- Searching for small molecules as antibacterials: Non-cytotoxic diarylureas analogues of triclocarban
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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.
- Catalano, Alessia,Iacopetta, Domenico,Rosato, Antonio,Salvagno, Lara,Ceramella, Jessica,Longo, Francesca,Sinicropi, Maria Stefania,Franchini, Carlo
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- COMPOSITIONS AND METHODS FOR THE TREATMENT OF CANCER
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This disclosure relates to compounds, pharmaceutical compositions comprising them, and methods of using the compounds and compositions for treating diseases related to Heat Shock Transcription Factor 1 (HSF1) activity and/or function. More particularly, this disclosure relates to methods of inhibiting HSF1 activity with these compounds and pharmaceutical compositions thereof, and methods of treating diseases associated with HSF1 activity and/or function, such as cancer.
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Paragraph 0183
(2020/07/08)
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- Unsymmetrically disubstituted urea derivatives: A potent class of antiglycating agents
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A series of unsymmetrically disubstituted urea derivatives 1-28 has been synthesized and screened for their antiglycation activity in vitro. Compounds 26 (IC50 = 4.26 ± 0.25 μM), 1 (IC50 = 5.8 ± 0.08 μM), 22 (IC50 = 4.26 ± 0.25 μM), 6 (IC50 = 6.4 ± 0.02 μM), 5 (IC50 = 6.6 ± 0.26 μM), 2 (IC50 = 7.02 ± 0.31 μM), 3 (IC50 = 7.14 ± 0.84 μM), 27 (IC50 = 7.27 ± 0.36 μM), 4 (IC50 = 8.16 ± 1.04 μM), 21 (IC50 = 8.4 ± 0.15 μM), 23 (IC50 = 9.0 ± 0.35 μM) and 13 (IC50 = 15.22 ± 6.7 μM) showed an excellent antiglycation activity far better than the standard (rutin, IC50 = 41.9 ± 2.3 μM). This study thus provides a series of potential molecules for further studies of antiglycation agents.
- Khan, Khalid M.,Saeed, Sumayya,Ali, Muhammad,Gohar, Madiha,Zahid, Javariya,Khan, Ambreen,Perveen, Shahnaz,Choudhary, M. Iqbal
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experimental part
p. 2447 - 2451
(2009/09/05)
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- Promotion of the [PPN][Rh(CO)4]-catalysed carbonylation of nitrobenzene by 2-hydroxypyridine and related molecules: An apparent bifunctional activation
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2-Hydroxypyridine and related molecules have a large activating effect on the previously reported [PPN][Rh(CO)4]-based catalytic system for the reductive carbonylation of nitrobenzene to methyl phenylcarbamate (PPN+=(PPh3)2N+). The effect is not due to the known 2-hydroxypyridine-2-pyridone tautomeric equilibrium, since 4-hydroxypyridine, for which the same tautomeric equilibrium exists, completely inhibits the reaction. A promoting effect of 2-hydroxypyridine is also observed in the reactions of a previously isolated metallacyclic complex, [PPN][Rh(CO)2ON(Ar)C(O)O], believed to be an intermediate in the catalytic reactions. However, the dependence of the rate of the catalytic reactions on the aniline concentration indicates that the effect found for the stoichiometric reaction cannot be the one that is relevant for the acceleration of the catalytic reactions. Thus, two different effects are present, both of which appear to be due to the proximal positions of a basic and an acidic site in the promoter molecules.
- Ragaini, Fabio,Gallo, Emma,Cenini, Sergio
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p. 109 - 118
(2007/10/03)
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- Synthesis and structure activity relationships in diphenylureas against Culex quinouefasciatus
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Substituted diphenylureas 1-23 have been synthesised from isocyanates generated from azides of benzoic acid and 4-chlorobenzoic acid with aniline, and 4-chloro-, 2-trifluoromethyl-, 3-trifluoromethyl, 4-phenoxy-, 2,4-dichloro-, 2,5-dichloro-, 3,4-dichloro-, 3-chloro-4-methoxy-, 3-chloro-2-methyl-, 3-chloro-4-methyl- and 4-nitro-anilines. All the compounds have been tested for insect growth regulating (IGR) activity against early third instar larvae of Culex quinquefasciatus, the human filariasis vector. Compounds 15 and 19 exhibit 100 percent emergence inhibition at 1 ppm concentration against Cx quinquefasciatus larvae. These compounds may play a useful role in mosquito control by maintaining the vector populations at a minimum level.
- Minatchy, S.,Mathew, Nisha
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p. 1066 - 1068
(2007/10/03)
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