3,4-Dihydro-2-phenyl-2H-pyrano[2,3-b]pyridines with potent antirhinovirus activity

Bargar, Thomas M.; Dulworth, Jacqueline K.; Kenny, Michael T.; Massad, Renee; Daniel, John K.; Wilson, Thomas E.; Sargent, Roger

doi:10.1021/jm00159a006

Cited by 17 publications

(13 citation statements)

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“…15) were identified as potent inhibitors of rhinovirus replication with median plaque EC 50 values of respectively 0.03, 0.006, and 0.006 mg/mL against 32 serotypes of rhinovirus tested. 163,164 Mechanism of action studies with MDL 20,610 indicated that the compound binds directly to the capsid with subsequent inhibition of uncoating. 165 …”

Section: Dibenzofuran and Dibenzosuberol Derivativesmentioning

confidence: 99%

Selective inhibitors of picornavirus replication

Palma

Vliegen

Clercq

et al. 2008

Medicinal Research Reviews

234

217

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Picornaviruses cover a large family of pathogens that have a major impact on human but also on veterinary health. Although most infections in man subside mildly or asymptomatically, picornaviruses can also be responsible for severe, potentially life-threatening disease. To date, no therapy has been approved for the treatment of picornavirus infections. However, efforts to develop an antiviral that is effective in treating picornavirus-associated diseases are ongoing. In 2007, Schering-Plough, under license of ViroPharma, completed a phase II clinical trial with Pleconaril, a drug that was originally rejected by the FDA after a New Drug Application in 2001. Rupintrivir, a rhinovirus protease inhibitor developed at Pfizer, reached clinical trials but was recently halted from further development. Finally, Biota's HRV drug BTA-798 is scheduled for phase II trials in 2008. Several key steps in the picornaviral replication cycle, involving structural as well as non-structural proteins, have been identified as valuable targets for inhibition. The current review aims to highlight the most important developments during the past decades in the search for antivirals against picornaviruses.

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Section: Dibenzofuran and Dibenzosuberol Derivativesmentioning

confidence: 99%

Selective inhibitors of picornavirus replication

Palma

Vliegen

Clercq

et al. 2008

Medicinal Research Reviews

234

217

View full text Add to dashboard Cite

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“…3) and 6-Chloro-2-(4-Chlorophenyl)-3,4-Dihydro-2H-1-Benzopyran (BW683C, Fig. 1) were synthesized by published methods (Bargar et al, 1986;Hopkins, 1982). Compound 2-(3,4-Dichlorophenoxy)-5-(Methylsulfonyl)Pyridine (MDL 055, Fig.…”

Section: Test Compoundsmentioning

confidence: 99%

Mechanism of action of the antiviral compound MDL 20,610

Kenny¹,

Torney²,

Dulworth³

1988

Antiviral Research

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The purpose of this study was to probe the antirhinovirus (RV) mechanism of action of MDL 20,610. Evaluation of the compound's effects on RV RNA synthesis, uncoating of neutral red-sensitized RV, plasma membrane penetration by RV, stabilization of RV against heat (56 degrees C) and low pH (5.0) inactivation, and studies with MDL 20,610-resistant RV mutants indicate that MDL 20,610 binds directly to the RV capsid with subsequent inhibition of acid-mediated virion uncoating.

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“…As the core intermediates to obtain 4-[(N-imidazol-2-ylmethyl)anilino]pyranopyridine derivatives, 4 types of 2,2-dimethyl-2H-1-pyranopyridines (8)(9)(10)(11)(12)(13)(16)(17)(18)(19)(20), [3,2-c], [3,2-b], [2,3-c], and [2,3-b], were prepared (Scheme 1). 7 To eliminate one of the chiral centers, we introduced dimethyl function at the 2-position instead of an acetal of 1.…”

Section: Chemistrymentioning

confidence: 99%

“…Because the treatment of 2-pyridinol with 3-chloro-3-methylbut-1-yne didn't give the desired O-alkylation product, alternative method was employed for the synthesis of the [2,3-b]isomers. The reaction of 3,5-dibromo-2-methoxypyridine 14 10 with n-BuLi and 3-methyl-2-butenal gave the allylic alcohol 15, followed by the treatment with 48% HBr in acetic acid provided the pyrano [2,3-b]pyridine 16. The bromine of pyranopyridines was further converted to nitrile via nucleophilic substitution with CuCN under microwave irradiation, or debrominated using n-BuLi.…”

Section: Chemistrymentioning

confidence: 99%

4-[(N-Imidazol-2-ylmethyl)anilino]pyranopyridine Analogs as Novel Anti-Angiogenic Agents

2005

Bulletin of the Korean Chemical Society

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(imidazol-2-ylmethyl)aniline moiety at the 4-position, were synthesized respectively, and evaluated for primary anti-angiogenic properties through primary cultured HUVEC tube formation assay. From this study, we found that the pyranopyridine ring, especially [3,2-b]-and [2,3-c]-isomer, can replace the benzopyran ring of the compound 1 and can be optimized through the introduction of substituents both on the pyranopyridine ring and the aniline moiety for the identification of a novel anti-angiogenic agent.

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3,4-Dihydro-2-phenyl-2H-pyrano[2,3-b]pyridines with potent antirhinovirus activity

Cited by 17 publications

References 0 publications

Selective inhibitors of picornavirus replication

Selective inhibitors of picornavirus replication

Mechanism of action of the antiviral compound MDL 20,610

4-[(N-Imidazol-2-ylmethyl)anilino]pyranopyridine Analogs as Novel Anti-Angiogenic Agents

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