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    Synthesis and biological studies of novel hydroxyacetophenone-tetrazole hybrids
    (Acg Publications, 2023) Disli, Ali; Yucesoy, Esin Eylem; Ozturk, Ali; Dilek, Gulay
    A series of novel hybrid compounds was synthesized where 2 '-hydroxyacetophenone and N-alkylated thiotetrazole were coupled via methylene spacers of different lengths. The structures of the compounds were characterized by spectroscopic techniques, including the 1H-and 13C-NMR, FT-IR, and HRMS methods. The antimicrobial activities of the title compounds were evaluated against clinical isolates of Gram-positive and negative bacterial and fungal species. All compounds showed a broad spectrum of antimicrobial activity and inhibited all bacteria and fungi that tested with MIC values ranging from 4 to 128 mu g/ml. 4a and 5d were the most active antibacterial members.
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    Synthesis, characterization, theoretical studies and antimicrobial activity of novel 1-(2-hydroxy-4-propoxy-3-propylphenyl)ethanones bearing thiotetrazole
    (Elsevier, 2021) Disli, Ali; Yucesoy, Esin Eylem; Erdogdu, Yusuf; Gulluoglu, Mehmet Tahir; Ozturk, Ali; Dilek, Gulay
    We report herein a joint experimental and theoretical investigation on the novel 1-(2-hydroxy-4-propoxy-3-propylphenyl)ethanone bearing 1-propyl-1H-tetrazol-5-thiol and 2-propyl-2H-tetrazole-5-thiol pharmacophores. In the experimental studies, 1-[4-(34(1-propyl-1H-tetrazol-5-y1)thio)propoxy)2-hydroxy-3-propylphenyliethanone and 1-[4-(34(2-propyl-2H-tetrazol-5-yl)thio)propoxy)-2-hydroxy-3propylphenyliethanone were synthesized and characterized by ATR-FTIR, (1) H NMR, C-13-APT, and HRMS. In the theoretical studies, the most stable conformations, vibrational and NMR spectra of these compounds were predicted by Quantum chemical calculations. Quantum chemical calculations were performed using the B3LYP functional with 3-21 G, and 6-311++G(d,p) basis sets. All quantum chemical calculations were utilized Gaussian 16 software. While torsional barriers of the compounds were determined by B3LYP/3-21 G, their geometry optimizations were performed by B3LYP functional with 3-21 G, and 6-311++G(d,p) basis sets. The harmonic vibrational frequencies, potential energy distribution (PED) and infrared intensities were predicted using the B3LYP/6-311++G(d,p). Theoretically predicted vibrational frequencies were compared with experimental results. Predicted NMR chemical shifts were obtained by the GIAO method using the B3LYP/6-311++G(d,p). The (1) H and (13) C experimental chemical shifts are consistent with the theoretical NMR chemical shift values. Antimicrobial activities of the title compounds were investigated against five bacterial strains (Staphylococcus aureus, Staphylococcus epidennidis, Escherichia coli, Pseudomonas aeruginosa, Stenotrophomonas maltophilia) and two fungal strains (Candida albicans, Aspergillus fumigatus). The compounds showed good antimicrobial activity and inhibited all tested bacteria and fungi. (C) 2021 Elsevier B.V. All rights reserved.