Studies on Synthesis of Some Novel Thioureides of 2-(4-Methyl-phenoxymethyl)benzoic Acid with Antimicrobial Activity

Abstract

Thioureides of 2-(4-methyl-phenoxymethyl)benzoic acid have been synthesised by reaction of 2-(4-methyl-phenoxymethyl)benzoyl isothiocyanate with primary aromatic amines. The mentionated isothiocyanate was obtained in the reaction of the 2-(4-methyl-phenoxymethyl)benzoic acid chloride with ammonium thiocyanate. The acid chloride was prepared by reacting the coresponding acid, the 2-(4-methyl-phenoxymethyl)benzoic acid, with thionyl chloride and the aforementioned acid from potassium para-cresolate with phtalide. The reaction conditions were established to ensure the best yields. These new thioureides have been characterized by means of elemental analysis, IR and NMR spectral studies.

Recent developments in chemistry, coordination, structure and biological aspects of 1-(acyl/aroyl)-3-(substituted) thioureas

“…Many reported examples have demonstrated the varied biological activities of thioureas, such as antitumor [7], antiviral [8], antimicrobial [9], antiparasitic [10], insecticidal [11], herbicidal [12], pesticidal and fungicidal properties [13,14]. The 1H-benzimidazol thiourea derivatives evolved as promising anti-HIV and antibacterial agents [15,16].…”

Competing intramolecular NHOC hydrogen bonds and extended intermolecular network in 1-(4-chlorobenzoyl)-3-(2-methyl-4-oxopentan-2-yl) thiourea analyzed by experimental and theoretical methods

“…These are promising potential compounds for developing novel chemosensors for selective and sensitive naked-eye recognition for anions [20,21]. Moreover, important new developments on biological [22] and pharmaceutical [23][24][25] applications of 1-acyl thioureas rely in the formation of proper hydrogen bonds with particular receptors [26].…”

New N-acyl Thiourea Derivatives: Synthesis, Standardized Quantification Method and In Vitro Evaluation of Potential Biological Activities

“…The synthesis of the 2-((4-methoxyphenoxy)methyl)benzoic acid (Scheme 1) and 2-((4-methoxyphenoxy)methyl)benzoic acid chloride (3) were presented in a previous article [35,72].…”

“…The benzo [d]thiazole-based N-acyl thiourea derivatives (1a-1g) were designed and synthesized according to a previously published method, with punctual modifications [34,35], characterized by in silico and experimental approaches and evaluated for their biological properties. Furthermore, a routine quality control method for quantitative evaluation of the most promising compound (1d) has been developed and validated by reversed-phase high-performance liquid chromatography (RP-HPLC).…”