CHEMISTRY & BIODIVERSITY – Vol. 6 (2009)
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yellow oil was dissolved in AcOEt and then treated with HCl (g) in AcOEt, The resulting HCl salt was
then filtered as a brownish yellow solid.
1-(6-{[4-(2,3,4-Trimethoxybenzyl)piperazin-1-yl]methyl}-4-(butylamino)quinoline-3-carbonyl)gua-
nidine Hydrochloride (7b). Yield: 0.08 g (36.9%). Brownish yellow solid. M.p. 194–1968. IR (KBr):
3385, 2958–2560, 1703, 1626, 1601, 1585, 1497, 1286, 1098, 935, 792. 1H-NMR (300 MHz, (D6)DMSOþ
D2O): 0.88 (t, J¼7.5, Me); 1.24–1.37 (m, CH2); 1.46–1.56 (m, CH2); 2.75 (t, J¼7.5, NCH2); 3.35–3.70 (m,
8 H, piperazine); 3.74 (s, MeO); 3.80 (s, MeO); 3.85 (s, MeO); 4.26 (s, CH2); 4.50 (s, CH2); 6.87 (d, J¼8.7,
1 arom. H); 7.30 (d, J¼8.7, 1 arom. H); 8.16 (d, J¼8.4, 1 arom. H); 8.28 (d, J¼8.7, 1 arom. H); 8.74 (s, 1
arom. H); 9.29 (s, 1 arom. H). ESI-MS: 564.3 ([MþH]þ ). Anal. calc. for C30H45Cl4N7O4 ·H2O: C 49.53,
H 6.51, N 13.48; found: C 49.72, H 6.56, N 13.24.
1-(4-(Phenylamino)-6-{[4-(2,3,4-trimethoxybenzyl)piperazin-1-yl]methyl}quinoline-3-carbonyl)gua-
nidine Hydrochloride (7c). Yield: 38.1%. Yellow solid. M.p. 262–2638. IR (KBr): 3385, 3001–2719, 1701,
1
1624, 1578, 1531, 1494, 1285, 1099, 934. H-NMR (300 MHz, (D6)DMSO): 3.05–3.60 (m, 8 piperazine
H); 3.76 (s, MeO); 3.82 (s, MeO); 3.87 (s, MeO); 4.23 (s, CH2); 4.50 (br. s, CH2); 6.88 (d, J¼8.7, 1 arom.
H); 7.32–7.37 (m, 2 arom. H); 7.42 (d, J¼7.2, 1 arom. H); 7.93 (d, J¼8.7, 1 arom. H); 8.14–8.17 (m, 1
arom. H); 8.48 (s, 1 arom. H); 8.57 (br. s, 1 NH); 8.91 (d, J¼6.3, 1 arom. H); 8.99 (s, 1 arom. H); 9.09 (br.
s, 1 NH); 13.27 (s, 1 NþH); 13.89 (s, 1 NþH). ESI-MS: 584.4 ([MþH]þ ). Anal. calc. for C32H41Cl4N7O4 ·
H2O: C 51.41, H 5.80, N 13.12; found: C 51.24, H 5.92, N 13.24.
1-(4-[(3-Methoxyphenyl)amino]-6-{[4-(2,3,4-trimethoxybenzyl)piperazin-1-yl]methyl}quinoline-3-
carbonyl)guanidine Hydrochloride (7e). Yield: 43.2%. Yellow solid. M.p. 279–2818. IR (KBr): 3377,
3077–2657, 2987, 1701, 1623, 1572, 1530, 1493, 1286, 1096, 806. 1H-NMR (300 MHz, (D6)DMSO): 3.35–
3.65 (m, 8 piperazine H); 3.75 (s, MeO); 3.77 (s, MeO); 3.81 (s, MeO); 3.86 (s, MeO); 4.25 (s, CH2); 4.28
(br. s, 1 NH); 4.59 (s, CH2); 6.87 (d, J¼8.7, 1 arom. H); 6.93 (s, 1 arom. H); 7.35 (d, J¼7.8, 1 arom. H);
7.95 (d, J¼8.4, 1 arom. H); 8.15 (d, J¼6.6, 1 arom. H); 8.51 (s, 1 arom. H); 8.65 (br. s, 1 NH); 8.88 (d, J¼
6.6, 1 arom. H); 8.98 (s, 1 arom. H); 9.00 (br. s, 1 NH); 9.19 (s, 1 arom. H); 13.24 (s, 1 NHþ ); 14.07 (s,
1 NHþ ). ESI-MS: 614.5 ([MþH]þ ). Anal. calc. for C33H43Cl4N7O5 ·2 H2O: C 49.82, H 5.95, N 12.32;
found: C 50.04, H 5.82, N 12.33.
