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S.J.C. Gutierrez et al. / Il Farmaco 60 (2005) 475–477
The Nb-3,4-methylenedioxy-benzoyltryptamine is a new com-
pound.
11.85 (1H, sl); 13C NMR (50 MHz, C5D5N) d: 26.0, 40.9,
55.4, 55.5, 98.9, 105.9, 112.0, 113.1, 115.7, 119.2, 119.3,
121.9, 123.5, 128.4, 133.9, 137.7, 159.4, 163.6, 165.2.
3.1.3. Nb-3,4-dimethoxy-benzoyltryptamine (2c)
3. Experimental procedures
Yield of the product was 63% as a white powder from
CHCl3/MeOH (1:1), with m.p. 182 °C (Lit. 182 °C) [5]; IR
mmax (KBr) cm–1: 1230, 1416, 1441, 1461, 1504, 1605, 2839,
2873, 2930, 3011, 3080, 3219, 3390; UV kmax MeOH nm:
3.1. Chemistry
Melting points are uncorrected and were determined on
an electrically heated metal block apparatus. UV spectra were
recorded on aVankel 50 UV–Vis spectrophotometer in MeOH
as solvent. IR spectra were obtained on a Bomen Michelson
spectrophotometer using KBr. 1H and 13C NMR spectra were
recorded in C51D5N on a Varian-Mercury 200 spectrometer at
200 MHz for H NMR and 50 MHz for 13C NMR and 2D
techniques. For the analytical TLC, precoated Merck silica
gel PF254 plates were used with a 0.25 mm layer. For column
chromatography, silica gel-60 Merck was used. The
tryptamine and benzoyl chlorides were purchased from
Sigma-Aldrich and used as received.
1
220, 260, 290; H NMR (200 MHz, C5D5N) d: 3.36 (2H, t
J = 7.4), 3.65 (3H, s), 3.72 (3H, s), 4.06 (2H, q, J = 8.8), 6.96
(1H, d, J = 8.2), 7.24 (1H, dt, J = 1.2; 7.0), 7.32 (1H, dt,
J = 1.4; 7.0), 7.60 (1H, d, J = 7.2), 7.60 (1H, d, J = 2.2), 7.87
(1H, sl), 7.93 (1H, m), 7.99 (1H, d J = 2.0), 9.13 (1H, t
J = 5.8); 13C NMR (50 MHz, C5D5N) d: 26.0, 41.5, 55.8, 56.9,
111.4, 111.8, 113.4, 119.1, 119.2, 121.0, 121.7, 123.4, 128.5,
128.7, 137.6, 149.5, 152.2, 167.4.
3.1.4. Nb-3,4-methylenedioxy-benzoyltryptamine (2d)
Yield of the product was 53% as a white powder from
CHCl3/MeOH (1:1) with m.p. 150 °C; IR mmax (KBr) cm–1:
1443, 1457, 1485, 1501, 1618, 1640, 2787, 2918, 2976, 3118,
3.1.1. Nb-4-methoxy-benzoyltryptamine (2a)
1
3342, 3401, 3416; UV kmax MeOH nm: 220, 260, 290; H
To a solution of triethylamine (1 ml) and chloroform
(20 ml), tryptamine was added until total solubilization. To
this solution a solution of p-anisoyl chloride (1 g) dissolved
in chloroform (10 ml) was added dropwise over 15 min with
magnetic stirring. The reaction mixture was left at room tem-
perature for 2 h. The solution was then washed with first 2%
HCl and then H2O, dried over anhydrous Na2SO4, filtered
and concentrated under vacuum, yielding a white powder. This
product was chromatographed on a silica gel column, eluted
with CHCl3/hexane (1:1 and 8:2), CHCl3 and CHCl3/MeOH
(98:02). After TLC analysis, fractions 10–21 were reunited
and crystallized from CHCl3/MeOH (1:1). The resulting mate-
rial (2a, 75% yield) was obtained as white crystals with melt-
ing point of 134 °C (Lit. 132.5–133.5 °C) [3]; IR mmax (KBr)
cm–1: 1179, 1257, 1437, 1455, 1507, 1607, 1615, 2847, 2937,
NMR (200 MHz, C5D5N) d: 3.35 (2H, t J = 8.0), 4.04 (2H, q
J = 6.0), 5.95 (2H, s), 6.91 (1H, d J = 8.6), 7.24 (1H, td J = 1.2;
7.0), 7.29 (1H, td J = 1.4; 7.0), 7.35 (1H, d J = 2.4), 7.59 (1H,
d J = 1.2), 7.86 (1H, m), 9.06 (1H, t J = 6.0); 13C NMR
(50 MHz, C5D5N) d: 26.3, 41.5, 102.5, 108.1, 108.4, 112.0,
113.2, 119.1, 119.2, 121.7, 122.6, 128.5, 137.6, 148.2, 149.7,
167.0.
