The syntheses and preliminary biological evaluation of a potentially bioreductive N-mustard and paclitaxel conjugate prodrug 3 targeting hypoxic tumor tissue are described. Aromatic nitro group was used as the bioreductive trigger. Generation of paclitaxel occurred after reduction via a subsequent mechanism of "cyclizationcyclizationextrusion". The prodrug was stable in PBS (pH = 7.4) and released paclitaxel after chemical reduction of the nitro functionality. In aerobic cytotoxicity assays, it exhibited diminished cytotoxicity and is a candidate for further biological evaluation. © 2013 Journal of Chinese Pharmaceutical Sciences, School of Pharmaceutical Sciences, Peking University.