131554-52-4

Usage

Chemical class

Thiazolidinedione drugs

Potential use

Treatment of diabetes and other metabolic disorders

Mechanism of action

Improves insulin sensitivity and lowers blood glucose levels in patients with type 2 diabetes

Chemical structure

Contains a 2,4-thiazolidinedione ring and a 4-chlorophenyl group

Possible interaction

May interact with specific receptors or enzymes involved in glucose metabolism

Research status

Further research needed to determine the full potential and safety for therapeutic use

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 39131-10-7 1,3-thiazolidine-2,4-dione potassium salt 

Downstream Products

• 154285-39-9 N-(4'-chlorophenacyl)-5-(3-bromobenzylidene)-thiazolidine-2,4-dione 
• 151956-14-8 N-(4'-chlorophenacyl)-5-(4-methylbenzylidene)-thiazolidine-2,4-dione 
• 443308-29-0 6-(4-chlorophenyl)-4,5-dihydro-2H-1,2,4-triazin-3-one 
• 61416-43-1 5-(4-chlorophenyl)-3H-oxazol-2-one 
• 23448-89-7 6-(4-chlorophenyl)-2H-1,2,4-triazin-3-one 

Relevant academic research and scientific papers

Studies on the synthetic and structural aspects of benzosuberones bearing 2, 4-thiazolidenone moiety as potential anti-cancer agents

Novel representative of the important group of biologically active benzosuberones bearing 2, 4-thiazolidenone moiety was synthesized as potential anticancer agents (6a-j). These compounds were synthesized in good yields from Knoevenagel condensation of co

Design, Synthesis, and Biological Evaluation of a Series of Oxazolone Carboxamides as a Novel Class of Acid Ceramidase Inhibitors

Acid ceramidase (AC) is a cysteine hydrolase that plays a crucial role in the metabolism of lysosomal ceramides, important members of the sphingolipid family, a diversified class of bioactive molecules that mediate many biological processes ranging from cell structural integrity, signaling, and cell proliferation to cell death. In the effort to expand the structural diversity of the existing collection of AC inhibitors, a novel class of substituted oxazol-2-one-3-carboxamides were designed and synthesized. Herein, we present the chemical optimization of our initial hits, 2-oxo-4-phenyl-N-(4-phenylbutyl)oxazole-3-carboxamide 8a and 2-oxo-5-phenyl-N-(4-phenylbutyl)oxazole-3-carboxamide 12a, which resulted in the identification of 5-[4-fluoro-2-(1-methyl-4-piperidyl)phenyl]-2-oxo-N-pentyl-oxazole-3-carboxamide 32b as a potent AC inhibitor with optimal physicochemical and metabolic properties, showing target engagement in human neuroblastoma SH-SY5Y cells and a desirable pharmacokinetic profile in mice, following intravenous and oral administration. 32b enriches the arsenal of promising lead compounds that may therefore act as useful pharmacological tools for investigating the potential therapeutic effects of AC inhibition in relevant sphingolipid-mediated disorders.

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.

NOVEL PYRIDAZONES AND TRIAZINONES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION

The invention provides novel compounds having the general formula wherein R1, R2, R3, X and a are as described in the description and in the claims, as well as or pharmaceutically acceptable salts thereof. The invention also contains compositions including the compounds and methods of using the compounds.

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 and antimicrobial activity of some novel thiazolidine-2,4-dione derivatives

In this study, a series of phenylethylsulfanyl-1,3-thiazolo-thiazolidine-2, 4-dione derivatives (VII a - f, VIIIa - f) and 5-methyl-[1,2,4]triazolyl- sulfanyl-1,3-thiazolo-thiazolidine-2,4-dione derivatives (IX a - f, Xa - f) were synthesized and evaluated for their antibacterial and antifungal activities against S. aureus (ATCC 25923), methicillin resistant S. aureus (MRSA ATCC 43300), B. subtilis (ATCC 6633), E. coli ( ATCC 23556) and C. albicans (ATCC10145). All the compounds were found active against used bacteria. ECV Editio Cantor Verlag.

Substituted 4,5-dihydro-1,2,4-triazin-3-ones,1,2,4-triazin-3-ones, and their use as fungicides and insecticides

This invention relates to dihydrotriazinones, triazinones and related compounds, compositions comprising such compounds and an agronomically acceptable carrier, and the use thereof as broad spectrum fungicides and insecticides. This invention also teaches

Substd. 4, 5-dihydro -1, 2, 4-triazine-3-one, 1, 2, 4-triazine-3-one, and their use as an insecticide and sterilizing agent

This invention relates to dihydrotriazinones, triazinones and related compounds, compositions comprising such compounds and an agronomically acceptable carrier, and the use thereof as broad spectrum fungicides and insecticides. This invention also teaches methods of preparing these compounds as well as methods of using the compounds as fungicides and insecticides.

Synthesis and Antidiabetic Activity of Some New Furochromonyl-2,4- thiazolidinediones

A new series of furochromone-2,4-thlazolidinedione derivatives (VIIa-h) was prepared by Knoevenagel reaction of substituted-2,4-thiazolidinediones (VIa-h) with Khellin-2-carboxaldehyde (IV). The prepared compounds were tested for their insulinotropic acti