I. Giorgi et al. / Bioorg. Med. Chem. 17 (2009) 1817–1830
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9H, arom); 5.97 (s, 2H, CH2–benzyl). MS: 412 (M+, 30), 189 (100)
m/z. Elemental analysis for C22H16N6OS: Calcd: C, 64.06; H, 3.91;
N, 20.38. Found: C, 63.95; H, 4.23; N, 20.22.
Compound 2f1: yield: 30%; mp 197–198 °C (95% EtOH); IR: 3326
(NH); 1689 (C@O). 1H NMR: 11.72 (br s, 1H exch., NH); 8.54 (m, 2H,
arom); 8.07 (d, J = 1.0 Hz, 1H, arom); 7.70 (d, J = 3.2 Hz, 1H, arom);
7.60–7.34 (m, 8H, arom); 6.79 (m, 1H, arom); 5.97 (s, 2H, CH2–ben-
zyl). MS: 396 (M+, 5), 233 (100) m/z. Elemental analysis for
C22H16N6O2: Calcd: C, 66.66; H, 4.07; N, 21.20. Found: C, 66.80;
H, 4.24; N, 21.28.
Compound 2f2: yield: 5%; mp 216–218 °C (95% EtOH); IR: 3126
(NH); 1685 (C@O). 1H NMR: 11.64 (br s, 1H exch., NH); 8.67 (s, 1H,
arom); 8.55 (m, 2H, arom); 7.89 (m, 1H, arom); 7.61–7.09 (m, 9H,
arom); 5.98 (s, 2H, CH2–benzyl). MS: 396 (M+, 2), 233 (100) m/z.
Elemental analysis for C22H16N6O2: Calcd: C, 66.66; H, 4.07; N,
21.20. Found: C, 66.74; H, 4.21; N, 21.33.
arom); 5.96 (s, 2H, CH2-benzyl); 3.86 (s, 3H, OCH3). MS: 436 (M+,
8), 233 (100) m/z. Elemental analysis for C25H20N6O2: Calcd: C,
68.80; H, 4.62; N, 19.25. Found: C, 69.10; H, 4.87; N, 19.46.
Compound 2k2: yield: 40%; mp 179–180 °C (95% EtOH); IR:
3245 (NH); 1677 (C@O). 1H NMR: 11.83 (br s, 1H exch., NH);
8.34 (m, 2H, arom); 7.70–7.24 (m, 12H, arom); 5.97 (s, 2H, CH2–
benzyl); 3.86 (s, 3H, OCH3). MS: 436 (M+, 5), 233 (100) m/z. Ele-
mental analysis for C25H20N6O2: Calcd: C, 68.80; H, 4.62; N,
19.25. Found: C, 68.99; H, 4.81; N, 19.25.
Compound 2k3: yield: 36%; mp 223–224 °C (95% EtOH); IR:
3240 (NH); 1670 (C@O). 1H NMR: 11.81 (br s, 1H exch., NH);
8.50 (m, 2H, arom); 8.10 (d, J = 7.6 Hz, 2H, arom); 7.57–7.35 (m,
8H, arom); 7.11(d, J = 7.6 Hz, 2H, arom); 5.97 (s, 2H, CH2–benzyl);
3.86 (s, 3H, OCH3). MS: 436 (M+, 7), 91 (100) m/z. Elemental anal-
ysis for C25H20N6O2: Calcd: C, 68.80; H, 4.62; N, 19.25. Found: C,
68.83; H, 4.67; N, 19.38.
Compound 2g: yield: 20%; mp 227–228 °C (95% EtOH); IR: 3239
(NH); 1672 (C@O). 1H NMR: 11.95 (br s, 1H exch., NH); 8.48 (m, 2H,
arom); 8.08 (d, J = 8.6 Hz, 2H arom); 7.68–7.32 (m, 11H, arom);
5.91 (s, 2H, CH2–benzyl). MS: 436 (M+, 5), 273 (100) m/z. Elemental
analysis for C24H18N6O: Calcd: C, 70.92; H, 4.46; N, 20.68. Found: C,
70.79; H, 4.25; N, 20.38.
Compound 2h1: yield: 80%; mp 193–194 °C (95% EtOH); IR:
3236 (NH); 1685 (C@O). 1H NMR: 12.16 (s, 1H exch., NH); 8.21
(m, 2H, arom); 7.82–7.28 (m, 12H, arom); 5.96 (s, 2H, CH2–benzyl).
MS: 424 (M+, 11), 273 (100) m/z. Elemental analysis for
C24H17FN6O: Calcd: C, 67.92; H, 4.04; N, 19.80. Found: C, 68.14;
H, 4.20; N, 20.18.
