Synthesis, characterization, theoretical calculations and biochemical evaluation of a novel oxime ligand with complexes

Synthesis, characterization, and density functional theory studies of hydrazone–oxime ligand derived from 2,4,6‐trichlorophenyl hydrazine and its metal complexes searching for new antimicrobial drugs

“…This matching clarified that the hydrazone-oxime (H 2 L) works either as univalent bidentate chelator, bonded with the metal ions via the nitrogen atoms of both deprotonated oxime and imino moieties as in all complexes except complexes (2) and (8). This chelation manner was attained by three evidences: (i) the missing of hydroxyl band signifying to the partaking of the deprotonated oxime moiety in the chelation to the metal ions, which is confirmed by a hypochromic shift in position of the N-O band (1,190) cm −1 [25,54] ; (ii) a bathochromic shifting in the intensity and location of imine and oxime C=N groups by 10-51 and 8-38 cm −1 consecutively; (iii) the appearing of new bands in the 507-613 and 411-489 cm −1 ranges for complexes could belong to the ν(M-N) and ν(M N) successively. [55] While in complexes (2) and (8) the hydrazone-oxime (H 2 L) work as a neutral bidentate fashion chelated with the VO 2+ and Cu 2+ ions via the imino and oximato nitrogen atoms, which was confirmed by the following evidences: (i) the bathochromic shifting of the ν(OH) group ascribing to the partaking of protonated oxime group in the chelation.…”

“…The purity of all compounds has been checked by thin-layer chromatography (TLC) using different mobile phases. The elemental analysis (C, H, N) of acetohydrazide (1) and its metal complexes were analyzed in the Micro-Analytical Laboratory, Cairo University, Egypt. The metal and chloride ions content were analyzed by standard analytical methods.…”

“…The antistructures and syn-structures of the hydrazone-oxime (1) to-metal charge-transfer (LMCT) transitions. The vanadyl (VO 2+ ) ion has one electron in d orbital giving rise to the term 2 D. In perfect octahedral field, this electron localizes in t 2g leading to 2 T 2g ground state, which when gains energy, it will be excited to e g orbital and so in an octahedral only one peaks is expected matching to the 2 T 2g !…”

“…[94] this binding produce aggregation of AmB molecules to form channels, and as a result, this leads to change the membrane permeability and causing finally leakage out of the cell and death. [1,95] In case of Cd 2+ complex (13), it is more polar, and the aggregation of its molecules in the cell membrane is not expected as AmB, which suggests another mode of action. In addition, Cd 2+ complex (13) showed potent activities against cells with different membrane structures, and these activities increase against yeast, which has glucan and mannan components in its cell wall.…”

“…Recently, compounds containing hydrazone and/or oxime linkage attracted the attention of many scholars because of their ability to form stable complexes with various transition metals, in addition to the presence of N-OH moiety, which could be enhance their chelation ability and make it more flexible in the reduction, oxidation, and conjugation with organic and inorganic compounds. These categories of compounds and their transition metal complexes showed biochemical [1] and bioactivity against pathogens resistant as antimicrobial, [2][3][4][5][6][7] antitumor, [3,4,8] anticancer, [9] anticandidal, [10] antitubercular, [11] antioxidant, and [4,12] anti-inflammatory analgesic [4,13] activities. Abdel-Aziz et al showed that the isoindoline-1,3-dione-based oximes and benzene-sulphonamide hydrazones have a selective inhibition of the tumor-associated carbonic anhydrase IX.…”