6
47
(
EI): m/z (%) = 198 (55), 131 (41), 103 (40). Anal.
H), 7.7 (d, 1H, NH), 11.1 (s, 1H, COOH); MS (EI): m/z
(%) = 289 (37), 145 (100), 117 (79). Anal. C H NO S
C H N O (C, H, N).
17
20
2
4
18 17
3
2: 2-[2-(3-Phenyl-2-propenoylamino)propanoylamino]-
(C, H, N, S).
3
-phenylpropionic acid: yield 58%. M.p. 190–191 °C. IR
8: 2-(3-Carboxy-2-propenoylamino)-3-phenylpropionic
acid: yield 72%. M.p. 179–181 °C. IR (KBr): ν =
–
1
(KBr): ν = 3 400 cm (CONH), 3 600–2 600 (COOH),
–1
1
1 760 (CO), 1 670 (CO), 1 600, 1 560; H-NMR (DMSO-
d ): δ = 1.2 (d, 3H, NCHCH ,), 2.8–3.2 (m, 2H, f-CH ),
3 500–2 500 cm (COOH), 1 740 (CO), 1 680 (CO), 1 650
1
(CH=CH); H-NMR (DMSO-d ): δ = 2.7–3.2 (m, 2H,
6
3
2
6
4
.5 (m, 2H, NHCHCO), 6.8 (d, 1H, f-CH=CH), 7.2–7.6
f-CH ), 4.5 (m, 1H, NHCHCOOH), 6.4 (d, 1H,
HOOC–CH=CH), 6.9 (d, 1H, HOOC–CH=CH), 7.2 (s,
2
(m, 11H, f, f-CH=CH), 8.2 (t, 2H, NH), 12.7 (s, 1H,
+
COOH); MS (FAB): m/z (%) = 367 (23) [(M + H) ].
Anal. C H N O (C, H, N).
5H, aromatic H), 8.9 (d, 1H, NH); MS (ESI): m/z (%) =
–
262 (100) [(M – H) ]. Anal. C H NO (C, H, N).
21
22
2
4
13 13
5
3
: N-[2-(3-Phenyl-2-propenoylamino)propanoyl]indo-
9:
2-(3-Carboxy-2-methyl-2-propenoylamino)-3-
1
line-2-carboxylic acid: yield 86%. H-NMR (DMSO-d ):
δ = 1.8 (d, 3H, CH ), 3.0 (d, 1H,), 3.4 (m, 1H,), 3.7 (t, 1H,
CO–CH-), 4.8 (q, 1H, CH –CH-), 6.5 (d, 1H, -CH=CH-),
phenylpropionic acid: yield 72%. M.p. 200–201.5 °C. IR
(KBr): ν = 3 500–2 500 cm (COOH), 1 730 (CO),
1 670 (CO), 1 450, 1 300; H-NMR (CDCl ): δ = 2.1 (s,
6
–
1
3
1
3
3
7
(
.8–6.9 (m, 9H, aromatic H), 7.9 (d, 1H, CH=CH); MS
EI): m/z (%) = 147 (100), 103 (42), 77 (28). Anal.
C H N O (C, H, N).
3H, CH ), 2.9–3.2 (m, H, f-CH ), 4.5 (m, 1H, NHCH-
3
2
COOH), 6.13 (s, 1H, CH=C), 7.3 (s, 5H, aromatic H), 8.6
(d, 1H, NH), 12.9 (s, 2H, COOH); MS (EI): m/z (%) =
218 (12), 213 (28), 185 (13). Anal. C H NO (C, H, N).
21 20 2 4
4:
2-[2-(2-Butenoylamino)propanoylamino]-3-phenyl-
1
4
15
5
propionic acid: yield 54%. M.p. 157–159 °C. IR (NaCl
10:
N-(3-Phenyl-2-propenoyl)indoline-2-carboxylic
–
1
cell): ν = 3 300 cm (CONH), 3 500–2 500 (COOH),
720 (CO), 1 670 (CO), 1 640 (CH=CH), 970 (CH=CH);
acid: yield 90%. M.p. 223–225 °C. IR (KBr): ν =
3 300–2 700 cm (COOH), 1 750 (CO), 1 650 (CO),
1 630 (CH=CH); H-NMR (DMSO-d ): δ = 3.3–3.6 (q,
–
1
1
1
1
H-NMR (DMSO-d ): δ = 1.2 (d, 3H, NCHCH ,), 1.8 (d,
6
3
6
3
H, CH –CH=CH), 2.9–3.2 (m, 2H, f-CH ), 4.4 (t, 2H,
2H, NCHCH ), 5.5 (d, 1H, NCHCOOH), 6.9–7.4 (m, 7H,
3
2
2
NHCHCO), 6.0 (d, 1H, CH –CH=CH), 6.6 (q, 1H,
CH –CH=CH), 7.2 (s, 5H, aromatic H), 8.0 (q, 1H, NH),
f-CH=CH), 7.5–7.8 (m, 3H, aromatic H), 8.2 (d, 1H,
3
–
aromatic H); MS (ESI): m/z (%) = 292 (100) [(M – H) ].
