Med Chem Res
compounds of the series (1b–j) were obtained in similar
manner.
N, 13.58; found: C, 50.17; H, 4.59; N, 13.38. IR (KBr),
v (cm-1): 3431 (O–H), 3334 (N–H), 2991 (Ar–H), 2749
(C–H), 1682 (C=O), 1355 (S–H). 1H NMR (DMSO) d
(ppm): 11.23 (brs,1H,OH), 11.02(d,1H,NH) 7.34–7.32(m,
6H,Ar–H), 4.25(d,1H,NH), 3.70(m,1H,CH), 3.17(d,2H,
CH2). 13C NMR (CDCl3) d (ppm):136.2 (C2-imidazole),
131.3 (C4-imidazole), 117.2 (C5-imidazole), 27.5 (C6-
methanediyl), 56.4 (C7-methanetriyl), 174.4 (C11-car-
bonyl), 141.3 (C14–Ar), 128.3 (C15–Ar), 129.3(C16–Ar),
137.6 (C17–Ar), 21.2 (C21–methyl). MS (m/z): 309 (M?).
2(S)-{[(4-methylphenyl)sulfonyl]amino}-3-
sulfanylpropanoic acid (1a)
Brown solid.Yield: 75 %. Mp: 124–126 °C. Analysis for
C10H17NO4S2 (275.344); calculated: C, 43.62; H, 4.76; N,
5.09; found: C, 43.22; H, 4.36; N, 5.01. IR (KBr), v (cm-1):
3420 (O–H), 3350 (N–H), 2991 (Ar–H), 2754 (C–H), 1692
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1
(C=O),1367 (S–H). H NMR (DMSO) d (ppm): 7.16–7.73
½aꢁD : -46.
(m,4H,Ar–H), 3.67–3.67–3.86 (m,2H,CH2), 2.34 (s,3H,CH3).
13C NMR (CDCl3) d (ppm): 141 (C1–Ar), 128.2 (C2–Ar),
129.5 (C3–Ar), 139.3 (C6–Ar), 21.4 (C9-methyl), 58.9 (C12-
methanetriyl), 25.1 (C13-methanediyl), 177.2 (C15-carbonyl).
3-(4-Hydroxyphenyl)-2(S)-{[(4-methylphenyl)sulfonyl]
amino}propanoic acid (1e)
25
MS m/z (%): 276 (M?). ½aꢁD : -18.
Brown solid. Yield: 39 %: mp 130–132 °C. Analysis for
C16H17NO5S (335.374); calculated: C, 57.30; H, 5.11; N,
4.18; found: C, 57.27; H, 5.06; N, 4.12. IR (KBr), v (cm-1):
3426 (O–H), 3356 (N–H), 2981 (Ar–H), 2774 (C–H), 1692
(C=O), 1362 (S–H). 1H NMR (DMSO) d (ppm): 11.27
(brs,1H,OH), 7.34–7.30 (m,8H,Ar–H),5.7 (s,1H,OH), 4.22
(d,1H,NH), 3.80 (m,1H,CH), 2.78 (d,2H,CH2), 2.34
(s,3H,CH3). 13C NMR (CDCl3) d (ppm): 141.2 (C1–Ar),
128.3 (C2–Ar), 129.2(C3–Ar), 137.6 (C4–Ar), 21.3 (C9-
methyl), 57.2 (C12-methanetriyl), 35.4 (C13-methanediyl),
130.3 (C15–Ar), 115.6 (C16–Ar), 155.5 (C17–Ar), 174.7
2(S)-{[(4-methylphenyl)sulfonyl]amino}-4-
(methylsulfanyl)butanoic acid (1b)
White solid. Yield: 64 %. Mp: 133–135 °C. Analysis for
C12H17NO4S2 (303.397); calculated: C, 47.50; H, 5.65; N, 4.62;
found: C, 47.43; H, 5.35; N, 4.42. IR (KBr), v (cm-1): 3446 (O–
H), 3350 (N–H), 2981 (Ar–H), 2754 (C–H), 1693 (C=O), 1358
(S–H). 1H NMR (DMSO) d (ppm): 7.17–7.67 (m,4H,Ar–H),
3.9 (d,1H,NH), 2.59–2.61 (m,1H,CH), 2.35 (s,3H,CH3), 2.07
(s,3H,CH3). 13C NMR (CDCl3) d (ppm): 141.4 (C1–Ar), 128.2
(C2–Ar), 129.3 (C3–Ar), 139.2 (C6–Ar), 21.4 (C9-methyl), 59.1
(C12-methanetriyl), 28.5 (C13-methanediyl), 29.2.5 (C14-
methanediyl), 16.2 (C16-methyl), 176.8 (C17-carbonyl). MS (m/
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(C20-carbonyl). MS (m/z): 335 (M?). ½aꢁD : -52.
