International Scholarly Research Notices

Research Article

Interaction of 5′-Guanosine Monophosphate with Organotin(IV) Moieties: Synthesis, Structural Characterization, and Anti-Inflammatory Activity

Table 2

, , and NMR spectral data of di- and triorganotin(IV) derivatives of (5′-GMP)2− at 300 MHz in DMSO-d6.
Ligand/Complex no.a (ppm)b
Na2(5′-GMP) (500 MHz)N(1)-H: 10.67 (s, 1H); NH2: 6.48 (s, 2H); H-8: 7.95 (s, 1H); H-1′: 5.70 (d, 5.0 Hz, 1H); H-2′: 4.40 (s, 1H); 2′-OH: 5.42 (d, 5.5 Hz) and 5.14 (d, 3.0 Hz, 1H); H-3′: 4.09 (d, 4.0 Hz, 1H); 3′-OH: 5.06 (t, 4.5 Hz, 1H); H-4′: 3.87 (d, 3.0 Hz, 1H); H-5′: 3.55−3.51 (m)d and 3.64−3.60 (m, 2H); C-2: 153.6; C-4: 151.3; C-5: 116.6; C-6: 156.7; C-8: 135.6; C-1′: 86.3; C-2′: 73.6; C-3′: 70.3; C-4′: 85.2; C-5′: 61.3
[Me2Sn(5′-GMP)·H2O N(1)-H: 10.74 (s, 1H); NH2: 6.52 (s, 2H); H-8: 7.95 (s, 1H); H-1′: 5.71 (s, 1H); H-2′: 4.44 (s, 1H); 2′-OH: 5.41 (s, 1H); H-3′: 4.14 (s, 1H); 3′-OH: 5.26 (s, 1H); H-4′: 4.00 (br s, 1H); H-5′: 3.46 (d, 3.0 Hz, 2H); H- : 0.63, 0.99 (s, 6H)c; C-2: 153.8; C-4: 151.9; C-5: 116.3; C-6: 157.2; C-8: 135.6; C-1′: 85.9; C-2′: 74.2; C-3′: 71.3; C-4′: 84.2; C-5′: 65.4; C- : 11.8, 13.9
[ -Bu2Sn(5′-GMP)·H2O N(1)-H: 10.74 (s, 1H); NH2: 6.63 (t, 3.5 Hz, 2H); H-8: 7.91 (s, 1H); H-1′: 5.76 (s, 1H); H-2′: 4.16 (s, 1H); 2′-OH: 5.53 (s, 1H); H-3′: 4.03 (s, 1H); 3′-OH: 4.48 (s, 1H); H-4′: 3.93 (br s, 1H); H-5′: 3.52 (s), 3.43 (d, 3.0 Hz, 2H); H- and H- : 1.34 (m, 8H)d; H- : 1.69 (m, 4H); H- : 0.91 (t, 6H)
[Ph2Sn(5′-GMP)·H2O N(1)-H: 10.76 (s, 1H); NH2: 6.58 (s, 2H); H-8: 7.92 (s, 1H); H-1′: 5.79 (s, 1H); H-2′: 4.46 (s, 1H); 2′-OH: 5.57 (s, 1H); H-3′: 4.10 (s, 1H); 3′-OH: 5.38 (s, 1H); H-4′: 3.91 (s, 1H)c; H-5′: 3.66 (br d, 2H); H-α: 7.80 (d, 7.1 Hz, 4H); H-β: 7.50 (d, 7.5 Hz, 4H); H-γ: 7.32 (br m, 2H); C-2: 153.9; C-4: 151.6; C-5: 116.5; C-6: 156.9; C-8: 135.1; C-1′: 86.0; C-2′: 73.6; C-3′:70.6; C-4′: 83.1; C-5′: 65.9; C- : 140.8; C-α: 136.1; C-β: 128.5; C-γ: 129.2; 119Sn: −225.1
