Journal
JOURNAL OF MOLECULAR STRUCTURE
Volume 1199, Issue -, Pages -Publisher
ELSEVIER
DOI: 10.1016/j.molstruc.2019.126991
Keywords
5-lodo-1,2,3-triazole; Halogen bonding; PDHc-E1 inhibitor; DFT calculation; Molecular docking
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Funding
- National Natural Science Foundation of China [21807084, 21867011]
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The binding mode of 5-((4-((4-chlorophenoxy)methyl)-5-iodo-1H-1,2,3-triazol-1-yl)methyl)-2-methylpyrimidin-4-amine (PA-1) was studied using a combination of X-ray crystallography, DFT calculation, and molecular docking approaches. The crystal structure of PA-1 primarily indicated the formation of intermolecular hydrogen bonding and halogen bonding between N-H center dot center dot center dot N and C-I center dot center dot center dot N. DFT calculation demonstrated that the geometric structure of PA-1 is in excellent agreement with the crystal structure. The frontier molecular orbital analysis indicated the important role of the 5-iodo-1,2,3-triazole and benzene ring in the biological activities of PA-1. Further molecular electrostatic potential surface analysis confirmed the possibility of iodine atom participating in the halogen bonding with the negatively charged center; this was validated by the molecular docking study, which showed that the iodine atom of PA-1 could form a halogen bonding with the O atom of Asp521 in the active site of E. coli. PDHc-E1. These findings demonstrate that halogen bonding interaction could be used for the further optimization of PA-1 to discover more potent PDHc-E1 inhibitors and antifungal compounds. (C) 2019 Elsevier B.V. All rights reserved.
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