SYNTHESIS AND IN VITRO ANTIVIRAL ACTIVITY EVALUATION OF 9-(2-AZIDO-2,3-DIDEOXY-β-D-THREO-PENTOFURANOSYL)ADENINE DERIVATIVES

REFERENCES

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• Compound 7: 1H NMR (300 MHz, DMSO-d 6) δ 8.75 (1H, s, H-2), 8.70 (1H, s H-8), 7.21–7.43 (15H, m, 5′O-Tr), 6.58 (1H, d, J = 6.3 Hz, H-1′), 4.95 (1H, ddd, J = 9.4, 6.9, 6.3 Hz, H-2′), 4.36–4.46 (1H, m, H-4′), 3.46-3.54 (1H, m, H-5′a), 3.20–3.36 (1H, m, H-5′b), 2.50–2.60 (1H, m, H-3′a), 2.20–2.33 (1H, m, H-3′b); 13C NMR (75 MHz, DMSO-d 6) δ 151.9, 151.6, 149.6, 145.8, 143.7, 131.2, 128.4, 128.1, 127.3, 86.4, 84.6, 78.2, 65.1, 61.6, 31.4; IR (KBr): 2114 cm−1; Anal. Calcd for C29H25N7O2Cl: C, 64.74; H, 4.50; N, 18.22. Found: C, 64.75; H, 4.50; N, 18.19
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• Compound 1a: 1H NMR (300 MHz, CDCl3) δ 8.38 (1H, s, H-8), 7.93 (1H, s H-2), 6.26 (1H, d, J = 6.2 Hz, H-1′), 6.08 (1H, bs, 6-NH), 4.90 (1H, bs, 5′-OH), 4.55 (1H, ddd, J = 11.2, 5.0, 3.8 Hz, H-2′), 4.30–4.39 (1H, m, H-4′), 4.10 (1H, bd, J = 12.2 Hz, H-5′a), 3.81 (1H, bd, J = 12.2 Hz, H-5′b), 3.20 (3H, bs, N-CH3), 2.63 (1H, ddd, J = 15.4, 6.5, 6.5 Hz, H-3′a), 2.44 (1H, ddd, J = 13.1, 6.7, 6.7 Hz, H-3′b); 13C NMR (75 MHz, CDCl3) δ 155.5, 153.1, 138.7, 120.0, 85.8, 79.5, 62.9, 62.6, 30.9, 27.6; IR (KBr): 2115 cm−1; HRMS (FAB+) calcd for C11H15N8O2 (M + H)+ 291.1318, found 291.1328
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• Compound 1b: 1H NMR (300 MHz, CDCl3) δ 8.30 (1H, s, H-8), 7.92 (1H, s H-2), 6.26 (1H, d, J = 6.1 Hz, H-1′), 4.53 (1H, ddd, J = 11.1, 4.8, 3.7 Hz, H-2′), 4.44 (1H, bs, 5′-OH), 4.29–4.36 (1H, m, H-4′), 4.09 (1H, dd, J = 12.4, 2.3 Hz, H-5′a), 3.81 (1H, bd, J = 12.4 Hz, H-5′b), 3.54 (6H, bs, N(CH3)2), 2.61 (1H, ddd, J = 15.5, 6.5, 6.5 Hz, H-3′a), 2.43 (1H, ddd, J = 12.7, 6.6, 6.6 Hz, H-3′b); 13C NMR (75 MHz, CDCl3) δ 155.0, 152.2, 150.0, 137.2, 120.4, 85.9, 79.3, 62.9, 62.7, 38.6, 30.7; IR (KBr): 2115 cm−1; HRMS (FAB+) calcd for C12H17N8O2 (M+H)+ 305.1474, found 305.1479
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• Compound 1c: 1H NMR (300 MHz, CDCl3) δ 8.45 (1H, s, H-8), 7.93 (1H, s H-2), 6.25 (1H, d, J = 6.2 Hz, H-1′), 6.05 (1H, bs, 6-NH), 4.55 (2H, ddd, J = 11.0, 4.9, 3.7 Hz, H-2′+5′-OH), 4.31–4.38 (1H, m, H-4′), 4.11 (1H, bd, J = 12.5 Hz, H-5′a), 3.78–3.85 (1H, m, H-5′b), 3.02 (1H, bm, cyclopropane), 2.65 (1H, ddd, J = 15.5, 6.5, 6.5 Hz, H-3′a), 2.45 (1H, ddd, J = 13.2, 6.6, 6.6 Hz, H-3′b), 0.91–0.98 (2H, m, cyclopropane), 0.65–0.70 (2H, m, cyclopropane); 13C NMR (75 MHz, CDCl3) δ 155.4, 152.9, 148.2, 138.8, 119.0, 84.4, 79.1, 62.3, 61.9, 30.3, 23.4, 7.0, 6.8; IR (KBr): 2113 cm−1; HRMS (FAB+) calcd for C13H17N8O2 (M + H)+ 317.1474, found 317.1472
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• Compound 1d: 1H NMR (300 MHz, CDCl3) δ 8.35 (1H, s, H-8), 7.93 (1H, s H-2), 6.25 (1H, d, J = 6.1 Hz, H-1′), 5.98 (1H, bs, 6-NH), 4.61 (1H, bs, 5′-OH), 4.55 (1H, ddd, J = 10.7, 4.9, 3.7 Hz, H-2′), 4.30–4.38 (1H, m, H-4′), 4.09 (1H, dd, J = 12.6, 2.2 Hz, H-5′a), 3.81 (1H, dd, J = 12.6, 3.3 Hz, H-5′b), 2.62 (1H, ddd, J = 15.3, 6.5, 6.5 Hz, H-3′a), 2.44 (1H, ddd, J = 13.1, 6.7, 6.7 Hz, H-3′b), 2.06–2.21 (2H, m, cyclopentane), 1.50–1.84 (7H, m, cyclopentane); 13C NMR (75 MHz, CDCl3) δ 154.6, 153.1, 138.6, 120.1, 86.1, 79.5, 62.9, 62.6, 52.4, 33.4, 30.6, 32.7; IR (KBr): 2112 cm−1; HRMS (FAB+) calcd for C15H21N8O2 (M + H)+ 345.1787, found 345.1777
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• Compound 1e: 1H NMR (300 MHz, CDCl3) δ 8.33 (1H, s, H-8), 7.93 (1H, s H-2), 6.24 (1H, d, J = 6.0 Hz, H-1′), 5.80 (1H, bs, 6-NH), 4.72 (1H, bs, 5′-OH), 4.54 (1H, ddd, J = 10.8, 4.8, 3.7 Hz, H-2′), 4.29–4.38 (1H, m, H-4′), 4.09 (1H, dd, J = 12.6, 2.2 Hz, H-5′a), 3.81 (1H, dd, J = 12.6, 3.2 Hz, H-5′b), 2.62 (1H, ddd, J = 15.2, 6.4, 6.4 Hz, H- 3′a), 2.44 (1H, ddd, J = 13.2, 6.7, 6.7 Hz, H-3′b), 2.04–2.16 (2H, m, cyclohexane), 1.20–1.86 (9H, m, cyclohexane); 13C NMR (75 MHz, CDCl3) δ 153.9, 153.1, 148.2, 138.4, 119.0, 85.0, 79.1, 62.5, 62.3, 49.1, 33.0, 30.5, 25.4, 24.7; IR (KBr): 2111 cm−1; HRMS (FAB+) calcd for C16H23N8O2 (M + H)+ 359.1944, found 359.1953
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