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

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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.

в: Molecules, Том 31, № 2, 08.01.2026.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

BibTeX

@article{af46990fa2df4e539f9ed2d9bd7bca10,

title = "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",

abstract = "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. {\textcopyright} 2026 by the authors.",

keywords = "1,2,3-triazole, density functional theory, FTIR spectroscopy, lupinine, molecular docking, X-ray diffraction, 1,2,3 triazole derivative, alkaloid, amino acid, benzene, triazole, absorption spectroscopy, article, binding site, catalysis, controlled study, drug analysis, Fourier transform infrared spectrometer, Fourier transform infrared spectroscopy, human cell, pharmacophore, X ray diffraction",

author = "D. Turdybekov and Z. Nurmaganbetov and A. Makhmutova and D. Baev and Y. Gatilov and D. Pankin and M. Smirnov and P. Bekisheva and K. Kopbalina",

note = "Export Date: 09 February 2026; Cited By: 0; Correspondence Address: Z. Nurmaganbetov; Laboratory of Synthesis of Biologically Active Substances, Institute of Organic Synthesis and Coal Chemistry, Karaganda, 100008, Kazakhstan; email: nzhangeldy@yandex.ru; A. Makhmutova; School of Pharmacy, Karaganda Medical University, Karaganda, 100012, Kazakhstan; email: almagul_312@mail.ru; CODEN: MOLEF",

year = "2026",

month = jan,

day = "8",

doi = "10.3390/molecules31020218",

language = "Английский",

volume = "31",

journal = "Molecules",

issn = "1420-3049",

publisher = "MDPI AG",

number = "2",

}

RIS

TY - JOUR

T1 - 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

AU - Turdybekov, D.

AU - Nurmaganbetov, Z.

AU - Makhmutova, A.

AU - Baev, D.

AU - Gatilov, Y.

AU - Pankin, D.

AU - Smirnov, M.

AU - Bekisheva, P.

AU - Kopbalina, K.

N1 - Export Date: 09 February 2026; Cited By: 0; Correspondence Address: Z. Nurmaganbetov; Laboratory of Synthesis of Biologically Active Substances, Institute of Organic Synthesis and Coal Chemistry, Karaganda, 100008, Kazakhstan; email: nzhangeldy@yandex.ru; A. Makhmutova; School of Pharmacy, Karaganda Medical University, Karaganda, 100012, Kazakhstan; email: almagul_312@mail.ru; CODEN: MOLEF

PY - 2026/1/8

Y1 - 2026/1/8

N2 - 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. © 2026 by the authors.

AB - 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. © 2026 by the authors.

KW - 1,2,3-triazole

KW - density functional theory

KW - FTIR spectroscopy

KW - lupinine

KW - molecular docking

KW - X-ray diffraction

KW - 1,2,3 triazole derivative

KW - alkaloid

KW - amino acid

KW - benzene

KW - triazole

KW - absorption spectroscopy

KW - article

KW - binding site

KW - catalysis

KW - controlled study

KW - drug analysis

KW - Fourier transform infrared spectrometer

KW - Fourier transform infrared spectroscopy

KW - human cell

KW - pharmacophore

KW - X ray diffraction

UR - https://www.mendeley.com/catalogue/4008b283-ebff-3aa8-b77e-e974a2e1b382/

U2 - 10.3390/molecules31020218

DO - 10.3390/molecules31020218

M3 - статья

C2 - 41599269

VL - 31

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 2

ER -

ID: 148491612