2740-94-5

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 18, p. 779, 1953 DOI: 10.1021/jo50013a002

InChI:InChI=1/C9H12N2S/c1-10-9(12)11-7-8-5-3-2-4-6-8/h2-6H,7H2,1H3,(H2,10,11,12)

Upstream product

• 593-51-1 methylamine hydrochloride 
• 622-78-6 Benzyl isothiocyanate 
• 74-89-5 methylamine 
• 79645-01-5 N₁,N₃-dimethyl-N₁-nitrosothiourea 
• 100-46-9 benzylamine 
• 2438-90-6 N,N'-dimethylthioperoxydicarbamic acid 
• 556-61-6 methyl thioisocyanate 

Downstream Products

• 83507-22-6 2-[(Z)-Benzylimino]-3-methyl-4-methylene-thiazolidin-5-one 
• 76070-78-5 C₁₀H₁₄N₄S*2ClH 
• 85464-41-1 2-[(Z)-Benzylimino]-4-chloro-3-methyl-thiazolidin-5-one 
• 85464-40-0 3-Benzyl-4-chloro-2-[(Z)-methylimino]-thiazolidin-5-one 
• 6957-05-7 N-methyl-N'-benzylurea 
• 1449280-36-7 1-benzyl-3,4,5-trimethyl-1H-imidazole-2(3H)-thione 
• 1449280-44-7 2-[[2-(benzyloxycarbonylamino)-3-phenyl-propanoyl]amino]-6-(1-benzyl-3,4,5-trimethyl-imidazol-3-ium-2-yl)sulfanyl-5-oxo-hexanoic acid bromide 

Relevant academic research and scientific papers

Catalytic Asymmetric Synthesis of Quaternary Barbituric Acids

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.

N-methylthioureas as new agonists of retinoic acid receptor-related orphan receptor

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.

A simple and green procedure for the synthesis of N-benzylthioureas

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.

Synthesis and biological evaluation of 3-benzyl-1-methyl- and 1-methyl-3-phenyl-isothioureas as potential inhibitors of iNOS

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.

A high-yielding and facile preparation of N-substituted thioureas by substitution of nitrosothioureas with alkylamines

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.

A convenient route to cyanoguanidines

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.

Synthesis of N,N'-disubstituted N''-2-(2-quinolinylmethylthio)ethylguanidines as potential anticancer agents

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.