Design, synthesis, and evaluation of cytotoxic activities of arylnaphthalene lignans and aza‐analogs

Abstract

A concise and versatile synthetic strategy for the total synthesis of arylnaphthalene lignans and aza-analogs was developed. The main objective was to develop synthetic tactics for the creation of the lactone and lactam unit that would give access to an array of synthetic, natural, and/or bioactive compounds through rather simple chemical manipulation. The flexibility and potentiality of these new processes were further illustrated by the total synthesis of retrojusticidin B (13b), justicidin C (14b), and methoxy-vitedoamine A (22a). In this study, a series of novel aryl-naphthalene lignans and aza-analogs were synthesized, and the cytotoxic activities of all compounds on cancer cell growth were evaluated. The target compounds were structurally characterized by 1 H NMR (nuclear magnetic resonance), 13 C NMR, infrared, highresolution mass spectrometry, and X-ray crystallography. The IC 50 values of these compounds on five tumor cell lines (A549, HS683, MCF-7, SK-MEL-28, and B16-F1) were obtained by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) colorimetric assay. Five of the compounds exhibited excellent activity compared to 5-fluorouracil and etoposide against the five cell lines tested, with IC 50 values ranging from 1 to 10 μM.

Biocatalytic Synthesis of Coumarin S-Glycosides: Towards Non-Cytotoxic Probes for Biomedical Imaging and Sensing

“…To use these S -glycosidic compounds in cellulo, the potential impact of the glycosidic linkage nature on the anticancer activity was assessed. The S -glycoside derivatives and the 7-MC were tested against four human cancer cell lines and a healthy one, namely A549 (lung carcinoma), HS-683 (glioma cancer), MCF-7 (breast adenocarcinoma), SK-MEL-28 (melanoma skin cancer), and HaCaT (keratinocyte normal skin), using MTT (thiazolyl blue tetrazolium bromide, Sigma-Aldrich, St. Louis, MO, USA) assay, as previously described in the literature [ 42 , 43 , 44 ]. The selected reference drugs were 5-fluorouracil (5-FU) and etoposide.…”

NMR Characterization of Lignans

“…), even though flaxseed represents the highest producer of lignans, estimated to be 60–700 times more abundant than other plants. Due to their differentiated employment as bioactive molecules, elicitation, rather than total synthesis procedures [ 15 , 16 ], has been applied in the view of a larger production procedure of compounds, but also to use them as a reference for structural characterization approaches. A subfamily of these compounds is made by dilignans, an uncommon subset of naturally occurring plant products.…”