Journal :   Asian Journal of Research in Chemistry

Volume No. :   10

Issue No. :  4

Year :  2017

Pages :   459-469

ISSN Print :  0974-4169

ISSN Online :  0974-4150


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Urea and Thiourea Derivatives of Dipeptides Conjugated Piperazine Analogue as A New Class of AGE’s Inhibitors: Synthesis and Molecular Docking Studies



Address:   D. M. Suyoga Vardhan, H. K. Kumara, H. Pavan Kumar, D. Channe Gowda*
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore – 570 006, Karnataka, India
*Corresponding Author
DOI No: 10.5958/0974-4150.2017.00075.X

ABSTRACT:
A novel class of urea and thiourea derivatives of dipeptides conjugated 2,3-dichlorophenyl piperazine were synthesized and evaluated for their AGE’s inhibition capacity. Antiglycation assay was performed by assessing fluorescence spectrum (exitation 370 nm), and change in fluorescence intensity (to emission 440 nm), based on AGEs were monitored by using spectrofluorimeter. Our results indicate that fluoro containing dipeptide-PZN derivatives have shown excellent curative potential. Interestingly, compounds 6, 7, 14, 15, 22, 23, 30 and 31 have shown excellent potency with IC50 values 13.5 ± 0.77, 8.0 ± 0.25, 14.5 ± 0.92, 7.8 ±0.44, 9.1 ± 0.41, 3.1 ± 0.45, 9.2 ± 0.80 and 2.5 ± 0.55, compared to the standard, rutin 41.9 µM. From our studies, we may draw certain conclusions like Lys containing dipeptides may serve as good antiglycating agents. On the other hand, it’s felt worthy to consider substitutions particularly at para position for the increase in potency. The IC50 values of the compounds were compared with the glide scores from the molecular studies. It was observed that the main interaction force of compounds with the active site was hydrophobic. The IC50 values and glide scores have exhibited better correlation. Thus, this synthetic novel urea and thioureas of dipeptide containing compounds may lead potent antiglycating agents.
KEYWORDS:
Amino acids, Piperazine, Conjugation, Urea, Thiourea, Antiglycation.
Cite:
D. M. Suyoga Vardhan, H. K. Kumara, H. Pavan Kumar, D. Channe Gowda. Urea and Thiourea Derivatives of Dipeptides Conjugated Piperazine Analogue as A New Class of AGE’s Inhibitors: Synthesis and Molecular Docking Studies. Asian J. Research Chem. 2017; 10(4):459-469.
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