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7.1.9.2. 2(R,S)-{2-[(1H-Benzoimidazole-2-carbonyl)-ami-
no]-benzoylamino}-3-phenyl-propionic acid (2). The col-
lected precipitate was analytically pure. TLC (AcOEt/MeOH
13H, Ar); 9.11 (d, 1H, –NH–CH<); 11.39 (s, 1H, –NH–);
13C-NMR (DMSO-d6) d 11.85, 36.05, 37.46, 53.87, 119.91,
120.00, 120.66, 122.21, 123.78, 126.10, 126.58, 127.25,
127.89, 128.00, 128.87, 131.96, 132.48, 137.80, 138.95,
141.76, 144.95, 148.30, 163.12, 168.47, 172.50. MS (ES)
m/z 441 [MH]+; MW: 440 (calcd. for C27H24N2O4).
1
2:1)—Rf: 0.62; m.p. 271–272 °C; H-NMR (DMSO-d6) d
3.10 (m, 2H, –CH2–); 4.73 (m, 1H, –CH<); 7.07–8.65 (m,
13H, Ar); 9.02 (d, 1H, –NH–CH<); 12.56 (s, 1H, –NH–);
13.46 (s, 1H, –NH); 13C-NMR (DMSO-d6) d 36.98, 54.73,
113.35, 121.26,123.58, 124.00, 125.26, 127.06, 128.87,
129.15, 129.73, 133.06, 135.54, 138.65, 138.81, 143.16,
145.99, 157.82, 168.55, 173.51. MS (ES) m/z 429 [MH]+;
MW: 428 (calcd. for C24H20N4O4).
7.1.9.7.
2(R,S)-{2-[(2-Acetylamino-cinnamoyl)-amino]-
benzoylamino}-3-phenyl-propionic acid (7). Purification
method: crystallization from AcOEt/Hexane; TLC
(AcOEt/MeOH 2:1)—Rf: 0.43; m.p. 126–127 °C; 1H-NMR
(DMSO-d6) d 2.04 (s, 3H, –CH3); 3.13 (m, 2H, –CH2–CH<);
4.59 (m, 1H, –CH<); 7.08–8.65 (m, 15H,Ar and –CH=); 9.02
(d, 1H, –NH–CH<); 9.83 (s, 1H, –NH–); 12.06 (s, 1H,
–NH–); 13C-NMR (DMSO-d6) d 23.47, 36.84, 54.90,
119.99, 120.28, 123.14, 127.11, 128.94, 129.04, 129.32,
129.65, 129.80, 130.34, 130.61, 130.91, 133.18, 134.37,
138.68, 140.14, 163.92, 169.02, 170.85, 173.31. MS (ES)
m/z 472 [MH]+; MW: 471 (calcd. for C27H25N3O5).
7.1.9.3. 2(R,S)-{2-[(Benzofuran-2-carbonyl)-amino]-ben-
zoylamino}-3-phenyl-propionic acid (3). Trituration with
hot MeOH afforded the titled compound in 52% yield. TLC
(AcOEt/MeOH 3:1)—Rf: 0.25; m.p. 256–257 °C; 1H-NMR
(DMSO-d6) d 3.30 m, 2H, –CH2–CH<); 4.78 (m, 1H, –CH<);
7.03–8.58 (m, 14H, Ar); 9.16 (d, 1H, –NH–CH<); 12.24 (s,
1H, –NH–); 13C-NMR (DMSO-d6) d 36.09, 53.80, 110.88,
111.85, 120.12, 120.32, 122.82, 123.08, 123.81, 126.13,
126.96, 127.29, 127.91, 128.17, 128.85, 132.22, 137.72,
138.08, 148.32, 154.25, 155.87, 168.13, 172.51. MS (ES)
m/z 429 [MH]+; MW: 428 (calcd. for C25H20N2O5).
7.1.9.8.
2(R,S)-{2-[(2-Nitrocinnamoyl)-amino]-benzoyl-
amino}-3-phenyl-propionic acid (8). Purification method:
crystallization from AcOEt/Hexane; TLC (AcOEt/MeOH
1
2:1)—Rf: 0.47; m.p. 196–198 °C; H-NMR (DMSO-d6) d
3.20 (m, 2H, –CH2–CH<); 4.69 (m, 1H, –CH<); 6.85 (d,
1H, =CH–CO– J= 15 Hz); 7.14–8.51 (m, 14H, Ar and =CH–
C6H5); 9.06 (d, 1H, –NH–CH<); 11.19 (s, 1H, –NH–); 13.00
(b, 1H, –OH); 13C-NMR (DMSO-d6) d 36.92, 54.87, 121.62,
122.00, 123.86, 125.35, 127.10, 127.67, 128.88, 129.74,
129.89, 130.18, 131.30, 132.68, 134.47, 136.54, 138.66,
139.00, 149.06, 163.32, 168.75, 173.54. MS (ES) m/z 460
[MH]+; MW: 459 (calcd. for C25H21N3O6).
