40176-02-1

Basic information

• Product Name: ethyl 2‐[5‐(4‐chlorobenzylidene)‐2,4‐dioxothiazolidin‐3‐yl]acetate
• Synonyms: ethyl 2‐[5‐(4‐chlorobenzylidene)‐2,4‐dioxothiazolidin‐3‐yl]acetate
• CAS NO: 40176-02-1
• Molecular Weight: 325.773
• Mol File: 40176-02-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: ethyl 2‐[5‐(4‐chlorobenzylidene)‐2,4‐dioxothiazolidin‐3‐yl]acetate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2‐[5‐(4‐chlorobenzylidene)‐2,4‐dioxothiazolidin‐3‐yl]acetate(40176-02-1)
• EPA Substance Registry System: ethyl 2‐[5‐(4‐chlorobenzylidene)‐2,4‐dioxothiazolidin‐3‐yl]acetate(40176-02-1)

Safety Data

• Hazardous Substances Data: 40176-02-1(Hazardous Substances Data)

Upstream product

• 105-39-5 chloroacetic acid ethyl ester 
• 71995-35-2 5-(4-Chlorophenylmethylene)-2,4-dioxothiazolidine potassium salt 
• 104-88-1 4-chlorobenzaldehyde 
• 24138-83-8 5-(4-chloro-benzylidene)-thiazolidine-2,4-dione 
• 105-36-2 ethyl bromoacetate 
• 39137-34-3 (2,4-thiazolidinedion-3-yl)acetic acid ethyl ester 

Relevant articles and documents

Design, synthesis, docking, ADMET profile, and anticancer evaluations of novel thiazolidine-2,4-dione derivatives as VEGFR-2 inhibitors

The anticancer activity of novel thiazolidine-2,4-diones was evaluated against HepG2, HCT-116, and MCF-7 cells. Among the tested cancer cell lines, HCT-116 was the most sensitive one to the cytotoxic effect of the new derivatives. In particular, compounds 18, 11, and 10 were found to be the most potent derivatives among all the tested compounds against the HepG2, HCT-116, and MCF-7 cancer cell lines, with IC50 values ranging from 38.76 to 53.99 μM. The most active antiproliferative derivatives (7–14 and 15–19) were subjected to further biological studies to evaluate their inhibitory potentials against VEGFR-2. The tested compounds displayed a good-to-medium inhibitory activity, with IC50 values ranging from 0.26 to 0.72 μM. Among them, compounds 18, 11, and 10 potently inhibited VEGFR-2 at IC50 values in the range of 0.26–0.29 μM, which are nearly three times that of the sorafenib IC50 value (0.10 μM). Although our derivatives showed lower activities than the reference drug, they could be useful as a template for future design, optimization, adaptation, and investigation to produce more potent and selective VEGFR-2 inhibitors with higher anticancer analogs. The ADMET profile showed that compounds 18, 11, and 10 do not violate any of Lipinski's rules and have a comparable intestinal absorptivity in humans. Also, the new derivatives could not inhibit cytochrome P3A4. Unlike sorafenib and doxorubicin, compounds 18, 11, and 10 are expected to have prolonged dosing intervals. Moreover, compounds 10 and 18 displayed a wide therapeutic index and higher selectivity against cancer cells as compared with their cytotoxicity against normal cells.

A class of carbonic anhydrase IX/XII–selective carboxylate inhibitors

A small series of 2,4-dioxothiazolidinyl acetic acids was prepared from thiourea, chloroacetic acid, aromatic aldehydes, and ethyl-2-bromoacetate. They were assayed for the inhibition of four physiologically relevant carbonic anhydrase (CA, EC 4.2.1.1) isoforms of human (h) origin, the cytosolic hCA I and II, and the transmembrane hCA IX and XII, involved among others in tumorigenesis (hCA IX and XII) and glaucoma (hCA II and XII). The two cytosolic isoforms were not inhibited by these carboxylates, which were also rather ineffective as hCA IX inhibitors. On the other hand, they showed submicromolar hCA XII inhibition, with KIs in the range of 0.30–0.93 μM, making them highly CA XII-selective inhibitors.

Synthesis of thiazolidindione-2,4-carboxylic acids

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