390
S. A. Manohara Reddy et al. / Bioorg. Med. Chem. 19 (2011) 384–392
736 and 675 cmꢀ1
.
1H NMR (400 MHz, CDCl3), d: 0.90 (t, 3H, CH3),
4.1.21. 8-(7-Nitro-3-octylquinoxalin-2-yl)octanoic acid (3c)
Pale brown solid. Yield: 52%. Rf 0.77 (ethyl acetate/methanol;
20:80). Mp 55–57 °C; IR (KBr): 3400–2500 (b, –OH of –COOH),
3093 (–CH–, aromatic), 2922 (–CH2–, asymmetric), 2854 (–CH2–,
symmetric), 1726 (s, –C@O of –COOH), 1618 (–C@N), 1575 and
1462 (–NO2), 1340, 1166, 1076 (–C–N), 1006, 954, 839, 731 and
661 cmꢀ1. MS-EI: for C24H35N3O4, calcd 429.26, found 429 m/z (M)+.
1.20–1.37 (m, 18H, (CH2)n), 1.45–1.65 (m, 6H, (CH2)n), 2.35 (m, 2H,
CH2COOH), 7.60 (s, 1H, COOH) ppm. 13C NMR (100 MHz, DMSO-d6),
d: 13.83 (CH3), 22.01, 23.85, 24.40, 25.87, 28.43, 31.12, 33.61,
38.96, 39.16, 39.37, 39.58, 39.78, 39.99, 122.89, 136.22 (C-9,
C-10), 148.93 (C@O), 174.47 (COOH) ppm. MS-CI: for C19H32N2O3,
calcd 336.47, found 337 m/z (M+1) +; MS-EI: 337.30 m/z (M+1)+.
4.1.15. 8-(5-Octyl-2-oxo-2H-imidazol-4-yl)octanehydrazide (2a)
Colourless solid (needles). Yield: 40%. Rf 0.78 (chloroform/meth-
anol; 80:20). Mp 112–116 °C. IR (KBr); 3317 (–NH), 3178, 3041
(–CH–, aromatic), 2918 (–CH2–, asymmetric), 2848 (–CH2–,
symmetric), 1629 (s, –C@O of –CONH–), 1533, 1464 (–C@N),
4.1.22. 8-(3-Octylquinoxalin-2-yl)octanehydrazide (3d)
Pale yellow solid (needles). Yield: 20%. Rf 0.79 (chloroform/ethyl
acetate/methanol; 80:06:14). Mp 113–115 °C. IR (KBr): 3317
(–NH), 3041 (–CH–, aromatic), 2920 (–CH2–, asymmetric), 2850
(–CH2–, symmetric), 1735 (s, –C@O of –CONHNH2), 1602 (–C@N),
1089 (–C–N), 949, 771, 725 and 617 cmꢀ1
.
MS-EI: for
1533, 1465, 1377, 1014 (–C–N), 950, 760, 723 and 617 cmꢀ1
.
C
19H34N4O2, calcd 350.27, found 348 m/z (Mꢀ2)+.
MS-EI: for C24H38N4O, calcd 398.30, found 397 m/z (Mꢀ1)+.
4.1.16. 2-(Nitrooxy)ethyl 8-(5-octyl-2-oxo-2H-imidazol-4-
yl)octanoate (2b)
4.1.23. 8-(4-Octyl-1,2,5-oxadiazol-3-yl)octanoic acid (4)
Colourless solid. Yield: 44%. Rf 0.40 (ethyl acetate/methanol;
12:88). Mp 120–125 °C. IR (KBr): 3400–2500 (b, –OH of –COOH),
2926 (–CH2–, asymmetric), 2852 (–CH2–, symmetric), 1720 (s, –C
@O of –COOH), 1604, 1442 (–C@N), 1188, 1033 (–C–N), 918 (–N–
Pale brownish liquid. Yield: 47%. IR (neat); 3200, 2926 (–CH2–,
asymmetric), 2859 (–CH2–, symmetric), 1712 (s, –C@O of –
COOCH2CH2–), 1640 (–C@N), 1562 and 1455 (–ONO2, asymmetric
and symmetric), 1376, 1274, 1172, 1108 (–C–N), 900, 852, 759,
O) and 740 cmꢀ1 1H NMR (400 MHz, CDCl3), d: 0.89 (t, 3H, CH3),
.
