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Table 1 The physicochemical, elemental and spectral characteristics of synthesized thiazolidine-2,4-dione derivatives

From: Synthesis, biological evaluation and in-silico ADME studies of novel series of thiazolidin-2,4-dione derivatives as antimicrobial, antioxidant and anticancer agents

Compound

Physicochemical and spectral characteristics

(E)-5-(4-(4-oxo-3-phenylthiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 280–282; Rf value: 0.56*; % yield: 74; IR (KBr pellets) cm−1: 3448.73 (N–H str.), 1770.59 (C=O str.), 1497.42 (C=C str., aromatic ring), 1661.76 (C=C str., aliphatic), 2943.38 (C–H str., aliphatic), 1255.61 (C–N str.), 847.82 (C–H oop bend., aromatic), 663.15 (C–S bend.) 1101.06 (C–C str., aromatic ring); 1H-NMR (δ, DMSO): 7.10–7.88 (m, 9H, Ar–H), 7.94 (s, 1H, –CH=), 3.44, 3.46 (d, 2H, –CH2 of thiazolidine-4-one), 6.77 (s, 1H, –CH of thiazolidine-4-one) 12.59 (s, 1H, NH); M. Formula: C19H14N2O3S2; MS: m/z 383.04 (M+); Elemental analysis (CHN) Theoretical calc: C, 59.67; H, 3.69; N, 7.32 Found: C, 59.7; H, 3.67; N, 7.30

(E)-5-(4-(3-amino-4-oxothiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 208–210; Rf value: 0.61**; % yield: 60; IR (KBr pellets) cm−1: 3472.36 (N–H str.), 1690.31 (C=O str.), 1524.13 (C = C str., aromatic ring), 1637.59 (C=C str., aliphatic), 3119.42 (C–H str., aromatic ring), 3003.75 (C–H str., aliphatic), 1336.47 (C–N str.), 801.42 (C–H oop bend., aromatic), 628.31 (C–S bend.) 1149.31 (C–C str., aromatic ring) 3313.97, 3382.58 (N–H str., aliphatic amine); 1H-NMR (δ, DMSO): 6.98–7.78 (m, 4H, Ar–H), 7.95 (s, 1H, –CH=), 3.45, 3.58 (d, 2H, –CH2 of thiazolidine-4-one), 5.22 (s, 1H, –CH of thiazolidine-4-one), 3.79 (s, 2H, –NH2 group), 12.61 (s, 1H, NH); M. Formula: C13H11N3O3S2; MS: m/z 323.21 (M+ + 2); Elemental analysis (CHN) Theoretical calc: C, 48.59; H, 3.45; N, 13.08 Found: C, 48.62; H, 3.44; N, 13.10

(E)-5-(4-(4-oxo-3-(phenylamino)thiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 282–284; Rf value: 0.51**; % yield: 65; IR (KBr pellets) cm−1: 3477.42 (N–H str.), 3357.17 (N–H str., secondary amine), 1694.69 (C=O str.), 1518.27 (C=C str., aromatic ring), 1649.21 (C=C str., aliphatic), 3191.78 (C–H str., aromatic ring), 2950.88 (C–H str., aliphatic), 1274.86 (C–N str.), 801.86 (C–H oop bend., aromatic), 631.19 (C–S bend.), 1166.66 (C–C str., aromatic ring); 1H-NMR (δ, DMSO): 6.68–7.506 (m, 9H, Ar–H), 7.61 (s, 1H, –CH=), 3.32, 3.34 (d, 2H, –CH2 of thiazolidine-4-one), 5.71 (s, 1H, –CH of thiazolidine-4-one), 9.61 (s, 1H, NH adjacent to phenyl ring), 12.51 (s, 1H, NH of thiazolidine ring); M. Formula: C19H15N3O3S2; MS: m/z 398.27 (M+ + 1); Elemental analysis (CHN) Theoretical calc: C, 57.42; H, 3.80; N, 10.57 Found: C, 57.40; H, 3.79; N, 10.55

