Convenient synthesis and anticancer evaluation of novel pyrazolyl-thiophene, thieno[3,2-b]pyridine, pyrazolo[3,4-d]thieno[3,2-b]pyridine and pyrano[2,3-d]thieno[3,2-b]pyridine derivatives was written by Masaret, Ghada S.. And the article was included in Journal of Heterocyclic Chemistry in 2021.Quality Control of Ethyl 4-chloro-3-oxobutanoate The following contents are mentioned in the article:
The newly synthesized 3-(3-amino-5-(phenylamino)-4-(phenylcarbamoyl)thiophen-2-yl)-3-oxopropanoate was utilized as a precursor for the synthesis of pyrazolyl-thiophene derivative, I which undergoes cyclization upon treatment with benzaldehyde derivatives to provide pyrazolo[3,4-d]thieno[3,2-b]pyridines II [Ar = 4-MeC6H4, 4-MeOC6H4, 4-ClC6H4]. Basic treatment of pyrazolyl-thiophene derivative with Ph isothiocyanate followed by subsequent addition of chloroacetone and/or Et bromoacetate yielded the thiazolylidene-pyrazolyl thiophenes. In addition, the building block 3-(3-amino-5-(phenylamino)-4-(phenylcarbamoyl)thiophen-2-yl)-3-oxopropanoate was converted into the corresponding thieno[3,2-b]pyridine compounds through its reactions with (DMF-DMA) and/or heating in sodium ethoxide. Moreover, the reaction of 7-hydroxy-5-oxo-N-phenyl-2-(phenylamino)-4,5-dihydrothieno[3,2-b]pyridine-3-carboxamide with 2-arylidenemalononitrile produced the new annulated pyrano[2,3-d]thieno[3,2-b]pyridines II. The prepared thiophene-based compounds pyrazolyl-thiophene I , thieno[3,2-b]pyridine, pyrazolo[3,4-d]thieno[3,2-b]pyridine II and pyrano[2,3-d]thieno[3,2-b]pyridine derivatives III were evaluated against HepG2, PC3, and MCF-7 cancer cells, and normal fibroblast cell (WI38). The pyrazolo[3,4-d]thieno[3,2-b]pyridine II [Ar = 4-ClC6H4] and pyrano[2,3-d]thieno[3,2-b]pyridine compounds III [Ar = 4-ClC6H4] presented promising cytotoxic activities against HepG2 cancer cell line without any human toxicity. Docking study for the synthesized thiophene compounds I, II, III delivered valuable insights about the binding interactions with the crystal structure of NS5B enzyme with PDB ID (4TLR). This study involved multiple reactions and reactants, such as Ethyl 4-chloro-3-oxobutanoate (cas: 638-07-3Quality Control of Ethyl 4-chloro-3-oxobutanoate).
Ethyl 4-chloro-3-oxobutanoate (cas: 638-07-3) belongs to organic chlorides. An organic chloride is an organic compound containing at least one covalently bonded atom of chlorine. Their wide structural variety and divergent chemical properties lead to a broad range of names and applications. Organochlorine compounds are lipophylic, meaning they are more soluble in fat than in water. This gives them a high tenancy to accumulate in the food chain (biomagnification).Quality Control of Ethyl 4-chloro-3-oxobutanoate
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics