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Vol. 30 No. 2 (2018): Vol 30 Issue 2

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Design, Synthesis, Single X-Ray Crystal Structure, DFT and Molecular Docking Studies of Novel Clip Type-Pyridyltetrazole Analogues

https://doi.org/10.14233/ajchem.2018.20954
M. Surendra Babu
Department of Chemistry, GITAM Deemed to be University, Hyderabad Campus, Rudaram, Sangareddy-502 329, India
K. Santhosh Reddy
Department of Chemistry, GITAM Deemed to be University, Hyderabad Campus, Rudaram, Sangareddy-502 329, India
Kalyan Sundar Ghosh
Department of Chemistry, National Institute of Technology, Hamirpur-177 005, India
Bijaya Ketan Sahoo
Department of Chemistry, GITAM Deemed to be University, Hyderabad Campus, Rudaram, Sangareddy-502 329, India
Ch. Himasekar
Department of Chemistry, Rayalaseema University, Kurnool-518 002, India
Shaik Mustafa
Department of Chemistry, GITAM Deemed to be University, Hyderabad Campus, Rudaram, Sangareddy-502 329, India

Corresponding Author(s) : Shaik Mustafa

mustaff_02@yahoo.co.in

Asian Journal of Chemistry, Vol. 30 No. 2 (2018): Vol 30 Issue 2

Abstract

Novel clip type-pyridyltetrazole analogs of 1,3-bis(5-(pyridin-2-yl)-1H-tetrazol-1-yl)propan-2-ol (3A) and 1,3-bis(5-(pyridin-2-yl)-2H-tetrazol-2-yl) propan-2-ol (3B) have been synthesized by the reaction of 2-(1H-tetrazol-5-yl)pyridine (2) with 0.5 equivalent of epichlorohydrine in DMF using K2CO3 as a base. Relevant monomers of 1-chloro-3-(5-(pyridin-2-yl)-1H-tetrazol-1-yl)propan-2-ol (3C) and 1-chloro-3-(5-(pyridin-2-yl)-2H-tetrazol-2-yl)propan-2-ol (3D) have been synthesized by reaction of compound 2 with one equivalent of epichlorohydrine in DMF using K2CO3 as a base. The compounds 3C and 3D are further modified by the reaction sequences to obtain the ligands 1-(2-(hydroxymethyl)phenoxy)-3-(5-(pyridin-2-yl)-1H-tetrazol-1-yl)propan-2-ol (3G) and 1-(2-(hydroxymethyl)phenoxy)-3-(5-(pyridin-2-yl)-2H-tetrazol-2-yl)propan-2-ol (3H) respectively. The eight synthesized compounds (3A-3H) were characterized by 1H NMR, 13C NMR, IR and Mass spectroscopy. The compound 3A, was crystallized in triclinic primitive system space group P2(1)/c with a = 8.9442 Å, b = 9.2097 Å, c = 11.3558 Å, V = 814.68 Å, R1 = 0.0213 at 298 K. The compounds 3A and 3B were optimized, HOMO/LUMO and molecular electrostatic potential studies were carried by DFT calculations with B3LYP/6.311G** method. The molecular docking studies were performed on 3A, 3B, 3G and 3H and the studies reveal that all the compounds exist in crescent shapes.

Keywords

Clip type-pyridyltetrazole Epichlorohydrine Salicylaldehyde DFT studies Molecular docking
Babu, M. S., Reddy, K. S., Ghosh, K. S., Sahoo, B. K., Himasekar, C., & Mustafa, S. (2018). Design, Synthesis, Single X-Ray Crystal Structure, DFT and Molecular Docking Studies of Novel Clip Type-Pyridyltetrazole Analogues. Asian Journal of Chemistry, 30(2), 333–342. https://doi.org/10.14233/ajchem.2018.20954
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