3,3′-Di(1,3-thiazolidine-4-one) system. V. Synthesis and pharmacological properties of 3,3′(1,2-ethanediyl)bis-(2-heteroaryl-1,3-thiazolidine-4-one) derivatives

Configurational assignments of the diastereomers of 3,3′‐(1,2‐ethanediyl)bis[2‐(3‐fluorophenyl)‐5‐methyl‐4‐thiazolidinone] derivative with four stereogenic centers

“…The presence of multiple sets of signals with different intensities and the analogy with the magnetic behavior of compounds A with corresponding geometry, allow the chemical shifts of each isomer to be exactly assigned (Table 3). In fact, the trans/cis relationship of dl 4 is supported by two sets of 2,2'-CH (5.51, 5.56 ppm) and 5,5'-CH (3.92, 4.04 ppm) signals as already explained for enantiomeric pair dl 2 of type A with the same trans/cis relationship. However, the mixture shows additional single signals for 2,2'-CH (5.53 ppm) and 5,5'-CH (4.02 ppm) attributable to isomer with the trans/trans geometry (see discussion for dl 1 ).…”

“…However, the mixture shows additional single signals for 2,2'-CH (5.53 ppm) and 5,5'-CH (4.02 ppm) attributable to isomer with the trans/trans geometry (see discussion for dl 1 ). Thus we can deduce that B 1 mixture is formed by meso 1 with configuration 2R5R,2'S5'S and dl 4 enantiomeric pair with configurations 2R5R,2'S5'R and 2S5S,2'R5'R. In addition the 1 H nmr spectrum allows dl 4 :meso 1 60:40 ratio to be measured.…”

“…Thus we can deduce that B 1 mixture is formed by meso 1 with configuration 2R5R,2'S5'S and dl 4 enantiomeric pair with configurations 2R5R,2'S5'R and 2S5S,2'R5'R. In addition the 1 H nmr spectrum allows dl 4 :meso 1 60:40 ratio to be measured.…”

“…Since the 2 and 2' carbons bear the same substituent (Ar) and 5 and 5' also bear the same substituent (CH 3 ), the number of possible stereoisomers is reduced from sixteen to ten, namely four enantiomeric pairs dl [1][2][3][4] and two meso forms meso [1][2] . They can display trans/trans, trans/cis or cis/cis geometries with respect to the Ar/CH 3 disposition of each thiazolidinone ring ( Table 1).…”

Synthesis and Antimicrobial Activities of Novel Series of 3‐(4‐(2‐substituted thiazol‐4‐yl)phenyl)‐2‐(4‐methyl‐2‐substituted thiazol‐5‐yl)thiazolidin‐4‐one Derivatives

“…Thiazolidinones have also received considerable attention because of their biological importance . The thiazolidinone nucleus containing compounds show anti‐inflammatory , anticonvulsant , hypnotic and anti‐tubercular , and antimicrobial and anticancer activities. In view of these observations and as a continuation of our previous work on thiazolidinone , it was thought to synthesize new thiazole based 1,3‐thiazolidin‐4‐one by the condensation of 2‐substituted‐4‐methylthiazole‐5‐carbaldehyde with 4‐(2‐substituted thiazol‐4‐yl)benzene‐amine and thioglycolic acid.…”