Chemistry
Structural characterization of synthesized compounds: 3-((1,3-dioxoisoindolin-2-yl)methyl)thiazolidine-2,4-dione (LPSF/FT-01) (3) C12H8N2O4S. White solid. Melting point (m.p.): 172°C. Yield: 67 %. IR (KBr, cm− 1): 3005 (C-H), 1730 (C = O), 1676 (C = O), 1315 (C–N). H1 NMR (300 MHz, DMSO-d6) δ 7.88 (m, 4H, J = 20.7 Hz, ArH), 5.33 (s, 2H, –CH2), 4.19 (s, 2H, –CH2). 13C-NMR (300 MHz, DMSO-d6): δ 171.1 (C = O), 170.8, 166.3, 134.8, 123.4, 43.5 (CH2), 33.5. MS m/z (%): 275.95, calculated 276.02.
5-(4-(1H-imidazol-1-yl)benzylidene)-3-((1,3-dioxoisoindolin-2-yl)methyl)thiazolidine-2,4-dione (LPSF/FT-07) (7a) C22H14N4O4S. Yellow solid. m.p.: 263°C. Yield: 44 %. IR (KBr, cm− 1): 3136 (C-H), 1732 (C = O), 1598 (C = C), 1320 (C-N), 724 (C-H). H1 NMR (300 MHz, DMSO-d6): δ 8,39 (s, 1H, -CH), 7,89 (m, 8H, J = 42,3 Hz, ArH), 7,74 (d, 2H, J = 8,1 Hz, ArH), 7,14 (s, 1H, ArH), 5,51 (s, 2H, -CH2). 13C-NMR (300 MHz, DMSO-d6): δ 166.3, 166.0, 164.4, 138.0, 135.6, 134.8, 132.3, 131.7, 131.2, 131.0, 130.3, 123.4, 120.5, 117.6, 43.8 (CH2). MS m/z (%): (M + H) + 431.03, calculated 430.07.
3-((4-((3-((1,3-dioxoisoindolin-2-yl)methyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)(methyl)amino)propanenitrile (LPSF/FT-08) (7b) C23H18N4O4S. Orange solid. m.p.: 241°C. Yield: 61 %. IR (KBr, cm-1): 2917 (C-H), 2248 (-CN), 1721 (C = O), 1582 (C = C), 1319 (C-N). H1 NMR (300 MHz, DMSO-d6): δ 7,88 (m, 5H, J = 34,2 Hz, FtH), 7,45 (d, 2H, J = 9,6 Hz, ArH), 6,91 (d, 2H, J = 9,3 Hz, ArH), 5,48 (s, 2H, -CH2), 3,77 (t, 2H, J = 13,5 Hz, CH2), 3,04 (s, 3H, CH3), 2,76 (t, 2H, J = 12,9 Hz, CH2). 13C-NMR (300 MHz, DMSO-d6): δ 170.8, 166.3, 166.2, 164.6, 149.97, 134.8, 134.2, 132.4, 131.1, 123.3, 120.4, 112.3, 47.1, 43.5 (CH2), 33.4, 14.9. MS m/z (%): 446.07, calculated 446.1.
5-(3-bromobenzylidene)-3-((1,3-dioxoisoindolin-2-yl)methyl)thiazolidine-2,4-dione (LPSF/FT-18) (7c) C19H11BrN2O4S. White solid. m.p.: 210°C. Yield: 68 %. IR (KBr, cm-1): 3088 (C-H), 1748 (C = O), 1602 (C = C), 1313 (C-N), 723 (C-H). H1 NMR (400 MHz, CDCl3): δ 7,89 (m, 2H, J = 8,4 Hz, ArH), 7,82 (s, 1H, CH), 7,75 (m, 2H, J = 8 Hz, ArH), 7,61 (t, 1H, J = 3,6 Hz, ArH), 7,55 (dt, 1H, J = 11,2 Hz, ArH), 7,41 (d, 1H, J = 8,4 Hz, ArH), 7,34 (t, 1H, J = 16 Hz, ArH), 5,67 (s, 2H, CH2). 13C-NMR (400 MHz, CDCl3): δ 166.5, 164.7, 135.0, 134.5, 133.5, 132.9, 131.5, 130.6, 128.3, 123.9, 123.3, 122.3, 43.5 (CH2). MS m/z (%): (M + H)+ 442.9, calculated 441.96.
