16655-20-2Relevant articles and documents
Searching for small molecules as antibacterials: Non-cytotoxic diarylureas analogues of triclocarban
Catalano, Alessia,Iacopetta, Domenico,Rosato, Antonio,Salvagno, Lara,Ceramella, Jessica,Longo, Francesca,Sinicropi, Maria Stefania,Franchini, Carlo
, p. 1 - 13 (2021/03/15)
Triclocarban (TCC), a broad-spectrum lipophilic antimicrobial agent, is a diarylurea derivative that has been used for more than 60 years as a major ingredient of toys, clothing, food packaging materials, food industry floors, medical supplies and especially of personal care products, such as soaps, toothpaste and shampoo. In September 2016, the U.S. FDA banned nineteen antimicrobial ingredients, including TCC, in over-the-counter consumer antiseptic wash products, due to their toxicity. Withdrawal of TCC has prompted efforts to search for new antimicrobial compounds. In this paper, we present the synthesis and biological evaluation, as antibiotic and non-cytotoxic agents, of a series of diarylureas, analogues of TCC. These compounds are characterized by an intriguingly simple chemistry and can be easily synthesized. Among the synthesized compounds, 1ab and 1bc emerge as the most interesting compounds as they show the same activity of TCC (MIC = 16 μg/mL) against Staphylococcus aureus, and a higher activity than TCC against Enterococcus faecalis (MIC = 32 μg/mL versus MIC = 64 μg/mL). Moreover, 1ab and 1bc show no cytotoxicity towards the human mammary epithelial cells MCF-10A and embryonic kidney epithelial cells Hek-293, in opposition to TCC, which exhibits a marked cytotoxicity on the same cell lines and shows a good antitumor activity on a panel of cell lines tested.
Antischistosomal activity of N,N′-arylurea analogs against Schistosoma japonicum
Yao, Houzong,Liu, Fengyou,Chen, Jinglei,Li, Yan,Cui, Jinhao,Qiao, Chunhua
supporting information, p. 1386 - 1390 (2016/02/19)
Although the antischistosomal activities of N,N′-arylurea analogs were reported, systematic structure-activity relationships have not been conducted. In this Letter, we reported the design, synthesis and evaluation of 45 N,N′-arylurea analogs. Among these prepared compounds, 13 compounds were urea linker modified and 32 were N,N′-arylurea derivatives. The activity evaluation revealed 12 analogs exhibited IC50 values lower than 22.6 μM, and 7 of them had IC50 less than 10 μM against the juvenile Schistosoma japonicum in vitro. Their worm killing potency was even higher against adult worm. Unfortunately, low to moderate worm burden reduction of 0-33.4% was recorded after administration of a single oral dose of 200 mg/kg or 400 mg/kg to mice harboring S. japonicum.
