Synthesis, characterization, crystallographic, binding, in silico and antidiabetic studies of novel 2,4-thiazolidinedione-phenothiazine molecular hybrids

α‐Amylase Inhibitors Based on Thiazolidinone Skeleton: A Promising Approach in Diabetes Management

“…Molecular docking studies with pig pancreatic α-amylase (PDB ID: 1UA3) established the significant interactions of the tested derivatives within the enzyme's active cleft with high binding energies. Doddagaddavalli and coauthors [99] synthesized phenothiazine-thiazolidinedione hybrids 42 a-t and assessed for antidiabetic potential using α-amylase and glucose uptake assays. In molecular docking analysis, potential interactions of the derivatives within the active site of pancreatic α-amylase enzyme (PDB ID: 2QV4).…”

“…Doddagaddavalli and coauthors [99] synthesized phenothiazine‐thiazolidinedione hybrids 42 a – t and assessed for antidiabetic potential using α‐amylase and glucose uptake assays. In vitro results displayed that compounds 42 m – p presented more inhibition with IC 50 values in the range of 83.7–60.8 μM as compared to the positive control, Acarbose (IC 50 =101.7 μM), while compound 42 o exhibited maximum inhibition among the series with IC 50 values 60.8 μM.…”

Rhodanine Derivatives Containing 5‐Aryloxypyrazole Moiety as Anti‐inflammatory and Anticancer Agents

“…These molecules have been reported as, e. g., PTP1B inhibitors, [11,12] anti-bacterial activity [13] and potential anticancer activity. [14,15] In our previous work, a large variety of rhodanine-based 5-aryloxy pyrazoles derivatives (e. g. 5 a-g, 6 ad and 7 a-m) (Figure 1) were synthesized and investigated for antibacterial activity. [16,17] Continuing our studies on rhodanine as promising applicants, we aim to exploit the biological evaluation of these compounds (5 a-g, 6 a-d and 7 a-m) for their anti-inflammatory and anticancer activities.…”

“…As one of the thiazolidines subtypes, rhodanines (2‐thioxothiazolidin‐4‐ones) have been attracting much attention in medicinal chemistry. These molecules have been reported as, e. g., PTP1B inhibitors, [11,12] anti‐bacterial activity [13] and potential anticancer activity [14,15] . In our previous work, a large variety of rhodanine‐based 5‐aryloxy pyrazoles derivatives (e. g. 5 a – g , 6 a – d and 7 a – m ) (Figure 1) were synthesized and investigated for antibacterial activity [16,17] .…”

Tetrazolopyrimidine-tethered phenothiazine molecular hybrids: synthesis, biological and molecular docking studies

“…Literature reveals that phenothiazine-integrated drugs can specifically hamper mitotic kinesin KSP/Eg5 to cause mitotic arrest, further inhibiting tumor cell proliferation. 25 A diverse range of phenothiazineintegrated chemical entities exhibit notable chemical behaviour and biological potencies including anti-inflammatory, 26 anticancer, [27][28][29][30] antifungal, 31 antitubercular, 32 antimalarial, 33 anti-diabetic, 34 and antioxidant. 35 Particularly, in connection with anticancer traits, an analysis of chlorpromazine, a drug tethered with phenothiazine pharmacophore, exposed that it could extend the tamoxifen cytotoxicity effect on breast cancer cells.…”