4-((3-((1,3-dioxoisoindolin-2-yl)methyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl acetate (LPSF/AA-FT-02) (9e) C21H14N2O6S. Yellow solid. m.p.: 263°C. Yield: 56,7 %. IR (KBr, cm− 1): 1745 (C = O), 1722 (C = O), 1585 (C = C), 725 (C-H). H1 NMR (300 MHz, DMSO-d6): δ 7,87 (m, 5H, J = 28,2 Hz, CH, FtH), 7,46 (d, 2H, J = 8,4 Hz, ArH), 6,91 (d, 2H, J = 9 Hz, ArH), 5,49 (s, 2H, -CH2), 2,29 (s, 3H, -CH3). 13C-NMR (300 MHz, DMSO-d6): δ 166.43, 166.36, 164.62, 160.27, 134.81, 133.94, 132.65, 131.18, 123.69, 123.41, 116.41, 115.87, 43.77. MS m/z (%): (M + H)+ 423.9, calculated 422.05.
N -(4-((3-((1,3-dioxoisoindolin-2-yl)methyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)acetamide (LPSF/FT-03) (9f) C21H15N3O5S. Yellow solid. m.p.: 277°C. Yield: 80.4 %. IR (KBr, cm− 1): 3382 (N-H), 1745 (C = O), 1717 (C = O), 1580 (C = C), 726 (C-H). H1 NMR (300 MHz, DMSO-d6): δ 7,88 (m, 5H, J = 24,3 Hz, CH, FtH), 7,74 (d, 2H, J = 8,7 Hz, ArH), 7,55 (d, 2H, J = 9 Hz, ArH), 5,49 (s, 2H, -CH2), 2,07 (s, 3H, -CH3). 13C-NMR (300 MHz, DMSO-d6): δ 168.8, 166.3, 164.5, 141.5, 134.8, 133.2, 131.3, 131.2, 127.1, 123.4, 119.1, 118.0, 43.7 (CH2), 40.3, 24.1. MS m/z (%): (M + H)+ 422.02, calculated 421.07.
5-((2,3-dihydrobenzofuran-6-yl)methylene)-3-((1,3-dioxoisoindolin-2-yl)methyl)thiazolidine-2,4-dione (LPSF/FT-04) (9g) C21H14N2O5S. Yellow solid. m.p.: 255.9°C. Yield: 75,5 %. IR (KBr, cm− 1): 1779 (C = O), 1736 (C = O), 1594 (C = C), 710 (C-H). H1 NMR (300 MHz, CDCl3): δ 7,88 (m, 3H, J = 12,3 Hz, CH, FtH), 7,74 (m, 2H, J = 8,7 Hz, ArH), 7,30 (dd, 2H, J = 9,6 Hz, ArH), 6,85 (d, 1H, J = 9 Hz, ArH), 5,66 (s, 2H, -CH2), 4, 66 (t, 2H, J = 17,7 Hz), 3,26 (t, 2H, J = 17,7 Hz). 13C-NMR (300 MHz, CDCl3): δ 166.5, 162.6, 135.2, 134.4, 132.4, 131.5, 128.7, 127.0, 125.7, 123.8, 116.4, 110.2, 72.1, 43.3 (CH2), 29.1 (CH3). MS m/z (%): 406.06, calculated 406.11.
