Benzothiazole-Containing Analogues of Triclocarban with Potent Antibacterial Activity

Abstract

Triclocarban (TCC) is a polychlorinated, aromatic, antimicrobial agent commercially used since the 1950s in personal care products for the prevention of spoilage and infections. Humans are frequently exposed to TCC due to its widespread use, leading to its substantial release into the aquatic environment. With the recent ban of TCC from some personal care products, implemented in 2016, many replacement antimicrobial compounds have been studied by researchers. Herein, we report the synthesis and biological activity of a series of diarylureas, analogues of TCC that bear the benzothiazole nucleus as one of the two aryl moieties. Among the studied compounds, 2bF and 2eC showed the highest antimicrobial activity against Staphylococcus aureus, being also more active than TCC, with MIC values of 8 µg/mL versus 16 µg/mL of TCC. Moreover, compound 2bB was much more active than TCC against Enterococcus faecalis, a Gram-positive bacterium that is, unfortunately, strongly responsible for nosocomial infections. Finally, interesting results were found for compound 2bG that, even though less active than the others, exerts an interesting bactericidal action.

Recent insights into antibacterial potential of benzothiazole derivatives

“…Out of the studied compounds, 83a demonstrated excellent activity ( MIC = 8 μg/ml), which was 8 times higher than the reference compound TCC (MIC = 64 μg/ml) against E. faecalis . Compounds 83b and 83c exhibited two times more activity (MIC = 8 μg/ml) than reference compound triclocarban (MIC = 16 μg/ml) against S. aureus [ 61 ].

Scheme 18 Chemical reaction involved in the preparation of phenyl urea clubbed benzothiazole analogues ( 83a-c )

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Thidiazuron: New Trends and Future Perspectives to Fight Xylella fastidiosa in Olive Trees

“…TDZ ( N -phenyl- N ′-1,2,3-thiadiazol-5-ylurea) is a substituted diphenylurea compound [ 46 ]. Belonging to the diarylurea class, it may be easily synthesized [ 47 , 48 ], and is also characterized by a low-cost [ 49 ]. It was first reported to have cytokinin activity in 1982 [ 50 ] and since then, TDZ has been used as a growth regulator for abscission of green-turgid leaves of cotton to facilitate the picking of bolls [ 2 ].…”

Benzothiazole‐based apoptosis inducers: A comprehensive overview and future prospective

“…In this regard, nitrogen and sulfur‐containing heterocycles are explored widely. Among them, benzothiazole and amino‐benzothiazole are very privileged heterocycles exhibiting a wide spectrum of pharmacological activity such as antibacterial, [ 6 ] antimicrobial, [ 7 ] antifungal, [ 8 ] antiviral, [ 9 ] antidiabetic, [ 10 ] analgesics, [ 11 ] anticonvulsant, [ 12 ] and antiproliferative activities. [ 13,14 ] Thus, benzothiazoles are model structures with a natural affinity for a variety of biological receptors, making them ideal core scaffolds for the design and synthesis of targeted molecules.…”