3.1.5. Nb-3,4,5-trimethoxy-benzoyltryptamine (5e)
Yield of the product was 80%, white powder from
CHCl3/MeOH (1:1), with a m.p. 214 °C (Lit. 165 °C [6];
200–202 °C [7]); IR mmax (KBr) cm–1: 1127, 1233, 1413, 1458,
1503, 1586, 1635, 2855, 2938, 2959, 3013, 3297, 3363; UV
kmax MeOH nm: 230, 260, 270; 1H NMR (200 MHz, C5D5N)
d: 3.35 (2H, t J = 8.0), 3.64 (3H, s), 3.89 (3H, s), 4.05 (2H, q
J = 6.0), 7.24 (1H, td J = 1.2; 7.0), 7.29 (1H, td J = 1.4; 7.0),
7.36 (1H, d J = 2.0), 7.61 (1H, m), 7.62 (1H, s), 7.88 (1H, d
J = 2.0), 9.25 (1H, t J = 6.0); 13C NMR (50 MHz, C5D5N) d:
26.2, 41.6, 55.9, 60.5, 105.7, 112.0, 113.3, 119.1, 119.2, 121.7,
123.4, 128.6, 131.5, 137.6, 141.2, 153.6, 167.3.
1
2977, 3011; UV kmax MeOH nm: 235, 247, 256; H NMR
(200 MHz, C5D5N) d: 3.36 (1H, s), 3.64 (3H, s), 4.07 (2H, q,
J = 8.0), 7.01 (1H, d, J = 8.8), 7.25 (1H, dt, J = 1.2; 7.0), 7.29
(1H, dt, J = 1.4; 7.0), 7.35 (1H, d, J = 2.4), 7.60 (1H, d,
J = 7.2), 7.89 (1H, d, J = 8.0), 8.31 (1H, d, J = 8.8), 9.09 (1H,
t, J = 6.0), 11.8 (1H, s); 13C NMR (50 MHz, C5D5N) d: 26.4,
41.4, 55.2, 112.0, 113.3, 113.9, 119.1, 119.2, 123.3, 128.5,
128.5, 129.7, 162.3, 167.3.
3.2. Pharmacology
3.1.2. Nb-2,4-dimethoxy-benzoyltryptamine (2b)
The tissues were suspended in 6 ml organ baths under a
resting load of 1.0 g at 37 °C. Force generation was moni-
tored using an isometric transducer (7003-UGO BASILE)
coupled to a polygraph (7070-UGO BASILE). The modified
Krebs solution: NaCl (117.0), KCl (4.7), MgSO4·7H2O (1.3),
NaH2PO4·H2O (1.2), CaCl2·H2O (2.5), glucose (11.0),
NaHCO3 (25.0) was bubbled with a 95% O2 and 5% CO2 gas
mixture before use. Drugs—NaHCO3, KCl, MgSO4·7H2O
(Reagen); acetylcholine, CaCl2·H2O, NaCl, MgCl2·6H2O,
NaH2PO4·H2O, glucose (Merck) and histamine (Sigma-
Yield of the product was 65%, orange solid from
CHCl3/MeOH (1:1), with m.p. 116 °C (Lit. reported as oil)
[4]; IR mmax (KBr) cm–1: 1206, 1437, 1466, 1497, 1604, 1634,
2850, 2975, 3016, 3111, 3228, 3369; UV kmax MeOH nm:
225, 255, 287; 1H NMR (200 MHz, C5D5N) d: 3.25 (2H, t,
J = 6.8), 3.53 (3H, s), 3.67 (3H, s), 4.08 (2H, q, J = 6.4), 6.57
(1H, d, J = 2.2), 6.68 (1H, d, J = 7.8), 7.25 (1H, dt, J = 1.2;
7.0), 7.29 (1H, dt, J = 1.4; 7.0), 7.40 (1H, d, J = 1.6), 7.62
(1H, d, J = 8.2), 8.37 (1H, t, J = 5.2), 8.61 (1H, d, J = 8.6),