3-((1,3-dioxoisoindolin-2-yl)methyl)-5-(4-(diphenylamino)benzylidene)thiazolidine-2,4-dione (LPSF/FT-06) (9h) C31H21N3O4S. Yellow solid. m.p.: 133°C. Yield: 95,3 %. IR (KBr, cm− 1): 3033 (C-H), 1730 (C = O), 1582 (C = C), 1291 (C-N), 725 (C-H). H1 NMR (300 MHz, CDCl3): δ 7,88 (m, 2H, J = 9 Hz, FtH), 7,82 (s, 1H, CH), 7,74 (m, 2H, J = 8,1 Hz, FtH), 7,32 (m, 6H, J = 24,3 Hz, ArH), 7,15 (m, 6H, J = 22,5 Hz, ArH), 7,01 (d, 2H, J = 8,7 Hz, ArH), 5,66 (s, 2H, CH2). 13C-NMR (300 MHz, CDCl3): δ 166.5, 165.3, 150.2, 146.2, 134.7, 134.4, 131.8, 131.5, 131.2, 129.6, 129.6, 129.0, 126.2, 125.9, 125.1, 125.0, 124.7, 123.8, 120.47, 119.3, 116.1, 43.3 (CH2). MS m/z (%): 531.38, calculated 531.12.
3-((1,3-dioxoisoindolin-2-yl)methyl)-5-((3-phenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-dione (LPSF/FT-09) (9i) C22H14N4O4S. Yellow solid. m.p.: 214°C. Yield: 84,3 %. IR (KBr, cm− 1): 3321 (N-H), 3015 (C-H), 1710 (C = O), 1610 (C = C), 1318 (C-N). H1 NMR (300 MHz, DMSO-d6): δ 13,82 (s, 1H, NH), 8,24 (s, 1H, CH), 7,87 (m, 4H, J = 27,9 Hz, ArH), 7,61 (t, 6H, J = 39 Hz, ArH), 5,46 (s, 2H, CH2). 13C-NMR (300 MHz, DMSO-d6): δ 166.3, 165.8, 164.3, 134.8, 131.1, 129.0, 128.5, 123.3, 117.1, 112.5, 43.7 (CH2). MS m/z (%): (M + H)+ 431.19, (M + Na)+ 453.23, calculated 430.07.
5-((2-chloro-6-methylquinolin-3-yl)methylene)-3-((1,3-dioxoisoindolin-2-yl)methyl)thiazolidine-2,4-dione (LPSF/FT-12) (9j) C23H14ClN3O4S. Yellow solid. m.p.: 356°C. Yield: 72,2 %. IR (KBr, cm− 1): 1781 (C = O), 1731 (C = O), 1654 (C = C), 1310 (C-N). H1NMR (400 MHz, DMSO-d6): δ 8,10 (s, 1H, ArH), 7,86 (m, 4H, J = 22,8 Hz, ArH), 7,56 (s, 1H, ArH), 7,40 (dd, 2H, J = 10 Hz, ArH), 722 (d, 1H, J = 8 Hz, ArH), 5,46 (s, 2H, CH2), 2,48 (m, 3H, J = 5,6 Hz, CH3). 13C-NMR (300 MHz, CDCl3): δ 167.6, 166.6, 165.1, 160.6, 142.9, 137.3, 135.1, 134.1, 132.1, 131.3, 129.0, 128.7, 124.6, 123.6, 122.4, 119.2, 115.4, 43.8 (CH2), 20.4 (CH3). MS m/z (%): (M + H)+ 464.03, calculated 463.03.
3-((1,3-dioxoisoindolin-2-yl)methyl)-5-(4-(pyrimidin-5yl)benzylidene)thiazolidine-2,4-dione (LPSF/FT-15) (9k) C23H14N4O4S. Yellow solid. m.p.: 288°C. Yield: 87,3 %. IR (KBr, cm− 1): 3014 (C-H), 1749 (C = O), 1597 (C = C), 1312 (C-N), 727 (C-H). H1NMR (300 MHz, CDCL3): δ 9,25 (s, 1H, ArH), 8,99 (s, 2H, ArH), 7,96 (s, 1H, CH), 7,90 (m, 4H, J = 8,4 Hz, ArH), 7,72 (m, 4H, J = 45,3 Hz, ArH), 5,69 (s, 2H, CH2). 13C-NMR (300 MHz, CDCl3): δ 166.5, 164.8, 158.0, 154.8, 134.5, 133.6, 133.4, 133.0, 131.5, 131.1, 127.6, 123.8, 121.8, 43.5 (CH2). MS m/z (%): (M + H)+ 443.24, calculated 442.07.