(E)-5-(4-(3-(2-chlorophenyl)-4-oxothiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 222–224; Rf value: 0.63*; % yield: 62; IR (KBr pellets) cm−1: 3335.73 (N–H str.), 1743.82 (C=O str.), 1520.84 (C=C str., aromatic ring), 1693.17 (C=C str., aliphatic), 3186.47 (C–H str., aromatic ring), 2981.68 (C–H str., aliphatic), 1293.41 (C–N str.), 836.53 (C–H oop bend., aromatic), 623.85 (C–S bend.), 761.83 (C–Cl bend., o-substitution on phenyl ring) 1069.19 (C–C str., aromatic ring); M. Formula: C19H13ClN2O3S2; MS: m/z 415.47 (M+ − 1); Elemental analysis (CHN) Theoretical calc: C, 54.74; H, 3.14; N, 6.72 Found: C, 54.76; H, 3.15; N, 6.70

(E)-5-(4-(3-dodecyl-4-oxothiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 160–162; Rf value: 0.57**; % yield: 70; IR (KBr pellets) cm−1: 3393.96 (N–H str.), 1692.08 (C=O str.), 1515.19 (C=C str., aromatic ring), 1612.17 (C=C str., aliphatic), 3160.90 (C–H str., aromatic ring), 3020.88 (C–H str., aliphatic), 1296.92 (C–N str.), 841.16 (C–H oop bend., aromatic), 661.02 (C–S bend.), 1067.74 (C–C str., aromatic ring) 2915.30 (C–H str., side chain); 1H NMR (δ, DMSO): 7.04–7.65 (m, 4H, Ar–H), 7.95 (s, 1H, –CH=), 3.87, 3.99 (d, 2H, –CH2 of thiazolidine-4-one), 4.90 (s, 1H, –CH of thiazolidine-4-one), 12.53 (s, 1H, NH), 1.23–2.88 (m, 20H, CH2), 0.90 (t, J=85 Hz, 3H, CH3), 3.71 (m, 2H, CH2 adjacent to CH=N); M. Formula: C25H34N2O3S2; MS: m/z 476.1 (M+-1); Elemental analysis (CHN) Theoretical calc: C, 63.26; H, 7.22; N, 5.90 Found: C, 63.25; H, 7.24; N, 5.91

(E)-5-(4-(3-(furan-2-ylmethyl)-4-oxothiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 127–129; Rf value: 0.56*; % yield: 60; IR (KBr pellets) cm−1: 3437.28 (N–H str.), 1760.34 (C=O str.), 1549.27 (C=C str., aromatic ring), 1660.96 (C=C str., aliphatic), 3199.60 (C–H str., aromatic ring), 2901.27 (C–H str., aliphatic), 1339.28 (C–N str.), 844.33 (C–H oop bend., aromatic), 660.47 (C–S bend.), 1096.59 (C–C str.), 1018.24 (C–O–C str., furan ring); 1H NMR (δ, DMSO): 7.12–7.95 (m, 4H, Ar–H), 7.97 (s, 1H, –CH=), 3.76, 3.97 (d, 2H, –CH2 of thiazolidine-4-one), 6.59 (s, 1H, –CH of thiazolidine-4-one), 12.58 (s, 1H, NH), 4.79 (s, 2H, –CH2 adjacent to furan ring), 7.21 (d, 1H, CH of furan ring at 3rd position), 7.12 (t, 1H, CH of furan ring at 4th position), 8.17 (d, 1H, CH of furan ring adjacent to O); M. Formula: C17H12N2O4S2; Elemental analysis (CHN) Theoretical calc: C, 54.83; H, 3.25; N, 7.52 Found: C, 54.85; H, 3.22; N, 7.53

