Abstract
The tetrahydropyridine (THP) ring system has received considerable focus due to its excellent ability to act as a pharmacophore. It is recognized as a major constituent in natural alkaloids. THP derivatives have been reported for a diverse range of biological activities. Recent synthetic works contain syntheses of monosubstituted, disubstituted, trisubstituted, highly functionalized, and condensed structures. In this review, we summarize the recent literature dealing with the bioactive nature of this important heterocycle.
Highlights
Active heterocyclic compounds are abundantly found in nature. 1 Among heterocyclic compounds, pyridine and partially reduced dihydropyridine and tetrahydropyridine (THP) have emerged as excellent templates for various bioactive molecules. 2,3 Three structural isomers of THP are 1,2,3,6-tetrahydropyridine, 1,2,3,4tetrahydropyridine, and 3,4,5,6-tetrahydropyridine
Arecoline and betanin III are the two natural biologically active THP compounds containing alkaloid and glycoside, respectively. 4−6 The most famous THP-containing neurotoxin is 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine, which causes parkinsonism disease. 7,8 THP-based droperidole and tazomeline act as drugs used for the treatment of Alzheimer disease and schizophrenia. 9,10 Various THP derivatives have shown antiinflammatory, 11,12 antianginal, antimicrobial, antifungal, antioxidant, anticancer, and antihypoxic activities
Different types of methods have been developed for the synthesis of THPs, such as [4 + 2] cycloaddition reactions, 24 multicomponent reactions, 25,26 radical cyclization of Baylis–Hillman adducts, aza-Morita–Baylis–Hillman reactions, and two-component reactions of aldimines and tetrahydropyrandiol. 27−29 THPs are used in the synthesis of piperidine derivatives. 30
Summary
Active heterocyclic compounds are abundantly found in nature. 1 Among heterocyclic compounds, pyridine and partially reduced dihydropyridine and tetrahydropyridine (THP) have emerged as excellent templates for various bioactive molecules. 2,3 Three structural isomers of THP are 1,2,3,6-tetrahydropyridine, 1,2,3,4tetrahydropyridine, and 3,4,5,6-tetrahydropyridine. 71 N -Alkyl/aryl substituted thiazolidinone arecoline analogues as muscarinic M 1 receptor agonists were synthesized by Sadashiva et al Compound 73 was most potent (affinity, Ki = 19 ± 1.97 μ M; potency, IC 50 = 48 ± 6.23 μ M) in this series and contained diphenylamine attached to the nitrogen of thiazolidinone moiety. It was active in reversing scopolamine-induced memory loss.
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