7.1.9.4. 2(R,S)-{2-[(Benzo[b]thiophene-2-carbonyl)-ami-
no]-benzoylamino}-3-phenyl-propionic acid (4). Crystalli-
zation from MeOH afforded the titled compound in 63%
yield. TLC (AcOEt/MeOH 3:1)—Rf: 0.33; m.p. 207–
209 °C; 1H-NMR (DMSO-d6) d 3.28 (m, 2H, –CH2–CH<);
4.80 (m, 1H, –CH<); 7.09–8.51 (m, 14H, Ar); 9.21 (d, 1H,
–NH–CH<); 12.31(s, 1H, –NH–); 13C-NMR (DMSO-d6) d
36.01, 53.91, 119.65, 120.13, 122.77, 122.94, 125.03,
125.08, 125.45, 126.20, 126.60, 127.96, 128.19, 128.87,
132.38, 137.73, 138.51, 138.70, 139.32, 140.33, 159.41,
168.43, 172.46. MS (ES) m/z 445 [MH]+; MW: 444 (calcd.
for C25H20N2O4S).
7.1.9.9.
3-Phenyl-2(R,S)-[2-(cinnamoylamino)-benzoyl-
amino]-propionic acid (9). Purification method: crystalliza-
tion from MeOH; TLC (AcOEt/MeOH 3:1)—Rf: 0.29; m.p.
1
209–211 °C; H-NMR (DMSO-d6) d 3.23 (m, 2H, –CH2–
CH<); 4.70 (m, 1H, –CH<); 6.79 (d, 1H, =CH–CO–
J = 15 Hz); 7.15–8.55 (m, 14H, Ar and =CH–C6H5); 9.07 (d,
1H, –NH–CH<); 11.11 (s, 1H, –NH–); 13C-NMR (DMSO-
d6) d 36.00, 53.91, 120.57, 120.79, 122.17, 122.61, 126.22,
127.98, 128.70, 128.86, 129.77, 131.78, 134.23, 137.76,
138.49, 140.89, 163.29, 168.05, 172.70. MS (ES) m/z 415
[MH]+; MW: 414 (calcd. for C25H22N2O4).
7.1.9.5. 2(R,S)-{2-[(1H-Indene-2-carbonyl)-amino]-ben-
zoylamino}-3-phenyl-propionic acid (5). The collected pre-
cipitate was analytically pure. TLC (AcOEt/MeOH
1
2:1)—Rf: 0.59; m.p. 209–210 °C; H-NMR (DMSO-d6) d
3.07 (m, 2H, –CH2–CH<); 3.69 (s, 2H, –CH2– ind); 4.72 (m,
1H, –CH<); 7.04–8.60 (m, 14H, Ar and –CH=); 9.07 (d, 1H,
–NH–CH<); 11.79 (s, 1H, –NH–); 13C-NMR (DMSO-d6) d
37.07, 38.40, 55.01, 120.42, 120.65, 123.24, 123.88, 125.03,
126.99, 127.59, 127.86, 128.79, 128.93, 129.80, 133.04,
137.18, 138.81, 139.84, 142.55, 143.26, 144.59, 162.58,
169.22, 173.36. MS (ES) m/z 427 [MH]+; MW: 426 (calcd.
for C26H22N2O4).
7.1.9.10. 3-Phenyl-2(R,S)-{2-[(quinoline-2-carbonyl)-ami-
no]-benzoylamino}-propionic acid (10). Purification
method: crystallization from EtOH 95%; TLC
(AcOEt/MeOH 2:1)—Rf: 0.41; m.p. 206–207 °C; 1H-NMR
(DMSO-d6) d 3.22 (m, 2H, –CH2–CH<); 4.79 (m, 1H,
–CH<); 6.98–8.74 (m, 15H, Ar); 9.03 (d, 1H, –NH–CH<);
12.84 (s, 1H, –NH–); 12.95 (b, 1H, –OH); 13C-NMR
(DMSO-d6) d 36.96, 54.69, 119.24, 120.84, 122.59, 123.73,
126.97, 128.77, 129.10, 129.22, 129.70, 130.16, 131.47,
132.71, 138.66, 138.70, 138.99, 146.45, 150.24, 163.19,
168.65, 173.56. MS (ES) m/z 440 [MH]+; MW: 439 (calcd.
for C26H21N3O4).
7.1.9.6. 2(R,S)-{2-[(3-Methyl-1H-indene-2-carbonyl)-ami-
no]-benzoylamino}-3-phenyl-propionic acid (6). Trituration
with Et2O afforded the titled compound in 58% yield. TLC
(AcOEt/MeOH 2:1)—Rf: 0.50; m.p. 127–129 °C; 1H-NMR
(DMSO-d6) d 2.53 (s, 3H, –CH3); 3.23 (m, 2H, –CH2–CH<);
3.62 (s, 2H, –CH2– ind); 4.71 (m, 1H, –CH<); 7.06–8.59 (m,