3-(5-(1H-imidazol-1-yl) pent-1-en-1-yl)-9-ethyl-9H-carbazole: synthesis, characterization (IR, NMR), DFT, antimicrobial-antioxidant activities and docking study.

3-(5-(1H-imidazol-1-yl) pent-1-en-1-yl)-9-ethyl-9H-carbazole called as compound 1 was synthesized and characterized by proton and carbon-13 nuclear magnetic resonance (1H- and 13C- NMR) and Fourier transform infrared (FTIR) spectroscopic methods. Density Functional Theory/Becke, 3-parameter (DFT/B3LYP), for compound 1 were performed with 6-311++G(d,p) method. Optimized geometry, frontier molecular orbitals (HOMO; highest occupied molecular orbital; LUMO: lowest unoccupied molecular orbital), IR and NMR parameters of compound 1 were obtained. The evaluations reveal that the calculation results support the experimental results. In addition, the antimicrobial (a microwell dilution method) and antioxidant activities (2,2-Diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis-(3-ethylbenzothiazoline-6-sulfonate) (ABTS) ferric ion reducing antioxidant power (FRAP) of compound 1 were evaluated. According to the results obtained, it showed higher antimicrobial activity (Minimal inhibition concentration (MIC): 78.12 µg/mL) against B. subtilis subsp. Spizizenii. Morever, molecular docking studies were carried out to investigate the interactions of an antimicrobial agent on some important enzymes played important roles in nucleic acid (Deoxyribo nucleic acid (DNA) synthesis, cell wall synthesis, protein synthesis, and metabolism etc. The compound 1 was strongly bound to tyrosyl-tRNA synthetase enzyme (binding energy: -11.18 and Ki: 6.37 nM) and Beta-Ketoacyl-Acp Synthase III enzyme (binding energy: -10.29 and Ki: 28.47 nM).Communicated by Ramaswamy H. Sarma.

HIV-1-RT inhibition activity of Satureja spicigera (C.KOCH) BOISS. Aqueous extract and docking studies of phenolic compounds identified by RP-HPLC-DAD.

AIDS is a global disease caused by HIV, affecting millions of people and causing death. The current limitations of antiretroviral therapy used in the therapy of HIV/AIDS have led to the need to search for new and effective drugs from natural products, especially plants. Herewith, using the present study, the detection of HIV-1-RT inhibition of aqueous extract of Satureja spicigera (C.KOCH) BOISS. was performed for the first time. Besides, total phenolic content (TPC), analysis of phenolic constituents by RP-HPLC-DAD and antioxidant capacity by DPPH and Ferric reducing antioxidant power (FRAP) methods were determined for the first time. In addition, molecular docking studies were carried out between HIV-1-RT and phenolic substances, the presence of which was determined in the aqueous extract, for the determination of the phenolics that may be responsible for HIV-1-RT activity. HIV-1-RT inhibition was defined as IC50 : 22.83 µg/ml. Benzoic acid, vanillin, rutin, and chlorogenic acid were present as main phenolics in quantities of 621.96, 505.87, 349.33, and 323.23 µg phenolic/g extract, respectively. Further, TPC, DPPH, and FRAP were calculated as in the order of 151.69 mg GAE/g extract, 23.77 µg/ml, and 445.7 µmol TE/g extract. Chlorogenic acid (-8.48 kcal/mol) was found to be the most effective ligand in docking studies, with a value close to positive standard nevirapine (-9.35 kcal/mol). Hereby, although the aqueous extract of S. spicigera can be used as a natural antioxidant, the crude extract or its phenolics have the potential to be used in the treatment of AIDS due to its high HIV-1-RT activity. PRACTICAL APPLICATIONS: In this study, anti-HIV-1-RT and antioxidant activity and total phenolic content of Satureja spicigera aqueous extract were determined. In addition, HPLC analysis of some phytochemicals and the activities of these phytochemicals against HIV-1-RT enzyme was determined by molecular docking studies. The results showed that the aqueous extract of S. spicigera and some of the phytochemicals it contains have the potential to be used as a natural product against HIV infection or in the treatment of AIDS.