5-(Alkylsulfonyl)salicylanilides as potential dental antiplaque agents

Abstract

A series of 22 5-(alkylsulfonyl)salicylanilides was synthesized and evaluated for in vitro antibacterial and antiplaque activity against Actinomyces viscosus and Streptococcus mutans, adherent microorganisms implicated in periodontal disease and dental caries. The minimum inhibitory concentrations of 25 salicylanilides (including 5-acyl-, 5-alkyl-, and 5-(alkylsulfonyl)-4'-bromo- and -4'-(trifluoromethyl)salicylanilides) were found to correlate (r = 0.94) with estimated log D values. Several salicylanilides, such as 5-(decylsulfonyl)- and 5-(dodecylsulfonyl)-4'-(trifluoromethyl)salicylanilides (15 and 19) were found to exhibit high levels of in vitro antibacterial and antiplaque activity against A. viscosus and S. mutans.

Salicylanilides and Their Derivates as Perspective Anti-tuberculosis Drugs: Synthetic Routes and Biological Evaluations

“…ii) Dry benzene is an unsuitable solvent because of health risks and the possible formation of undesired by-products [28]. v) Salicylic acid reacts in acetone with a mixture of trifluoroacetic acid (TFA) and trifluoroacetic acid anhydride (TFAA) resulting in formation of 2,2-dimethyl-4H-benzo[d] [1,3]dioxin-4-one [31]. iv) The hydroxyl group on the starting salicylic acid can be protected as in methyl ethers and salicylic acid is activated using thionyl chloride (reflux 1 h), followed by coupling with aniline at room temperature.…”

“…Salicylanilides (N-substituted hydroxy benzamides) are wellknown organic pharmacological compounds with numerous biological activities, which were initially investigated for their antimicrobial [1] and antifungal activities [2], as well as their usefulness as topical antimycotics and antiplaque agents [3]. Salicylanilides have also found use as molluscicidal [4] or anthelmintic agents [5] in human and veterinary practise.…”

Supervised Learning

“…The two-and three-dimensional models for the Wilson and Famini example [26] have α values near zero which correspond to the MLR used in the original analysis. The example data set from Clark and co-workers [27], on the other hand, which was also originally fitted by MLR gives an α value of 0.55 corresponding to a PLS model. The charge-transfer data shown in the last two sections has also been modelled by continuum regression.…”

Crystal Structure of the 5-Chloro Salicylamides: Three Different Types of the H-bonding Influenced Linear Chain Formation in the Solid State

“…N-Phenyl and N-benzyl salicylamides were investigated for their antimicrobial [1], antifungal [2], and various antiviral properties [3]. These compounds were also used as topical antimycotics and antiplaque [4], molluscicidal [5] and anthelmentic agents [6].…”