Convenient synthesis of carbamates, S-alkyl thiocarbamates, and N,N′-disubstituted urea derivatives of methoxycarbonylsulfenyl isocyanate

Torrico-Vallejos, Sonia; Erben, Mauricio F.; Hey‐Hawkins, Evamarie; Védova, Carlos O. Della

doi:10.1016/j.tetlet.2011.08.027

Cited by 7 publications

(1 citation statement)

References 43 publications

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“…Previous work in our laboratory resulted in the development of the one-pot procedure for the Hofmann rearrangement of aromatic or aliphatic amides, which led to the synthesis of a series of carbamates and cyclic ureas 15 . With regard to the synthesis of these classes of compounds, different protocols have been reported in the literature 16 , 17 . Carbamate derivatives with a recognizable –O–CO–NH– moiety encompass multiple applications in bioorganic and medicinal chemistry 18–24 .…”

Section: Introductionmentioning

confidence: 99%

α-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives

Popović‐Djordjević

Jevtić

Grozdanić

et al. 2017

Journal of Enzyme Inhibition and Medicinal Chemistry

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The inhibitory activities of selected cyclic urea and carbamate derivatives (1–13) toward α-glucosidase (α-Gls) in in vitro assay were examined in this study. All examined compounds showed higher inhibitory activity (IC50) against α-Gls compared to standard antidiabetic drug acarbose. The most potent was benzyl (3,4,5-trimethoxyphenyl)carbamate (12) with IC50 = 49.85 ± 0.10 µM. In vitro cytotoxicity of the investigated compounds was tested on three human cancer cell lines HeLa, A549 and MDA-MB-453 using MTT assay. The best antitumour activity was achieved with compound 2 (trans-5-phenethyl-1-phenylhexahydro-1H-imidazo[4,5-c]pyridin-2(3H)-one) against MDA-MB-453 human breast cancer cell line (IC50 = 83.41 ± 1.60 µM). Cyclic ureas and carbamates showed promising anti-α-glucosidase activity and should be further tested as potential antidiabetic drugs. The PLS model of preliminary QSAR study indicated that, in planing the future synthesis of more potent compounds, the newly designed should have the substituents capable of polar interactions with receptor sites in various positions, while avoiding the increase of their lipophilicity.

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Section: Introductionmentioning

confidence: 99%

α-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives

Popović‐Djordjević

Jevtić

Grozdanić

et al. 2017

Journal of Enzyme Inhibition and Medicinal Chemistry

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Synthesis of Unsymmetrical Ureas andS-Thiocarbamates under Catalyst-free Conditions in a [BMIM]BF₄Ionic Liquid

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Bis(thiocarbamates): Synthesis and Substituent Effects on the Barrier to N‐CO Rotation

Maouati

Sanhoury

Merlet

et al. 2015

Heteroatom Chemistry

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Convenient synthesis of carbamates, S-alkyl thiocarbamates, and N,N′-disubstituted urea derivatives of methoxycarbonylsulfenyl isocyanate

Cited by 7 publications

References 43 publications

α-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives

α-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives

Synthesis of Unsymmetrical Ureas andS-Thiocarbamates under Catalyst-free Conditions in a [BMIM]BF₄Ionic Liquid

Bis(thiocarbamates): Synthesis and Substituent Effects on the Barrier to N‐CO Rotation

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Convenient synthesis of carbamates, S-alkyl thiocarbamates, and N,N′-disubstituted urea derivatives of methoxycarbonylsulfenyl isocyanate

Cited by 7 publications

References 43 publications

α-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives

α-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives

Synthesis of Unsymmetrical Ureas andS-Thiocarbamates under Catalyst-free Conditions in a [BMIM]BF4Ionic Liquid

Bis(thiocarbamates): Synthesis and Substituent Effects on the Barrier to N‐CO Rotation

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Synthesis of Unsymmetrical Ureas andS-Thiocarbamates under Catalyst-free Conditions in a [BMIM]BF₄Ionic Liquid