724 and 629 cmꢀ1
.
1H NMR (400 MHz, CDCl3), d: 0.89 (t, 3H,
1.25–1.35 (m, 20H, (CH2)n), 1.60–1.65 (m, 4H, (CH2)n), 2.30 (m,
2H, CH2COOH), 2.50–2.60 (m, 4H, (CH2)n), 7.50 (s, 1H, COOH)
CH3), 1.20–1.40 (m, 16H, (CH2)n), 1.60–1.99 (m, 6H, (CH2)n), 2.35
(m, 2H, CH2COO–), 3.7–4.79 (m, 4H, COOCH2CH2–) ppm. MS-EI:
for C19H34N4O2, calcd 425.25, found 425 m/z (M)+.
ppm: MS-EI: for
C18H32N2O3, calcd 324.24, found 323 m/z
(M ꢀ 1)+. MS-CI: 323 m/z (Mꢀ1)+.
4.1.17. N-(2-4-Chlorophenyl)-4-oxothiazolidin-3-yl-8-(5-octyl-
2-oxo-2H-imidazol-4-yl)-octanamide (2c)
4.1.24. 8-(5-Octyl-3-thioxo-2,3-dihydro-1,2,4-triazin-6-yl)
octanoic acid (5)
Colourless solid. Yield: 10%. Rf 0.65 (ethyl acetate/methanol;
20:80). Mp 139–142 °C. IR (KBr); 3394 (–NH), 3090 (–CH–, aro-
matic), 2918 (–CH2–, asymmetric), 2850 (–CH2–, symmetric),
1690 and 1651 (s, –C@O of –CONH– and –CO–CH2–S–), 1590,
1465 (–C@N–), 1309, 1274, 1087 (–C–N–), 970, 842, 736, 675
Yellow solid. Yield: 56%. Rf 0.77 (ethyl acetate/methanol; 20:80).
Mp 131–136 °C; IR (KBr): 3400–2500 (b, –OH of –COOH), 2928
(–CH2–, asymmetric), 2856 (–CH2–, symmetric), 1739 (s, –C@O of
–COOH), 1680, 1577 (–C@N), 1444, 1383, 1255 (–C@S), 1184, 1091
(–C–N), 985, 767, 725, 651 and 597 cmꢀ1. 1H NMR (400 MHz, CDCl3),
d: 0.90 (t, 3H, CH3), 1.30–1.45 (m, 16H, (CH2)n), 1.65 (m, 4H, (CH2)n),
2.05 (m, 2H, CH2COOH), 2.15–2.35 (m, 4H, (CH2)n), 7.8 (br s, 1H, NH),
9.05 (s, 1H, COOH) ppm. MS-EI: for C19H33N3O2S, calcd 367.23, found
365 m/z (Mꢀ2)+.
and 582 cmꢀ1 1H NMR (400 MHz, CDCl3), d: 3.73–3.90 (d, 2H, S–
.
CH2–CO), 6.1 (s, 1H, CH), 7.25–7.55 (m, 4H, aromatic), 8.58 (br s,
1H, NH) ppm. MS-EI: for C28H39ClN4O3S, calcd 546.24, found
547 m/z (M+1)+.
4.1.18. 8-(3-Octylquinoxalin-2-yl)octanoic acid (3)
4.1.25. 8-(3-Octyl-5,7-dioxo-6,7-dihydro-5H-1,4-diazepine-2-
yl)octanoic acid (6)
Pale yellowish brown solid. Yield: 45%. Rf 0.43 (ethyl acetate/
methanol; 12:88). Mp 58–60 °C. IR (KBr): 3400–2500 (b, –OH of
–COOH), 3061 (–CH–, aromatic), 2926 (–CH2–, asymmetric), 2852
(–CH2–, symmetric), 1730 (s, –C@O of –COOH), 1566 (–C @N),
Pale yellow solid. Yield: 60%. Rf 0.77 (ethyl acetate/methanol;
40:60). Mp 128–133 °C. IR (KBr); 3400–2500 (b, –OH of –COOH),
3365, 3175, 2924 (–CH2–, asymmetric), 2852 (–CH2–, symmetric),
1712 (s, –C@O of –COOH), 1650, 1591 (–C@N), 1460, 1406, 1260,
1103 (–C–N), 962, 858, 765 and 657 cmꢀ1 1H NMR (400 MHz,
.
