473910-47-3

Upstream product

• 98-88-4 benzoyl chloride 
• 169908-34-3 methyl (2R,4R)-N-benzoyl-2-phenylthiazolidine-4-carboxylate 
• 196930-46-8 (4R)-2-phenyl-1,3-thiazolidine-4-carboxylic acid 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 125813-73-2 (2R,4R)-N-benzoyl-2-phenylthiazolidine-4-carboxylic acid 

Downstream Products

• 711016-37-4 dimethyl 3,5-diphenyl-1H,3H-pyrrolo[1,2-c]thiazole-6,7-dicarboxylate-2,2-dioxide 
• 1426937-90-7 C₂₀H₁₉NO₂S 
• 138037-09-9 dimethyl 2-phenyl-5-styryl-1H-pyrrole-3,4-dicarboxylate 

Relevant academic research and scientific papers

Chiral 6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c]thiazoles with anti-breast cancer properties

The synthesis and biological evaluation of 6,7-bis(hydroxymethyl)-1H,3H- pyrrolo[1,2-c]thiazoles as anticancer agents against MCF7 breast cancer cell lines is reported. The design of the new compounds has been guided considering (3R)-6,7-bis(hydroxymethyl)-5-methyl-3-phenyl-1H,3H-pyrrolo[1,2-c]thiazole as the lead compound due to its good performance against MCF7 breast cancer cell lines (IC50 = 1.0 μM). The structural changes included the removal of the phenyl group at C-3, the replacement of this group by a 3,4,5-trimethoxyphenyl group, the removal of the methyl group at C-5 from the lead scaffold and the replacement of this group by a phenyl substituent. Overall, these studies showed that the combined presence of a phenyl group at C-3 and a methyl group at C-5 in the 1H,3H-pyrrolo[1,2-c]thiazole ring system is essential to ensure high cytotoxicty against MCF7 breast cancer cell lines. To probe whether the absolute configuration of the lead compound might affect the anticancer activity, its enantiomer was prepared and the activity against MCF7 cells was evaluated. (3S)-6,7-Bis(hydroxymethyl)-5-methyl-3-phenyl-1H,3H- pyrrolo[1,2-c]thiazole proved to be the most active compound so far studied, with IC50 value of 0.5 μM.

Cycloaddition reactions of 3-aryl-5-phenyl-5H,7H-thiazolo[3,4-c]oxazol-4-ium-1-olates

Intermolecular 1,3-dipolar cycloaddition of (5R)- and (5S)-3,5-diphenyl-5H,7H-thiazolo[3,4-c]oxazol-4-ium-1-olates, (5R)- and (5S)-3-(p-methoxyphenyl)-5-phenyl-5H,7H-thiazolo-[3,4-c]oxazol-4-ium-1-olates with a range of dipolarophiles is described. New chiral 5-aryl-3-phenyl-1H,3H-pyrrolo[1,2-c]thiazoles with R and S configuration were obtained. The structure of methyl (3R)-3-phenyl-5-(p-methoxyphenyl)-1H,3H-pyrrolo[1,2-c]thiazole-6-carboxylate was determined by X-ray crystallography. The synthesis of 7,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazole-6,7-dicarboxylates was also achieved.