M. Schlitzer et al. / Bioorg. Med. Chem. 10 (2002) 615–620
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127.3, 128.3, 129.3, 129.6, 130.0, 131.2, 132.0, 132.6,
133.2, 136.9, 138.0, 157.3, 171.2, 171.5, 198.8. MS (EI):
m/z 516 (21), 441 (27). Anal. calcd for C31H35N3O5: C,
70.30; H, 6.66; N, 7.93; found: C, 70.69; H, 6.99; N,
7.86.
128.2, 129.3, 129.6, 130.0, 131.3, 132.6, 132.9, 136.2,
136.9, 138.1, 168.9, 170.1, 174.8, 198.7. MS (EI): m/z
666 (100, M+), 535 (32), 327 (38), 266 (39). Anal. calcd
for C42H58N3O4: C, 75.41; H, 8.74; N, 6.28; found: C,
75.18; H, 8.57; N, 6.45.
N-[4-[3-Benzoyl-4-[(4-methylphenyl)acetylamino]phenyla-
mino]-4-oxobutyl]pentadecanoic acid amide (5). From N-
[2-[3-Benzoyl-4-[(4-methylphenyl)acetylamino]phenyl]-
Ng-tert-butyloxycarbonyl-g-aminobutyric acid amide
(12b) (1.06 g, 2.0 mmol) and pentadecanoic acid (0.484
g, 2.0 mmol) as described for 4. Purification: column
chromatography ethyꢁl acetate/n-hexane 3:2. Yield:
0.560 g (43%); mp115 C. IR (KBr): n 3297, 2922, 2852,
1645, 1549 cmꢀ1. 1H NMR (CDCl3): d 0.81 (t, J=7 Hz,
3H), 1.20 (m, 22H), 1.50 (m, 2H), 1.75 (m, 2H), 2.07 (t,
J=8 Hz, 2H), 2.21 (m, 2H)), 2.26 (s, 3H), 3.24 (m, 2H),
3.60 (s, 2H), 5.80 (m, 1H), 7.10 (m, 2H), 7.16 (m, 2H),
7.40 (m, 2H), 7.49 (m, 1H), 7.55 (m, 1H), 7.65 (m, 2H),
7.96 (m, 1H), 8.43 (m, 1H), 9.20 (s, 1H), 10.47 (s, 1H).
13C NMR (CDCl3): d 14.1, 21.1, 22.7, 25.8, 26.6, 29.27,
29.3, 29.34, 29.5 29.6, 29.7, 31.9, 34.6, 36.8, 38.5, 45.0,
122.3, 124.1, 124.4, 125.2, 128.3, 129.3, 129.6, 130.1,
132.6, 133.1, 136.0, 137.0, 138.1, 170.1, 171.1, 174.7,
198.8. MS (EI): m/z 653 (18, M+), 346 (15), 311 (20),
212 (21), 140 (64), 127 (100). Anal. calcd for
C41H55N3O4: C, 75.31; H, 8.48; N, 6.43; found: C,
75.54; H, 8.06; N, 6.62.
N-[3-[3-Benzoyl-4-[(4-methylphenyl)acetylamino]phenyla-
mino]-3-oxopropyl]octadecanoic acid amide (8). From N-
stearoyl-b-alanine (0.355 g, 1.0 mmol) and N-(4-amino-
2-benzoylphenyl)-(4-methylphenyl)acetamide
(11a)
(0.344 g, 1.0 mmol) according to general procedure.
Purification: column chromatography ethyl acetate/n-
ꢁ
hexane 3:2. Yield: 0.435 g (64%); mp95 C. IR (KBr): n
3300, 3057, 2920, 2851, 1649, 1542 cmꢀ1
.
1H NMR
(CDCl3): d 0.80 (t, J=7 Hz, 3H), 1.17 (m, 28H), 1.41
(m, 2H), 1.99 (t, J=7 Hz, 2H), 2.25 (s, 3H), 2.43 (m,
2H), 3.40 (m, 2H), 3.58 (s, 2H), 6.28 (m, 1H), 7.08 (m,
2H), 7.14 (m, 2H), 7.37 (m, 2H), 7.46 (m, 1H), 7.51 (m,
1H), 7.60 (m, 2H), 7.78 (m, 1H), 8.36 (m, 1H), 8.92 (s,
2H), 10.38 (s, 1H). 13C NMR (CDCl3): d 14.1, 21.1,
22.7, 25.7, 29.1, 29.2, 29.3, 29.4, 29.5, 29.6, 29.7, 31.9,
35.2, 35.4., 36.4, 36.6, 44.9, 117.3, 117.4, 122.4, 124.2,
124.3, 125.2, 126.2, 126.3, 128.1, 128.2, 128.3 129.1,
129.2, 129.6, 130.0, 131.1, 131.3, 132.6, 132.9, 136.0,
137.0, 138.0, 170.2, 173.9, 174.0, 198.4. MS (EI): m/z
681 (53, M+), 549 (73), 344 (31), 212 (100). Anal. calcd
for C43H59N3O4: C, 75.73; H, 8.72; N, 6.16; found: C,
75.68; H, 8.70; N, 6.55.
