776
J.C.J.M.D.S. Menezes et al. / European Journal of Medicinal Chemistry 46 (2011) 773e777
bath and conc. HCl (1.0 mL) was added. Extraction with diethyl
ether or filtration on a Buchner funnel afforded the crude cinna-
mates, 8e21 which were further purified by recrystallization.
3.3.8. Trans-hexadecyl-3-(4-hydroxy-3-methoxyphenyl)
propenoate (15)
Colorless solid; m.p. 69 ꢂC (methanol) (lit [26,2]. 61e63 ꢂC);
identical with ref [26] and [2].
3.3.1. Trans-tetradecyl-3-(4-hydroxyphenyl) propenoate (8)
Colorless solid; m.p. 89 ꢂC (methanol) (lit. [9] 88e90 ꢂC); HRE-
SIMS: m/z 383.2554 (M þ Na)þ; Calcd for C23H36O3Naþ: 383.2557.
Identical with ref [9].
3.3.9. Trans-hexadecyl-3-(3,5-dimethoxy-4-hydroxyphenyl)
propenoate (16)
Colorless solid; m.p. 60 ꢂC (methanol); HRESIMS: m/z 471.3078
(M þ Na)þ; Calcd for C27H44O5Naþ: 471.3081. Identical with ref [2].
3.3.2. Trans-tetradecyl-3-(4-methoxyphenyl) propenoate (9)
Colorless solid; m.p. 51 ꢂC (methanol); UV (MeOH): 309,
226 nm; IR (KBr, cmꢃ1): 2916, 1707 (CO), 1606, 1517, 1182, 825; 1H
3.3.10. Trans-hexadecyl-3-phenylpropenoate (17)
Colorless solid; m.p. 38 ꢂC (Petroleum ether) (lit [27].
39.6e40.6 ꢂC); UV (MeOH): 276, 217 nm; IR (KBr, cmꢃ1): 2924,
NMR (300 MHz, CDCl3)
d
: 0.88 (t, J ¼ 6.6 Hz, 3H, H-140), 1.26 (bs,
22H, H-30-130), 1.69 (m, 2H, H-20), 3.84 (s, 3H, OCH3), 4.18
(t, J ¼ 6.6 Hz, 2H, H-10), 6.31 (d, J ¼ 15.9 Hz, 1H, H-2), 6.90
(d, J ¼ 8.8 Hz, 2H, H-6, 8), 7.48 (d, J ¼ 8.8 Hz, 2H, H-5, 9), 7.64
(d, J ¼ 15.9 Hz, 1H, H-3); HRESIMS: m/z 397.2704 (M þ Na)þ; Calcd
for C24H38O3Naþ: 397.2713.
1717 (CO), 1638, 1310, 1167, 766; 1H NMR (300 MHz, CDCl3)
d: 0.88
(t, J ¼ 6.6 Hz, 3H, H-160), 1.25 (bs, 26H, H-30-150), 1.69 (m, 2H, H-20),
4.20 (t, J ¼ 6.6 Hz, 2H, H-10), 6.44 (d, J ¼ 15.9 Hz, 1H, H-2), 7.37e7.53
(m, 5H, Ar-H), 7.68 (d, J ¼ 15.9 Hz, 1H, H-3); 13C NMR (75 MHz,
CDCl3) d
: 14.1 (C-160), 22.7 (C-150), 25.9 (C-30), 28.7 (C-20), 29.2 (C-
40), 29.3 (C-130), 29.7 (C-50-120), 31.9 (C-140), 64.7 (C-10), 118.3 (C-2),
128.0 (C-5, 9), 128.8 (C-6, 8), 130.2 (C-4), 134.5 (C-7), 144.5 (C-3),
3.3.3. Trans-tetradecyl-3-(3,4-dihydroxyphenyl)propenoate (10)
Colorless solid; m.p. 106 ꢂC (methanol) (lit [9,24]. 108e109 ꢂC);
HRESIMS: m/z 399.2508 (M þ Na)þ; Calcd for C23H36O4Naþ:
399.2506. Identical with ref [9] and [24].
167.1 (C-1); HRESIMS: m/z 395.2924 (M
þ
Na)þ; Calcd for
C25H40O2Naþ: 395.2921.
