54568-11-5

Usage

InChI:InChI=1/C7H11N3/c1-4-5(2)9-7(8)10-6(4)3/h1-3H3,(H2,8,9,10)

Upstream product

• 420-04-2 CYANAMID 
• 23652-87-1 4-amino-3-methyl-3-penten-2-one 
• 113-00-8 guanidine nitrate 
• 815-57-6 3-Methyl-2,4-pentanedione 
• 593-85-1 diguanidine carbonate 
• 1522-25-4 4-hydroxy-3-methylpent-3-en-2-one 

Downstream Products

• 873411-48-4 4-acetylamino-N-(4,5,6-trimethyl-pyrimidin-2-yl)-benzenesulfonamide 
• 1104066-58-1 2-(2,6-dibromophenyl)-3-(4,5,6-trimethylpyrimidin-2-yl)thiazolidin-4-one 
• 70826-02-7 N-phenethyl-N'-(4,5,6-trimethyl-pyrimidin-2-yl)-guanidine 

Relevant academic research and scientific papers

Design, microwave-assisted synthesis and HIV-RT inhibitory activity of 2-(2,6-dihalophenyl)-3-(4,6-dimethyl-5-(un)substituted-pyrimidin-2-yl)th iazolidin-4-ones

A series of novel thiazolidin-4-ones bearing a hydrophobic substituent at 5-position on the 4,6-dimethyl-pyrimidine ring at N-3 (5c-i and 6c-i) were designed on the prediction of QSAR studies, synthesized in good yields of 60.1-85.3% by microwave-assisted one-pot protocol with the combination of using dicyclohexylcarbonimide (DCC) as the promotor, and evaluated as HIV-1 reverse transcriptases inhibitors. The results of in vitro HIV-1 RT kit assay showed that some of the new compounds, such as 5c, 6c, 5d, 6d, 5g, 5h and 6i, could effectively inhibit RT activity. Among them, compounds 5c and 6c where ethyl group existed at 5-position on N-3 pyrimidine ring were the best ones with the IC50 value of 0.26 μM and 0.23 μM, respectively. Structure-activity relationship analysis of these analogues suggested that the overall hydrophobicity and steric factor were important to the anti-HIV RT activity. The mechanism of the intramolecular cycloamidation promoted by DCC was also investigated with the key uncyclized intermediate 13.

Synthesis and evaluation of 2-(2,6-dihalophenyl)-3-pyrimidinyl-1,3-thiazolidin-4-one analogues as anti-HIV-1 agents

A series of 2-(2,6-dihalophenyl)-3-(substituted pyrimidinyl)-1,3-thiazolidin-4-ones were designed on the prediction of quantitative structure-activity relationship (QSAR) studies, synthesized, and evaluated as HIV-1 reverse transcriptase inhibitors. Our attempts in correlating the identified molecular surface features related properties for modeling the HIV-1 RT inhibitory activity resulted in some statistically significant QSAR models with good predictive ability. The results showed that compounds 4m and 4n were highly active in inhibiting HIV-1 replication with EC50 values in the range of 22-28 nM in MT-4 as well as in CEM cells with selectivity indexes of >10,000. The derived models collectively suggest that the compounds should be compact without bulky substitution on its peripheries for better HIV-1 RT inhibitory activity. These models also indicate a preference for hydrophobic compounds to obtain good HIV-1 RT inhibitory activity.

THE REACTION OF β-AMINOENONES WITH CYANAMIDE. A HIGH EFFICIENT SYNTHESIS OF 2-AMINOPIRIMIDINES.

β-aminoenones react with cyanamide, molar ratio 1:2, to yield 2-aminopyrimidines in nearly quantitative yields.