Novel Pyrimidine-Triazole Schiff Bases: Synthesis, Antifungal Activities, DFT and Molecular Docking

Li, Mou-Cui; Ren, Ying-Hui; Han, Yu-Ying; Dong, Yang-Ming; Wu, Shao-Jie; Zhang, Wen-Hui; Qi, Le; Lu, Yi-Ming; Ma, Hai-Xia

Mou-Cui Li, Ying-Hui Ren, Yu-Ying Han, Yang-Ming Dong, Shao-Jie Wu, Wen-Hui Zhang, Le Qi, Yi-Ming Lu, Hai-Xia Ma

Novel Pyrimidine-Triazole Schiff Bases: Synthesis, Antifungal Activities, DFT and Molecular Docking

Abstract:

Seven 4-amino-5-substituted-1,2,4-triazole-3-thione Schiff base compounds were synthesized reacting 4-amino-5-substituted-1,2,4-triazole-3-thione with dichloro-substituted 5-pyrimidines, and the structures were verified by elemental analysis and spectroscopic techniques (FT-IR, 1H NMR). Additionally, in vitro antifungal activities of the compounds (named F1~F2; A1~A5) against Grape anthracnose and Wheat gibberellic have been evaluated. The compounds of F1, A4 and A5 were found to be potentially effective antifungal agents against Grape anthracnose, while the others showed the low bioactivity. The antifungal activity of all compounds against Wheat gibberellic were superior to that of fluconazole (standard drug, SD). Particularly, compounds of F1, A1, A4 and A5 exhibited a broad-spectrum antifungal activity against two fungus as compared to the others. Therefore, molecular docking study was carried out to explore the potential interaction between ligands and Fusarium graminearum (PDB ID: 5E9H). The results showed that four compounds had higher affinity compared with fluconazole and form the stable complex with the receptor. Besides, the frontier molecular orbitals (FMOs) and molecular electrostatic potentials (MEP) of four compounds with broad-spectrum antimicrobial activity were also calculated with DFT/ B3LYP /6-31G (d, p) method. The energy gap values (△ELUMO-HOMO) of all the synthesized compounds ranged from 3.307-3.375 eV, which was lower than that of SD (6.248 eV). Additionally, according to MEP the electrophile reaction of 5-substituted groups was beneficial to improving the biological activity against Wheat gibberellic and Grape anthracnose.

Keywords:
Schiff base; 1;2;4-triazole; DFT; molecular docking; antifungal activity

Issue: 2021, Volume 72, Issue 4

Pages: 65-74

Publication date: 2021/10/29

https://doi.org/10.37358/RC.21.4.8457

Download Pdf Article

This article is published under the Creative Commons Attribution 4.0 International License

Citation Styles

Cite this article as:
LI, M., REN, Y., HAN, Y., DONG, Y., WU, S., ZHANG, W., QI, L., LU, Y., MA, H., Novel Pyrimidine-Triazole Schiff Bases: Synthesis, Antifungal Activities, DFT and Molecular Docking, Rev. Chim., 72(4), 2021, 65-74.

Vancouver
Li M, Ren Y, Han Y, Dong Y, Wu S, Zhang W, Qi L, Lu Y, Ma H. Novel Pyrimidine-Triazole Schiff Bases: Synthesis, Antifungal Activities, DFT and Molecular Docking. Rev. Chim.[internet]. 2021 Apr;72(4):65-74. Available from: https://doi.org/10.37358/RC.21.4.8457

APA 6th edition
Li, M., Ren, Y., Han, Y., Dong, Y., Wu, S., Zhang, W.,... Ma, H. (2021). Novel Pyrimidine-Triazole Schiff Bases: Synthesis, Antifungal Activities, DFT and Molecular Docking. Revista de Chimie, 72(4), 65-74. https://doi.org/10.37358/RC.21.4.8457

Harvard
Li, M., Ren, Y., Han, Y., Dong, Y., Wu, S., Zhang, W., Qi, L., Lu, Y., Ma, H. (2021). 'Novel Pyrimidine-Triazole Schiff Bases: Synthesis, Antifungal Activities, DFT and Molecular Docking', Revista de Chimie, 72(4), pp. 65-74. https://doi.org/10.37358/RC.21.4.8457

IEEE
M. Li, Y. Ren, Y. Han, Y. Dong, S. Wu, W. Zhang, L. Qi, Y. Lu, H. Ma, "Novel Pyrimidine-Triazole Schiff Bases: Synthesis, Antifungal Activities, DFT and Molecular Docking". Revista de Chimie, vol. 72, no. 4, pp. 65-74, 2021. [online]. https://doi.org/10.37358/RC.21.4.8457

Text
Mou-Cui Li, Ying-Hui Ren, Yu-Ying Han, Yang-Ming Dong, Shao-Jie Wu, Wen-Hui Zhang, Le Qi, Yi-Ming Lu, Hai-Xia Ma,
Novel Pyrimidine-Triazole Schiff Bases: Synthesis, Antifungal Activities, DFT and Molecular Docking,
Revista de Chimie,
Volume 72, Issue 4,
2021,
Pages 65-74,
ISSN 2668-8212,
https://doi.org/10.37358/RC.21.4.8457.
(https://revistadechimie.ro/Articles.asp?ID=8457)
Keywords: Schiff base; 1;2;4-triazole; DFT; molecular docking; antifungal activity

RIS
TY - JOUR
T1 - Novel Pyrimidine-Triazole Schiff Bases: Synthesis, Antifungal Activities, DFT and Molecular Docking
A1 - Li, Mou-Cui
A2 - Ren, Ying-Hui
A3 - Han, Yu-Ying
A4 - Dong, Yang-Ming
A5 - Wu, Shao-Jie
A6 - Zhang, Wen-Hui
A7 - Qi, Le
A8 - Lu, Yi-Ming
A9 - Ma, Hai-Xia
JF - Revista de Chimie
JO - Rev. Chim.
PB - Revista de Chimie SRL
SN - 2668-8212
Y1 - 2021
VL - 72
IS - 4
SP - 65
EP - 74
UR - https://doi.org/10.37358/RC.21.4.8457
KW - Schiff base
KW - 1
KW - 2
KW - 4-triazole
KW - DFT
KW - molecular docking
KW - antifungal activity
ER -

BibTex
@article{RevCh2021P65,
author = {Li Mou-Cui and Ren Ying-Hui and Han Yu-Ying and Dong Yang-Ming and Wu Shao-Jie and Zhang Wen-Hui and Qi Le and Lu Yi-Ming and Ma Hai-Xia},
title = {Novel Pyrimidine-Triazole Schiff Bases: Synthesis, Antifungal Activities, DFT and Molecular Docking},
journal = {Revista de Chimie},
volume = {72},
number = {4},
pages = {65-74},
year = {2021},
issn = {2668-8212},
doi = {https://doi.org/10.37358/RC.21.4.8457},
url = {https://revistadechimie.ro/Articles.asp?ID=8457}
}

<<<< back

PUBLISHING SECTION

Author Guidelines

* Paper Drafting

* Paper Template

* Ethical Statement

* Paper Submission

Ghidul Autorului (ro)

Open Access & Archiving Policy

Search Authors

LATEST NEWS
	NUMAR OMAGIAL PETRU PONI.. detalii
	Revista de Chimie - 70 de ani de aparitie neintrerupta.. detalii
	English-Romanian Dictionary for Mechanical Engineering (download pdf)