18085-24-0Relevant academic research and scientific papers
Occurrence of urea-based soluble epoxide hydrolase inhibitors from the plants in the order Brassicales
Kitamura, Seiya,Morisseau, Christophe,Harris, Todd R.,Inceoglu, Bora,Hammock, Bruce D.
, (2017)
Recently, dibenzylurea-based potent soluble epoxide hydrolase (sEH) inhibitors were identified in Pentadiplandra brazzeana, a plant in the order Brassicales. In an effort to generalize the concept, we hypothesized that plants that produce benzyl glucosinolates and corresponding isothiocyanates also produce these dibenzylurea derivatives. Our overall aim here was to examine the occurrence of urea derivatives in Brassicales, hoping to find biologically active urea derivatives from plants. First, plants in the order Brassicales were analyzed for the presence of 1, 3-dibenzylurea (compound 1), showing that three additional plants in the order Brassicales produce the urea derivatives. Based on the hypothesis, three dibenzylurea derivatives with sEH inhibitory activity were isolated from maca (Lepidium meyenii) roots. Topical application of one of the identified compounds (compound 3, human sEH IC50= 222 nM) effectively reduced pain in rat inflammatory pain model, and this compound was bioavailable after oral administration in mice. The biosynthetic pathway of these urea derivatives was investigated using papaya (Carica papaya) seed as a model system. Finally, a small collection of plants from the Brassicales order was grown, collected, extracted and screened for sEH inhibitory activity. Results show that several plants of the Brassicales order could be potential sources of urea-based sEH inhibitors.
Synthesis of symmetrical and asymmetrical phenethyl thiourea compounds as nonnucleoside inhibitors of HIV-1 reverse transcriptase
Venkatachalam,Uckun, Faith M.
, p. 2039 - 2056 (2005)
Synthesis of symmetrical and asymmetrical phenethyl thioureas was accomplished in two steps with an overall yield of 75-80%. Condensation of a substituted phenethyl amine with thiocarbonyldiimidazole, followed by treatment with one more equivalent of the phenethylamine in DMF, yielded the desired symmetrical phenethyl thiourea compound as a crystalline solid. In the case of asymmetrical thiourea derivatives, different amines were selected and condensed using a similar procedure. A series of 45 thioureas was synthesized. Copyright Taylor & Francis, Inc.
Rapid and highly efficient synthesis of thioureas in biocompatible basic choline hydroxide
Azizi, Najmedin,Farhadi, Elham
, p. 548 - 554 (2017/09/27)
A straightforward and convenient synthesis of symmetrical thiourea derivatives by the reaction of primary amines and carbon disulfide in biocompatible basic choline hydroxide is presented. A variety of biologically important thiourea derivatives can be obtained in good to excellent yields without a tedious work-up under mild reaction conditions. A series of primary aliphatic and aromatic amines with different substituted functional groups have been converted to thiourea derivatives under milder reaction conditions and short reaction times.
Green process development for the synthesis of aliphatic symmetrical N,N'-disubstituted thiourea derivatives in aqueous medium
Jangale, Asha D.,Kumavat, Priyanka P.,Wagh, Yogesh B.,Tayade, Yogesh A.,Mahulikar, Pramod P.,Dalal, Dipak S.
supporting information, p. 236 - 244 (2015/10/29)
A highly efficient green process for the synthesis of N,N'-disubstituted aliphatic thiourea derivatives using primary aliphatic amines and carbon disulfide in aqueous medium at room temperature via a nonisothiocyanate route is described. This protocol illustrates the rapid preparation of N,N'-disubstituted aliphatic thiourea derivatives in excellent yields with some advantages such as no catalyst and simple workup without any side product formation. Moreover the new route is concise, chromatography-free, and adaptable to pilot-scale preparation.
Green Process Development for the Synthesis of Aliphatic Symmetrical N,N ′-Disubstituted Thiourea Derivatives in Aqueous Medium
Jangale, Asha D.,Kumavat, Priyanka P.,Wagh, Yogesh B.,Tayade, Yogesh A.,Mahulikar, Pramod P.,Dalal, Dipak S.
supporting information, p. 376 - 385 (2015/10/29)
A highly efficient green process for the synthesis of N,N′-disubstituted aliphatic thiourea derivatives using primary aliphatic amines and carbon disulfide in an aqueous medium at room temperature via a nonisothiocyanate route is described. This protocol illustrates the rapid preparation of N,N′-disubstituted aliphatic thiourea derivatives in excellent yields with some advantages such as no catalyst and simple workup without any side product formation. Moreover, the new route is concise, does not require chromatography, and is adaptable to pilot-scale preparation. GRAPHICAL ABSTRACT.
A concise synthesis of substituted thiourea derivatives in aqueous medium
Maddani, Mahagundappa R.,Prabhu, Kandikere R.
supporting information; experimental part, p. 2327 - 2332 (2010/07/02)
(Figure Presented) An efficient method for the synthesis of symmetrical and unsymmetrical substituted thiourea derivatives by means of simple condensation between available building blocks such as amines and carbon disulfide in aqueous medium is presented. This protocol works smoothly with aliphatic primary amines to afford various di- and trisubstituted thiourea derivatives. The present method is also useful in synthesizing various substituted 2-mercapto imidazole heterocycles. This method proceeds through a xanthate (amino dithiol deivative) intermediate, unlike isothiocyanate as in an earlier known method.
1-(Methyldithiocarbonyl)imidazole: A useful thiocarbonyl transfer reagent for synthesis of substituted thioureas
Mohanta, Pramod K.,Dhar, Sanchita,Samal,Ila,Junjappa
, p. 629 - 637 (2007/10/03)
1-(Methyldithiocarbonyl)imidazole 1 and its N-methyl quaternary salt 2 have been shown to be efficient methyldithiocarbonyl and thiocarbonyl transfer reagents for the synthesis of dithiocarbamates, symmetrical and unsymmetrical mono-, di- and tri-substituted thioureas in high yields under mild and simple non-hazardous reaction conditions. (C) 2000 Elsevier Science Ltd.
Enzyme induction and comparative oxidative desulfuration of isothiocyanates to isocyanates
Lee, Mei-Sie
, p. 1072 - 1078 (2007/10/03)
Enzyme induction of oxidative metabolism of isothiocyanates to isocyanates by rat liver microsomes and comparative metabolic conversion of some isothiocyanates were investigated. Metabolic activity was assayed by trapping the isocyanate metabolites from isothiocyanates with the inclusion of 2-aminofluorene to form the respective mixed ureas as previously described for the 2-naphthyl isothiocyanate. Male F344 rats were fed either a conventional grain diet for induction with Aroclor 1254 or AIN 76A diet without antioxidant beginning 2 weeks before treatment with Aroclor 1254, β- naphthoflavone, isosafrole, or phenobarbital. Enzymes responsible for the metabolism of 1- and 2-naphthyl isothiocyanate were inducible by all four agents, Aroclor being the best under the current induction protocol and metabolic conversion assay procedure. On the other hand, enzymes responsible for the metabolism of benzyl isothiocyanate were induced only by Aroclor and, to a lesser extent, by phenobarbital. For the comparative metabolic conversion studies, using the microsomes from Aroclor-treated rats fed a conventional grain diet, the rates of metabolic conversion followed the order of 1-naphthyl >> phenyl > benzyl and phenethyl >> propyl, ethyl, and methyl isothiocyanates.
