title: 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.
abstract: 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.
authors: Organic Chemistry Division II, Indian Institute of Chemical Technology (CSIR), Tarnaka, Hyderabad 500607, India. lnagarapuiict@yahoo.com
authors: Lingaiah
authors: L
authors: Nagarapu
authors: Hanmant K
authors: HK
authors: Gaikwad
authors: Rajashaker
authors: R
authors: Bantu
authors: Sheeba Rani
authors: SR
authors: Manikonda
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D055162:Biocatalysis; D002175:Candida / Q000201:enzymology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008049:Lipase / Q000378:metabolism*; D015394:Molecular Structure; D010879:Piperazines / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D011804:Quinolines / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: C560932:2-(2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl)-1H-pyrrolo(3,4-b)quinolin-3(2H)-one; D000970:Antineoplastic Agents; D010879:Piperazines; D011804:Quinolines; D008049:Lipase