11a-N-Tosyl-5-deoxi-pterocarpan (LQB-223), a promising prototype for targeting MDR leukemia cell lines

• Aza-deoxi-pterocarpans exhibited antineoplastic effect on MDR leukemia cell lines.
• LQB-223 is the most promising prototype for targeting these cells.
• LQB-223 is a candidate for treatment of unresponsive leukemias with a lower chance of side effects.
• The tosyl group (a sulfonamide) is very important for the biological activity.

Aza-deoxi-pterocarpans (1) were synthesized through palladium-catalyzed aza-arylation of dihydronaphtalen, and showed antineoplastic effect on MDR leukemic cell lines (K562, Lucena-1 and FEPS). Compounds 1c–d were prepared to identify the pharmacophoric group responsible for the activity as well as compounds 2a–c were prepared to evaluate the structural requirements in the D-ring. LQB-223 (1b) is the most promising antileukemic agent since it was the most active on MDR cells without detectable toxicity to normal immune system cells.

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