Compound 2h2: yield: 21%; mp 210–211 °C (95% EtOH); IR:
3242 (NH); 1675 (C@O). 1H NMR: 11.97 (s, 1H exch., NH); 8.49
(m, 2H, arom); 7.91 (m, 2H, arom); 7.56–7.34 (m, 10H, arom);
5.98 (s, 2H, CH2–benzyl). MS: 424 ((M+, 10), 273 (100) m/z. Ele-
mental analysis for C24H17FN6O: Calcd: C, 67.92; H, 4.04; N,
19.80. Found: C, 68.19; H, 4.28; N, 20.01.
Compound 2h3: yield: 25%; mp 260–261 °C (95% EtOH); IR:
3252 (NH); 1674 (C@O). 11.90 (s, 1H exch., NH); 8.49 (m, 2H,
arom); 8.15 (m, 2H, arom); 7.57–7.37 (m, 10H, arom); 5.99 (s,
2H, CH2–benzyl). MS: 424 (M+, 9) 395 (100) m/z. Elemental analy-
sis for C24H17FN6O: Calcd: C, 67.92; H, 4.04; N, 19.80. Found: C,
67.99; H, 4.12; N, 19.98.
Compound 2i1: yield: 15%; mp 210–211 °C (95% EtOH); IR: 3238
(NH); 1688 (C@O). 1H NMR: 12.31 (s, 1H exch., NH); 8.09 (m, 2H,
arom); 7.68–7.36 (m, 12H, arom); 5.96 (s, 2H, CH2–benzyl). MS:
405 (31) 139 (100) m/z. Elemental analysis for C24H17ClN6O: Calcd:
C, 65.38; H, 3.89; N, 19.06. Found: C, 65.11; H, 4.12; N, 19.17.
Compound 2i2: yield: 35%; mp 219–220 °C (95% EtOH); IR: 3241
(NH); 1685 (C@O). 1H NMR: 11.98 (br s, 1H exch., NH); 8.48 (m, 2H,
arom); 8.14 (s, 1H, arom); 8.05 (d, J = 7.2 Hz, 1H); 7.79–7.36 (m,
10H, arom); 5.99 (s, 2H, CH2–benzyl). MS: 440 (M+, 15) 178 (100)
m/z. Elemental analysis for C24H17ClN6O: Calcd: C, 65.38; H, 3.89;
N, 19.06. Found: C, 65.37; H, 4.00; N, 19.21.
Compound 2i3: yield: 58%; mp 220–221 °C (95% EtOH); IR: 3259
(NH); 1674 (C@O). 1H NMR: 11.87 (br s, 1H exch., NH); 8.35 (m, 2H,
arom); 8.12 (d, J = 7.0 Hz, 2H, arom); 7.70–7.34 (m, 10H, arom);
5.99 (s, 2H, CH2-benzyl). MS: 440 (M+, 82) 160 (100) m/z. Elemen-
tal analysis for C24H17ClN6O: Calcd: C, 65.38; H, 3.89; N, 19.06.
Found: C, 65.41; H, 3.92; N, 19.10.
Compound 2l: yield: 32%; mp > 300 °C (95% EtOH); IR: 3266
(NH); 1671 (C@O). 1H NMR1H NMR: 11.81 (br s, 1H exch.,
NH); 8.51 (m, 2H, arom); 8.03 (d, J = 3.8 Hz, 2H, arom); 7.60–
7.37 (m, 10H, arom); 5.99 (s, 2H, CH2–benzyl); 2.44 (s, 3H,
CH3). MS: 420 (M+, 4), 91 (100) m/z. Elemental analysis for
C25H20N6O: Calcd: C, 71.41; H, 4.79; N, 19.99. Found: C,
71.33; H, 4.86; N, 19.94.
Compound 2m1: yield: 20%; mp 178–180 °C (MeOH); IR: 3221
(NH); 1675 (C@O). 1H NMR: 12.38 (br s, 1H exch., NH); 8.03–
7.76 (m, 6H, arom); 7.52–7.35 (m, 8H, arom); 5.95 (s, 2H, CH2-ben-
zyl). MS: 474 (M+, 8), 173 (100) m/z. Elemental analysis for
C25H17F3N6O: Calcd: C, 63.29; H, 3.61; N, 17.71. Found: C, 63.15;
H, 3.47; N, 17.62.
