New enaminone-based to the sesquiterpenic: TiCl4-catalyzed synthesis, spectral characterization, crystal structure, Hirshfeld surface analysis, DFT studies and cytotoxic activity

International audienceIn this work, the compound 2 named ethyl (1,1-dichloro-1a,5,5,7-tetramethyl-8-oxo-1a,2,3,4,5,5a,8,9-octahydro-1H-benzo[a]cyclopropa[b][7]annulen-6-yl)glycinate (C20H29Cl2NO3) was synthesized from the α,β-unsaturated sesquiterpenicketone1 using the azido-Schmidt reaction catalyzed by titanium tetrachloride (TiCl4). The structure of the newly synthesized enaminone 2 was fully identified on the basis of its HRMS, FT-IR, UV-Visible, NMR (1 H & 13 C) spectral data, and X-ray crystallography. The compounds 1 and 2 were evaluated for their cytotoxic activity in four human cancer cell lines, fibrosarcoma (HT-1080), lung carcinoma (A-549), and breast (MCF-7 and MDA-MB-231). Data showed that compound 1 wasthe most activeagainst HT-1080 and A-549 cells with IC50 values between 13.28 and 16.41 µM.Thetheoretical Study Theory (DFT) was used to predict the molecular proprieties which lead to the highest potential of cytotoxic effect, in accordance to the experimental spectroscopic data

Palladium‐catalyzed site‐selective C7 oxidative arylation of 4‐EWG‐1 H ‐Indazoles

International audienceAn efficient palladium‐catalyzed oxidative arylation of substituted 1$H$‐indazole with various arenes and heteroarenes as coupling partners is reported. A site selective C7 oxidative arylation was perfectly achieved with a directing electron‐withdrawing groups (EWG) located at the C4 position of the 1$H$‐indazole. The desired products are obtained in moderate to good yields from 4‐NO$_2$ or 4‐CO$_2$ Me 1$H$‐indazoles and various (hetero)aryls as coupling partners in the presence of Pd(OAc)$_2$ as catalyst, phenanthroline as ligand, Ag$_2$ CO$_3$ as oxidant and NaOH as the base. Density functional theory was also conducted for reaction mechanism comprehension. This approach provides a highly effective, direct, and atom economical way to build C7‐ (het)arylated 1$H$‐indazole compounds

Selective synthesis of novel quinolones-amino esters as potential antibacterial and antifungal agents : Experimental, mechanistic study, docking and molecular dynamic simulations

A new selective synthesis of novel quinoline carboxamides was developed by the N-alkylation reaction of methyl (2-oxo-1,2- dihydroquinolin-4-yl)-L-alaninate via phase transfer catalysis in a basic medium at room temperature. The compounds were obtained in excellent yields (70-90%) and characterized by H-1, (CNMR)-C-13 spectroscopy and mass spectra. In addition, theoretical studies at B3LYP/6-311G(d,p) level were carried out to explain the observed selectivity of the N-alkylation reaction of compound 2 . The biological activities of the synthesized compounds were studied using some bacterial and fungal strains. The results show that compounds 3h and 3i exhibit stronger antibacterial activity against Bacillus subtilis and Staphyloccocus aureus. Compound 3e showed high antifungal activity against Candida Albicans compared to other substituted quinoline carboxamides. Molecular docking and molecular dynamics studies were also carried out to investigate the binding affinities of some compounds with the target proteins, and the results were in good correlation with the experimental findings. (C) 2021 Elsevier B.V. All rights reserved.Peer reviewe