Molecules 2009, 14
3149
13C-NMR(75 MHz) δ: 172.2, 171.4, 167.0, 157.7(d, 2JFC = 25.7 Hz), 149.8, 139.4(d, 1JFC = 226.9 Hz),
2
131.2(d, JFC = 33.7 Hz), 60.9, 60.1, 51.5, 49.6, 29.9, 26.5, 14.2, 14.1; IR(KBr, cm-1) ν: 3304, 3213,
2924, 1725, 1675, 1546, 1468, 1416, 1379, 1250, 1176, 1023; MS(ESI) m/z: 372 (M-);
[
α
]
8.7 +12.40 (c
D
1.0, DMF).
(S)-methyl 2-(2-5-(fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)-3-(1H-indol-3-yl)pro-
1
panoate (2k-1). Yield: 50%; m.p. 205-206 ºC; H-NMR(300 MHz) δ: 11.84(s, 1H, NH of 5-FU),
10.90(s, 1H, NH of indole), 8.72(d, 1H, NH, J = 7.2 Hz), 7.93(d, 1H, FC=CH, 3JFH = 6.8 Hz), 7.48(d,
1H, Ar-H, J = 7.5 Hz), 7.33(d, 1H, Ar-H, J = 8.1 Hz), 7.16(d, 1H, =CHN, J = 2.2 Hz), 7.07(t, 1H, Ar-
H, J = 8.1, 6.9 Hz), 6.99(t, 1H, Ar-H, J = 7.5, 6.9 Hz), 4.54(dd, 1H, NCH, J = 7.2, 6.6 Hz), 4.33(d, 2H,
NCH2, J = 16.5 Hz), 3.56(s, 3H, OCH3), 3.19-3.03(m, 2H, CCH2, J = 7.5, 6.0, 14.4 Hz); 13C-NMR(75
MHz) δ: 172.2, 166.9, 157.8(d, 2JFC = 25.7 Hz), 149.9, 139.4(d, 1JFC = 228.1 Hz), 136.3, 131.3(d, 2JFC
= 33.8 Hz), 127.3, 124.1, 121.2, 118.7, 118.2, 111.7, 109.2, 53.6, 52.1, 49.5, 27.4; IR(KBr, cm-1) ν:
3386, 3312, 3069, 2977, 1702, 1545, 1381, 1233, 1062; MS(ESI) m/z: 387(M-);
[
α
]
17.9 +36.4 (c 1.0,
D
DMF).
(R)-methyl 2-(2-5-(fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)-3-(1H-indol-3-yl)pro-
1
panoate (2k-2). Yield: 53%; m.p. 205-206 ºC; H-NMR(300 MHz) δ: 11.84(d, 1H, NH of 5-FU,
4JFH = 5.1 Hz), 10.90(s, 1H, NH of indole), 8.72(d, 1H, NH, J = 7.5 Hz), 7.93(d, 1H, FC=CH,
3JFH = 6.9 Hz), 7.48(d, 1H, Ar-H, J = 7.8 Hz), 7.34(d,1H, Ar-H, J = 8.1 Hz), 7.16(s, 1H, =CHN),
7.07(t, 1H, Ar-H, J = 7.2, 7.8 Hz), 6.99(t, 1H, Ar-H, J = 7.2 Hz), 4.55(dd, 1H, NCH, J = 6.9, 6.6 Hz),
4.33(d, 2H, NCH2, J = 16.5 Hz), 3.57(s, 3H, OCH3), 3.20-3.03(m, 2H, CCH2, J = 7.5, 6.0, 14.8 Hz);
13C-NMR(75 MHz) δ: 172.2, 166.9, 157.8 (d, 2JFC = 25.7 Hz), 149.9, 139.4(d, 1JFC = 228.2 Hz), 136.3,
2
131.3(d, JFC = 33.8 Hz), 127.3, 124.1, 121.2, 118.7, 118.2, 111.7, 109.2, 53.5, 52.1, 49.5, 27.4;
IR(KBr, cm-1) ν: 3392, 3320, 3075, 1732, 1648, 1542, 1446, 1385, 1355, 1248, 1219,1099, 744;
MS(ESI) m/z: 387(M-);
[
α
]
17.8 -36.4 (c 1.0, DMF).
D
(S)-methyl 2-(2-5-(fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)-3-(4-hydroxyphenyl)
1
propanoate (2l). Yield: 72%; m.p. 192-193 ºC; H-NMR(300 MHz) δ: 11.85(s, 1H, NH of 5-FU),
9.28(s, 1H, OH), 8.68(d, 1H, NH, J = 7.5 Hz), 7.94(d, 1H, FC=CH, 3JFH = 6.9 Hz), 6.99 (d, 2H, Ar-H,
J = 8.4 Hz), 6.66 (d, 2H, Ar-H, J = 8.4 Hz), 4.39(dd, 1H, NCH, J = 6.3, 7.5 Hz), 4.31(d, 2H, NCH2,
J = 16.8 Hz), 3.59(s, 3H, OCH3), 2.93-2.77(m, 2H, CH2Ar, J = 6.3, 8.1, 13.8 Hz); 13C-NMR(75 MHz)
δ: 171.9, 166.9, 157.7(d, 2JFC = 25.7 Hz), 156.3, 149.8, 139.4(d, 1JFC = 226.9 Hz), 131.2(d, 2JFC = 33.8
Hz), 130.3, 127.0, 115.3, 54.4, 52.0, 49.5, 36.3; IR(KBr, cm-1) ν: 3271, 1739, 1712, 1661, 1552, 1516,
1451, 1386, 1231, 1164, 778; MS(ESI) m/z: 364(M+);
]
17.8 +16.6 (c 1.0, DMF).
D
(R)-ethyl 2-(2-5-(fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)-3-(4-hydroxyphenyl)
1
propanoate (2m). Yield: 70%; m.p. 156-158 ºC; H-NMR(300 MHz) δ: 11.82(s, 1H, NH of 5-FU),
9.23(s, 1H, OH), 8.63(d, 1H, NH, J = 7.5 Hz), 7.94(d, 1H, FC=CH, 3JFH = 6.6 Hz), 6.99(d, 2H, Ar-H,
J = 8.4 Hz), 6.65(d, 2H, Ar-H, J = 8.4 Hz), 4.36(dd, 1H, NCH, J = 7.5, 6.9 Hz), 4.31(d, 2H, NCH2,
J = 16.8 Hz), 4.02(q, 2H, OCH2, J = 7.2 Hz), 2.89-2.77(m, 2H, CH2Ar, J = 7.5, 6.0, 13.8 Hz), 1.10(t,