1-(4-[(4-Ethoxyphenyl)amino]-6-{[4-(2,3,4-trimethoxybenzyl)piperazin-1-yl]methyl}quinoline-3-
carbonyl)guanidine Hydrochloride (7f). Yield: 52.7%. Brownish yellow solid. M.p. 257–2608. IR (KBr):
3382, 2982–2560, 1700, 1623, 1581, 1532, 1451, 1286, 1100, 926, 802. 1H-NMR (300 MHz, (D6)DMSO):
1.34 (t, J¼6.6, Me); 3.22–3.63(m, 8 piperazine H); 3.75 (s, MeO); 3.81 (s, MeO); 3.86 (s, MeO); 4.05 (q,
J¼6.9, CH2O); 4.24 (s, CH2); 4.34 (br. s, CH2); 6.87 (d, J¼8.7, 1 arom. H); 6.95 (d, J¼8.7, 1 arom. H);
7.29 (d, J¼8.7, 1 arom. H); 7.34 (d, J¼8.7, 1 arom. H); 8.00 (s, 1 arom. H); 8.15 (d, J¼8.7, 1 arom. H); 8.28
(d, J¼9, 1 arom. H); 8.45 (br. s, 1 NH); 8.49 (s, 1 arom. H); 8.91 (s, 1 arom. H); 9.19 (br. s, 1 NH); 11.58 (s,
1 NH); 12.71 (s, 1 NH); 13.25 (s, 1 NHþ ); 13.96 (s, 1 NHþ ). ESI-MS: 628.3 ([MþH]þ ). Anal. calc. for
C34H45Cl4N7O5 ·H2O: C 51.59, H 5.98, N 12.39; found: C 51.24, H 6.07, N 12.24.
1-(4-(p-Toluidino)-6-{[4-(2,3,4-trimethoxybenzyl)piperazin-1-yl]methyl}quinoline-3-carbonyl)gua-
nidine Hydrochloride (7g). Yield: 36.4%. Yellow solid. M.p. 260–2618. IR (KBr): 3384, 3075–2659, 1701,
1623, 1570, 1530, 1494, 1286, 1204, 1097, 930, 805. 1H-NMR (300 MHz, (D6)DMSO): 2.50 (s, Me); 3.35–
3.65 (m, 8 piperazine H); 3.75 (s, MeO); 3.81 (s, MeO); 3.86 (s, MeO), 4.22 (br. s, CH2); 4.30 (br. s,
1 NH); 4.58 (s, CH2); 6.87 (d, J¼8.7, 1 arom. H); 7.35 (d, J¼8.4, 1 arom. H); 7.94 (d, J¼8.4, 1 arom. H);
8.15 (d, J¼7.8, 1 arom. H); 8.50 (s, 1 arom. H); 8.59 (br. s, 1 NH); 8.90 (d, J¼6.6, 2 arom. H); 9.09 (br. s,
1 NH); 9.19 (s, 1 arom. H); 13.25 (s, 1 NHþ ); 13.96 (s, 1 NHþ ). ESI-MS: 598.3 ([MþH]þ ). Anal. calc.
for C33H43Cl4N7O4 ·H2O: C 52.04, H 5.96, N 12.87; found: C 51.84, H 6.07, N 12.74.
1-(4-[(3,4-Dimethylphenyl)amino]-6-{[4-(2,3,4-trimethoxybenzyl)piperazin-1-yl]methyl}quinoline-
3-carbonyl)guanidine Hydrochloride (7i). Yield: 46.1%. Light-yellow solid. M.p. 210–2138. IR (KBr):
3445, 2935, 2813, 1621, 1585, 1518, 1498, 1287, 1095, 874, 806. 1H-NMR (300 MHz, CDCl3): 2.12 (s, Me);
2.15 (s, Me); 2.17–2.52 (m, 8 piperazine H); 3.34 (s, CH2); 3.44 (s, CH2); 3.85 (s, MeO); 3.87 (s, 2 MeO);
6.63 (d, J¼8.4, 2 arom. H); 6.74 (d, J¼7.8, 1 arom. H); 6.81 (s, 1 arom. H); 6.96 (dd, J¼3.6, 8.4, 1 arom.
H); 7.56 (s, 1 arom. H); 7.90 (d, J¼9, 1 arom. H); 8.04 (br. s, 1 NH); 8.21 (br. s, 1 NH); 9.49 (s, 1 arom. H).
13C-NMR (300 MHz, (D6)DMSO): 19.14; 19.78; 52.87; 52.94; 56.06; 56.56; 60.82; 61.22; 62.72; 76.62;
77.04; 77.25; 77.47; 107.06; 114.31; 119.71; 119.78; 123.66; 124.17; 125.17; 127.12; 127.61; 130.32; 132.32;
132.38; 132.72; 133.88; 137.52; 141.18; 142.36; 147.79; 151.28; 152.64; 152.91; 161.91; 178.05. ESI-MS: