Repository of Research and Investigative Information

Repository of Research and Investigative Information

Ilam University of Medical Sciences

Synthesis, bioactivity and binding energy calculations of novel 3-ethoxysalicylaldehyde based thiosemicarbazone derivatives

Thu Oct 6 08:20:01 2022

(2020) Synthesis, bioactivity and binding energy calculations of novel 3-ethoxysalicylaldehyde based thiosemicarbazone derivatives. Bioorganic chemistry. p. 103924. ISSN 1090-2120 (Electronic) 0045-2068 (Linking)

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Official URL: https://www.ncbi.nlm.nih.gov/pubmed/32442818

Abstract

In recent decade, the entrance of alpha-N-heterocyclic thiosemicarbazones derivates (Triapne, COTI-2 and DpC) in clinical trials for cancer and HIV-1 has vastly increased the interests of medicinal chemists towards this class of organic compounds. In the given study, a series of eighteen new (3a-r) 3-ethoxy salicylaldehyde-based thiosemicarbazones (TSC), bearing aryl and cycloalkyl substituents, were synthesized and assayed for their pharmacological potential against carbonic anhydrases (hCA I and hCA II), cholinesterases (AChE and BChE) and alpha-glycosidase. The hCA I isoform was inhibited by these novel 3-ethoxysalicylaldehyde thiosemicarbazone derivatives (3a-r) in low nanomolar levels, the Ki of which differed between 144.18 +/- 26.74 and 454.92 +/- 48.32 nM. Against the physiologically dominant isoform hCA II, the novel compounds demonstrated Kis varying from 110.54 +/- 14.05 to 444.12 +/- 36.08 nM. Also, these novel derivatives (3a-r) effectively inhibited AChE, with Ki values in the range of 385.38 +/- 45.03 to 983.04 +/- 104.64 nM. For BChE was obtained with Ki values in the range of 400.21 +/- 35.68 to 1003.02 +/- 154.27 nM. For alpha-glycosidase the most effective Ki values of 3l, 3n, and 3q were with Ki values of 12.85 +/- 1.05, 16.03 +/- 2.84, and 19.16 +/- 2.66 nM, respectively. Moreover, the synthesized TCSs were simulated using force field methods whereas the binding energies of the selected compounds were estimated using MM-GBSA method. The findings indicate the present novel 3-ethoxy salicylaldehyde-based thiosemicarbazones to be excellent hits for pharmaceutical applications.

Item Type: Article
Creators:
CreatorsEmail
Ishaq, M.UNSPECIFIED
Taslimi, P.UNSPECIFIED
Shafiq, Z.UNSPECIFIED
Khan, S.UNSPECIFIED
Ekhteiari Salmas, R.UNSPECIFIED
Zangeneh, M. M.UNSPECIFIED
Saeed, A.UNSPECIFIED
Zangeneh, A.UNSPECIFIED
Sadeghian, N.UNSPECIFIED
Asari, A.UNSPECIFIED
Mohamad, H.UNSPECIFIED
Keywords: 3-ethoxysalicylaldehyde Bioactivity Molecular simulations Synthesis Thiosemicarbazone competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Divisions:
Page Range: p. 103924
Journal or Publication Title: Bioorganic chemistry
Journal Index: Pubmed
Volume: 100
Identification Number: https://doi.org/10.1016/j.bioorg.2020.103924
ISSN: 1090-2120 (Electronic) 0045-2068 (Linking)
Depositing User: مهندس مهدی شریفی
URI: http://eprints.medilam.ac.ir/id/eprint/2796

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