2(S)-{[(4-methylphenyl)sulfonyl]amino}-3-
phenylpropanoic acid (1f)
25
z): 303 (M?). ½aꢁD : ?126.
White solid.Yield 56 %. Mp: 141–143 °C. Analysis for
C16H17NO4S (319.375); calculated: C, 60.17; H, 5.37; N,
4.39; found: C, 60.12; H, 5.27; N, 4.29. IR (KBr), v (cm-1):
3426 (O–H), 3341(N–H), 2989 (Ar–H), 2754 (C–H), 1690
(C=O), 1370 (S–H). 1H NMR (DMSO) d (ppm): 11.26
(brs,1H,OH), 7.31–7.28(m,9H,Ar–H), 4.20–4.18(d,1H,NH),
3.80(m,1H,CH), 2.90–2.88 (d,2H,CH2), 2.32(s,3H,CH3).
13C NMR (CDCl3) d (ppm): 141.2 (C1–Ar), 128.2 (C2–Ar),
129.2 (C3–Ar), 137.4 (C4–Ar), 21.3 (C9-methyl), 57.4 (C12-
methanetriyl), 35.6 (C13-methanediyl), 136.3 (C14–Ar),
127.1 (C15-Ar), 128.7 (C16-Ar), 125.4 (C17–Ar), 174.7 (C20-
3-(1H-indol-3-yl)-2(S)-{[(4-methylphenyl)sulfonyl]
amino}propanoic acid (1c)
Off white solid. Yield: 72 %. Mp: 136–138 °C. Analysis for
C18H18N2O4S (358.411); calculated: C, 60.32; H, 5.06; N, 7.82;
found: C, 60.12; H, 4.96; N, 7.62. IR (KBr), v (cm-1): 3427 (O–
H), 3340 (N–H), 2998 (Ar–H), 2751 (C–H), 1678 (C=O), 1360
1
(S–H). H NMR (DMSO) d (ppm): 11.18 (s,1H,OH), 9.76
(d,1H,NH), 7.17–7.12 (m,9H,Ar–H), 4.22 (d,1H,NH), 3.80
(m,1H,CH), 2.76 (d,2H,CH2), 2.30 (s,3H,CH3). 13C NMR
(CDCl3) d (ppm):122.7 (C2-indole), 109.5 (C3-Indole), 127.2
(C4-indole), 118.4 (C5-indole), 119.2 (C6-indole), 121.4 (C7-
indole),111.2 (C8-indole), 136.3 (C9-indole), 29.1 (C10-meth-
anediyl), 58.3 (C11-methanetriyl), 174.4 (C15-carbonyl), 141.2
(C18–Ar), 128.3 (C19–Ar), 129.3 (C20–Ar), 137.2 (C21–Ar),
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carbonyl). MS (m/z): 319 (M?). ½aꢁD : -44.
3-Hydroxy-2(S)-{[(4-methylphenyl)sulfonyl]amino}
propanoic acid (1g)
25
21.3 (C25-methyl). MS (m/z): 358 (M?). ½aꢁD : -68.
Off white solid. Yield 53 %. Mp: 127–129 °C. Analysis for
C10H13NO5S (259.278); calculated: C, 46.32; H, 5.05; N,
5.40; found: C, 46.22; H, 4.95; N, 5.36. IR (KBr), v (cm-1):
3417 (O–H), 3350 (N–H), 29877 (Ar–H), 2761 (C–H),
1602 (C=O), 1368 (S–H). 1H NMR (DMSO) d (ppm):
11.22 (s,1H,OH), 7.43–7.40 (d,4H,Ar–H), 4.18 (d,1H,NH),
3-(1H-imidazol-4-yl)-2(S)-{[(4-methylphenyl)sulfonyl]
amino}propanoic acid (1d)
Paleyellow solid. Yield: 55 %. Mp: 117–119 °C. Analysis
for C13H15N3O4S (309.34); calculated: C, 50.47; H, 4.89;
123