Synthesis of 6-[(hydroxyimino)phenyl)]methyl]-1-[(1-methylethyl)sulfonyl]-1H-imidazo[4,5-b]pyridin-2-amine. An aza analogue of enviroxime

doi:10.1002/JHET.5570270656

Paper

Synthesis of 6-[(hydroxyimino)phenyl)]methyl]-1-[(1-methylethyl)sulfonyl]-1H-imidazo[4,5-b]pyridin-2-amine. An aza analogue of enviroxime

Published Sep 1, 1990 · J. L. Kelley, E. W. McLean, Ronda Davis

Journal of Heterocyclic Chemistry

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Abstract

6-[[(Hydroxyimino)phenyl]methyl]-1-[(1-methylethyl)sulfonyl]-1H-imidazo[4,5-b]pyridin-2-amine (1), an aza analogue of enviroxime, was synthesized in eight steps from 6-hydroxynicotinic acid (2). Acid 2 was nitrated, chlorinated with phosphorus pentachloride, and subjected to Friedel-Crafts aroylation to give 6-chloro-5-nitro-3-pyridyl phenyl ketone (5). Amination of 5 was followed by reduction of the nitro group and condensation with ethoxycarbonylisothiocyanate to give 6-benzyl-2-ethoxycarbonylamino-1H-imidazo[4,5-d]pyridine (8). The ethoxycarbonyl moiety of 8 was cleaved, N-1 was isopropylsulfonylated, and the carbonyl moiety was condensed with hydroxylamine to give 1. Compound 1 was inactive against rhinovirus 1B and poliovirus type 1.

Study Snapshot

6-[(hydroxyimino)phenyl]methyl]-1-[(1-methylethyl)sulfonyl]-1H-imidazo[4,5-b]pyridin-2-amine] was synthesized and found inactive against rhinovirus 1B and poliovirus type

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis of 6-[(hydroxyimino)phenyl)]methyl]-1-[(1-methylethyl)sulfonyl]-1H-imidazo[4,5-b]pyridin-2-amine. An aza analogue of enviroxime

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References

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6-dimethylamino-9-(aminoacylamidobenzyl)purines show in vitro anti-viral activity against rhinovirus serotype 1B, with a IC50 value of 17 M.

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Minimal hydrophobicity in drug design is crucial for preventing CNS penetration and reducing side effects, while maintaining efficacy.

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Combinations of HuIFN- or HuIFN- and enviroxime show potent antiviral synergy against RV2 and RV9, warranting further clinical study.

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The developed HPLC assay accurately quantitates enviradene in plasma, with high and persistent plasma concentrations in dogs after oral administration, and its bioavailability is increased by concomitant food administration.

Chapter 12. Antiviral Agents

Antiviral agents have made significant progress in treating respiratory diseases, with acyclovir showing promise for treating herpes and other DNA viruses.

Citations

Discovery and development of 2-aminobenzimidazoles as potent antimalarials.

2-aminobenzimidazoles with a phenol moiety show high potency against Plasmodium falciparum malaria and low cytotoxicity, offering potential as new antimalarials.

A novel application of the Ullmann coupling reaction for the alkylsulfenylation of 2-amino-imidazo[1,2-a]pyridine

The Ullmann coupling reaction provides a novel and efficient method for incorporating alkylthiol groups at C-3 in heterocyclic systems, using copper bronze in pyridine.