Synthesis and evaluation of thiazolidine-2,4-dione/benzazole derivatives as inhibitors of protein tyrosine phosphatase 1B (PTP-1B): Antihyperglycemic activity with molecular docking study

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.…”

Synthesis, SAR and docking studies of substituted aryl phenylthiazolyl phenylcarboxamide as potential protein tyrosine phosphatase 1B (PTP1B) inhibitors

“…PTP1B inhibitors containing thiazolyl and carboxyl group are known (Douty et al., ; Ganou et al., ; Hidalgo‐Figueroa et al., ; Mahapatra et al., ; Wan et al., ). Therefore, we replaced sulfonyl moiety in the compound I by benzoyl group (region B) to afford compound II and to see its impact on the PTP1B inhibitory activity.…”

“…() successfully exploited the presence of a secondary PTP1B‐specific non‐catalytic, arylphosphate‐binding site located close to the active site to design selective bidentate PTP1B inhibitors that can simultaneously occupy the active site and the nearby non‐catalytic site. Since then number of PTP1B inhibitors targeting both of these binding sites have been reported notably benzooxathiazole derivatives(Petry, Baringhaus, Hoelder, & Mueller, ), isothiazolidinone (Douty et al., ), hydroxyphenylazole derivatives (Liang et al., ), thiazolidine‐2,4‐dione derivative (Hidalgo‐Figueroa et al., ; Mahapatra, Kumar, & Kumar, ), and thiazolyl derivatives (Ganou et al., ). These inhibitors although show high PTP1B‐binding affinity but contain less cellular potency because of poor membrane permeability which is associated with targeting active site by highly acidic phosphotyrosine mimetics (Maheshwari et al., ).…”

Design, Synthesis, Antihyperglycemic Studies, and Docking Simulations of Benzimidazole-Thiazolidinedione Hybrids

“…e ΔC t values were calculated in every sample for each gene of interest as follows: C t gene of interest-C t reference gene with 36B4 as the reference gene (mRNA of reference remained stable throughout the experiments). Fluctuations in the relative expression levels of individual specific genes (ΔΔC t ) were measured and graphed [2,12]. Normoglycemic mice (ICR strain) were divided into 3 groups of 6 mice (n � 6).…”

“…Drugs that improve insulin resistance are effective in controlling hyperglycemia. Peroxisome proliferator-activated receptor isotype gamma (PPARc) is the protein target of thiazolidine-2,4-diones, a class of insulin-sensitizing drugs used as antihyperglycemic agents [2]. PPARc controls target genes involved in several biological processes, for example, the facilitated glucose transporter GLUT-4 [3].…”