849052-66-0

Basic information

• Product Name: 4-Thiazolidinecarboxylic acid, 2-[4-(acetylamino)phenyl]-, (4R)-
• CAS NO: 849052-66-0
• Molecular Formula: C12H14N2O3S
• Molecular Weight: 266.321
• Mol File: 849052-66-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-Thiazolidinecarboxylic acid, 2-[4-(acetylamino)phenyl]-, (4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Thiazolidinecarboxylic acid, 2-[4-(acetylamino)phenyl]-, (4R)-(849052-66-0)
• EPA Substance Registry System: 4-Thiazolidinecarboxylic acid, 2-[4-(acetylamino)phenyl]-, (4R)-(849052-66-0)

Safety Data

• Hazardous Substances Data: 849052-66-0(Hazardous Substances Data)

Upstream product

• 52-90-4 L-Cysteine 
• 122-85-0 para-acetamidobenzaldehyde 

Downstream Products

• 72679-40-4 (R)-2-(4-Acetylamino-phenyl)-3-((S)-3-mercapto-2-methyl-propionyl)-thiazolidine-4-carboxylic acid 
• 1208224-25-2 (4R)-2-(4-acetylamino-phenyl)-thiazolidine-3,4-dicarboxylic acid 3-(9H-fluoren-9-ylmethyl)ester 
• 1071160-18-3 C₃₅H₅₇N₃O₄S 
• 72679-39-1 (R)-2-(4-Acetylamino-phenyl)-3-((S)-3-benzoylsulfanyl-2-methyl-propionyl)-thiazolidine-4-carboxylic acid 
• 110078-88-1 (2R,4R)-3-Acetyl-2-(4-acetylamino-phenyl)-thiazolidine-4-carboxylic acid 
• 1071160-14-9 C₃₄H₅₇N₃O₄S 
• 948052-65-1 (4R)-2-(4-acetylamino-phenyl)-thiazolidine-4-carboxylic acid hexadecylamide 
• 1071160-12-7 C₃₂H₅₃N₃O₄S 
• 1071160-11-6 C₃₁H₅₁N₃O₄S 
• 948052-63-9 (4R)-2-(4-acetamidophenyl)-N-dodecylthiazolidine-4-carboxamide 
• 1071160-10-5 C₂₉H₄₇N₃O₄S 
• 948052-48-0 C₁₇H₂₂N₂O₅S 

Relevant articles and documents

Discovery of 2-arylthiazolidine-4-carboxylic acid amides as a new class of cytotoxic agents for prostate cancer

To improve the selectivity and antiproliferative activity of previously reported serine amide phosphates (SAPs), we designed a new series of 4-thiazolidinone amides, in which the 4-thiazolidinone moiety was introduced as a phosphate mimic. However, these 4-thiazolidinone derivatives demonstrated less cytotoxicity in prostate cancer cells despite improved selectivity over RH7777 cells. To further optimize the thiazolidinone analogues in terms of cytotoxicity and selectivity, we made closely related structural modifications, which led us to the discovery of a new class of 2-arylthiazolidine-4-carboxylic acid amides. These compounds were potent cytotoxic agents with IC50 values in the low micromolar concentration range and demonstrated enhanced selectivity in receptor-negative cells compared to SAPs and 4-thiazolidinone amides.

Synthesis and antiproliferative activity of thiazolidine analogs for melanoma

We have previously described 2-aryl-thiazolidine-4-carboxylic acid amides as a novel class of antiproliferative agents for prostate cancer. Screening these compounds with melanoma cell lines revealed that several of them have potent antiproliferative activity and selectivity against melanoma. To further improve the potency and selectivity, we synthesized a new series of analogs and tested them in two melanoma cell lines and fibroblast cells (negative controls). Comparison of anticancer effects of these compounds with a standard chemotherapeutic agent, sorafenib, showed that they are very effective in killing melanoma cells with low micromolar to nanomolar antiproliferative activity and provide us a new lead for developing potential drugs for melanoma.