Study of Structural, Vibrational, and Molecular Docking Properties of (1S,9aR)-1-({4-[4-(Benzyloxy)-3-methoxyphenyl]-1H-1,2,3-triazol-1-yl}methyl)octahydro-2H-quinolizine
Turdybekov D. Nurmaganbetov Z. Makhmutova A. Baev D. Gatilov Y. Pankin D. Smirnov M. Bekisheva P. Kopbalina K.
January 2026Multidisciplinary Digital Publishing Institute (MDPI)
Molecules
2026#31Issue 2
A promising direction for the creation of new biologically active derivatives of the alkaloid lupinine is the synthesis of “hybrid molecules” that combine a fragment of the alkaloid and the pharmacophore of 1,2,3-triazole in their structure. From a biological perspective, this work presents the first X-ray diffraction study of a single crystal of (1S,9aR)-1-({4-[4-(Benzyloxy)-3-methoxyphenyl]-1H-1,2,3-triazol-1-yl}methyl)octahydro-2H-quinolizine, a new, recently synthesized 1,2,3-triazole derivative of lupinine. A comparison of theoretically predicted and experimentally observed structural parameters was carried out. The FTIR spectroscopy study and vibrational properties calculations allowed us to interpret the FTIR absorption spectrum and localize specific vibrational modes in quinolizidine, 1,2,3-triazole, and benzene rings. Such information can be fruitful for further characterization of the synthesis process and products. The molecular docking of the compound was performed. It was shown that the studied molecules are capable of interacting with the Mpro binding site via non-covalent and hydrophobic interactions with subsites S3 (Met165, Glu166, Leu167, Pro168) and S5 (Gln189, Thr190, Gln192), which ensure the stabilization of the Mpro substrate. Blocking of the active site of the enzyme in the region of the oxyanion hole does not occur, but stable stacking interactions with the π-system of one of the catalytic amino acids, His41, are observed.
1,2,3-triazole , density functional theory , FTIR spectroscopy , lupinine , molecular docking , X-ray diffraction
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Department of Physics, Abylkas Saginov Karaganda Technical University, Karaganda, 100027, Kazakhstan
Laboratory of Synthesis of Biologically Active Substances, Institute of Organic Synthesis and Coal Chemistry, Karaganda, 100008, Kazakhstan
School of Pharmacy, Karaganda Medical University, Karaganda, 100012, Kazakhstan
Synchrotron Radiation Facility—Siberian Circular Photon Source “SKlF” Boreskov Institute of Catalysis of Siberian Branch of the Russian Academy of Sciences, Koltsovo, 630559, Russian Federation
Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, 630090, Russian Federation
Center for Optical and Laser Materials Research, St. Petersburg State University, Ulianovskaya 5, St. Petersburg, 198504, Russian Federation
Faculty of Physics, St. Petersburg State University, Universitetskaya Nab. 7/9, St. Petersburg, 199034, Russian Federation
Department of Physics and Nanotechnology, E.A. Buketov Karaganda National Research University, Universitetskaya 28, Karaganda, 100024, Kazakhstan
Department of Physics
Laboratory of Synthesis of Biologically Active Substances
School of Pharmacy
Synchrotron Radiation Facility—Siberian Circular Photon Source “SKlF” Boreskov Institute of Catalysis of Siberian Branch of the Russian Academy of Sciences
Novosibirsk Institute of Organic Chemistry
Center for Optical and Laser Materials Research
Faculty of Physics
Department of Physics and Nanotechnology
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