Chemoenzymatic synthesis with lipase catalyzed resolution and evaluation of antitumor activity of (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one

Synthesis, characterization, resolution and evaluation of novel (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one derivatives are described. Enantiomerically pure compounds were isolated in good to excellent yield with high enantiomeric excess under mild reaction conditions by using Candida antarctica B (CAL-B) and Candida rugosa (CRL) Lipases. Newly synthesized and resolved compounds were screened for their antitumor activity against cancer cells such as human neuroblastoma SK–N–SH and human lung carcinoma A549 cell line in vitro. The results have shown that the compound 1 S-(−) alcohol was more effective in inhibiting the tumor cell growth. Synthesis and resolution of (±)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3, 4-b]quinolin-3(2H)-one (1) in good to excellent yield. Newly isolated compounds were evaluated for their antitumor activity against the human cancer cell lines. [Display omitted] ► Synthesized and characterized the novel derivatives of (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl) propyl]-1H-pyrrolo [3,4-b] quinolin-3(2H)-one in good to excellent yields. ► Synthesized racemic derivatives were resolved by using Candida antarctica B (CAL-B) and Candida rugosa (CRL) Lipases. ► All newly synthesized and resolved isomers were evaluated for their antitumor activity against cancer cells such as human neuroblastoma SK–N–SH and human lung carcinoma A549 cell lines. ► The results have shown that the compound 1 S-(−) alcohol was more effective in inhibiting the tumor cell growth.