Synthesis and antiallergic activity of dimethyl-2-(phenylcarbamoyl)ethylsulfonium p-toluenesulfonate derivatives.

doi:10.1021/JM970285Z

Paper

Synthesis and antiallergic activity of dimethyl-2-(phenylcarbamoyl)ethylsulfonium p-toluenesulfonate derivatives.

Published Aug 1, 1998 · Yukio Tada, I. Yamawaki, S. Ueda

Journal of medicinal chemistry

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7

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0

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Abstract

The derivatives of dimethyl-2-(phenylcarbamoyl)ethylsulfonium p-toluenesulfonates were synthesized and evaluated for antiallergic activity. The 2,3-dihydroxyethoxy group was introduced to the phenyl ring from the standpoint of lipophilicity and electronic effects of substituent. The IgE-induced rat passive cutaneous anaphylaxis (PCA) was inhibited by oral administration of several substituted 2-[(4-propoxyphenyl)carbamoyl]ethyldimethylsulfonium p-toluenesulfonate derivatives. Among them (+/-)-2-[N-[4-(3-ethoxy-2-hydroxypropoxy)phenyl]carbamoyl]ethyldimeth ylsulfonium p-toluenesulfonate (1a, IPD-1151T) was found to possess considerable activity in the PCA test, and it was launched as Suplatast tosilate in Japan.

Non-RCT

Animal Study

Study Snapshot

Dimethyl-2-(phenylcarbamoyl)ethylsulfonium p-toluenesulfonate derivatives show antiallergic activity, with Suplatast tosilate being the most effective.

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 antiallergic activity of dimethyl-2-(phenylcarbamoyl)ethylsulfonium p-toluenesulfonate derivatives.

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References

Citations

Synthesis and structural characterization of 2,3-bis(hydroxymethyl)-2,3-dinitro-1,4-butanediol tetra p -toluenesulfonate

The synthesized compound has a melting point of 400.25 K and decomposition temperature of 510.70 K, making it a promising candidate for a novel anti-inflammatory agent.

Substituted 2-phenyl-benzimidazole derivatives: novel compounds that suppress key markers of allergy.

These novel compounds show potential for treating various forms of asthma by suppressing key markers of allergy, including IgE response and IL-4, IL-5, and CD23 expression.

Optimal Lipophilicity of Sulfonium p-Toluenesulfonate as Anti-allergic Drug

The optimal lipophilicity of sulfonium compounds for anti-allergy drugs is approximately zero, with optimal values being 0.07 and 0.06.

Lead Optimization of Dimethyl(2-phenoxyethyl)sulfonium p-Toluenesulfonate for the Development of an Anti-allergic Agent

The lead compound 2-[4-(3-ethoxy-2-hydroxypropoxy)phenoxy]ethyldimethyl-sulfonium p-toluenesulfonate (11) shows potential as an anti-allergic agent for type I allergic diseases, with potential toxicity and

Lead Evolution in Development of an Anti-allergic Agent ; Dimethyl(2-phenoxyethyl)sulfonium p-Toluenesulfonate as the Secondary Lead Compound

Dimethyl(2-phenoxyethyl)sulfonium p-toluenesulfonate (5) shows potential as an anti-allergic agent for type I allergic diseases, with potential correlations between hydrophobicity and anti-allergic activity.