asymmetric transformations and are also being utilized in the synthesis of unnatural oligomers as scaffolds for various biological applications such as antidiabetic, anticancer, antimalarial, antiviral, antimicrobial, anti-inflammatory and antibacterial activities. Consequently, the efficient synthesis of these heterocycles has been received significant attention and different strategies for their syntheses have been developed. Among all the methods for the synthesis, the [3+2] cycloaddition of azomethineylides with substituted olefins is a most powerful method to rapidly obtain highly substituted pyrrolidine rings. It is intended to present a brief description of the methods for the synthesis and biological activities of pyrrolidine derivatives.
Synthesis and Biological Study of Some New Pyrrolidines
مجلة التربية والعلم, 2007
A series of Schiff bases N-Arylidene benzylamie (1-6) have been prepared, and through 1,3-anionic cycloaddition under strong basic conditions were added to benzoquinone to afford the fused new pyrrolidines (7-12). The spectroscopic methods were used to confirm the structures of the new products, as well as melting points. The suggested mechanisms of most of the reactions were investigated theoretically on the basis of the values of heat of formation and steric energy of the products. A preliminary biological activity on E. coli and Staph. aureus of the products had also been tested.
Synthesis and biological evaluation of pyrrole-2-carboxamide derivatives: oroidin analogues
Medicinal Chemistry Research, 2014
A novel series of pyrrolidine-2-carbonitrile and 4-fluoropyrrolidine-2-carbonitrile derivatives was designed, synthesized, and found to act as dipeptidyl peptidase-4 (DPP-4) inhibitors. From this series of compounds, compound 17a was identified as an efficacious, safe, and selective inhibitor of DPP-4. In vivo studies in ICR and KKAy mice showed that administration of this compound resulted in decreased blood glucose in these mice after an oral glucose challenge. Compound 17a showed high DPP-4 inhibitory activity (IC 50 = 0.017 lM), moderate selectivity against DPP-4 (selective ratio: DPP-8/DPP-4 = 1324; DPP-9/DPP-4 = 1164), and good efficacy in oral glucose tolerance tests in ICR and KKAy mice. These in vivo anti-diabetic properties and its desirable pharmacokinetic profile in Sprague-Dawley rats demonstrate that compound 17a is a promising candidate for development as an anti-diabetic agent.
Bioorganic & Medicinal Chemistry Letters, 2000
ÐTwo series of anhydride modi®ed cantharidin analogues were synthesised and screened for their phosphatase inhibition (PP1 and PP2A) and cytotoxicity in various cancer cell lines (Ovarian A2780, ADDP; Osteosarcoma 143B; and Colon HCT116 and HT29). One series was synthesised by a novel, high yielding one-pot hydrogenation-ring-opening-esteri®cation procedure, the other by acid catalysed acetal formation. Analogues 5±7 and 9 displayed moderate PP2A selectivity (ca. 5-to 20-fold) and inhibition typically in the low mM range (comparable, in some cases to cantharidin). The anticancer activity of these analogues varied with the cell line under study; however, many of them showed selective cytotoxicity for the colon tumour cell lines.