[(Me3Sn)2(5′-GMP)·H2O N(1)-H: 10.67 (s, 1H); NH2: 6.49 (s, 2H); H-8: 7.93 (s, 1H); H-1′: 5.70 (s, 1H); H-2′: 4.44 (s, 1H); 2′-OH: 5.37 (s, 1H); H-3′: 4.15 (s, 1H); 3′-OH: 5.22 (s, 1H); H-4′: 3.98 (d, 7.5 Hz, 1H); H-5′: 3.36 (br d, 2H); H-α: 0.63, 0.76, 0.98 (s, 18H)
[( -Pr3-Sn)2(5′-GMP)·H2O N(1)-H: 10.76 (s, 1H); NH2: 6.60 (s, 2H); H-8: 7.73 (s, 1H); H-1′: 5.68 (d, 6.0 Hz, 1H); H-2′: 4.36, (4.48) (s, 1H); 2′-OH: 5.55 (s, 1H); H-3′: 4.07 (s, 1H); 3′-OH: 5.41 (s, 1H); H-4′: 3.94 (br s, 1H); H-5′: 3.73 (br s, 2H); H-α: 1.08 (m, 6H); H-β (a): 1.65 (d, 9.0 Hz, 18H); H-β (b): 0.90 (t, 6.0 Hz, 18 H); C-2: 153.8; C-4: 151.5; C-5: 116.5; C-6: 156.9; C-8: 134.7; C-1′: 85.8; C-2′: 73.7; C-3′: 70.8; C-4′: 83.6; C-5′: 64.4; C-α: 24.2; C-β (a): 19.0, (19.2); C-β (b): 18.8, (18.5); 119Sn: −255.7
[( -Bu3Sn)2(5′-GMP)·H2O N(1)-H: 10.67 (s, 1H); NH2: 6.51 (s, 2H); H-8: 7.62 (s, 1H); H-1′: 5.69 (s, 1H); H-2′: 4.26 (s, 1H); 2′-OH: 5.50 (s, 1H); H-3′: 3.96 (d, 18 Hz, 1H); 3′-OH: 5.11 (br s, 1H); H-4′: 3.71 (br s, 1H); H-5′: 3.40 (s, 2H); H-α: 1.05 (s, 12H); H-β: 1.57 (s, 12H); H-γ: 1.26 (d, 6.0 Hz, 12H); H-δ: 0.82 (s, 18H); C-2: 153.8; C-4: 151.6; C-5: 116.5; C-6: 156.9; C-8: 134.2; C-1′: 85.7; C-2′: 73.9; C-3′: 70.9; C-4′: 83.4; C-5′: 64.7; C-α: 19.9; C-β: 27.8; C-γ: 26.8 [83.0 Hz]b; C-δ: 13.7
[(Ph3Sn)2(5′-GMP)·H2O N(1)-H: 10.66 (s, 1H); NH2: 6.51 (s, 2H); H-8: 7.75 (s, 1H); H-1′: 5.69 (s, 1H); H-2′: 4.41 (s, 1H); 2′-OH: 5.42 (s, 1H); H-3′: 4.10 (s, 1H); 3′-OH: 5.19 (s, 1H); H-4′: 3.96 (s, 1H); H-5′: 3.41, (3.17), (s, 2H); H-α + H-β + H-γ: 7.00–7.32 (br m, 30H)d; C-2: 153.7; C-4: 151.9; C-5: 116.5; C-6: 156.9; C-8: 135.1; C-1′: (85.1); C-2′: (73.6); C-3′: (70.4); C-4′: (83.1); C-5′: (65.0); C- : 142.8, 142.1; C-α: 136.2, 136.1; C-β: 128.0, (127.7); C-γ: 128.3, (128.8); 119Sn: −225.8
aAccording to Experimental section; bhomonuclear proton-proton coupling multiplet abbreviations given in parentheses: s: singlet; d: doublet; t: triplet; br: broad; m: multiplet; cfused singlet; doverlapping multiplets; weak signals in parantheses; resonances H-β (a) and H-β (b) may be interchanged(see Scheme 2).