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SYNTHESIS, CRYSTAL STRUCTURE, AND DFT STUDY OF 4-(2-CHLOROBENZYL)-1-(5-NITRO-2-(PYRROLIDIN-1-YL)PHENYL)- [1,2,4]TRIAZOLO[4,3-a]QUINAZOLIN-5(4H)-ONE

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Abstract

4-(2-Chlorobenzyl)-1-(5-nitro-2-(pyrrolidin-1-yl)phenyl)-[1,2,4]triazolo[4,3-a]quinazo-lin-5(4H)-one is a derivative of quinazolinones with antitumor, antibacterial, anti-inflammatory, and antimicrobial effects. Using diabetic jujube as a raw material, the title compound is synthesized by substitution and cyclization steps. The structure of the target compound is confirmed by FTIR, 1H and 13C NMR, and MS spectroscopies. The precise structure of the 4-(2-chlorobenzyl)-1-(5-nitro-2-(pyrrolidin-1-yl)phenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one compound is analyzed by single crystal X-ray diffraction (XRD). The molecular structure is further calculated using density functional theory (DFT) and the result is compared with the XRD value. The molecular electrostatic potential and frontier molecular orbitals of the title compound are investigated using DFT. In addition, the obtained atomic coordinates for the single crystal of the compound are then applied in a molecular docking simulation, and the title compound is found to participate in a number of important binding interactions in the SHP2 binding sites.

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Funding

The authors would like to thank the Guizhou Provincial Natural Science Foundation ([2020]1Y393).

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Authors and Affiliations

  1. School of Pharmaceutical Sciences, Guizhou University, Guiyang, Guiyang, People’s Republic of China

    Q. Ren, Y. Liu, Z. -X. Zhou & C. -S. Zhao

  2. Guizhou Engineering Laboratory for Synthetic Drugs, Guiyang, People’s Republic of China

    Q. Ren, P. -Y. Huang, Y. Liu, Z. -X. Zhou & C. -S. Zhao

  3. Chemistry and Chemical Engineering, Guizhou University, Guiyang, People’s Republic of China

    P. -Y. Huang

  4. Guizhou Provincial Engineering Technology Research Center for Chemical Drug R&D, Guizhou Medical University, Guiyang, People’s Republic of China

    W. -K. Liao

  5. Department of Dermatology, Affiliated Hospital of Guizhou Medical University, Guiyang, People’s Republic of China

    Z. -X. Zhou

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  1. Q. Ren
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Correspondence to Q. Ren, Z. -X. Zhou or C. -S. Zhao.

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Text © The Author(s), 2021, published in Zhurnal Strukturnoi Khimii, 2021, Vol. 62, No. 9, pp. 1571-1581.https://doi.org/10.26902/JSC_id80768

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Ren, Q., Huang, P.Y., Liu, Y. et al. SYNTHESIS, CRYSTAL STRUCTURE, AND DFT STUDY OF 4-(2-CHLOROBENZYL)-1-(5-NITRO-2-(PYRROLIDIN-1-YL)PHENYL)- [1,2,4]TRIAZOLO[4,3-a]QUINAZOLIN-5(4H)-ONE. J Struct Chem 62, 1472–1482 (2021). https://doi.org/10.1134/S0022476621090171

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