(E)-5-(4-(4-oxo-3-(m-tolyl)thiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 141–143; Rf value: 0.61**; % yield: 61; IR (KBr pellets) cm−1: 3423.62 (N–H str.), 1694.32 (C=O str.), 1514.80 (C=C str., aromatic ring), 1645.13 (C=C str., aliphatic), 3117.59 (C–H str., aromatic ring), 2966.25 (C–H str., aliphatic), 1335.01 (C–N str.), 824.35 (C–H oop bend., aromatic), 680.72 (C–S bend.), 1108.60 (C–C str.) 2873.73 (C–H str., side chain); M. Formula: C20H16N2O3S2; Elemental analysis (CHN) Theoretical calc: C, 60.59; H, 4.07; N, 7.07 Found: C, 60.60; H, 4.06; N, 7.07

(E)-5-(4-(4-oxo-3-(p-tolyl)thiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 191–193; Rf value: 0.54*; % yield: 61; IR (KBr pellets) cm−1: 3471.71 (N–H str.), 1689.58 (C=O str.), 1538.27 (C=C str., aromatic ring), 1646.90 (C=C str., aliphatic), 3163.62 (C–H str., aromatic ring), 3022.64 (C–H str., aliphatic), 1328.53 (C–N str.), 809.91 (C–H oop bend., aromatic), 679.58 (C–S bend.), 1140.25 (C–C str. aromatic ring) 2946.07 (C–H str., side chain); 1H NMR (δ, DMSO): 7.03–7.75 (m, 8H, Ar–H), 7.94 (s, 1H, –CH=), 3.76, 3.97 (d, 2H, –CH2 of thiazolidine-4-one), 6.46 (s, 1H, –CH of thiazolidine-4-one), 12.55 (s, 1H, NH), 2.73(s, 3H, CH3, p-position); M. Formula: C20H16N2O3S2; Elemental analysis (CHN) Theoretical calc: C, 60.59; H, 4.07; N, 7.07 Found: C, 60.62; H, 4.09; N, 7.05

(E)-5-(4-(3-(2,4-dimethylphenyl)-4-oxothiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 231–233; Rf value: 0.59**; % yield: 60; IR (KBr cm−1): 3498.49 (N–H str.), 1743.71 (C=O str.), 1542.27 (C=C str., aromatic ring), 1696.07 (C=C str., aliphatic), 3178.82 (C–H str., aromatic ring), 3029.83 (C–H str., aliphatic), 1268.36 (C–N str.), 838.86 (C–H oop bend., aromatic), 661.91 (C–S bend., thiazolidine ring), 1038.69 (C–C str.) 2978.93 (C–H str., side chain); 1H NMR (δ, DMSO): 7.20–7.42 (m, 7H, Ar–H), 7.49 (s, 1H, –CH=), 3.68, 3.75 (d, 2H, –CH2 of thiazolidine-4-one), 6.48 (s, 1H, –CH of thiazolidine-4-one), 12.61 (s, 1H, NH), 2.23(s, 3H, CH3, p-position), 2.16 (s, 3H, CH3 o-position); M. Formula: C21H19N2O3S2; Elemental analysis (CHN) Theoretical calc: C, 61.44; H, 4.22; N, 6.82 Found: C, 61.45; H, 4.23; N, 6.81

(E)-5-(4-(3-(2,6-dimethylphenyl)-4-oxothiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 145–147; Rf value: 0.63**; % yield: 56; IR (KBr cm−1): 3475.21 (N–H str.), 1687.76 (C=O str.), 1508.71 (C=C str., aromatic ring), 1546.87 (C=C str., aliphatic), 2997.90 (C–H str., aromatic ring), 2948.20 (C–H str., aliphatic), 1232.86 (C–N str., thiazolidine ring), 629.87 (C–S bend.), 1094.67 (C–C str.) 2821.33 (C–H str., side chain); 1H NMR (δ, DMSO): 7.15–7.30 (m, 7H, Ar–H), 7.95 (s, 1H, –CH =), 3.93, 4.05 (d, 2H, –CH2 of thiazolidine-4-one), 6.52 (s, 1H, –CH of thiazolidine-4-one), 12.49 (s, 1H, NH), 2.12 (s, 6H, CH3 o-position); M. Formula: C21H19N2O3S2; Elemental analysis (CHN) Theoretical calc: C, 61.44; H, 4.22; N, 6.82 Found: C, 61.42; H, 4.21; N, 6.83

