Efficient Synthesis of a New Class of <i>N</i>-Nucleosides of 4<i>H</i>-Thiochromeno[2,3-<i>d</i>]pyrimidine-10-Sulfone as Potential Anticancer and Antibacterial Agents

Abstract

A highly practical and efficient preparation of 6-methy-4H-thiochromene and 7-methyl-thiochromene[2,3-d]pyrimidine derivatives was developed via a multi-component reaction of 3-methyl-thiophenol (1), aldehydes (2), and malononitrile (3). A series of pyrimidine nucleoside, thiochromene[2,3-d]pyrimidine and thiochromene[2,3-d]pyrimidine-10-sulfone was efficiently obtained. These hybrid compounds were evaluated as potential antibacterial and anticancer agents and showed encouraging biological activities. Some of these derivatives showed broad-spectrum antitumour activity against the nine tumour subpanels tested, and demonstrated significant activity in the in vitro antitumour screening expressed by MG-MID log 10 GI 50 value of −4.55, −4.67 and −4.73 of compounds 9a, 9b and 9c, respectively.