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Carbohydrate Moiety and HIV-1 RT
1191
Found: 526.0; HPLC Rt: 9.14 min, % purity 97.1; Anal. calcd. for
C22H25BrFN3O4S: C, 50.2; H, 4.79; N, 7.98 Found: C, 49.66; H, 4.80;
N, 8.03.
({[(4S, 1R, 5R)-7,7-dimethyl-2, 6, 8-trioxa-4-(phenylmethoxy) bicyclo
oct-3-yl]methyl}[2-(2-fluorophenyl)ethyl]amino[(5-bromo(2-pyri-
[3.3.0]
dyl)amino] methane-1-thione (8). [a]D ¼ À0.074ꢀ(c 1, MeOH); M.p.:
64–65ꢀC; H NMR (CDCl3) d: 9.10 (brs, 1H, NH), 8.30–8.27 (m, 2H,
1
ArH), 7.73–7.69 (dd, 1H, J ¼ 2.7 Hz, 2.1 Hz, ArH), 7.40–6.99 (m, 9H,
ArH), 6.10–6.08 (d, 1H, J ¼ 3.9 Hz, H-1), 4.73–4.69 (d, 1H, J ¼ 12 Hz,
OCH2Ph), 4.68–4.67 (d, 1H, J ¼ 3.6 Hz, H-5), 4.53–4.49 (d, 1H,
J ¼ 11.7 Hz, OCH2Ph), 4.43–3.65 (m, 6H, H-3,4, CH2-N-CH2),
3.19–3.07 (m, 2H, Ar-CH2, –CH2-N), 1.48, 1.32 (2s, 6H, 2 ꢁ CH3);
13C NMR (CDCl3): 181.0, 162.5, 159.3, 152.1, 148.4, 138.8, 136.6,
131.2, 131.2, 128.5, 128.3, 128.2, 128.1, 127.6, 125.1, 124.3, 117.6,
115.2, 115.0, 113.9, 112.0, 105.0, 82.0, 78.7, 71.8, 52.5, 51.2, 26.7, 26.2;
LCMS (ESI) calcd. for(M þH) 617.5, Found: 617.2; HPLC Rt: 13.6 min,
% purity 99.8; Anal. calcd. for C29H31BrFN3O4S: C, 56.50; H, 5.07; N,
6.82 Found: C, 56.14; H, 5.09; N, 6.84.
({[(4S, 1R, 5R)-7,7-dimethyl-2, 6, 8-trioxa-4-(phenylmethoxy) bicyclo
[3.3.0] oct-3-yl] methyl}[2-(2-fluorophenyl)ethyl] amino[(5-chloro(2-pyridyl)
amino] methane-1-thione (9). [a]D ¼ À0.077ꢀ(c 1, MeOH); M.p.: 59–60ꢀC;
1H NMR (CDCl3) d: 9.14 (brs, 1H, NH), 8.31–8.28 (d, 1H, J ¼ 9 Hz,
ArH), 8.18–8.17 (d, 1H, J ¼ 2.4 Hz, ArH), 7.58–7.55 (dd, 1H, J ¼ 2.4,
2.7 Hz, ArH), 7.38–6.97 (m, 9H, ArH), 6.08–6.07 (d, 1H, J ¼ 3.6 Hz,
H-1), 4.71–4.67 (d, 1H, J ¼ 11.7 Hz, OCH2Ph), 4.66–4.65 (d, 1H,
J ¼ 3.9 Hz, H-5), 4.51–4.47 (d, 1H, 11.7 Hz, OCH2Ph), 4.42–3.63 (m,
6H, H-3,4, CH2-N-CH2), 3.22–3.03 (m, 2H, Ar-CH2, –CH2-N), 1.45,
1.30 (2s, 6H, 2 ꢁ CH3); 13C NMR (CDCl3) d: 181.1, 162.5, 159.3, 151.7,
146.1, 136.6, 136.2, 131.3, 128.5, 128.4, 128.3, 128.1, 127.7, 125.9, 124.2,
117.2, 115.3, 115.0, 112.1, 105.0, 82.0, 81.7, 78.7, 71.8, 52.5, 51.2, 26.7,
26.2; LCMS (ESI) calcd. for(M þH) 572.1, Found: 572.2; HPLC
Rt: 34.1 min, % purity 96.3; Anal. calcd. for C29H31ClFN3O4S: C,
60.89; H, 5.46; N, 7.34. Found: C, 60.52; H, 5.52; N, 7.54.
({[(4S, 1R, 5R)-7,7-dimethyl-2, 6, 8-trioxa-4-(phenylmethoxy) bicyclo
[3.3.0] oct-3-yl] methyl}[2-(2-fluorophenyl)ethyl] amino[(5-methyl(2-pyri-
dyl) amino] methane-1-thione (10). [a]D ¼ À0.053ꢀ (c 1, MeOH); M.p.:
50–52ꢀC; H NMR (CDCl3): 8.78 (brs, 1H, ArH), 8.03 (brs, 2H, ArH),
1
7.45–7.41 (dd, 1H, J ¼ 2.1, 2.4 Hz, ArH), 7.37–696 (m, 9H, ArH),
6.04–6.03 (d, 1H, J ¼ 3.9 Hz, H-1), 4.70–4.66 (d, 1H, J ¼ 12 Hz,
OCH2Ph), 4.63–4.62 (d, 1H, J ¼ 3.9 Hz, H-5), 4.53–4.49 (d, 1H,
11.7 Hz, OCH2Ph) 420–3.73 (m, 6H, H-3,4, CH2-N-CH2), 3.21–3.06
(m, 2H, Ar-CH2, –CH2-N), 2.52 (s, 3H, Ar-CH3), 1.45, 1.29 (2s, 6H,