(E)-5-(4-(3-(2-fluorophenyl)-4-oxothiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 121–123; Rf value: 0.53*; % yield: 69; IR (KBr cm−1): 3397.62 (N–H str.), 1690.56 (C=O str.), 1556.85 (C=C str., aromatic ring), 1621.56 (C=C str., aliphatic), 3022.29 (C–H str., aromatic ring), 2942.43 (C–H str., aliphatic), 1308.11 (C–N str.), 831.66 (C–H oop bend., aromatic), 666.00 (C–S bend.), 1196.21 (C–C str.), 1016.77 (C-F bend., o-substitution on phenyl ring); 1H NMR (δ, DMSO): 7.19–7.21 (m, 8H, Ar–H), 7.951 (s, 1H, –CH=), 3.694, 3.961 (d, 2H, –CH2 of thiazolidine-4-one), 6.39 (s, 1H, –CH of thiazolidine-4-one), 12.57 (s, 1H, NH); M. Formula: C19H13FN2O3S2; MS: m/z 401.03 (M+ + 1); Elemental analysis (CHN) Theoretical calc: C, 56.99; H, 3.27; N, 7.00 Found: C, 57.00; H, 3.25; N, 7.01

(E)-5-(4-(3-(4-bromophenyl)-4-oxothiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 119–121; Rf value: 0.59**; % yield: 73; IR (KBr cm−1): 3381.80 (N–H str.), 1746.01 (C=O str.), 1512.02 (C=C str., aromatic ring), 1672.91 (C=C str., aliphatic), 3110.07 (C–H str., aromatic ring), 2966.14 (C–H str., aliphatic), 1243.62 (C–N str.), 1156.04 (C–C str.), 826.49 (C–H oop bend., aromatic), 680.92 (C–Br bend., p-substitution on phenyl ring); 1H NMR (δ, DMSO): 7.21–7.49 (m, 8H, Ar–H), 7.952 (s, 1H, –CH=), 3.691, 3.981 (d, 2H, –CH2 of thiazolidine-4-one), 6.51 (s, 1H, –CH of thiazolidine-4-one), 12.63 (s, 1H, NH); M. Formula: C19H13BrN2O3S2; MS: m/z 459.91 (M+-1); Elemental analysis (CHN) Theoretical calc: C, 49.41; H, 3.27; N, 7.00 Found: C, 49.48; H, 3.25; N, 7.01

(E)-5-(4-(3-(3-nitrophenyl)-4-oxothiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 159–161; Rf value: 0.58*; % yield: 74; IR (KBr cm−1): 3380.87 (N–H str.), 1717.77 (C=O str.), 1541.24 (C=C str., aromatic ring), 1663.52 (C=C str., aliphatic), 3007.25 (C–H str., aromatic ring), 2885.82 (C–H str., aliphatic), 1250.32 (C–N str.), 618.67 (C–S bend.), 1079.45 (C–C str.), 1220.79 (N–O str., m-substitution on phenyl ring), 1436.75 (N=O str., m-substitution on phenyl ring); 1H NMR (δ, DMSO): 7.211–7.523 (m, 8H, Ar–H), 7.950 (s, 1H, –CH=), 4.098, 4.132 (d, 2H, –CH2 of thiazolidine-4-one), 6.49 (s, 1H, –CH of thiazolidine-4-one), 12.61 (s, 1H, NH); M. Formula: C19H13N3O5S2; Elemental analysis (CHN) Theoretical calc: C, 53.39; H, 3.07; N, 9.83 Found: C, 53.41; H, 3.05; N, 9.85

