Journal
JOURNAL OF MOLECULAR STRUCTURE
Volume 1227, Issue -, Pages -Publisher
ELSEVIER
DOI: 10.1016/j.molstruc.2020.129412
Keywords
Type-2 diabetes mellitus (T2DM); Dihydropyrimidine (DHPM); Hypoglycemia; Streptozotocin (STZ)
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Funding
- Durban University of Technology
- National Research Foundation, South Africa [98884]
- Department of Chemistry, VNIT, Nagpur - DST FIST Project [SRTST/CS1-279/201.6]
- SERB, DST, Government of India [ECR/2016/001820]
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A series of potential anti-diabetic compounds were synthesized and evaluated in vivo using a diabetic rat model, showing significant hypoglycemic effects in some of the compounds. Crystal structure analysis revealed hydrogen bonding interactions and ring motifs in the synthesized compounds.
In an effort to identify an anti-diabetic agent, a series of methyl/ethyl 4-(hydroxyphenyl)-6-methyl-2-oxo/thioxo-1,2,3,4 tetrahydropyrimidine-5-carboxylate analogues (4a-h) have been synthesized, purified, and characterized by using Fourier-Transform Infrared Spectroscopy (FT-IR) and NMR (H-1 and C-13). The synthesized compounds were screened for anti-hyperglycemic activity using Streptozotocin (STZ) induced diabetic rat model. The anti-hyperglycemic activity of dihydropyrimidine (DHPM) compound is mainly analyzed with the variation of substituents present on the phenyl ring and urea/thiourea group on pharmacophoric features. Further, the crystal structure and supramolecular characteristics of two compounds 4c and 4f were analyzed through a single-crystal X-ray method and the Hirshfeld Surface Analysis, which shows hydrogen bonding through N-H center dot center dot center dot O and N-H center dot center dot center dot S interactions with the formation of ring motif in the crystal structure. It is interesting to note that among the title compounds, the 4a, 4e, 4f, and 4g significantly displayed a better hypoglycemic effect in vivo rat model study. (C) 2020 Elsevier B.V. All rights reserved.
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