Synthesis and Antitumor Activity of a Series of Sulfone Analogues of 1,4-Naphthoquinone

Article abstract of DOI:10.1021/jm00139a017

A series of novel subsituted thiochromones and thiochroman-4-ones was synthesized.Compounds were designed as anlogues of naphthoquinone and as potential "bioreductive alkylating agents" and were tested for antitumor activity.The lead compound, 3-(chloromethyl)thiochromone 1,1-dioxide (4), inhibited Ehrlich ascites tumor growth by 100percent in CF₁ male mice at 10 (mg/kg) day ip.Similarly, 18 of the 29 related compounds demonstrated good activity in this tumor screen.Few definitive structure-activity correlations were evident regarding the nature of the 3-substituent.How ever, the 2,3 double bond and a sulfone or sulfoxide were required for activity.Four of the compounds synthesized showed marginal but significant activity against P-388 lymphocytic leukemia.