- 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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- Method for synthesizing asymmetric disubstituted urea through catalytic oxidation and carbonylation
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The invention discloses a novel method for directly synthesizing asymmetric disubstituted urea compounds. The method comprises the step of adding a palladium catalyst into a solvent polyethylene glycol or a polyethylene glycol water solution under the action of alkali, an iodine compound and an oxidant so as to catalyze direct cross coupling reaction of primary amine and carbon monoxide, so as to prepare the asymmetric disubstituted urea compounds. The method for preparing the asymmetric disubstituted urea compounds through the coupling reaction has the advantages that the catalyst is wide in source and environment-friendly; a substrate is wide in source, cheap and easy to process; a carbonyl is stable in source and cheap and does not generate waste; a ligand is not required in the reaction, and the reaction activity is good; reaction conditions are mild, and the reaction selectivity is high; the substrate has good functional group consistency and is wide in application range; and a reaction medium is environment-friendly and can be circularly recycled. The separation yield of a target product can reach up to about 97% under optimized reaction conditions.
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Paragraph 0091; 0092
(2017/12/28)
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- Skin wash compositions comprising triclocarban and surfactants
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The compositions of the present invention are useful for the topical delivery of a wide variety of active ingredients. These compositions are particularly useful for treating conditions such as acne and its attendant skin lesions, blemishes, and other imperfections. These compositions are nonirritating to the skin and also provide skin feel benefits. These compositions can be in the form of leave-on products and products that are rinsed or wiped from the skin after use.
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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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- Compositions
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The problem of providing a storage stable anti-calculus toothpaste comprising a tripolyphosphate salt is remedied by incorporating more than 4% of the salt and having the pH from about 8 to about 10. A tripolyphosphate salt may also be combined with a noncationic anti-bacterial agent such as triclosan to provide a composition having anti-calculus and anti-plaque activity.
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- Process for the preparation of N-aryl-N'-(mono- or di substituted)-urea derivatives
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The invention relates to a new method for the preparation of N-aryl-N'-(mono- or disubstituted)-urea derivatives having the general formula (I), STR1 wherein Aryl is an optionally substituted phenyl group, and R1 and R2 each stand for an optionally substituted alkyl, cycloalkyl, alkoxy or phenyl group, or R1 and R2 may form, together with the adjacent nitrogen atom, a nitrogen-containing heterocyclic group which may contain a further hetero atom, or one of R1 and R2 may also stand for hydrogen, with the proviso that if one of R1 and R2 is an optionally substituted phenyl group, the other may represent only hydrogen atom or an optionally substituted alkyl or alkoxy group, by reacting a carbamate of the general formula (II) with an amine of the general formula (III), or a carbamate of the general formula (IV) with an amine of the general formula (V), wherein R1, R2 and Aryl are as defined above and X is a lower alkoxy, phenoxy or substituted phenoxy group, in the presence of a tertiary amine catalyst. According to the invention a tertiary alkylamine containing altogether at least 6 carbon atoms and minimum one alkyl chain with at least 4 carbon atoms or a mixture of such tertiary alkylamines is applied as catalyst.
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