103753-40-8

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 100-14-1 4-nitrobenzyl chloride 

Downstream Products

• 1537868-52-2 (5Z)-5-(3,4,5-trimethoxybenzylidene)-3-(4-nitrobenzyl)thiazolidine-2,4-dione 
• 1537868-51-1 (5Z)-5-(3-bromo-4-methoxybenzylidene)-3-(4-nitrobenzyl)thiazolidine-2,4-dione 
• 1537868-50-0 (5Z)-5-(3-bromobenzylidene)-3-(4-nitrobenzyl)thiazolidine-2,4-dione 
• 1213236-05-5 C₁₇H₁₁ClN₆O₄S₃ 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of N-substituted indole-thiazolidinedione analogues as potential pancreatic lipase inhibitors

Pancreatic Lipase (PL) is a key enzyme responsible for the digestion of 50%–70% of dietary triglycerides, hence its inhibition is considered as a viable approach for the management of obesity. A series of indole-TZD hybrid analogues were synthesized, characterized and evaluated for their PL inhibitory activity. Knoevenagel condensation of various substituted indole-3-carboxaldehyde with substituted thiazolidinediones resulted in the formation of titled analogues. Analogues 6d and 6e exerted potent PL inhibitory activity (IC50-6.19 and 8.96?μM, respectively). Further, these analogues exerted a competitive mode of PL inhibition. Moreover, molecular modelling studies were in agreement with the in vitro results (Pearson's r?=.8682, p?.05). The fluorescence spectroscopic analysis further supported the strong binding affinity of these analogues with PL. A molecular dynamics study (20?ns) indicated that these analogues were stable in a dynamic environment. Thus, the present study highlighted the potential role of indole-thiazolidinedione hybrid analogues as potential PL inhibitors and further optimization might result in the development of new PL inhibitory lead candidates.

Synthesis of Novel Hybrids of Thiazolidinedione-Triazoles as Potential Lipase and α-Glucosidase Inhibiting Agents

Novel thiazolidinedione-triazole analogs (5a-5n, 6) were synthesized and screened for pancreatic lipase and intestinal α-glucosidase inhibitory activity. Analogs with nitro and fluoro benzyl substitutions at thiazolidinedione moiety 5a (IC50 28

Novel Furochromone Derivatives: Synthesis and Anticancer Activity Studies

Medicinal plant extracts have been used for medical purposes throughout human history. In this study, khellin, having furochromone structure, which is obtained from a well-known traditional medicinal plant, was selected. A series of furochromonyl compounds (K1–K14) were synthesized for their anticancer activities. Furochromonyl compounds (K1–K14) were synthesized by Knoevenagel reaction of substituted 2,4-thiazolidinediones (Ia–j)/rhodanines (Ik–n) with khellin-2-carboxaldehyde (V), and their cytotoxicity was investigated in 22 cancer cell lines, which were originated from tissues such as the liver, breast, colon, and cervix. As the first step, two hepatocellular carcinoma cell lines Huh7 and PLC/PRF/5 (Alexander cells) were treated with 10?μM of each compound for 72?h, and then sulforhodamine B assay was performed to analyze their anti-growth activities. Ethyl 2-(5-((4,9-dimethoxy-5-oxo-5H-furo[3,2-g]chromen-7-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetate (K11) was found as the most cytotoxic compound of primary screening. Afterwards, 12 hepatocellular carcinoma, seven breast cancer, two colon cancer, and a cervical cancer cell lines were selected to test K11 for 72?h at multiple concentrations to determine 50% effective doses. Results showed that the 14 cell lines were affected by K11 quantities lower than 10?μM. The structure of K11, which is particularly effective on breast cancers, can be used to slow down the progression of tumors. Furthermore, the discovery of more effective compounds can be carried out on the basis of this structure.

Synthesis and in vitro cytotoxicity evaluation of β-carboline-linked 2,4-thiazolidinedione hybrids: potential DNA intercalation and apoptosis-inducing studies

