Synthesis and antiviral activity of 3-substituted imidazo[1,2-a]pyridines.

Elhakmaoui, Ahmed; Gueiffier, Alain; Milhavet, J. C.; Blache, Yves; Chapat, Jean‐Pierre; Chavignon, Olivier; Teulade, Jean‐Claude; Snoeck, Robert; Andrei, Gracíela; Clercq, Erik De

doi:10.1016/s0960-894x(01)80538-2

Cited by 82 publications

(23 citation statements)

References 7 publications

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“…In the past, intensive attention was mainly devoted to the Imidazo[1,2-a]pyridines (IP), Imidazo[1,2-a]pyrimidines (IPM), (Elkakmaoui et al, 1994;Gudmundsson and Johns, 2007;Liang et al, 2007;Scribner et al, 2007;Hayakawa et al, 2007;Warshakoon et al, 2006); Imidazo[1,2-a]thiazoles (IT) and Imidazo[1,2-a]thiazoles (ISO) (Andreani et al, 1995(Andreani et al, , 1996(Andreani et al, , 1999(Andreani et al, , 2000(Andreani et al, , 2001(Andreani et al, , 2005 bioactivity (Scheme 1). However, from a chemical point of view, a second isomeric structure is possible.…”

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confidence: 99%

Synthesis, characterization, and urease inhibition of 5-substituted-8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-diones

et al. 2010

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5-Substituted-8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-dione and its anilines, amino pyridines and hydrazides derivatives were prepared in a good to excellent yields. In the first step 8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-dione (1) was prepared by reacting 4-methyl-2-aminopyridine, with diethylmalonate. Compounds substituted pyrido[1,2-a]pyrimidine-2,4(3H)-diones (PPMDO) (2)-(17) were prepared by condensing 8-methyl-2H-pyrido[1,2-a] pyrimidine-2,4(3H)-dione in the presence of triethylorthoformte (TEF) and dimethylformamide (DMF), with respective amino components viz. 2-aminoacetophenone, 3-aminoacetophenone, 4-aminoacetophenone, 2,4,6-trimethylaniline, 2-fluoroaniline, 3-fluoroaniline, 4-fluoroaniline, 2-aminothiophenol, 2-amino-4-methylpyridine, 2-amino-5-methylpyridine, 2-amino-5-nitropyridine, Benzoic hydrazide, 4-nitrobenzoic hydrazide, 4-bromobenzoic hydrazide, 4-chlorobenzoic hydrazide and 4-hydroxybenzoic hydrazide, respectively. The chemical structures of all the compounds were elucidated by IR, 1 H-NMR, 13 C-NMR and elemental analysis data. The synthesized compounds were screened for their in vitro urease inhibition activity, by the phenol hypochlorite method. These compounds were found to exhibit either no or low to moderate or significant activity. The compounds (9) and (14) showed comparatively much higher activity. However, the compound (9) was found to be the most active one.

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and urease inhibition of 5-substituted-8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-diones

et al. 2010

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“…Preparation of the nucleosides analogs was achieved according to our previously described procedure. [5][6][7] Thus the alcohol 13 was converted to the corresponding halide in refluxing thionyl chloride. After evaporation to dryness, the residue was dissolved in acetonitrile and refluxed in the presence of the suitable thiol and pyridine to give the attempted derivatives (14-33) (Scheme 1).…”

Section: Chemistrymentioning

confidence: 99%

“…1 From the reported acyclo-C-nucleosides, 2 the 1-methylpseudouridine (5) showed activity against HSV-1. Recently, Tanaka et al 3a have reported synthesis and antiviral activity of an acyclo-N-nucleoside derivative of pyrimidine, bearing a phenylthio group at the position 6, called HEPT (6). This compound showed a marked anti-HIV-1 activity and was 20-fold less toxic for the bone marrow than azidothymidine (AZT).…”

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confidence: 99%

“…In previous studies, we have described the preparation 5 and activity of 3-[[(hydroxyethyl)thio]-methyl]-7-methylimidazo[1,2-a]pyridine (9) against TKvaricella-zoster virus. 6 In contrast, some derivatives in the imidazo[1,2-a]-pyrimidine series were devoid of antiviral activity. 7 In this work, we report the synthesis and the antiviral activity of side-chain-modified imidazo[1,2-a]pyridinic and -pyrimidinic derivatives and the influence of the antiviral activity of the nature and position of various substituents in the imidazo[1,2-a]pyridinic ring system.…”

