Design and synthesis of novel cytotoxic agents based on combined framework of quinoline and nimesulide

Functionalization of quinoline aldehydes, derived from nimesulide framework was carried out using Morita–Baylis–Hillman (MBH) chemistry. A number of novel quinoline‐based diverse MBH adducts was prepared via the reaction of derivatives of 2‐chloroquinoline‐3‐carbaldehyde and various activated alkenes in good yields. Many of these compounds were found to be potent when tested against human prostate cancer (Pc‐3) cell line in vitro. Among all the compounds tested N‐(2‐chloro‐3‐(2‐cyano‐1‐hydroxyallyl)‐7‐phenoxyquinolin‐6‐yl)formamide (IC₅₀ = 1.2 μg mL^?1) was identified as the most potent compound in this series. J. Heterocyclic Chem., (2012).