3.3.11. 3.3.Trans-octadecyl-3-(3,4-dihydroxyphenyl)propenoate(18)
Colorless solid; m.p. 108 ꢂC (methanol) (lit [24]. 110e112 ꢂC); UV
(MeOH): 328, 219 nm; IR (KBr, cmꢃ1): 3481 (OH), 3311 (OH), 2918,
1684 (CO),1606,1284,1180, 974, 815; 1H NMR (300 MHz, DMSO-d6)
3.3.4. Trans-tetradecyl-3-(4-hydroxy-3-methoxyphenyl)
propenoate (11)
Colorless solid; m.p. 70 ꢂC (methanol) (lit [25]. 76 ꢂC); identical
with ref [25].
d
: 0.84 (t, J ¼ 6.6 Hz, 3H, H-180), 1.22 (bs, 30H, H-30-170), 1.61 (m, 2H,
H-20), 4.09 (t, J ¼ 6.45 Hz, 2H, H-10), 6.25 (d, J ¼ 15.9 Hz,1H, H-2), 6.75
(d, J ¼ 8.1 Hz, 1H, H-8), 7.0 (dd, J ¼ 8.1, 1.8 Hz, 1H, H-9), 7.04
(d, J ¼ 1.8 Hz, 1H, H-5), 7.45 (d, J ¼ 15.9 Hz, 1H, H-3), 9.17 (s, 1H, OH),
3.3.5. Trans-tetradecyl-3-(3,5-dimethoxy-4-hydroxyphenyl)
propenoate (12)
Colorless solid; m.p. 62 ꢂC (methanol); UV (MeOH): 327, 240 nm; IR
9.61 (s, 1H, OH); 13C NMR (75 MHz, DMSO-d6) : 13.4 (C-180), 21.6
d
(KBr, cmꢃ1): 3554 (OH), 2917,1709 (CO),1639,1516,1181, 843; 1H NMR
(C-170), 24.9 (C-30), 27.8 (C-20), 28.2 (C-40, 150), 28.5 (C-50-140), 30.8
(C-160), 63.2 (C-10), 113.5 (C-2), 114.2 (C-8), 115.2 (C-5), 120.8 (C-9),
125.0 (C-4), 144.5 (C-3), 145.1 (C-6), 147.9 (C-7), 166.1 (C-1); HRE-
SIMS: m/z 455.3135 (M þ Na)þ; Calcd for C27H44O4Naþ: 455.3132.
(300 MHz, CDCl3)
d
: 0.87 (t, J ¼ 6.6 Hz, 3H, H-140), 1.25 (bs, 22H, H-30-
130), 1.69 (m, 2H, H-20), 3.91 (s, 6H, 2 ꢄ OCH3), 4.18 (t, J ¼ 6.6 Hz, 2H, H-
10), 5.81 (s, 1H, OH), 6.30 (d, J ¼ 15.9 Hz, 1H, H-2), 6.77 (s, 2H, H-5, 9),
7.58 (d, J ¼ 15.9 Hz, 1H, H-3); 13C NMR (75 MHz, CDCl3)
d
: 14.1 (C-140),
22.7 (C-130), 25.9 (C-30), 28.8 (C-20), 29.2 (C-40), 29.3 (C-110), 29.6 (C-50-
100), 31.9 (C-120), 56.3 (2 ꢄ OCH3), 64.6 (C-10),105.1 (C-5, 9),116.1 (C-2),
126.0 (C-4), 137.1 (C-7), 144.8 (C-3), 147.2 (C-6, 8), 167.2 (C-1); HRE-
SIMS: m/z 443.2762 (M þ Na)þ; Calcd for C25H40O5Naþ: 443.2768.
3.3.12. Trans-octadecyl-3-(4-hydroxy-3-methoxyphenyl)
propenoate (19)
Colorless solid; m.p.104 ꢂC (methanol) (lit [28].110 ꢂC); identical
with ref [28].
