ABSTRACT
A series of new sinomenine derivatives were designed, synthesized, and evaluated in tumor inhibitory activity, such as human triple negative breast cancer cell line (MDA-MB-231), glioma cell line (A172), human lung cancer cell line (A549), human colon cancer cell line (HCT-8). The modifications were carried out on rings A and C of the sinomenine by esterificating on phenolic hydroxyl with good yields. The highlight of this work was that the synthetic procedures were concise and sinomenine derivatives demonstrated promising antitumor activities.
Subject(s)
Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacology , Morphinans/chemical synthesis , Morphinans/pharmacology , Antineoplastic Agents/chemistry , Cell Line, Tumor , Cell Proliferation/drug effects , Cell Survival/drug effects , Drug Design , Drug Screening Assays, Antitumor , Humans , Molecular Structure , Morphinans/chemistry , Nuclear Magnetic Resonance, Biomolecular , Structure-Activity RelationshipABSTRACT
Four new polyisoprenylated benzoylphloroglucinol derivatives, hyperscabrones J-M (1-4), were isolated from the air-dried aerial parts of Hypericum scabrum. Their structures were elucidated by spectroscopic methods and were subsequently confirmed by comparing with data of known compounds. The absolute configuration of the bicyclo[3.3.1]nonane-2,4,9-trione core was defined by the experimental and calculated electronic circular dichroism (ECD) spectra. The evaluation of their hepatoprotective activities against paracetamol-induced HepG2 cell damage showed that compounds 2 and 4 exhibited significant hepatoprotection at 10µM.