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Synthesis of Acyclo-C-nucleosides in the Imidazo[1,2-a]pyridine and Pyrimidine Series as Antiviral Agents

et al. 1996

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“…6) As a result, numerous two-and three-component approaches for their synthesis have been reported. [7][8][9][10][11][12][13][14] Biopolymers, especially cellulose and its derivatives, 15) have some unique properties, which make them attractive alternatives for conventional organic or inorganic supports for catalytic applications. Among others, they are extremely inert, inexpensive, biodegradable and environmentally benign allowing various reaction conditions to be employed.…”

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Cellulose Sulfuric Acid Catalyzed One-Pot Three-Component Synthesis of Imidazoazines

Shaabani

Maleki

Rad

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Imidazoazines have been synthesized by a one-pot three-component condensation reaction of an aldehyde, a 2-aminoazine and an isocyanide in the presence of the cellulose sulfuric acid, as an effective bio-supported catalyst in excellent yields. The reaction work-up is simple and the catalyst can be easily separated from the product and reused in several times.Key words cellulose sulfuric acid; bio-supported catalyst; imidazo[1,2-a]pyridine; isocyanide; multi-component reaction Imidazo[1,2-a]pyridines, as an important class of versatile pharmaceutically and biologically active compounds spanning applications in anti-inflammatory 1,2) and antibacterial agents, 3) inhibitors of gastric acids secretion, 4) calcium channel blockers, 5) and antiulcer based therapies. 6) As a result, numerous two-and three-component approaches for their synthesis have been reported. [7][8][9][10][11][12][13][14] Biopolymers, especially cellulose and its derivatives, 15) have some unique properties, which make them attractive alternatives for conventional organic or inorganic supports for catalytic applications. Among others, they are extremely inert, inexpensive, biodegradable and environmentally benign allowing various reaction conditions to be employed. Cellulose is the most abundant natural material in the world and it has been widely studied during the past decades because it is a biodegradable material and a renewable resource.In recent years, the emphasis of science and technology is shifting more towards environmentally friendly and sustainable resources and processes; in this regard, biopolymers are attractive candidates to explore for supported catalysis. 16,17) Several interesting biopolymers for example alginate, 18) gelatin, 19,20) starch 21) and chistosan 22) derivatives have been utilized as a support for catalytic applications.During the course of our studies on the development of new routes for the synthesis of organic compounds using solid acid catalysts in organic transformations [23][24][25][26][27] and our interest in isocyanide-based MCRs, [28][29][30][31] we developed the synthesis of imidazoazines 4a-j via the three-component condensation of an aldehyde 1, a 2-aminoazine 2 and an isocyanide 3 in the presence of catalytic amount of cellulose sulfuric acid at room temperature (Chart 1). ExperimentalApparatus Melting points were measured on an Electrothermal 9100 apparatus and are uncorrected. The elemental analyses were performed with an Elementar Analysensysteme GmbH VarioEL. Mass spectra were recorded on a FINNIGAN-MAT 8430 mass spectrometer operating at an ionization potential of 70 eV. IR spectra were recorded on a Shimadzu IR-470 spectrometer.1 H-and 13 C-NMR spectra were recorded on a BRUKER DRX-300 AVANCE spectrometer at 300.13 and 75.47 MHz, respectively. All the products (except 4g) are known compounds, which were identified by IR and 1 H-NMR spectral data and comparing their melting points with literature reports.Preparation of Cellulose Sulfuric Acid To a magnetically stirred mixture of 5.00 g of cellulos...

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Synthesis and antiviral activity of 3-substituted imidazo[1,2-a]pyridines.

Cited by 82 publications

References 7 publications

Synthesis, characterization, and urease inhibition of 5-substituted-8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-diones

Synthesis, characterization, and urease inhibition of 5-substituted-8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-diones

Synthesis of Acyclo-C-nucleosides in the Imidazo[1,2-a]pyridine and Pyrimidine Series as Antiviral Agents

Cellulose Sulfuric Acid Catalyzed One-Pot Three-Component Synthesis of Imidazoazines

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