Synthesis and biological evaluation of 2,3-diarylimidazo[1,2-a]pyridines as antileishmanial agents

Marhadour, Sophie; Marchand, Pascal; Pagniez, Fabrice; Bazin, Marc‐Antoine; Picot, Carine; Lozach, Olivier; Ruchaud, Sandrine; Antoine, Maud; Meijer, Laurent; Rachidi, Najma; Pape, Patrice Le

doi:10.1016/j.ejmech.2012.10.048

Cited by 63 publications

(37 citation statements)

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“…Furthermore heterocyclic (Scheme 2, 3am to 3ao) and napthyl methyl ketones (3ap) furnishes the oxidative products in good yields. Next, we studied the reaction with varying the substitution on compound 1, where substituted imidazo[1,2-a]pyridine substrates bearing electron donating groups such as p-Me, p-OMe, 3,4(-O-CH 2 -O-) on the phenyl ring (Scheme 3, 3ba to 3da), furnished 15 the corresponding products in high yields. Substrates bearing halide substitution were also well tolerated and gave the corresponding products in good yields (Scheme 3, 3ea to 3ga).…”

Section: Resultsmentioning

confidence: 99%

“…Imidazo[1,2-a]pyridine compounds are prominent among Nfused heterocycles and have shown interesting biological 15 activities. 1 Based on the diverse biological activities of these compounds i.e.…”

Section: Introductionmentioning

confidence: 99%

“…In view of the prominence gained by the direct C-H bond functionalization reactions coupled with significance of iodine as 15 an alternate to metal catalysts and also our continued interest on the synthesis of bioactive heterocycles, 12 we have planned for the oxidative coupling of IP compounds and ketones in order to functionalize the imidazo[1,2-a]pyridines without involving any transition metal catalysts as they are known to pose 20 environmental problem and should be avoided wherever possible. Further, it is highly desirable to develop the green protocols to access the bioactive molecules.…”

Section: Introductionmentioning

confidence: 99%

“…In conclusion, a highly efficient and selective I 2 -DMSO promoted oxidative cross-coupling in presence of PTSA has been developed with the use of imidazo[1,2-a]pyridines and methyl ketones for the construction of 1-phenyl-2-(2-phenylimidazo[1,2a]pyridin-3-yl)ethane-1,2-diones (3) with a new C-C bond 15 formation. This tandem oxidative cross coupling proved easy to operate and could sequentially promote three mechanistically distinct reactions in a one pot without use of any metal catalyst.…”

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I₂–DMSO–PTSA: a simple and metal free oxidative cross coupling of imidazo[1,2-a]pyridines and methylketones

et al. 2015

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A simple, highly efficient and selective oxidative cross coupling of imidazo[1,2-a]pyridine (IP) compounds (1) and methylketones (2), promoted by molecular iodine in DMSO in presence of catalytic amount of PTSA have been realized in one pot reaction. This strategy has provided a general route for the synthesis of 1-Aryl-2-(2-phenylimidazo[1,2-a]pyridin-3-yl)ethane-1,2-diones 10 (3) with a new C-C bond formation through Kornblum oxidation followed by nucleophilic attack of IP compounds (1) on the insitu formed phenylglyoxal. Simple reaction conditions, no metal catalysts and selective product formation are the advantages of this protocol.This approach not only streamlines the existing synthesis of useful molecular entities, but also contributes to the way chemists 40 think about chemical reactivity and plan the synthesis. Further, functionalization of imidazo[1,2-a]pyridines at 2 and 3 position is of very significant as substitution at these positions reported 6 great impact in terms of biological activity. A growing repertoire of C-H bond functionalization reactions have been reported 45 lately, including arylation, alkylation, alkenylation, insertion, amination, oxidation, borylation, and halogenation. 7 Despite significant advances in method development, the application of C-H functionalization for the synthesis of structurally complex molecules remains a formidable challenge to the chemical 50 community. Notably, the development of transition-metal free cross-coupling reactions is a highly topical and significant research area in organic synthesis as the transition metals add additional costs and generate stoichiometric amounts of metal salts as waste. 55 Scheme 1: Previous reports (1a-d) and present work (1e) In this context, a very useful methods have been reported on Suzuki cross-coupling reaction for direct arylation of imidazole heterocycles 8 promoted by Pd(OAc) 2 (Scheme 1a) and recently 60 as a light yellow solid; Yield 75%; m.p. 118-120°C; IR (KBr): 75 3110, 2983, 2861, 1694, 1625, 1229, 778 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ 9.81 (d, J = 6.40 Hz, 1H), 7.85 (d, J = 8.85 Hz, 1H), 7.29 (d, J = 7.93 Hz, 2H), 7.66 (t, J = 7.78 Hz, 1H), 7.60 (t, J = 6.71 Hz, 1H), 7.43 (t, J = 7.47 Hz, 2H), 7.23 (t, J = 6.71 Hz, 1H), 6.83 (s, 1H), 6.72 (d, J = 7.78 Hz, 1H), 6.44 (d, J = 7.78 Hz, 80 1H), 5.91 (s,

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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I₂–DMSO–PTSA: a simple and metal free oxidative cross coupling of imidazo[1,2-a]pyridines and methylketones

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“…Imidazo[1,2‐ a ]pyridines are valuable heterocycles due to their biological potential in a wide range of activities, presumably as a function of the ring substituents. However, to date, there are no reports about direct role of this scaffold and its participation as QS activity modulator.…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Imidazo[1,2‐a]pyridines with Carboxamide Group Substitution andIn silicoEvaluation of their Interaction with a LuxR‐type Quorum Sensing Receptor

Lara

Salgado-Zamora

Bazin

et al. 2018

Journal of Heterocyclic Chem

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Quorum sensing, an important process of bacterial communication, is involved in the development of complex behavior and expression of virulence factors that become important due to its key role in infection process. In this manuscript, docking studies were used as a preliminary screening to identify main interactions between LuxR receptor (CviR) of Chromobacterium violaceum as model and N‐acyl L‐homoserine lactones. Thus, following this approach, a library of imidazo[1,2‐a]pyridines bearing carboxamide and urea moieties was designed, evaluated on this in silico model previously validated, and synthesized to generate new potential quorum sensing inhibitors. The present article summarizes survey to develop these new molecules with potential biological activity, based on interaction analysis ligand‐receptor.

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Tricyclohexylphosphine Tetrafluoroborate

Ricard

Gagnon

2016

Encyclopedia of Reagents for Organic Synthesis

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Synthesis and biological evaluation of 2,3-diarylimidazo[1,2-a]pyridines as antileishmanial agents

Cited by 63 publications

References 30 publications

I₂–DMSO–PTSA: a simple and metal free oxidative cross coupling of imidazo[1,2-a]pyridines and methylketones

I₂–DMSO–PTSA: a simple and metal free oxidative cross coupling of imidazo[1,2-a]pyridines and methylketones

Design and Synthesis of Imidazo[1,2‐a]pyridines with Carboxamide Group Substitution andIn silicoEvaluation of their Interaction with a LuxR‐type Quorum Sensing Receptor

Tricyclohexylphosphine Tetrafluoroborate

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Synthesis and biological evaluation of 2,3-diarylimidazo[1,2-a]pyridines as antileishmanial agents

Cited by 63 publications

References 30 publications

I2–DMSO–PTSA: a simple and metal free oxidative cross coupling of imidazo[1,2-a]pyridines and methylketones

I2–DMSO–PTSA: a simple and metal free oxidative cross coupling of imidazo[1,2-a]pyridines and methylketones

Design and Synthesis of Imidazo[1,2‐a]pyridines with Carboxamide Group Substitution andIn silicoEvaluation of their Interaction with a LuxR‐type Quorum Sensing Receptor

Tricyclohexylphosphine Tetrafluoroborate

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Product

Resources

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I₂–DMSO–PTSA: a simple and metal free oxidative cross coupling of imidazo[1,2-a]pyridines and methylketones

I₂–DMSO–PTSA: a simple and metal free oxidative cross coupling of imidazo[1,2-a]pyridines and methylketones