Novel Synthesis, Cytotoxic Evaluation, and Structure−Activity Relationship Studies of a Series of α-Alkylidene-γ-lactones and Lactams
Citations Over TimeTop 10% of 2005 papers
Abstract
5-Alkyl- and 5-arylalkyl-3-methylenedihydrofuran-2-ones 13a-e, 3-alkylidenedihydrofuran-2-ones 18a-c, and 3-methylenepyrrolidin-2-ones 16a-e were synthesized utilizing ethyl 2-diethoxyphosphoryl-4-nitroalkanoates 9a-e as common intermediates. All obtained compounds were tested against L-1210, HL-60, and NALM-6 leukemia cells. The highest cytotoxic activity was observed for 3-methylenefuranones 13d,e bearing benzyl or 3,4-dimethoxyphenylmethyl substituents at position 5, with IC(50) values of 5.4 and 6.0 microM, respectively. Contrary to the literature reports, no enhancement in activity due to the presence of a hydroxy group was found when the cytotoxicity of furanones 13a,b,d and 5-(1'-hydroxyalkyl)-3-methylenedihydrofuran-2-ones 6a,b,d was compared. The anticancer activity of pyrrolidinones 16a-e and 3-alkylidenefuranones 18a-c was much weaker than that of furanones 13a-e.
Related Papers
- → Efficient synthesis of N-substituted lactams from (N-arylsulfonyloxy) amines and cyclic ketones(1989)32 cited
- → Six-Step Total Synthesis of Azaspirene(2017)14 cited
- → Stereoselective synthesis of homochiral pyrrolidinones and cis, cis-bis-β-lactams from (+)-(1S,2S)-2-amino-1-phenylpropan-1,3-diol(1996)34 cited
- → Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues(2003)20 cited
- Synthesis of a new spirocyclic γ-lactam derivatives from 3-halogeno-3-trifluoroacetyl-1-methyl-2-pyrrolidinones(2007)