6307-40-0

Usage

General Description

2-amino-6-(methylsulfanyl)pyrimidin-4(3H)-one, also known as 2-amino-6-mercaptopyrimidin-4-one, is a chemical compound with the molecular formula C5H6N4OS. It is a pyrimidine derivative with a sulfur atom attached to the sixth position of the pyrimidine ring. 2-amino-6-(methylsulfanyl)pyrimidin-4(3H)-one has several potential industrial and pharmaceutical applications, as it is a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. It is also used in the production of dyes, pigments, and other specialty chemicals. Additionally, its properties make it a potential candidate for use in the development of new drugs and materials.

Upstream product

• 6973-81-5 2-amino-6-mercaptopyrimidin-4(3H)-one 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

Structural studies of pterin-based inhibitors of dihydropteroate synthase

Dihydropteroate synthase (DHPS) is a key enzyme in bacterial folate synthesis and the target of the sulfonamide class of antibacterials. Resistance and toxicities associated with sulfonamides have led to a decrease in their clinical use. Compounds that bi

Monocyclic Pteridine Analogues. Inhibition of Escherichia coli Dihydropteroate Synthase by 6-Amino-5-nitrosoisocytosines

A variety of 5,6-disubstituted isocytosine derivatives were evaluated in vitro as inhibitors of dihydropteroate synthase from Escherichia coli.A number of 6-(alkylamino)-5-nitrosoisocytosines have in vitro potency equivalent with or superior to that of therapeutically effective sulfonamide inhibitors of the synthase.The sulfonamide drugs are known to complete for the p-aminobenzoic acid binding site of the synthase, and kinetic analysis of inhibition of the synthase by 6-(methylamino)-5-nitrosoisocytosine (16; I50 = 1.6 μM) and by the 6-(3-phenoxypropyl)amino analogue (33; I50 = 3.7 μM) indicated that the nitrosoisocytosine inhibitors compete with the pteridine substrate for the enzyme.Structure-activity studies demonstrated that the enzyme surface has a low tolerance for steric bulk in the region surrounding the isocytosine 6-amino function.However, this steric intolerance may be counterbalanced to a significant degree by positive allosteric interactions achieved by certain analogues that have a 6-(ω-phenylalkyl)amino substituent.For example, 6--5-nitrosoisocytosine (28) is as effective an inhibitor (I50 = 1.4 μM) as the 6-methylamino compound 16.Although several members of the 5-nitroso series were potent synthase inhibitors, none of the nitrosoisocytosines exhibited significant antibacterial activity.This observation may reflect poor transport of these compounds through the bacterial cell wall or, alternatively, may result from a rapid metabolic inactivation process.