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A new class of hybrid anticancer agents inspired by the synergistic effects of curcumin and genistein: Design, synthesis, and anti-proliferative evaluation
- Source :
- Bioorganic & Medicinal Chemistry Letters. 25:4553-4556
- Publication Year :
- 2015
- Publisher :
- Elsevier BV, 2015.
-
Abstract
- Inspired by the synergistic effects of dietary natural products with different scaffolds on the inhibition of cancer cell proliferation, incorporation of central (1E,4E)-1,4-penta-dien-3-one linker (an optimal substitute for the central metabolically unstable diketone linker of curcumin), 1-alkyl-1H-imidazol-2-yl (a promising bioisostere of terminal aryl group in curcumin), and chromone (the common pharmacophore in genistein and quercetin) into one chemical entity resulted in ten new hybrid molecules, 3-((1E,4E)-5-(1-alkyl-1H-imidazol-2-yl)-3-oxopenta-1,4-dien-1-yl)-4H-chromen-4-ones. They were synthesized through a three-step transformation using acid-catalyzed aldol condensation as key step. The WST-1 cell proliferation assay showed that they have greater anti-proliferative potency than curcumin, quercetin, and genistein on both androgen-dependent and androgen-independent human prostate cancer cells.
- Subjects :
- Curcumin
Clinical Biochemistry
Pharmaceutical Science
Genistein
Antineoplastic Agents
Pharmacology
Biochemistry
Structure-Activity Relationship
chemistry.chemical_compound
Cell Line, Tumor
Drug Discovery
Humans
Structure–activity relationship
Molecular Biology
Cell Proliferation
Dose-Response Relationship, Drug
Molecular Structure
Organic Chemistry
Drug Synergism
chemistry
Drug Design
Chromone
Cancer cell
Molecular Medicine
Bioisostere
Drug Screening Assays, Antitumor
Pharmacophore
Linker
Subjects
Details
- ISSN :
- 0960894X
- Volume :
- 25
- Database :
- OpenAIRE
- Journal :
- Bioorganic & Medicinal Chemistry Letters
- Accession number :
- edsair.doi.dedup.....1da0c3657d8d6dcbd618ed3c869e4202