Structure-activity studies of 5-[[4-(4,5-dihydro-2-oxazolyl) phenoxy]alkyl]-3-methylisoxazoles: inhibitors of picornavirus uncoating.

doi:10.1021/JM00385A021

Paper

Structure-activity studies of 5-[[4-(4,5-dihydro-2-oxazolyl) phenoxy]alkyl]-3-methylisoxazoles: inhibitors of picornavirus uncoating.

Published Feb 1, 1987 · G. Diana, R. C. Oglesby, V. Akullian

Journal of medicinal chemistry

Q1 SJR score

25

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

A series of substituted phenyl analogues of 5-[[4-(4,5-dihydro-2-oxazolyl) phenoxy]alkyl]-3-methylisoxazoles has been synthesized and evaluated in vitro against several human rhinovirus (HRV) serotypes. Substituents in the 2-position greatly enhanced activity when compared to the unsubstituted compound. Many of these compounds exhibited mean MICs (MIC) against five serotypes as low as 0.40 microM. The mean MIC correlated well (r = 0.83) with the MIC80 (the concentration that inhibited 80% of the serotypes tested). A quantitative structure-activity relationship study indicated a strong dependency of MIC on lipophilicity (log P) in combination with inductive effects (sigma m) and bulk factors (MW).

In Vitro Study

Study Snapshot

Substituted phenyl analogues of 5-[[4-(4,5-dihydro-2-oxazolyl) phenoxy]alkyl]-3-methylisoxazoles show enhanced activity against human rhinovirus serotypes, with low mean MICs and strong

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

Structure-activity studies of 5-[[4-(4,5-dihydro-2-oxazolyl) phenoxy]alkyl]-3-methylisoxazoles: inhibitors of picornavirus uncoating.

Sign up to use Study Snapshot

References

Citations

A rearrangement of 3-hydroxyazetidines into 2-oxazolines.

This novel rearrangement sequence of 3-hydroxyazetidines into 2-oxazolines provides high yields and can be scaled-up for a new class of macrocycles.

WIN compounds: on the way to efficient antipicornaviral agent. A historical survey

WIN compounds, such as pleconaril, show potential as efficient antipicornaviral agents by blocking viral uncoating and attachment to host cell receptors.

The Evolution of Pleconaril: Modified O-Alkyl Linker Analogs Have Biological Activity towards Coxsackievirus B3 Nancy

Novel compounds synthesized from pleconaril show strong anti-Coxsackievirus B3 Nancy activity, offering new possibilities for the synthesis of new selective anticoxsackievirus compounds.

The human rhinovirus: human‐pathological impact, mechanisms of antirhinoviral agents, and strategies for their discovery

Antirhinoviral agents from synthetic and natural origin can effectively block viral replication and protect host cells, with potential for efficient lead structure discovery.

Antiinflammatory property of 3-aryl-5-(n-propyl)-1,2,4-oxadiazoles and antimicrobial property of 3-aryl-5-(n-propyl)-4,5-dihydro-1,2,4-oxadiazoles: their syntheses and spectroscopic studies.

3-aryl-5-(n-propyl)-1,2,4-oxadiazoles show antiinflammatory properties and show potential antimicrobial activity against Staphylococcus aureus, Mycobacterium smegmatis, and Candida albicans.

Structure–Activity Relationship Studies of Ethyl 2-[(3-Methyl-2,5-dioxo(3-pyrrolinyl))amino]-4-(trifluoromethyl)pyrimidine-5-carboxylate: An Inhibitor of AP-1 and NF-κB Mediated Gene Expression

Ethyl 2-[(3-methyl-2,5-dioxo(3-pyrrolinyl))amino]-4-(trifluoromethyl)pyrimidine-5-carboxylate] is a novel and potent inhibitor of AP-1 and NF-B

Novel inhibitors of AP-1 and NF-kappaB mediated gene expression: structure-activity relationship studies of ethyl 4-[(3-methyl-2,5-dioxo(3-pyrrolinyl))amino]-2-(trifluoromethyl)++ +pyrimidi ne-5-carboxylate.

The 2-(2′-thienyl) substituted compound (11), identified as the most potent inhibitor of AP-1 and NF-B mediated gene expression, is a novel compound.

Chemotherapy of respiratory viruses: prospects and challenges.

Chemotherapy offers potential for treating respiratory viruses, but current treatments are insufficient for the most common infections.