Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles.

doi:10.1021/JM00401A009

Paper

Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles.

Published Jun 1, 1988 · I. Ager, A. C. Barnes, G. Danswan

Journal of medicinal chemistry

Q1 SJR score

112

Citations

2

Influential Citations

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Abstract

4H-Imidazo[2,1-c][1,4]benzoxazine-2-carboxylic acid (3) was found to possess potent activity in the IgE-induced rat passive cutaneous anaphylaxis model which may be predictive of clinical antiallergic activity. Compared to disodium cromoglycate (DSCG, 1), 3 was less active following iv administration but unlike DSCG showed very significant oral activity. To explore the structural requirements for this activity, a range of tricyclic compounds was prepared and their activities were measured. Individual 2-carboxylic acids derived from imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles showed iv activities up to 10(3) times as potent as DSCG and many of them showed significant oral activity. From these, imidazo[1,2-a]quinoxaline-2-carboxylic acid 114 has been chosen for further development.

Non-RCT

Animal Study

Highly Cited

Study Snapshot

Imidazo[1,2-a]quinoxaline-2-carboxylic acid 114 shows significant oral antiallergic activity, with potential for further development as a clinical treatment for IgE-induced rat anaphylaxis.

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 and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles.

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References

Citations

Palladium supported on alumina as a highly active heterogeneous catalyst for direct arylation of 6-substituted imidazo[2,1-b]thiadiazole via C H bond activation reaction

This study presents a fast, eco-friendly, and reusable method for the green synthesis of 5,6-disubstituted imidazo[2,1-b]thiadiazole derivatives using a heterogeneous palladium catalyst in triethylammonium ionic liquid

Access to 2,3‐Unsubstituted Imidazo[2,1‐b][1,3]benzothiazole Using Ethylene Glycol as a C2 Precursor and Subsequent Regioselective C3 Functionalization

Ethylene glycol as a C2 precursor can be used to synthesize 2,3-unsubstituted imidazo[2,1b][1,3]benzothiazoles, which can be regioselectively converted to 3substituted imidazo[

A Glycerol promoted, regioselective synthesis of 6‐aryl substituted Imidazo[2,1‐b]thiazole and imidazo[2,1‐b]‐1,3,4‐thiadiazole through a one‐step domino process under green conditions

This study presents a green, efficient, and cost-effective strategy for synthesizing Imidazo[2,1b]thiazole and Imidazo[2,1b][1,3,4]thiadiazole using glycerol as a sustainable solvent.

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

Iodine and DMSO can be used as environmentally friendly alternatives to expensive metal and non-metal reagents in organic synthesis, offering a more sustainable solution for valuable chemical scaffolds.

A Three-Component, One-Pot Synthesis of Novel Benzimidazo[2,1-b]Thiazoles from Thiobarbituric Acid under Thermal and Microwave-Assisted Conditions

This study presents a three-component, one-pot synthesis of novel benzimidazo[2,1-b]thiazoles from thiobarbituric acid, offering potential for antitumor, antimicrobial, and antibacterial properties in pharmaceutical chemistry.

Rejuvenating the [1, 2, 3]-triazolo [1,5-a]quinoxalin-4(5H)-one scaffold: Synthesis and derivatization in a sustainable guise and preliminary antimicrobial evaluation

The [1,2,3]-triazolo [1,5-a]quinoxalin-4(5H)-one scaffold has been rejuvenated using eco-friendly catalysts and reaction conditions, allowing for extensive decoration activity and preliminary antimicrobial evaluation.

Design, synthesis and biological evaluation of benzo-[d]-imidazo-[2,1-b]-thiazole and imidazo-[2,1-b]-thiazole carboxamide triazole derivatives as antimycobacterial agents

The imidazo-[2,1-b]-thiazole derivatives show selective inhibition of Mycobacterium tuberculosis, with no acute cellular toxicity observed.

Syntheses and Applications of 1,2,3-Triazole-Fused Pyrazines and Pyridazines

1,2,3-triazole-fused pyrazine and pyridazines are useful in medicinal chemistry, as fluorescent probes, and as structural units in polymers.