Facile synthesis, Spectral investigation, in vitro and in silico studies of Thiophenecarboxamide-α,β-unsaturated ketone hybrids

•The synthesis of TCKs is very simple and inexpensive method.•The antidiabetic activity of TCKs is superior to acarbose.•The TCK1 showed 5 hydrogen bonding interaction with α-amylase enzyme.•The binding energy of TCK2 with cyclooxygenase-2 is −10.02 kcal/mol.•All TCKs obey the lipinski rule and phys...

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Bibliographic Details
Published inJournal of molecular structure Vol. 1308; p. 138060
Main Authors Bharathi, Manikkam, Shreedevi, S., Sribalan, Rajendran
Format Journal Article
LanguageEnglish
Published Elsevier B.V 15.07.2024
Subjects
ADMET
Anti-inflammatory
Antidiabetic
Molecular docking, DFT
Protox-II
Thiophenecarboxamide
Molecular docking, DFT
Protox-II
Anti-inflammatory
ADMET
Antidiabetic
Thiophenecarboxamide
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Summary:•The synthesis of TCKs is very simple and inexpensive method.•The antidiabetic activity of TCKs is superior to acarbose.•The TCK1 showed 5 hydrogen bonding interaction with α-amylase enzyme.•The binding energy of TCK2 with cyclooxygenase-2 is −10.02 kcal/mol.•All TCKs obey the lipinski rule and physiochemical pharmacokinetics parameters. Thiophenecarboxamide-α,β-unsaturated ketone (TCKs) hybrids were synthesized and scrupulously characterized by nuclear magnetic resonance spectroscopy (NMR) by the theoretical and experimental methods, Electrospray ionization mass (ESI-MS), Fourier transform infrared (FT-IR) and ultraviolet-visible spectroscopic techniques by experimental and theoretical methods. The anti-inflammatory and antidiabetic activities were tested for TCKs using protein anti-denaturation and the α-amylase inhibitory methods respectively. The molecular docking studies for TCKs were inspected and data were supported by their molecular parameters that were determined using density functional theory calculations (DFT). The obtained results of TCKs showed a lower band gap and higher electrophilicity index values. Molecular docking studies were investigated against the α-amylase and cyclooxygenase enzymes to compare the tentative results. The TCKs showed very good hydrogen bonding interactions with amino acid residues of the enzymes. In addition, ADMET study, Protox-II toxicity predictions were performed to check the pharmacological properties of TCKs. [Display omitted]
ISSN:0022-2860
DOI:10.1016/j.molstruc.2024.138060