CDCl3), d: 0.90 (t, 3H, CH3), 1.26–1.48 (m, 16H, (CH2)n), 1.60–1.70
(m, 4H, (CH2)n), 1.86 (m, 2H, CH2), 2.35 (m, 2H, CH2COOH), 3.0
(m, 4H, (CH2)2), 7.63–7.80 (m, 4H, aromatic), 8.0 (s, 1H, COOH)
ppm. MS-EI: for C24H36N2O2, calcd 384.55, found 385.30 m/z
(M+1)+.
1132, 1091 (–C–N), 964, 763, 725, 688, 651 and 582 cmꢀ1 1H
.
NMR (400 MHz, CDCl3), d: 0.90 (t, 3H, CH3), 1.22–1.40 (m, 16H,
(CH2)n), 1.52–1.68 (m, 4H, (CH2)n), 2.35 (m, 2H, CH2COOH), 3.0
(d, 2H, CO–CH2–CO), 9.50 (s, 1H, COOH) ppm. MS-EI: for
C21H34N2O4, calcd 378.25, found 375 m/z (Mꢀ3)+.
4.1.19. 8-(7-Methyl-3-octylquinoxalin-2-yl)octanoic acid (3a)
Pale brown solid. Yield: 54%. Rf 0.28 (ethyl acetate/methanol;
20:80). Mp 60–62 °C. IR (KBr): 3400–2500 (b, –OH of –COOH),
3051 (–CH–, aromatic), 2922 (–CH2–, asymmetric), 2852 (–CH2–,
symmetric), 1718 (s, –C@O of –COOH), 1620 (–C@N), 1251
(–CH3), 1114 (–C–N), 1006, 887, 827, 723 and 657 cmꢀ1. MS-EI:
for C25H38N2O2, calcd 398.58, found 400 m/z (M+2)+.
4.1.26. Methyl 8-(5-(2-acetoxyoctyl)-2,2-dimethyl-1,3-dioxolan-
4-yl)octanoate (7)
Pale brownish liquid. Yield: 40%. IR (neat); 2926 (–CH2–,
asymmetric), 2857 (–CH2–, symmetric), 1732 (s, –C@O of –COOCH3
and –OCOCH3), 1457, 1373, 1241, 1172, 1092, 1030, 832, 726 and
642 cmꢀ1 1H NMR (400 MHz, CDCl3), d: 0.90 (t, 3H, CH3), 1.30–
.
1.50 (m, 16H, (CH2)n), 1.65 (m, 4H, (CH2)n), 1.90-2.10 (m, 2H,
CH2COO–), 2.35 (m, 2H, CH2), 3.35–4.00 (s, 3H, OCH3), 4.70–5.10
(d, 2H, methylenedioxy protons) ppm. MS-EI: for C22H40O6, calcd
400.28, found 400 m/z (M)+.
4.1.20. 8-(7-Chloro-3-octylquinoxalin-2-yl)octanoic acid (3b)
Pale brown solid. Yield: 40%. Rf 0.85 (ethyl acetate/methanol;
20:80). Mp 60–67 °C; IR (KBr): 3400–2500 (b, –OH of –COOH),
3057 (–CH–, aromatic), 2922 (–CH2–, asymmetric), 2852 (–CH2–,
symmetric), 1716 (s, –C@O of –COOH), 1602 (–C@N), 1564, 1471,
1309, 1172, 1082 (–C–N), 1010, 925, 831, 721 and 659 cmꢀ1. MS-
EI: for C24H35ClN2O2, calcd 418.24, found 416 m/z (Mꢀ2)+.
4.1.27. Acetonide of 9,10-dihydroxy-methyl-12-acetylricinoleic
acid (7a)
Pale orange liquid. Yield: 38%. IR (neat); 2930 (–CH2–, asym-
metric), 2857 (–CH2–, symmetric), 1738 (s, –C@O of –COOCH3