Arylidene pyruvic acids motif in the synthesis of new thiopyrano[2,3-d]thiazoles as potential biologically active compounds

Abstract

Arylidene pyruvic acids motif in the synthesis of new thiopyrano[2,3-d]thiazoles as potential biologically active compoundsAbstract: Novel rel-(5R,6S,7S)-2- oxo-5,7-diaryl-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazol-6-yl-oxo-acetic acids were synthesized in 52-70% yields via regioselective and diastereoselective hetero-Diels-Alder reaction of 5-arylidene-4-thioxo-2-thiazolidinones with a series of arylidene pyruvic acids. The synthesized compounds were evaluated for anticancer activity in NCI60 cancer cell lines and for antiexudative activity on the carrageenan edema model in rats. Biological screening data led to identification of 3e as having moderate antitumor activity on the colon cancer HT-29 cell line and of 3b as having promising antiexudative effect.

Arylidene Pyruvic Acids Motif in the Synthesis of New 2H,5H-Chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazoles via Tandem Hetero-Diels–Alder-Hemiacetal Reaction

“…[19] Thus, the starting 5-(2-hydroxybenzylidene)-4-thioxo-2-thiazolidinones 1a-b were synthesized via Knoevenagel condensation (ethanol medium in the presence of ethylendiaminediacetate). [18] The APAs were synthesized by the reaction of the corresponding aromatic aldehyde with a pyruvic acid in aqueous methanol solution. [20] The reactions between 5-(2-hydroxybenzylidene)-4-thioxo-2-thiazolidinones 1a-b and arylidene pyruvic acids 2a-c followed by the tandem hetero-Diels-Alder and hemiacetal formation processes, affording tetracyclic fused 6-…”

“…Furthermore, previously synthesized compounds could be employed as templates for search of biologically active compounds. [18] Hence, the aim of the presented Letter was the synthesis of new 2H,5H-chromeno [4',3':4,5]thiopyrano [2,3-d]thiazoles via a novel hetero-Diels-Alder-hemiacetal reaction.…”

New thiopyrano[2,3-d][1,3]thiazole derivatives as potential antiviral agents

“…The synthesis of 2-oxo-3,7-dihydro-2Н-thiopyrano [2,3- (6)(7)(8)(9)(10)(11)(12)(13) 16 , 6-carboxymethylene-2-oxo-3,5,6,7-tetrahydro-2h-…”

Thiopyrano[2,3-d]Thiazoles as New Efficient Scaffolds in Medicinal Chemistry

“…Currently, the list of dienophiles for the synthesis of thiopyrano [2,3-d]thiazole derivatives has significantly expanded. Thus, the use of cynnamic acids [26] and their amides [27], aroylacrylic [28] and arylidene pyruvic [29] acids as well as dimethyl acetylenedicarboxylate [30], propiolic acid and its ethyl ester [26], acroleine [31], 2-norbornene [15] and 5-norbornene-2,3-dicarboxylic acid imides [16] as dienophiles allowed to obtain new thiopyrano[2,3-d]thiazoles 8-15 as promising biologically active compounds based on the "thiazolidinone" matrix (Scheme 4). It should be noted that the presence of chiral centers in the structure of thiopyrano[2,3-d]thiazole cycle causes certain features of stereochemistry in the hetero-Diels-Alder reaction.…”