Synthesis and SAR studies of very potent imidazopyridine antiprotozoal agents

Biftu, Tesfaye; Feng, Danqing; Fisher, Michael H.; Liang, Gui-Bai; Qian, Xiaoxia; Scribner, Andrew; Dennis, Richard; Lee, Shuliang; Liberator, Paul; Brown, C. M.; Gurnett, Anne; Leavitt, Penny; Thompson, D. R.; Mathew, John; Misura, Andrew S.; Samaras, Samantha; Tamas, Tamas; Sina, Joseph F.; McNulty, Kathleen A.; McKnight, Crystal; Schmatz, Dennis M.; Wyvratt, Matthew J.

doi:10.1016/j.bmcl.2006.01.092

Cited by 89 publications

(40 citation statements)

References 4 publications

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“…They have found widespread application in medicinal chemistry 2 and materials science. 3 They are also found in many pharmaceutical compounds ( Figure 1), such as saripidem 4 (anxiolytic, I), olprinone 5 (to treat acute heart failure, II), zolimidine 6 (antiulcer, III), and zolpidem 7 (hypnotic, IV), which exhibit antifungal, 8 antiinflammatory, 9 antitumor, 10 antiviral, 11 antibacterial, 12 antiprotozoal, 13 antipyretic, 14 analgesic, 15 antiapoptotic, 16 hypnoselective, and anxioselective activities. 17 Consequently, there is considerable interest from the pharmaceutical industry, synthetic chemists and this has stimulated the development of numerous methods for their preparation.…”

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confidence: 99%

Iron(II)-Catalyzed Denitration Reaction: Synthesis of 3-Methyl-2-arylimidazo[1,2-a]pyridine Derivatives from Aminopyridines and 2-Methylnitroolefins

Hao

Yang

Gao

et al. 2012

Synlett

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A variety of ways to synthesize imidazo[1,2-a]pyridines have been reported and many approaches are devoted to the functionalization of imidazo[1,2-a]pyridines. However, the use of a denitration reaction in the synthesis of imidazo[1,2-a]pyridines has not been reported. We report here the iron-catalyzed synthesis of 3-methyl-2-arylimidazo [1,2-a] pyridine derivatives from aminopyridines and 2-methyl-nitroolefins. The procedure, using FeCl 2 as catalyst, is simple and inexpensive. Various functional groups are tolerated and provide the products in good yields.

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confidence: 99%

Iron(II)-Catalyzed Denitration Reaction: Synthesis of 3-Methyl-2-arylimidazo[1,2-a]pyridine Derivatives from Aminopyridines and 2-Methylnitroolefins

Hao

Yang

Gao

et al. 2012

Synlett

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“…The required sulfone 5 was successfully synthesised in gram quantities as reported previously by us and others [9,23,28]. The required aminoalkyne linker 6a was then prepared in multi-gram quantities starting with selective propargylation of diethylene glycol 9a .…”

Section: Resultsmentioning

confidence: 97%

“…TgCDPK1 has previously been identified as a target of compound 2 [9,28]. Empty vector (the AD vector without TgCDPK1 and containing a stop codon immediately downstream of the multiple cloning site) was used as a negative control.…”

Section: Resultsmentioning

confidence: 99%

A Modular Approach to Triazole-Containing Chemical Inducers of Dimerisation for Yeast Three-Hybrid Screening

et al. 2013

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The yeast three-hybrid (Y3H) approach shows considerable promise for the unbiased identification of novel small molecule-protein interactions. In recent years, it has been successfully used to link a number of bioactive molecules to novel protein binding partners. However despite its potential importance as a protein target identification method, the Y3H technique has not yet been widely adopted, in part due to the challenges associated with the synthesis of the complex chemical inducers of dimerisation (CIDs). The development of a modular approach using potentially “off the shelf” synthetic components was achieved and allowed the synthesis of a family of four triazole-containing CIDs, MTX-Cmpd2.2-2.5. These CIDs were then compared using the Y3H approach with three of them giving a strong positive interaction with a known target of compound 2, TgCDPK1. These results showed that the modular nature of our synthetic strategy may help to overcome the challenges currently encountered with CID synthesis and should contribute to the Y3H approach reaching its full potential as an unbiased target identification strategy.

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“…1 For example, they exhibit good anti-cancer, 2 anti-inflammatory, 3 anti-bacterial, 4 anti-protozonal, 5 anti-viral, 6 anti-ulcer, 7 anti-fungal, 8 and anxiolytic properties. In addition, imidazo[1,2-a]pyridines have been found to be the core structure of many natural products and marketed drugs, including alpidem, 9 necopidem, 10 saripidem, 11 zolpidem (Ambien ®), 12 olprinone, 13 DS-1, 14 minodronic acid, 15 divalpon, 16 and Zolimidine.…”

Section: Introductionmentioning

confidence: 99%

Metal-free, efficient hydrazination of imidazo[1,2-a]pyridine with diethyl azodicarboxylate in neutral media

et al. 2015

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Synthesis and SAR studies of very potent imidazopyridine antiprotozoal agents

Cited by 89 publications

References 4 publications

Iron(II)-Catalyzed Denitration Reaction: Synthesis of 3-Methyl-2-arylimidazo[1,2-a]pyridine Derivatives from Aminopyridines and 2-Methylnitroolefins

Iron(II)-Catalyzed Denitration Reaction: Synthesis of 3-Methyl-2-arylimidazo[1,2-a]pyridine Derivatives from Aminopyridines and 2-Methylnitroolefins

A Modular Approach to Triazole-Containing Chemical Inducers of Dimerisation for Yeast Three-Hybrid Screening

Metal-free, efficient hydrazination of imidazo[1,2-a]pyridine with diethyl azodicarboxylate in neutral media

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