ChemInform Abstract: Synthesis of Acyclo‐C‐nucleosides in the Imidazo(1,2‐a)pyridine and ‐ pyrimidine Series as Antiviral Agents.

Gueiffier, Alain; Lhassani, Mohammed; Elhakmaoui, Ahmed; Snoeck, R.; Andreï, Graciela; Chavignon, Olivier; Teulade, Jean‐Claude; Kerbal, Abdelali; Essassi, E. M.; Debouzy, Jean‐Claude; Witvrouw, Myriam; Blache, Yves; Balzarini, Jan; Clercq, E. De; Chapat, Jean‐Pierre

doi:10.1002/chin.199643123

Cited by 3 publications

(3 citation statements)

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“…Our synthesis of 3 begins with a Vilsmeier−Haack formylation of imidazo[1,2- a ]pyridine 5 to give the aldehyde 6 , following the approach of Almirante et al as modified by Gueiffier et al By washing the crude product with water, we were able to isolate clean 6 without chromatographic purification. In the next step, ethyl azidoacetate 7 , readily prepared from ethyl bromoacetate and sodium azide, was condensed with 6 using sodium ethoxide dissolved in ethanol .…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Chiral High Performance Liquid Chromatographic Resolution and Enantiospecific Activity of a Potent New Geranylgeranyl Transferase Inhibitor, 2-Hydroxy-3-imidazo[1,2-a]pyridin-3-yl-2-phosphonopropionic Acid

et al. 2010

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3-(3-Pyridyl)-2-hydroxy-2-phosphonopropanoic acid (3-PEHPC, 1) is a phosphonocarboxylate (PC) analogue of 2-(3-pyridyl)-1-hydroxyethylidenebis(phosphonic acid) (risedronic acid, 2), an osteoporosis drug that decreases bone resorption by inhibiting farnesyl pyrophosphate synthase (FPPS) in osteoclasts, preventing protein prenylation. 1 has lower bone affinity than 2 and weakly inhibits Rab geranylgeranyl transferase (RGGT), selectively preventing prenylation of Rab GTPases. We report here the synthesis and biological studies of 2-hydroxy-3-imidazo[1,2-a]pyridin-3-yl-2-phosphonopropionic acid (3-IPEHPC, 3), the PC analogue of minodronic acid 4. Like 1, 3 selectively inhibited Rab11 vs. Rap 1A prenylation in J774 cells, and decreased cell viability, but was 33-60x more active in these assays. After resolving 3 by chiral HPLC (>98% ee), we found that (+)-3-E1 was much more potent than (-)-3-E2 in an isolated RGGT inhibition assay, approximately 17x more potent (LED 3 microM) than (-)-3-E2 in inhibiting Rab prenylation in J774 cells and >26x more active in the cell viability assay. The enantiomers of 1 exhibited a 4-fold or smaller potency difference in the RGGT and prenylation inhibition assays.

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Section: Resultsmentioning

confidence: 99%

“…Imidazo[1,2-a]pyridin-3-carbaldehyde (6). 19,20 To DMF (120 mL, 1.55 mol) cooled to 2 °C, freshly distilled phosphorus oxychloride (61 mL, 0.65 mol) was slowly added. The temperature was allowed to gradually rise to room temperature.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Chiral High Performance Liquid Chromatographic Resolution and Enantiospecific Activity of a Potent New Geranylgeranyl Transferase Inhibitor, 2-Hydroxy-3-imidazo[1,2-a]pyridin-3-yl-2-phosphonopropionic Acid

et al. 2010

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“…Imidazo [1,2-a]pyridines exhibit a broad range of biological proprieties [23e25] including antiviral [26], anticancer [27,28], antifungal [29], anti-inflammatory activities [30] and they have also been incorporated into compounds useful for imaging Ab aggregates in patients with Alzheimer's disease [31,32].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, biological evaluation and molecular modeling studies of imidazo[1,2- a ]pyridines derivatives as protein kinase inhibitors

Lawson

Rodrigo

Baratte

et al. 2016

European Journal of Medicinal Chemistry

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Ionic Liquids: A New Strategy in Pharmaceutical Synthesis

Siódmiak¹,

Marszałł

Proszowska³

2012

MROC

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The industrial synthesis of pharmaceutical compounds often involves the use of organic solvents. Unfortunately, these reaction media are responsible for organic contaminations in the final product. In recent years, ionic liquids (ILs) have become the "green alternatives" of volatile organic solvents. Thus, the application of ILs instead of conventional reagents offer a new opportunity to solve problems of environmentally harmful solvents. This mini-review discusses a new application of ILs in laboratory-scale pharmaceutical synthesis.

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ChemInform Abstract: Synthesis of Acyclo‐C‐nucleosides in the Imidazo(1,2‐a)pyridine and ‐ pyrimidine Series as Antiviral Agents.

Cited by 3 publications

References 1 publication

Synthesis, Chiral High Performance Liquid Chromatographic Resolution and Enantiospecific Activity of a Potent New Geranylgeranyl Transferase Inhibitor, 2-Hydroxy-3-imidazo[1,2-a]pyridin-3-yl-2-phosphonopropionic Acid

Synthesis, Chiral High Performance Liquid Chromatographic Resolution and Enantiospecific Activity of a Potent New Geranylgeranyl Transferase Inhibitor, 2-Hydroxy-3-imidazo[1,2-a]pyridin-3-yl-2-phosphonopropionic Acid

Synthesis, biological evaluation and molecular modeling studies of imidazo[1,2- a ]pyridines derivatives as protein kinase inhibitors

Ionic Liquids: A New Strategy in Pharmaceutical Synthesis

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