(E)-5-(4-(3-(4-chloro-2-nitrophenyl)-4-oxothiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 117–119; Rf value: 0.51*; % yield: 67; IR (KBr cm−1): 1509.11 (C=C str., aromatic ring), 2972.95 (C–H str., aromatic ring), 2885.16 (C–H str., aliphatic), 1249.06 (C–N str.), 622.84 (C–S bend., thiazolidine ring), 1074.34 (C–C str.), 1176.56 (N–O str., o-substitution on phenyl ring), 1437.32 (N=O str., o-substitution on phenyl ring), 640.18 (C–Cl bend., p-substitution on phenyl ring); 1H NMR (δ, DMSO): 7.092–7.269 (m, 7H, Ar–H), 7.953 (s, 1H, –CH =), 3.76, 3.88 (d, 2H, –CH2 of thiazolidine-4-one), 6.53 (s, 1H, –CH of thiazolidine-4-one), 12.46 (s, 1H, NH), M. Formula: C19H12ClN3O5S2; MS: m/z 462.1 (M+); Elemental analysis (CHN) Theoretical calc: C, 49.41; H, 2.62; N, 9.10 Found: C, 49.43; H, 2.61; N, 9.11

(E)-5-(4-(3-(2-methoxyphenyl)-4-oxothiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 131–133; Rf value: 0.67**; % yield: 65; IR (KBr cm−1): 3449.87 (N–H str.), 1748.92 (C=O str.), 1536.40 (C=C str., aromatic ring), 1659.37 (C=C str., aliphatic), 3138.14 (C–H str., aromatic ring), 3011.17 (C–H str., aliphatic), 1323.04 (C–N str.), 835.87 (C–H oop bend., aromatic), 659.25 (C–S bend.), 1101.58 (C–C str.), 1033.96 (O–CH3 str., o-substitution on phenyl ring); 1H NMR (δ, DMSO): 7.063–7.595 (m, 8H, Ar–H), 7.949 (s, 1H, –CH=), 3.99, 4.02 (d, 2H, –CH2 of thiazolidine-4-one), 5.88 (s, 1H, –CH of thiazolidine-4-one), 12.53 (s, 1H, NH), 3.795 (s, 3H, OCH3, o-position); M. Formula: C20H16N2O4S2; MS: m/z 413.24 (M+ + 1); Elemental analysis (CHN) Theoretical calc: C, 58.24; H, 3.91; N, 6.79 Found: C, 58.25; H, 3.90; N, 6.80

(E)-5-(4-(3-(3-methoxyphenyl)-4-oxothiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 196–198; Rf value: 0.61**; % yield: 65; IR (KBr cm−1): 3438.44 (N–H str.), 1741.31 (C=O str.), 1543.46 (C=C str., aromatic ring), 1664.46 (C=C str., aliphatic), 2899.96 (C–H str., aliphatic), 3089.91 (C–H str., aromatic ring), 1381.07 (C–N str.), 822.62 (C–H oop bend., aromatic), 649.37 (C–S bend.), 1115.13 (C–C str.), 1025.29 (O-CH3 str., m-substitution on phenyl ring); 1H NMR (δ, DMSO): 7.208–7.393 (m, 8H, Ar–H), 7.95 (s, 1H, –CH=), 3.61, 3.92 (d, 2H, -CH2 of thiazolidine-4-one), 6.16 (s, 1H, –CH of thiazolidine-4-one), 12.50 (s, 1H, NH), 2.89 (s, 3H, OCH3, m-position); M. Formula: C20H16N2O4S2; MS: m/z 413.63 (M+ + 1); Elemental analysis (CHN) Theoretical calc: C, 58.24; H, 3.91; N, 6.79 Found: C, 58.23; H, 3.88; N, 6.78

