title: Synthesis of polyfunctionalized piperidone oxime ethers and their cytotoxicity on HeLa cells.
abstract: A series of twenty 2,6-diarylpiperidin-4-one O-methyloximes were synthesized with fluoro/chloro/bromo/methyl/methoxy/ethoxy/isopropyl substituents on various positions of the phenyl at C-2 and C-6 in association with/without methyl substituent on the secondary amino group and methyl/ethyl/isopropyl substituents on the active methylene centers. Regardless of their substitution all compounds predominantly exist in the chair conformation except 3m, which adopts a twist-boat conformation. All the synthesized compounds were evaluated for their in vitro antiproliferative activity against human cervical carcinoma (HeLa) cell line. The cytotoxicity of the test compounds was determined by measuring the number of live cells after 24 h of treatment by MTT assay method. This preliminary SAR suggests some lead molecules 3c-f, 3j-k, 4d-g, and 4i with a scope of further structural optimization of the piperidone pharmacophore toward the development of anticancer drug synthesis.
authors: Department of Biomedicinal Chemistry, Inje University, Gimhae 621 749, Gyeongnam, South Korea.
authors: Paramasivam
authors: P
authors: Parthiban
authors: Ramjee
authors: R
authors: Pallela
authors: Se-Kwon
authors: SK
authors: Kim
authors: Dong Ho
authors: DH
authors: Park
authors: Yeon Tae
authors: YT
authors: Jeong
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects*; D004987:Ethers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005260:Female; D006367:HeLa Cells; D006801:Humans; D010091:Oximes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D010881:Piperidones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D002583:Uterine Cervical Neoplasms / Q000188:drug therapy
chemical_list: D000970:Antineoplastic Agents; D004987:Ethers; D010091:Oximes; D010881:Piperidones