We have recently reported the discovery of 2-amino-3-cyano-7-dimethylamino-4-(3-methoxy-4,5-methylenedioxyphenyl)-4H-chromene (1a) as potent apoptosis inducers using a novel cell- and caspase-based HTS assay and the SAR of the 4-position with a dimethylamino group in the 7-position. These chromenes were found to be active in the HUVEC tube formation assay, suggesting that this series of compounds may have antivascular activity, and several compounds were also found to be highly active in anti-cancer in vivo tumor models. More recently, we have described the SAR of the 7-position and the 5, 6, 8-positions of 4-aryl-4H-chromenes as inducers of apoptosis. The SAR revealed that disubstitution at the 7,8-positions was preferred over the 5,6 or 6,7-positions. Herein we will report in detail the chem., in vitro and in vivo characterization of compounds with a fused ring at the 7, 8-positions.