(E)-5-(4-(3-(4-methoxyphenyl)-4-oxothiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 130–132; Rf value: 0.64**; % yield: 70; IR (KBr cm−1): 3361.69 (N–H str.), 1693.75 (C=O str.), 1509.86 (C=C str., aromatic ring), 1606.81 (C=C str., aliphatic), 2922.73 (C–H str., aliphatic), 1395.80 (C–N str.), 651.12 (C–S bend., thiazolidine ring), 1027.91 (O–CH3 str., o-substitution on phenyl ring); 1H NMR (δ, DMSO): 7.206–7.445 (m, 8H, Ar–H), 7.827 (s, 1H, –CH=), 3.86, 3.91 (d, 2H, –CH2 of thiazolidine-4-one), 6.951 (s, 1H, –CH of thiazolidine-4-one), 12.45 (s, 1H, NH), 3.33 (s, 3H, OCH3, p-position); M. Formula: C20H16N2O4S2; MS: m/z 414.93 (M+ + 2); Elemental analysis (CHN) Theoretical calc: C, 58.24; H, 3.91; N, 6.79 Found: C, 58.21; H, 3.89; N, 6.77

(E)-5-(4-(3-(4-fluorophenyl)-4-oxothiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 150–152; Rf value: 0.57*; % yield: 60; IR (KBr cm−1): 3414.71 (N–H str.), 1800.02 (C=O str.), 1501.61 (C=C str., aromatic ring), 1660.40 (C=C str., aliphatic), 3064.39 (C–H str., aromatic ring), 2924.57 (C–H str., aliphatic), 1288.86 (C–N str., thiazolidine ring), 824.35 (C–H oop bend., aromatic), 660.68 (C–S bend., thiazolidine ring), 1095.34 (C–C str.), 1019.92 (C-F str., p-substitution on phenyl ring); 1H NMR (δ, DMSO): 7.12–7.69 (m, 8H, Ar–H), 7.951 (s, 1H, –CH=), 3.90, 3.98 (d, 2H, -CH2 of thiazolidine-4-one), 6.82 (s, 1H, –CH of thiazolidine-4-one), 12.51 (s, 1H, NH);M. Formula: C19H13FN2O3S2; MS: m/z 401.5 (M+ + 1); Elemental analysis (CHN) Theoretical calc: C, 56.99; H, 3.27; N, 7.00 Found: C, 56.97; H, 3.26; N, 7.03

(E)-5-(4-(3-(4-nitrophenyl)-4-oxothiazolidin-2-yl)benzylidene)thiazolidin-2,4-dione: m.p. oC: 144–146; Rf value: 0.60*; % yield: 70; IR (KBr cm−1): 3391.53 (N–H str.), 1788.47 (C=O str.), 1502.43 (C=C str., aromatic ring), 1660.13 (C=C str., aliphatic), 3115.33 (C–H str., aromatic ring), 2977.35 (C–H str., aliphatic), 1300.51 (C–N str.), 823.74 (C–H oop bend., aromatic), 663.28 (C–S bend.), 1097.38 (C–C str.), 1200.58 (N–O str., p-substitution on phenyl ring), 1388.68 (N=O str., p-substitution on phenyl ring); 1H NMR (δ, DMSO): 7.29–7.70 (m, 8H, Ar–H), 7.951 (s, 1H, -CH =), 3.90, 4.01 (d, 2H, -CH2 of thiazolidine-4-one), 6.52 (s, 1H, –CH of thiazolidine-4-one), 12.59 (s, 1H, NH); M. Formula: C19H13N3O5S2; Elemental analysis (CHN) Theoretical calc: C, 53.39; H, 3.03; N, 9.83 Found: C, 53.35; H, 3.05; N, 9.87[]

  1. TLC mobile phase=*n-Hexane: Ethyl Acetate:: 1: 1, **n-Hexane: Ethyl Acetate:: 3: 7