Glycine Site NMDA Antagonists
271
Table 4. Continued.
1H-NMR, δ (ppm), J (Hz)
Cpd.
Mp. (°C)
IR (KBr)
1.36 (ddd, 1 H, J = 12.5, 8.5, 4.5, CHabcd), 1.38 (s, 9 H, -C(CH3)3), 2.29 (dm, 1 H, J = 12.5,
CHabcd), 2.58 (t, J = 12.5, -CH2-), 3.08 (t, J = 12.5, -CH2-), 3.68 (dd, 1 H, J = 12.5, 4.5, CHabcd),
4.93 (m, 1 H, CHabcd) 6.48 (d, 1 H, J = 5.0, NH, exchange), 6.56 (d, 1 H, J = 2.5, Ar-H), 6.62 (d,
1 H, J = 5.0, NH, exchange), 6.74 (d, 1 H, J = 2.5, Ar-H), 7.08 (d, 2 H, J = 8.0, Ar-H), 7.26 (d,
2 H, J = 8.0, Ar-H), 8.07 (s, 1 H, NH, exchange), [DMSO-d6, 90 MHz]
>260
dec.
3350
s
(-NH), 2970 s
(-CH2-), 1685 s (-C=O),
1650 s (-NHCO)
trans 16
1.38 (s, 9 H, -C(CH3)3), 1.39 (ddd, 1 H, J = 12.5, 8.5, 4.5, CHabcd), 1.58 (quin, 2 H, J = 12.5,
-CH2-), 2.33 (dm, 1 H, J = 12.5, CHabcd), 2.42 (t, 2 H, J = 12.5, -CH2-), 2.85 (t, 2 H, J = 12.5,
-CH2-), 3.67 (dd, 1 H, J = 12.5, 4.5, CHabcd), 4.97 (m, 1 H, CHabcd), 6.46 (d, 1 H, J = 5.0, NH,
exchange), 6.54 (d, 1 H, J = 2.5, Ar-H), 6.63 (d, 1 H, J = 2.5, Ar-H), 7.00 (d, 2 H, J = 10.0, Ar-
H), 7.16 (d, 2 H, J = 10.0, Ar-H), 8.16 (s, 1 H, NH, exchange), [DMSO-d6, 90 MHz]
>260
dec.
3360s (-NH), 2970
(-CH2-), 1685 s (-C=O),
1655 s (-NHCO)
s
trans 17
1.35 (s, 9 H, -C(CH3)3), 1.91 (m, 1 H, CHabcd), 2.36 (dm, 1 H, J = 12.5, CHabcd), 293 (t, 4 H, J =
10.0, 2x-CH2-), 3.73 (m, 1 H, CHabcd), 3.82 (t, 4 H, J = 10.0, 2x-CH2-), 4.91 (m, 1 H, CHabcd),
6.06 (d, 1 H, J = 5.0, NH, exchange), 6.52 (d, 1 H, J = 2.5, Ar-H), 6.55 (d, 2 H, J = 6.0, Ar-H),
6.56 (d, 1 H, J = 2.5, Ar-H), 7.13 (d, 2 H, J = 10.0, Ar-H), 7.92 (s, 1 H, NH, exchange), [DMSO-
d6, 200 MHz]
>260
dec.
3390 s (-NH), 2970 s
(-CH2-), 1685 s (-C=O),
1655 s (-NHCO)
cis 18
1.32 (ddd, 1 H, J = 12.5, 8.5, 4.5, CHabcd), 1.39 (s, 9 H, -C(CH3)3, 2.33 (d, 1 H, J = 12.5, CHabcd),
2.92 (t, 4 H, J = 10.0, 2x-CH2-), 3.76 (dd, 1 H, J = 12.5, 4.5, CHabcd), 3.89 (t, 4 H, J = 10.0, 2x-
CH2-), 4.88 (m, 1 H, CHabcd), 6.32 (d, 1 H, J = 5.0, NH, exchange), 6.50 (d, 2 H, J = 6.0, Ar-H),
6.56 (d, 1 H, J = 2.5, Ar-H), 6.82 (d, 1 H, J = 2.5, Ar-H), 7.08 (d, 2 H, J = 6.0, Ar-H), 7.81 (s,
1 H, NH, exchange), [DMSO-d6, 200 MHz]
>260
dec.
3390 s (-NH), 2970 s
(-CH2-), 1685 s (-C=O),
1655 s (-NHCO)
trans 18
trans 19
trans 20
1.37 (s, 9 H, -C(CH3)3), 1.38 (ddd, 1 H, J = 12.5, 8.5, 4.5, CHabcd), 2.35 (dm, 1 H, J = 12.0,
CHabcd), 2.58 (t, 4 H, J = 10.0, 2x-CH2-), 3.09 (t, 4 H, J = 10.0, 2x-CH2-), 3.41 (s, 2 H, -CH2-
NR2), 3.59 (dd, 1 H, J = 12.5, 4.5, CHabcd), 4.94 (m, 1 H, CHabcd), 6.52 (d, 1 H, J = 5.0, NH,
exchange), 6.55 (d, 1 H, J = 2.5, Ar-H), 6.75 (d, 1 H, J = 2.5, Ar-H), 7.09 (d, 2 H, J = 10.0, Ar-
H), 7.37 (d, 2 H, J = 10.0, Ar-H), 8.08 (s, 1 H, NH, exchange), [DMSO-d6, 200 MHz]
>260
dec.