N-[3-Benzoyl-4-[(4-methylphenyl)acetylamino]phenyl]ara-
chidic acid amide (6). From arachinic acid (0.312 g, 1.0
mmol) and N-(4-amino-2-benzoylphenyl)-(4-methylphe-
nyl)acetamide (11a) (0.344 g, 1.0 mmol) according to
general procedure. Purification: column chromato-
graphy ethyl acetate/n-hexane 2:3. Yield: 0.476 g (74%);
mp102 ꢁC. IR (KBr): n 3444, 2920, 2851, 1685, 1657
cmꢀ1. 1H NMR (CDCl3): d 0.81 (t, J=7 Hz, 3H), 1.16–
1.23 (m, 32H), 1.58 (m, 2H), 2.20 (t, J=8 Hz, 2H), 2.66
(s, 3H), 3.61 (s, 2H), 7.09 (m, 2H), 7.16 (m, 3H), 7.41
(m, 3H), 7.52 (m, 1H), 7.63 (m, 2H), 7.79 (m, 1H), 8.44
(m, 1H), 10.43 (s, 1H). 13C NMR (CDCl3): d 14.1, 21.1,
22.7, 25.5, 29.2, 29.3, 29.4, 29.5, 29.6, 29.65, 29.7, 31.9,
37.6, 45.0, 122.4, 124.3, 125.1, 128.3, 129.3, 129.6, 130.0,
131.1, 132.7, 136.2, 137.0, 138.0, 171.4, 174.0, 198.6. MS
(EI): m/z 638 (100, M+), 533 (39), 506 (68), 212 (31).
Anal. calcd for C42H59N2O3: C, 78.95; H, 9.15; N, 4.38;
found: C, 78.62; H, 8.78; N, 4.73.
N-[3-[3-Benzoyl-4-(phenylacetylamino)phenylamino]-3-
oxopropyl]hexadecanoic acid amide (9). From N-palmi-
toyl-b-alanine (0.490 g, 1.5 mmol) and N-(4-amino-2-
benzoylphenyl)phenylacetamide (11b) (0.495 g, 1.5
mmol) according to general procedure. Purification:
column chromatography: (1) ethyl acetate/n-hexane 2:3,
(2) ethyl acetate. Yield: 0.85 g (88%); mp117 ꢁC. IR
1
(KBr): n 3310, 2920, 2850, 1640, 1550 cmꢀ1. H NMR
(CDCl3): d 0.81 (t, J=7 Hz, 3H), 1.17 (m, 24H), 1.45
(m, 2H), 2.02 (t, J=7 Hz, 2H), 2.46 (m, 2H), 3.44 (m,
2H), 3.65 (s, 2H), 6.12 (m, 1H), 7.23 (m, 1H), 7.29 (m,
3H), 7.39 (m, 2H), 7.48–7.57 (m, 2H), 7.62 (m, 2H), 7.77
(m, 1H), 8.43 (m, 2H), 10.45 (s, 1H). 13C NMR
(CDCl3): d 14.1, 22.7, 25.6, 29.2, 29.3, 29.4, 29.5, 29.6,
29.62, 29.7, 31.9, 35.2, 36.7, 36.9, 45.4, 122.4, 124.2,
124.3, 125.3, 127.4, 128.3, 128.9, 129.4, 130.0, 132.6,
132.7, 134.2, 136.2, 138.0, 169.7, 170.0, 174.0, 198.6. MS
(EI): m/z 639 (100, M+), 330 (69), 312 (67), 212 (73).
Anal. calcd for C40H53N3O4: C, 75.08; H, 8.35; N, 6.57;
found: C, 74.77; H, 8.38; N, 6.89.
N-[3-[3-Benzoyl-4-[(4-methylphenyl)acetylamino]phenyla-
mino]-3-oxopropyl]-N-methylhexadecanoic acid amide
(7). From N-methyl-N-palmitoyl-b-alanine (0.341 g, 1.0
mmol) and N-(4-amino-2-benzoylphenyl)-(4-methylphe-
nyl)acetamide (11a) (0.344 g, 1.0 mmol) according to
general procedure. Purification: column chromato-
graphy ethyl acetate/n-hexane 3:2. Yield: 0.386 g (58%);
oil. 1H NMR (CDCl3): d 0.81 (t, J=7 Hz, 3H), 1.19 (m,
24H), 1.44 (m, 2H), 2.19 (t, J=8 Hz, 2H), 2.27 (s, 3H),
2.56 (m, 2H), 2.94 (s, 3H), 3.59 (m, 2H), 3.61 (s, 2H),
7.09 (m, 2H), 7.17 (m, 2H), 7.40 (m, 2H), 7.50 (m, 1H),
7.58 (m, 1H), 7.64 (m, 2H), 7.88 (m, 1H), 8.44 (m, 1H),
9.34 (s, 1H), 10.49 (s, 1H). 13C NMR (CDCl3): d 14.1,
21.1, 22.7, 24.9, 29.3, 29.4, 29.5, 29.6, 29.64, 29.7, 31.9,
33.5, 35.9, 36.2, 44.1, 45.1, 122.2, 124.0, 124.5, 125.4,
N-[3-[3-Benzoyl-4-(1-naphthoylamino)phenylamino]-3-ox-
opropyl]hexadecanoic acid amide (10). From N-palmi-
toyl-b-alanine (0.327 g, 1.0 mmol) and N-(4-amino-2-
benzoylphenyl)naphthaline1-carbonic acid amide (11c)
(0.36 g, 1.0 mmol) according to general procedure. Pur-
ification: column chromatography ethyl acetate/n-hex-
ane 3:2. Yield: 0.350 g (52%); mp52 ꢁC. IR (KBr): n
3411, 2925, 2853, 1645, 1550 cmꢀ1. 1H NMR (CDCl3): d
0.80 (t, J=7 Hz, 3H), 1.16 (m, 24H), 1.53 (m, 2H), 2.08
(t, J=8 Hz, 2H), 2.54 (m, 2H), 3.51 (m, 2H), 6.08 (m,
1H), 7.42 - 7.55 (m, 6H), 7.68 (m, 3H), 7.80 (m, 2H),
8.20 (s, 1H), 8.48 (m, 2H), 8.82 (m, 1H), 11.19 (s, 1H).
13C NMR (CDCl3): d 14.2, 22.8, 25.8, 29.3, 29.41, 29.43,