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Synthesis of new triterpenic monomers and dimers as potential antiproliferative agents and their molecular docking studies
- Source :
- European Journal of Medicinal Chemistry. 143:948-957
- Publication Year :
- 2018
- Publisher :
- Elsevier BV, 2018.
-
Abstract
- In the current investigation, new monomers of myrrhanone B and lupeolic acid were prepared via reaction of triterpenic acids with linkers in the presence of K2CO3. In addition, new bis-myrrhanone B homodimers, myrrhanone B-myrrhanol B heterodimers, and bis-myrrhanone β-boswellic acids heterodimer were prepared. Evaluation of these compounds on the proliferation of four different human cancer cell lines, viz., FaDu (pharynx carcinoma), A2780 (ovarian carcinoma), HT29 (colon adenocarcinoma) and A375 (malignant melanoma) has been performed. It is worth mentioning that compounds 4, 7, 8, 10, and 11 possess potent antiproliferative effect towards HT29 cancer cells with IC50 values of 8.1 μM, 5.4 μM, 8.8 μM, 6.8 μM, and 8.2 μM, respectively. In addition, these compounds display good to moderate antiproliferative activities towards A2780 and A375 with IC50 values ranging from 10.4 to 24.2 μM. Moreover, the molecular docking studies of most active compounds (4, 7, 8, 10 and 11) with six anti-cancer drug targets DHFR, VEGFR2, HER-2/neu, CDK6, hCA-IX and LOX also carried, in order to know the mode of binding interaction and energy of this class of compounds.
- Subjects :
- 0301 basic medicine
Stereochemistry
Antineoplastic Agents
01 natural sciences
Structure-Activity Relationship
03 medical and health sciences
chemistry.chemical_compound
Cell Line, Tumor
Ovarian carcinoma
Drug Discovery
medicine
Humans
Cell Proliferation
Pharmacology
Dose-Response Relationship, Drug
Molecular Structure
biology
010405 organic chemistry
Melanoma
Organic Chemistry
General Medicine
medicine.disease
Triterpenes
0104 chemical sciences
Molecular Docking Simulation
030104 developmental biology
Monomer
chemistry
Cell culture
Antiproliferative Agents
Cancer cell
biology.protein
Cyclin-dependent kinase 6
Drug Screening Assays, Antitumor
Dimerization
Human cancer
Subjects
Details
- ISSN :
- 02235234
- Volume :
- 143
- Database :
- OpenAIRE
- Journal :
- European Journal of Medicinal Chemistry
- Accession number :
- edsair.doi.dedup.....277625221f903c8cbdf0a3fce1352189