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Synthesis and cytotoxic activities of 2-substituted (25R)-spirostan-1,4,6-triene-3-ones via ring-opening/elimination and 'click' strategy
- Source :
- Bioorganicmedicinal chemistry letters. 25(17)
- Publication Year :
- 2015
-
Abstract
- To develop more effective antitumor steroidal drugs, we synthesized a library including twenty-two novel cytotoxic 2-alkyloxyl substituted (25R)-spirostan-1,4,6-triene-3-ones and corresponding 1,2,3-triazoles through an abnormal monoepoxide ring-opening/elimination and 'click' reactions. After the cytotoxic evaluations against HepG2, Caski and HeLa cell lines, three steroidal triazoles 5b, 5f and 5m in this library were found to possess potent anti-proliferative effects against Caski cells with the half-inhibitory concentrations (IC50) of 9.4-11.8 mu M. The high-efficient and straightforward process was attractive feature for facile preparation of anti-tumor steroidal triazoles. (C) 2015 Elsevier Ltd. All rights reserved.
- Subjects :
- Magnetic Resonance Spectroscopy
Stereochemistry
Clinical Biochemistry
Pharmaceutical Science
Antineoplastic Agents
Chemistry Techniques, Synthetic
Diosgenin
Ring (chemistry)
Biochemistry
HeLa
Inhibitory Concentration 50
Structure-Activity Relationship
Drug Discovery
Spirostans
Cytotoxic T cell
Humans
Molecular Biology
IC50
biology
Cycloaddition Reaction
Molecular Structure
Chemistry
Organic Chemistry
Hep G2 Cells
Triazoles
biology.organism_classification
Combinatorial chemistry
Cell culture
Molecular Medicine
Click Chemistry
Drug Screening Assays, Antitumor
Copper
HeLa Cells
Subjects
Details
- ISSN :
- 14643405
- Volume :
- 25
- Issue :
- 17
- Database :
- OpenAIRE
- Journal :
- Bioorganicmedicinal chemistry letters
- Accession number :
- edsair.doi.dedup.....ab318134ac705867a8412df69985eaa8