title: Synthetic and cytotoxic studies of alpha-methylene-gamma-butyrolactone bearing pyrimidines.
abstract: A total of ten pyrimidine alpha-methylene-gamma-butyrolactones were synthesized as potential antitumor agents on the basis of their possible action as Michael acceptors for DNA/RNA and cellular enzymes. The synthesis of these heterocycles involved a convenient Reformatsky-type reaction of pyrimidinyl ketones with ethyl alpha-(bromomethyl)acrylate. The preliminary in vitro cytotoxic assay indicated that these synthetic compounds were essentially active against the growth of KB, Hep-2, HeLa and Colo-205 cells. Among them, 5'-biphenyl-5'-(uracil-1-ylmethyl)-2'-oxo-3'-methylenetetrahydr ofuran (5f) demonstrated to be the most potent antileukemic agent.
authors.affiliation: School of Chemistry, Kaohsiung Medical College, Taiwan, Republic of China.
authors.forename: B R
authors.initials: BR
authors.lastname: Huang
authors.forename: K H
authors.initials: KH
authors.lastname: Lee
authors.forename: T L
authors.initials: TL
authors.lastname: Tseng
authors.forename: H M
authors.initials: HM
authors.lastname: Wang
authors.forename: C F
authors.initials: CF
authors.lastname: Chen
authors.forename: C C
authors.initials: CC
authors.lastname: Tzeng
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000494:pharmacology; D014407:Tumor Cells, Cultured / Q000187:drug effects
chemical_list: D000970:Antineoplastic Agents; D011743:Pyrimidines; C014096:alpha-methylene gamma-butyrolactone; D015107:4-Butyrolactone