A series of new β-carboline-thiazolidinedione hybrids was synthesized and assessed for in vitro cytotoxicity potential against selected human cancer cell lines, namely, PC-3, A549, MG-63, HCT-15, MDA-MB-231, A431, and PANC-1 along with a normal human cell line (L-132). Among this new series, compound 19e was found to exhibit promising cytotoxic effects against triple negative breast cancer cell line (MDA-MB-231) with IC50 value of 0.97 ± 0.13 μM. Hence, further mechanistic studies of the apoptosis-inducing effect of 19e were conducted on the MDA-MB-23 cell line. Moreover, characteristic apoptotic features such as membrane blebbing, chromatin condensation, and apoptotic body formation were observed with the effect of 19e on MDA-MB-231 cells using AO/EB and DAPI staining. The Annexin V-Alexa Flour 488/PI assay confirmed significant early apoptosis induction. Notably, DCFDA assay indicated that 19e induced ROS generation. Moreover, mitochondrial membrane potential collapse was observed through JC-1 staining by 19e. Furthermore, cell cycle analysis revealed that 19e arrested cells in the sub G1 phase. In addition, clonogenic and wound healing assays indicated inhibition of colony formation and cell migration by 19e in a dose-dependent manner. Next, molecular modelling and DNA binding affinity studies such as relative viscosity, circular dichroism and UV-visible spectroscopy denoted classic intercalation of 19e with CT-DNA with binding constant of 1 × 105 M?1.

Design, synthesis, biological evaluation and molecular modelling studies of novel diaryl substituted pyrazolyl thiazolidinediones as potent pancreatic lipase inhibitors

A series of novel diaryl substituted pyrazolyl 2,4-thiazolidinediones were synthesized via reaction of appropriate pyrazolecarboxaldehydes with 2,4-thiazolidinedione (TZD) and nitrobenzyl substituted 2,4-thiazolidinedione. The resulting compounds were screened in vitro for pancreatic lipase (PL) inhibitory activity. Two assay protocols were performed viz., methods A and B using p-nitrophenyl butyrate and tributyrin as substrates, respectively. Compound 11e exhibited potent PL inhibitory activity (IC50?=?4.81?μM and Xi50?=?10.01, respectively in method A and B), comparable to that of the standard drug, orlistat (IC50?=?0.99?μM and Xi50?=?3.72). Presence of nitrobenzyl group at N-3 position of TZD and nature of substituent at para position of phenyl ring at C-3 position of pyrazole ring notably affected the PL inhibitory activity of the tested compounds. Enzyme inhibition kinetics of 11e revealed its reversible competitive inhibition, similar to that of orlistat. Molecular docking studies validated the rationale of pharmacophoric design and are in accordance to the in vitro results. Compound 11e exhibited a potential MolDock score of ?153.349?kcal/mol. Further, the diaryl pyrazolyl wing exhibited hydrophobic interactions with the amino acids of the hydrophobic lid domain. Moreover, the carbonyl group at 2nd position of the TZD ring existed adjacent to Ser 152 (≈3??) similar to that of orlistat. A 10?ns molecular dynamics simulation of 11e–PL complex revealed a stable binding conformation of 11e in the active site of PL (Maximum RMSD?≈?3??). The present study identified novel thiazolidinedione based leads with promising PL inhibitory activity. Further development of the leads might result in potent PL inhibitors.

Synthesis and antimicrobial activity of novel 5-[(1H-indol-3-yl)methylene]thiazolidine-2,4-dione–[1,2,3]triazole hybrids

5-[(1H-Indol-3-yl)methylene]thiazolidine-2,4-dione–[1,2,3]triazole hybrid derivatives were synthesized by click chemistry reaction and screened for antimicrobial activity against Gram positive and Gram negative bacteria and fungal species. All synthesized

Structural exploration, synthesis and pharmacological evaluation of novel 5-benzylidenethiazolidine-2,4-dione derivatives as iNOS inhibitors against inflammatory diseases

In our previous work, 3I inhibited the LPS-induced iNOS activity and NO production in RAW 264.7 cells and improved joint inflammation and cartilage destruction in inflammatory model. In this study, we synthesized 59 derivatives and bioisosteres on the bas

Synthesis, in vitro anticancer activity and in silico study of new disubstituted thiazolidinedione derivatives

Thiazolidinediones are known to have antidiabetic activity, but new activities are being discovered every year; among these, their anticancer activity has received the most attention. In this study, we synthesized three new disubstituted thiazolidinedione

Synthesis and antidiabetic activity of morpholinothiazolyl-2,4- thiazolidindione derivatives

We report the synthesis and the in vitro insulin releasing and glucose uptake activity of the morpholino thiazolyl-2,4-thiazolidinediones (1-15). Compounds 5, 1115 (at lower concentration; 0.001mg/ml) were able to increase insulin release in the presence

Synthesis of some novel substituted arylidene and substituted benzylthiazolidine-2,4-dione analouges as chemotherapeutic agents

A series of 5-substituted arylidene and 3-substituted benzylthiazolidine-2, 4-dione derivatives were synthesized from thiazolidinedione and substituted benzyl chloride followed by the addition of substituted aromatic aldehydes. All the compounds 1a-e and