3.3.6. 3.3Trans-hexadecyl-3-(3,4-dihydroxyphenyl)propenoate (13)
Colorless solid; m.p. 102 ꢂC (methanol) (lit [24]. 110e111 ꢂC); UV
(MeOH): 329, 219 nm; IR (KBr, cmꢃ1): 3481 (OH), 3312 (OH), 2918,
3.3.13. Trans-octadecyl-3-(3,5-dimethoxy-4-hydroxyphenyl)
propenoate (20)
Colorless solid; m.p. 72 ꢂC (methanol) (lit [29]. 72e73 ꢂC); UV
(MeOH): 327, 236 nm; IR (KBr, cmꢃ1): 3533 (OH), 2917, 1708 (CO),
1684 (CO), 1606, 1286, 1180, 974, 815; 1H NMR (300 MHz, CDCl3)
d:
0.87 (t, J ¼ 6.6 Hz, 3H, H-160), 1.25 (bs, 26H, H-30-150), 1.67 (m, 2H,
H-20), 4.18 (t, J ¼ 6.75 Hz, 2H, H-10), 5.69 (bs, 2H, 2 ꢄ OH), 6.27
(d, J ¼ 15.9 Hz, 1H, H-2), 6.87 (d, J ¼ 8.1 Hz, 1H, H-8), 7.02 (dd, J ¼ 8.1,
1.8 Hz, 1H, H-9), 7.09 (d, J ¼ 1.8 Hz, 1H, H-5), 7.57 (d, J ¼ 15.9 Hz, 1H,
1638, 1516, 1181, 836; 1H NMR (300 MHz, CDCl3)
d: 0.87
(t, J ¼ 6.6 Hz, 3H, H-180), 1.25 (bs, 30H, H-30-170), 1.70 (m, 2H, H-20),
3.92 (s, 6H, 2 ꢄ OCH3), 4.19 (t, J ¼ 6.6 Hz, 2H, H-10), 5.78 (s, 1H, OH),
6.30 (d, J ¼ 15.9 Hz, 1H, H-2), 6.77 (s, 2H, H-5, 9), 7.59 (d, J ¼ 15.9 Hz,
H-3); 13C NMR (75 MHz, DMSO-d6)
d
: 13.4 (C-160), 21.6 (C-150), 24.9
1H, H-3); 13C NMR (75 MHz, CDCl3) : 14.1 (C-180), 22.7 (C-170), 25.9
d
(C-30), 27.7 (C-20), 28.1 (C-40, 130), 28.5 (C-50-120), 30.8 (C-140), 63.2
(C-10), 113.5 (C-2), 114.3 (C-8), 115.2 (C-5), 120.8 (C-9), 125.0 (C-4),
144.5 (C-6), 145.1 (C-3), 147.9 (C-7), 166.1 (C-1); HRESIMS: m/z
427.2815 (M þ Na)þ; Calcd for C25H40O4Naþ: 427.2819.
(C-30), 28.8 (C-20), 29.2 (C-40), 29.3 (C-150), 29.7 (C-50-140), 31.9
(C-160), 56.3 (2 ꢄ OCH3), 64.6 (C-10), 105.1 (C-5, 9), 116.1 (C-2), 126.0
(C-4), 137.1 (C-7), 144.8 (C-3), 147.2 (C-6, 8), 167.2 (C-1); HRESIMS:
m/z 499.3398 (M þ Na)þ; Calcd for C29H48O5Naþ: 499.3394.
3.3.7. Trans-hexadecyl-3-(3,4-dimethoxyphenyl) propenoate (14)
Colorless solid; m.p. 67 ꢂC (methanol); UV (MeOH): 322, 295,
235, 218 nm; IR (KBr, cmꢃ1): 2916, 1720 (CO), 1514, 1271, 976, 843;
3.3.14. Trans-octadecyl-3-phenylpropenoate (21)
Colorless solid; m.p. 45 ꢂC (petroleum ether) (lit [29]. 45e46 ꢂC);
UV (MeOH): 276, 218 nm; IR (KBr, cmꢃ1): 2920,1713 (CO),1639,1311,
1H NMR (300 MHz, CDCl3)
d
: 0.87 (t, J ¼ 6.6 Hz, 3H, H-160), 1.25 (bs,
1175, 766; 1H NMR (300 MHz, CDCl3)
d
: 0.88 (t, J ¼ 6.6 Hz, 3H, H-180),
26H, H-30-150), 1.69 (m, 2H, H-20), 3.91 (s, 6H, 2 ꢄ OCH3), 4.18
(t, J ¼ 6.6 Hz, 2H, H-10), 6.31 (d, J ¼ 15.9 Hz, 1H, H-2), 6.86
(d, J ¼ 8.4 Hz, 1H, H-8), 7.05 (d, J ¼ 1.8 Hz, 1H, H-5), 7.10 (dd, J ¼ 8.1,
1.8 Hz, 1H, H-9), 7.62 (d, J ¼ 15.9 Hz, 1H, H-3); HRESIMS: m/z
455.3149 (M þ Na)þ; Calcd for C27H44O4Naþ: 455.3132.
1.26 (bs, 30H, H-30-170), 1.69 (m, 2H, H-20), 4.20 (t, J ¼ 6.6 Hz, 2H, H-
10), 6.44 (d, J ¼ 15.9 Hz, 1H, H-2), 7.37e7.55 (m, 5H, Ar-H), 7.68 (d,
J ¼ 15.9 Hz, 1H, H-3); 13C NMR (75 MHz, CDCl3)
d
: 14.1 (C-180), 22.7
(C-170), 25.9 (C-30), 28.7 (C-20), 29.3 (C-40), 29.6 (C-150), 29.7 (C-50-
140), 31.9 (C-160), 64.7 (C-10),118.3 (C-2),128.0 (C-5, 9),128.8 (C-6, 8),