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A novel series of coumarin fused benzothiazepines has been synthesized via coupling of oaminothiophenol with in situ generated 3-benzylidenechroman-2,4-diones. These novel compounds were screened for their in vitro antioxidant activity against free radical form of ABTS and cytotoxic activity against U87 human glioma cells. Molecular modeling and QSAR analysis were performed to explore comprehensive structure-activity relationships.