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Stereoselective synthesis and anti-proliferative effects on prostate cancer evaluation of 5-substituted-3,4-diphenylfuran-2-ones.
- Source :
-
European journal of medicinal chemistry [Eur J Med Chem] 2013 Jul; Vol. 65, pp. 323-36. Date of Electronic Publication: 2013 May 14. - Publication Year :
- 2013
-
Abstract
- Series of 5-substituted-3,4-diphenylfuran-2-ones were stereoselectively prepared. Their potential anti-proliferative effects on prostate cancer and some of their cyclooxygenases (COXs) inhibitory activities were evaluated. Structure-activity relationship (SAR) data, acquired by substituent modification at the para-position and ortho-position of the C-3 phenyl ring and 5-substituted modification of the central furanone, showed that 3-(2-chloro-phenyl)-4-(4-methanesulfonyl-phenyl)-5-(1-methoxy-ethyl)-5H-furan-2-one (13p) was the most potent compound and could effectively reduce the proliferation of prostate cancer cells (PC3 cell IC50 = 20 μM; PC3 PCDNA cell IC50 = 5 μM; PC3 SKP2 cell IC50 = 5 μM; DU145 cell IC50 = 25 μM). The cell cycle analysis for 13p in DU145 indicated that 13p may induce G1 phase arrest.<br /> (Copyright © 2013 Elsevier Masson SAS. All rights reserved.)
- Subjects :
- Antineoplastic Agents chemical synthesis
Antineoplastic Agents chemistry
Apoptosis drug effects
Cell Proliferation drug effects
Cyclooxygenase 1 metabolism
Cyclooxygenase 2 metabolism
Cyclooxygenase Inhibitors chemical synthesis
Cyclooxygenase Inhibitors chemistry
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Furans chemical synthesis
Furans chemistry
Humans
Male
Molecular Structure
Prostatic Neoplasms pathology
Stereoisomerism
Structure-Activity Relationship
Tumor Cells, Cultured
Antineoplastic Agents pharmacology
Cyclooxygenase Inhibitors pharmacology
Furans pharmacology
Prostatic Neoplasms drug therapy
Subjects
Details
- Language :
- English
- ISSN :
- 1768-3254
- Volume :
- 65
- Database :
- MEDLINE
- Journal :
- European journal of medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 23735281
- Full Text :
- https://doi.org/10.1016/j.ejmech.2013.04.062