3
1
9
2.6 (s, 1H, COOH); MS (EI): m/z (%) = 139 (6), 111 (2),
5 (6), 69 (28). Anal. C H N O (C, H, N).
Anal. C H NO (C, H, N).
1
8
15
3
11: N-(3-Carboxy-2-propenoyl)indoline-2-carboxylic
acid: yield 99%. M.p. 194–197 °C. IR (KBr): ν =
16 20 2 4
5:
2-(3-Phenyl-2-propenoylamino)-3-phenylpropionic
–
1
acid: yield 82%. M.p. 158–160 °C. IR (KBr): ν =
3 500–2 500 cm (COOH), 1 740 (CO), 1 690 (CO);
–
1
1
3
1
300 cm (CONH), 3 400–2 500 (COOH), 1 720 (CO),
H-NMR (DMSO-d ): δ = 3.2–3.6 (m, 2H, NCHCH ),
6
2
1
660 (CO), 1 630 (CH=CH), 980 (CH=CH); H-NMR
5.4 (dd, 1H, NCHCOOH), 6.7 (d, 1H, HOOC–
CH=CH–CO), 7.1–7.3 (m, 4H, f, HOOC–CH=CH–CO),
8.1 (d, 1H, aromatic H); MS (ESI): m/z (%) = 260 (100)
(DMSO-d ): δ = 2.8–3.4 (m, 2H, f-CH ), 4.5–4.7 (q, 1H,
6 2
NHCHCOOH), 6.6 (d, 1H, f-CH=CH), 7.1–7.6 (m, 11H,
f, f-CH=CH), 8.4 (d, 1H, NH), 12.6 (s, 1H, COOH); MS
–
[(M – H) ]. Anal. C H NO (C, H, N).
1
3
11
5
–
(
ESI): m/z (%) = 294 (100) [(M – H) ]. Anal. C H NO
12: N-(3-Carboxy-2-methyl-2-propenoyl)indoline-2-
carboxylic acid: yield 72%. M.p. 88–90 °C. IR (KBr): ν
18
17
3
(
C, H, N).
: 2-(2-Methyl-3-phenyl-2-propenoylamino)-3-phenyl-
propionic acid: yield 90%. M.p. 140–143.5 °C. IR (NaCl
–
1
6
= 3 500–2 500 cm (COOH), 1 720 (CO), 1 650, 1 410;
1
H-NMR (DMSO-d ): δ = 2.13 (s, 3H, CH ) 3.1–3.6 (m,
6
3
–
1
cell): ν = 3 400 cm (CONH), 3 500–2 500 (COOH),
1H, NCHCH ), 5.1 (dd, 1H, NCHCOOH), 5.95 (s, 1H,
2
1
1
750 (CO), 1 670 (CO), 1 630 (CH=CH); H-NMR
C=CH), 7.0–7.3, 8.0 (m, 4H, aromatic H), 12.9 (s, 2H,
COOH); MS (EI): m/z (%) = 117 (100), 90 (40). Anal.
C H NO (C, H, N).
(CDCl ); δ 2.0 (s, 3H, CH ), 3.2 (t, 2H, f-CH ), 4.9 (q,
3
3
2
1
H, NHCHC), 6.4 (d, 1H, f-CH=C), 7.0–7.5 (d, 10H,
1
4
13
5
aromatic H), 8.0 (s, 2H, NH, COOH); MS (EI): m/z (%)
=
289 (28), 145 (100), 117 (85). Anal. C H NO (C, H,
3.2. Biology
19
19
3
N).
7
: 2-(3-Phenylthio-2-propenoylamino)-3-phenylpropionic
3.2.1. Inhibition assay
–1
acid: yield 98%. IR (NaCl cell): ν = 3 330 cm (CONH),
500–2 500 (COOH), 1 750 (CO), 1 660 (CO), 1 600
CH=CH); H-NMR (CDCl ): δ = 2.9–3.1 (d, 2H, f-CH ),
.9 (t, 1H, NHCHCOOH), 5.6–5.8 (dd, 1H, f-S–CH=CH),
.3–6.5 (dd, 1H, f-S–CH=CH), 7.0–7.5 (s, 10H, aromatic
Incubation mixtures contained 40 µg rabbit liver
homogenate, 0.3 M sodium chloride, 1 mM hippuryl–
histidyl–leucine (HHL) and 0.1 M potassium phosphate
buffer (pH 8.4) in a total volume of 0.2 mL. Inhibitors
dissolved in methanol were added at various concentra-
3
(
4
6
1
3 2