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      C3‐Functionalization of Imidazo[1,2‐ a]pyridines

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          Abstract

          Among nitrogen‐containing organic compounds, imidazo[1,2‐ a]pyridines, and especially C3‐functionalized imidazo[1,2‐ a]pyridines, have a wide range of industrial applications in the fields of optics, material science, and organometallics. This scaffolds also have various medicinal uses due to their antiviral, cytotoxic, antibacterial, fungicidal, and antiinflammatory activities as they are found in many commercially available drugs such as Alpidem, Miroprofen, and Zolimidine. In this review, we summarized and classified the latest synthetic methods for the preparation of C3‐functionalized imidazo[1,2‐ a]pyridines based on the type of the substituents on the 3‐position of imidazo[1,2‐ a]pyridine including C3‐alkylation, C3‐arylation, C3‐carbonylation, C3‐sulfenylation, C3‐selenation, C3‐ N‐Substitution, C3‐phosphonation, and C3‐halogenation.

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          Recent progress in the pharmacology of imidazo[1,2-a]pyridines.

          Imidazo[1,2-a]pyridine is a bicyclic system with a bridgehead nitrogen atom, of growing interest in medicinal chemistry. The paper deals with the recent progress realised in the comprehension of the pharmacological properties of this scaffold. From the many imidazo[1,2-a]pyridine analogues described in the literature, those discussed herein will be presented in three parts concerning first the enzyme inhibitors, then the receptor ligands and finally the anti-infectious agents.
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            Synthesis of imidazo[1,2-a]pyridines: a decade update

            Here we describe the various strategies for the synthesis of imidazo[1,2- a ]pyridines. Imidazopyridine is one of the important fused bicyclic 5–6 heterocycles and it is recognized as a “drug prejudice” scaffold due to its wide range of applications in medicinal chemistry. This moiety is also useful in material science because of its structural character. Synthesis of this moiety from the easily available chemicals is desirable due to its tremendous use in the various branches of chemistry. Here we report a review on the synthesis of this scaffold employing different strategies such as condensation, multicomponent reactions, oxidative coupling, tandem reactions, aminooxygenation, and hydroamination reactions.
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              Advancement of Imidazo[1,2-a]pyridines with Improved Pharmacokinetics and Nanomolar Activity Against Mycobacterium tuberculosis.

              A set of fourteen imidazo[1,2-a]pyridine-3-carboxamides was synthesized and screened against Mycobacterium tuberculosis H37Rv. The minimum inhibitory concentrations of twelve of these agents were ≤ 1 μM against replicating bacteria and five compounds (9, 12, 16, 17 and 18) had MIC values ≤ 0.006 μM. Compounds 13 and 18 were screened against a panel of MDR and XDR drug resistant clinical Mtb strains with the potency of 18 surpassing that of clinical candidate PA-824 by nearly 10 fold. The in vivo pharmacokinetics of compounds 13 and 18 were evaluated in male mice by oral (PO) and intravenous (IV) routes. These results indicate that readily synthesized imidazo[1,2-a]pyridine-3-carboxamides are an exciting new class of potent, selective anti-TB agents that merit additional development opportunities.
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                Author and article information

                Contributors
                (View ORCID Profile)
                Journal
                European Journal of Organic Chemistry
                Eur J Org Chem
                Wiley
                1434-193X
                1099-0690
                January 23 2020
                January 14 2020
                January 23 2020
                : 2020
                : 3
                : 269-284
                Affiliations
                [1 ] Endocrinology and Metabolism Research Center Endocrinology and Metabolism Clinical Sciences Institute Tehran University of Medical Sciences Tehran I.R. Iran
                [2 ] Faculty of Fouman College of Engineering University of Tehran Fouman I.R. Iran
                Article
                10.1002/ejoc.201901491
                ba537b2a-fc32-4577-a43c-9f7cd4bca989
                © 2020

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