Background: Resveratrol (RV) and its analogues Aza-stilbenes were found effective in exhibiting anticancer activity. Objective: The present study mainly focused on the green synthesis of novel imine stilbene analogues and evaluation of their anticancer activity besides their influence on hypoxia-induced gene expression in cancer cells. Method: Novel imine stilbenes, differing in number and/or position of hydroxyl and methoxy functional groups, have been synthesized using green chemistry mediated condensation reaction between aldehydes and amines in the ethanolic extract of Psoralea corylifolia hairy roots and tested for their anticancer potential. Results: Ethanol containing 1% hairy root extract facilitated instant reaction and yielded more than 99% product( s). MTT assay on HeLa cells treated with imine stilbene analogues revealed an increase in the inhibition of cell proliferation as compared to RV. Treatment of nontumor HEK293 cells with these compounds disclosed minimal toxicity implying the selective advantage of these compounds for cervical cancer therapy. Scratch assay on HeLa cells displayed inhibition of directional cell motility by these analogues and compound 3e [4-((E)-(4- hydroxyphenylimino)methyl)-2-methoxyphenol] recorded maximum inhibition. In reporter assay, as compared to untreated N-(2-Methoxy-2-oxoacetyl) glycine methyl ester (DMOG) induced cells, hypoxia response element- directed transcriptional activity has been significantly reduced in DMOG induced cells treated with imine stilbene analogues. Conclusion: Overall results indicated that four of the five imine stilbene analogues exhibited enhanced anticancer activity than that of the RV. As such, the novel synthetic compounds 3d, 3e and 3b endowed with potent anticancer activity than RV can serve as drug lead molecules.