Thiazolidine‐4‐one clubbed pyrazoles hybrids: Potent α‐amylase and α‐glucosidase inhibitors with NLO properties

Abstract

Molecular hybrids based on thiazolidin‐4‐one and pyrazolyl pharmacophore (THZP) as new antidiabetic agents were synthesized. Two sets of signals came into view in 1H NMR of THZP8‐THZP14 exhibited the presence of a configurational isomeric mixture of 2E,5Z (38.24%‐41.58%) and 2Z,5Z isomers (58.42%‐61.76%), which was further endorsed by density functional theory (DFT) studies. All the compounds exhibit promising nonlinear optical properties (NLO). Further, the biological potential of THZPs was explored in terms of α‐amylase and α‐glucosidase inhibition. DFT‐based descriptors were calculated to describe the reactivity, and a relationship was developed with biological activities. THZP9 and THZP14 showed remarkable inhibition of α‐amylase and α‐glucosidase with IC50 9.90μM and 4.84μM, respectively, as compared with standard drug acarbose.

α‐Glucosidase, α‐Amylase Inhibition, Kinetics and Docking Studies of Novel (2‐Chloro‐6‐(trifluoromethyl)benzyloxy)arylidene) Based Rhodanine and Rhodanine Acetic Acid Derivatives

“…Homology model was prepared for the enzyme from S. cerevisiae because a standard crystal structure is currently unavailable. [44] The protein sequence for yeast α-glucosidase (MAL12 and MAL32) was obtained from UniProt (https://www.uniprot.org). The homology model was constructed with the help of X-ray crystal structure of S. cerevisiae isomaltase (PDB ID code 3AXH of 1.80 Å resolution) which demonstrated 72 % identical and 84 % similar sequence with that of the α-glucosidase obtained from S. cerevisiaeas described in previous studies.…”

Synthesis, Characterization Of Thiazolidin-4-one, Oxazolidin-4-one And Imidazolidin-4-one Derivatives From 6-Amino-1, 3-dimethyluraciland Evaluation Of Their Antioxidant And Antimicrobial Agent

“…In this step, (0.0041 mol) of Schiff bases (1-6) and 2-mercaptoacetic acid (0.3 mL, 0.0041 mol) in THF (10 mL) was added gradually. The reaction mixture was then heated to reflux up on (18)(19)(20) h. After refluxing the reaction mixture was followed neutralized by addition of sodium bicarbonate solution 5% to remove unreacted 2-mercaptoacetic acid. The product was filtered and washed with water then further purification was done using recrystallized from ethanol.…”

Magnetized inorganic–bioorganic nanohybrid [nano Fe3O4‐SiO2@Glu‐Cu (II)]: A novel nanostructure for the efficient solvent‐free synthesis of thiazolidin‐2‐imines

“…Thiazolidine is a versatile five‐membered compound/motif in organic transformations that possess both nitrogen and sulfur heteroatoms. Beside their applications in organic chemistry, many classes of these heterocycles utilized in pharmacology and biology with a wide range of in facto or potent properties such as hepatitis C virus (HCV) protease inhibitors, [ 1 ] anticonvalsunt, [ 2 ] antioxidant, [ 3 ] antidiabetic and adipogenic, [ 4 ] α‐amylase and α‐glucosidase inhibitors, [ 5 ] class II histone deacetylase (HDAC) inhibitors (in cervical cancer treatment), [ 6 ] protein tyrosine phosphatase 1B (PTP‐1B) inhibitors (antihyperglycemic activity), [ 7 ] and antiparasitic [ 8 ] activities. Thiozolidine‐2‐imine motif, also observed in potent radioprotectors against γ‐radiation, [ 9 ] exhibited marked activity as antidepressants [ 10 ] and potent inducible nitric oxide synthase inhibitors.…”