- Catalytic Asymmetric Synthesis of Quaternary Barbituric Acids
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The catalytic asymmetric α-functionalization of prochiral barbituric acids, a subtype of pseudosymmetric 1,3-diamides, to yield the corresponding 5,5-disubstituted (quaternary) derivatives remains essentially unsolved. In this study 2-alkylthio-4,6-dioxopirimidines are designed as key 1,3-diamide surrogates that perform exceedingly in amine-squaramide catalyzed C-C bond forming reactions with vinyl ketones or Morita-Baylis-Hillmann-type allyl bromides as electrophiles. Mild acid hydrolysis of adducts affords barbituric acid derivatives with an in-ring quaternary carbon in unprecedented enantioselectivity, offering valuable materials for biological evaluations.
- Del Pozo, Sandra,Vera, Silvia,Oiarbide, Mikel,Palomo, Claudio
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supporting information
p. 15308 - 15311
(2017/11/06)
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- N-methylthioureas as new agonists of retinoic acid receptor-related orphan receptor
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Thirty two thiourea derivatives were prepared and their agonistic activities on the retinoic acid receptor-related orphan receptor α (RORα) were evaluated. The replacement of the 3-allyl-2-imino-thiazolidin- 4-one moiety of the lead compound CGP52608 (1) with various functional group substituted aromatic rings, improved the agonistic activity of RORα. Among the prepared derivatives, 1-methyl-3-(4-phenoxy-benzyl)-thiourea (32) showed 2.6-fold higher agonistic activity than CGP52608 in the RORα-activation assay.
- Park, Yohan,Hong, Suckchang,Lee, Myungmo,Jung, Hyojun,Cho, Won-Jea,Kim, Eun-Jin,Son, Ho-Young,Lee, Mi-Ock,Park, Hyeung-Geun
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p. 1393 - 1401
(2013/01/15)
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- A simple and green procedure for the synthesis of N-benzylthioureas
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A simple and efficient reaction protocol for the synthesis of N-benzylthioureas is described from benzylisothiocyanate (BITC: 94% pure/GC-MS), isolated from crushed papaya seeds.
- De Sequeira Aguiar, Lucia C.,Viana, Gil M.,Dos Santos Romualdo, Marcus V.,Costa, Marcio V.,Bonato, Bruno S.
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experimental part
p. 540 - 544
(2012/06/01)
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- Synthesis and biological evaluation of 3-benzyl-1-methyl- and 1-methyl-3-phenyl-isothioureas as potential inhibitors of iNOS
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Novel benzyl- and phenyl-isothioureidic derivatives have been synthesised and evaluated as inhibitors of nitric oxide synthesis, induced in lipopolysaccharide (LPS)-activated J774.A1 macrophage cell line. The most potent iNOS inhibitor resulting was 1-methyl-3-phenyl-S-methyl isothiourea 5l.
- Paesano, Nicola,Marzocco, Stefania,Vicidomini, Caterina,Saturnino, Carmela,Autore, Giuseppina,De Martino, Giovanni,Sbardella, Gianluca
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p. 539 - 543
(2007/10/03)
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- A high-yielding and facile preparation of N-substituted thioureas by substitution of nitrosothioureas with alkylamines
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High yields of N-mono- or di- alkyl substituted thioureas are readily achieved by the reaction of nitrosothioureas with alkylamines in acetonitrile at room temperature.
- Xian,Zhu,Li,Cheng
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p. 1957 - 1960
(2007/10/03)
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- A convenient route to cyanoguanidines
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A facile and versatile method for the preparation of cyanoguanidines 7 from amines 3 and isothiocyanates 4 via a methylation, cyanamide-treatment sequence is described.
- Novak, Lajos,Hanania, Michel,Kovacs, Peter,Kovacs, Csilla Erika,Kolonits, Pal,Szantay, Csaba
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p. 1757 - 1766
(2007/10/03)
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- Synthesis of N,N'-disubstituted N''-2-(2-quinolinylmethylthio)ethylguanidines as potential anticancer agents
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A simple method for obtaining the title compounds was found in the alkaline rearrangement of S-2-aminoethylisothirouronium salts, which were obtained from the condensation of thiourea or substituted thioureas with 2-bromoethylamine hydrobromide. No activity was found for the substituted guanidines against P388 lymphocytic leukemia in mice, or as H2-receptor antagonists.
- Foye,An,Maher
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p. 1168 - 1170
(2007/10/02)
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