128276-95-9

Upstream product

• 4651-91-6 3-cyano-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene 
• 140-29-4 phenylacetonitrile 
• 108-94-1 cyclohexanone 

Relevant academic research and scientific papers

Synthesis and DNase I inhibitory properties of some 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines

A series of six novel and six known thieno[2,3-d]pyrimidin-4-amines 2–13 were synthesized, and further were used as a starting material for preparation of a small series of eight novel thieno[2,3-d]pyrimidin-4-phthalimides 14–21. Eight compounds, five amine and three phthalimide derivatives, inhibited bovine pancreatic DNase I with an IC50 below 200 μM, being more effective than referent inhibitor crystal violet. Phthalimide derivatives 16, 18 and 19 exhibited higher DNase I inhibitory activity compared to their amine precursors 7, 10 and 11. Compound 19, as the most potent (IC50 = 106 ± 16 μM), offers a good starting point for a design of new DNase I inhibitors. The Pharma RQSAR model showed a significant enhancement of thieno[2,3-d]pyrimidines activity using aryl substituents at R1 position. The E-State RQSAR model clarified the most important structural fragments relevant for DNase I inhibition. Molecular docking and Site Finder module defined the thieno[2,3-d]pyrimidines interactions with the most important catalytic residues of DNase I, including Glu 39, His 134, Asp 168 and His 252. We also found that steric effects and increase of molecular volume play a vital role in DNase I inhibition.

Reaction of Nitriles under Acidic Conditions. Part VI. Synthesis of Condensed 4-Chloro- and 4-Aminopyrimidines from ortho-Aminonitriles

Condensation of a nitrile with benzene, furan and thiophene ortho-aminonitriles in the presence of dry hydrogen chloride yields condensed 4-chloropyrimidines, condensed 4-aminopyrimidines or a mixture of the two condensed pyrimidines in varying proportions depending upon the nature of the nitrile and the substrate, ortho-aminonitrile.