Compound 2m2: yield: 39%; mp 210 °C dec. (95% EtOH); IR:
3235 (NH); 1679 (C@O). 1H NMR: 12.29 (br s, 1H exch., NH);
8.49–8.35 (m, 4H, arom); 8.20 (d, J = 7.4, 1H, arom), 7.83 (t,
J = 7.6 Hz, 1H, arom); 7.58–7.36 (m, 8H, arom); 5.99 (s, 2H, CH2–
benzyl). MS: 474 (M+, 10), 173 (100) m/z. Elemental analysis for
C25H17F3N6O: Calcd: C, 63.29; H, 3.61; N, 17.71. Found: C, 63.45;
H, 3.55; N, 17.60.
Compound 2m3: yield: 25%; mp 230–231 °C (MeOH); IR: 3247
(NH); 1672 (C@O). 1H NMR: 12.14 (br s, 1H exch., NH); 8.48 (m,
2H, arom); 8.24 (d, J = 8.2 Hz, 2H, arom); 7.96 (d, J = 8.2 Hz, 2H,
arom), 7.59–7.32 (m, 8H, arom); 5.98 (s, 2H, CH2-benzyl). MS:
474 (M+, 12), 445 (100) m/z. Elemental analysis for C25H17F3N6O:
Calcd: C, 63.29; H, 3.61; N, 17.71. Found: C, 63.57; H, 3.74; N,
17.82.
Compound 2n: yield: 11%; mp 169–170 °C (95% EtOH); IR: 3262
(NH); 1696 (C@O). 1H NMR: 11.70 (br s, 1H exch., NH); 8.34 (m, 2H,
arom); 7.93 (m, 1H, arom); 7.63–7.15 (m, 11H, arom); 5.97 (s, 2H,
CH2-benzyl); 4.13 (q, J = 6.8 Hz, 2H, CH2); 1.30 (t, J = 6.8 Hz, 3H,
CH3). MS: 450 (M+, 2), 273 (100) m/z. Elemental analysis for
C26H22N6O2: Calcd: C, 69.32; H, 4.92; N, 18.66. Found: C, 69.45;
H, 4.81; N, 18.85.
Compound 2o: yield: 34%; mp 206–207 °C (95% EtOH); IR:
3283 (NH); 1701 (C@O). 1H NMR: 11.86 (br s, 1H exch., NH);
8.29 (m, 2H, arom), 7.78 (d, J = 2.6 Hz, 1H, arom), 7.67–7.21
(m, 10H, arom), 5.98 (s, 2H, CH2-benzyl), 3.80 (s, 3H, CH3).
MS: 471(M+, 2), 436 (100) m/z. Elemental analysis for
C25H19ClN6O2: Calcd: C, 63.76; H, 4.07; N, 17.85. Found: C,
63.54; H, 4.02; N, 17.98.
Compound 2j: yield: 44%; mp 178–180 °C (95% EtOH); IR: 3201
(NH); 1665 (C@O). 1H NMR: 12.24 (br s, 1H exch., NH); 8.11 (m, 2H,
arom); 7.97 (d, J = 7.8 Hz, 1H); 7.56–7.32 (m, 11H, arom); 5.96 (s,
2H, CH2–benzyl). MS: 405(M+-128, 90), 91 (100) m/z. Elemental
analysis for C24H17IN6O: Calcd: C, 54.15; H, 3.22; N, 15.79. Found:
C, 54.31; H, 3.12; N, 15.56.
Compound 2p: yield: 40%; mp 175–176 °C (95% EtOH); IR: 3227
(NH); 1682 (C@O). 1H NMR: 12.59 (s, 1H exch., NH); 8.42 (s, 1H
arom), 8.07–7.86 (m, 4H, arom), 7.56–7.36 (m, 8H, arom), 5.96 (s,
2H, CH2-benzyl). MS: 485(M+, 20), 215 (100) m/z. Elemental anal-
ysis for C24H16ClN7O3: Calcd: C, 59.33; H, 3.32; N, 20.18. Found:
C, 59.21; H, 3.55; N, 20.05.
Compound 2k1: yield: 34%; mp 198–200 °C (95% EtOH); IR:
3281 (NH); 1704 (C@O). 1H NMR: 11.70 (br s, 1H exch., NH);
8.34 (m, 2H, arom); 7.85 (d, J = 7.6 Hz, 1H); 7.53–7.17 (m, 11H,
Compound 2q1: yield: 30%; mp 195–196 °C (95% EtOH); IR:
3234 (NH); 1682 (C@O). 1H NMR: 12.51 (br s, 1H exch., NH);
8.30 (m, 2H, arom); 7.98–7.29 (m, 12H, arom); 5.95 (s, 2H, CH2–