Synthesis, Antiproliferative and Cytotoxic Activities, DNA Binding Features and Molecular Docking Study of Novel Enamine Derivatives

Abstract

Novel enamine derivatives were synthesized from the reaction of lactone and chalcones and their antiproliferative and cytotoxic activities against six cancer cell lines (e. g., HeLa, HT29, A549, MCF7, PC3 and Hep3B) and one normal cell lines (e. g., FL) were investigated along with their mode of interactions with CT‐DNA. Most of the enamine derivatives with IC50 values of 86–168 μM demonstrated much stronger antiproliferative activity than the starting molecules against the cancer cells. While, among the enamine derivatives, four compounds displayed higher cytotoxic potency than the control drugs (5‐fluorouracil and cisplatin) against the Hep3B cell lines, these compounds did not exhibit any significant toxicity against normal cells, FL. The UV/VIS spectral data suggest that eight compounds cause hypochromism with a slight bathochromic shift (∼6 nm), indicating that they bind to the DNA by way of an intercalative or minor groove binding mode. The binding constants of the compounds are in the range of 0.1×103 M−1–2.3×104 M−1. The antiproliferative activity of studied enamine derivatives could possibly be due to their DNA binding as well as their cytotoxic properties. In addition to these assays, the chalcones and enamine derivatives were investigated by molecular docking to calculate the synergistic effect of antiproliferative activities against six human cancer cell lines.

In–Vitro Anticancer and Antibacterial Activities of Brominated Indeno[1,2‐b]qinoline Amines Supported with Molecular Docking and MCDM**

“…Finally, when the simulation data of the compounds examined with the PDB ID: 1M17 target protein, the crystal structure of the epidermal growth factor receptor (EGFRK), [42] representing the MCF7 cell line in Figure S4, the docking results of all compounds were similar to the experimental results. The binding modes and interaction types are given in Figure S5 in the Supplementary Material.…”

The use of Marrubium vulgare L. plant extracts in the control of fungal plant pathogens

“…In the current study, anti-fungal properties of Marrubium vulgare L. extracts in different solvents against certain plant pathogenic fungi were determined. Today, diverse set of organic and inorganic molecules were synthesized in the laboratory conditions using different methodologies, and their multiple biological functions including anti-fungal properties were studied (Özbek et al, 2017;Gürdere et al, 2020;Özbek and Gürdere, 2020). However, in the present study, natural plant-based extracts were analyzed in terms of their antifungal activities.…”

Synthesis, antiproliferative activities, and DNA binding of coumarin‐3‐formamido derivatives

“…Coumarin-3-formamido derivatives (2)(3)(4)(5)(6)(7)(8)(9)(10)(11) were synthesized by coumarin-3-ethyl formate (1) and benzylamine, benzylamine substituted with fluorine, benzylamine substituted with methoxy groups, 1-methyl-5-aminomethylimidazole, 2-thiophenemethylamine, and 2-furfurylamine by aminolysis of esters as reported. [31] The structures of the synthesized compounds were confirmed by infrared (IR; Figures S1-S11), nuclear magnetic resonance (NMR;…”

“…On the basis of the IC 50 values (Table 1), a histogram ( Figure 3) was drawn to compare the antineoplastic activity and cytotoxicity of coumarin-3-ethyl formate (1), coumarin-3-formamide derivatives (2)(3)(4)(5)(6)(7)(8)(9)(10)(11), and DOX against axenic cancers cells more clearly.…”