3360 s (-NH), 2970 s
(-CH2-), 1690 s (-C=O),
1650 s (-NHCO)
1.31 (ddd, 1 H, J = 12.5, 8.5, 4.5, CHabcd), 2.26 (dm, 1 H, J = 12.5, CHabcd), 3.55 (dd, 1 H, J =
12.5, 4.5, CHabcd), 3.58 (m, 8 H, 4x-CH2-), 3.70 (m, 4 H, 2x-CH2-), 3.96 (m, 4 H, 2x-CH2-), 4.96
(m, 1 H, CHabcd), 6.41 (d, 1 H, J = 5.0, NH, exchange), 6.56 (d, 1 H, J = 2.5, Ar-H), 6.58-6.82
(m, 3 H, Arom.), 6.75 (d, 1 H, J = 2.5, Ar-H), 8.22 (s, 1 H, NH, exchange), [DMSO-d6,
90 MHz]
>260
dec.
3380 s (-NH), 2930 s
(-CH2-), 1720 s (-C=O),
1690 s (-NHCO)
1.28 (ddd, 1 H, J = 12.5, 8.5, 4.5, CHabcd), 2.24 (dm, 1 H, J = 12.5, CHabcd), 3.48 (m, 4 H, 2x-
CH2-), 3.53 (dd, 1 H, J = 12.5, 4.5, CHabcd), 3.55 (m, 8 H, 4x-CH2-), 3.75 (m, 4 H, 2x-CH2-), 4.00
(m, 4 H, 2x-CH2-), 4.95 (m, 1 H, CHabcd), 6.35 (d, 1 H, J = 5.0, NH, exchange), 6.54 (d, 1 H, J =
2.5, Ar-H), 6.55-6.80 (m, 3 H, Arom.), 6.75 (d, 1 H, J = 2.5, Ar-H), 8.18 (s, 1 H, NH, exchange),
[DMSO-d6, 90 MHz]
>260
dec.
3360 s (-NH), 2910 s
(-CH2-), 1725 s (-C=O),
1650 s (-NHCO)
trans 21
trans 22
trans 23
trans 24
1.29 (ddd, 1 H, J = 12.5, 8.5, 4.5, CHabcd), 1.42 (s, 9 H, -C(CH3)3), 2.28 (dm, 1 H, J = 12.5,
CHabcd), 3.52 (dd, 1 H, J = 12.5, 4.5, CHabcd), 4.92 (m, 1 H, CHabcd), 6.32 (d, 1 H, J = 5.0, NH,
exchange), 6.54 (d, 1 H, J = 2.5, Ar-H), 6.72 (d, 1 H, J = 5.0, NH, exchange), 6.78 (d, 1 H, J =
2.5, Ar-H), 7.26-7.36 (m, 4 H, Ar-H), 8.54 (s, 1 H, NH, exchange), [DMSO-d6, 90 MHz]
>260
dec.
3360 s (-NH), 2910 s
(-CH2-), 1725 s (-C=O),
1650 s (-NHCO)
1.26 (ddd, 1 H, J = 12.5, 8.5, 4.5, CHabcd), 1.37 (s, 9 H, -C(CH3)3), 2.28 (dm, 1 H, J = 12.5,
CHabcd), 3.48 (m, 1 H, CHabcd), 3.96 (d, 2 H, -CH2-NHCO-), 4.89 (m, 1 H, CHabcd), 6.31 (s, 1 H,
NH, exchange), 6.52 (d, 1 H, J = 2.5, Ar-H), 6.67 (d, 1 H, J = 5.0, NH, exchange), 6.84 (d, 1 H, J
= 2.5, Ar-H), 7.16 (d, 2 H, J = 5.0, Ar-H), 7.38 (d, 2 H, J = 5.0, Ar-H), 8.49 (s, 1 H, NH,
exchange), [DMSO-d6, 90 MHz]
>260
dec.
3360 s (-NH), 2970 s
(-CH2-), 1690 s (-C=O),
1670 s (-NHCO)
1.58 (ddd, 1 H, J = 13.3, 12.5, 3.7, CHabcd), 2.08 (dm, 1 H, J = 13.3, CHabcd), 2.38 (s, 1 H, Ar-
CH3), 3.76 (d, 1 H, J = 10.6, CHabcd), 4.70 (s, 1 H, NH), 4.72 (m, 1 H, CHabcd), 6.64 (d, 1 H, J =
1.6, Ar-H), 6.80 (s, 2 H, NH), 6.69 (d, 1 H, J = 1.6, Ar-H), 7.58 (d, 2 H, J = 8.0, Ar-H), 7.77 (d,
2 H, J = 8.0, Ar-H), [DMSO-d6, 400 MHz]
>260
dec.
3400 s (-NH), 3030, m
(-OH) 1660 s (-CONH),
1350 m (-SO2-)
1.57 (ddd, 1 H, J = 13.2, 12.6, 3.5, CHabcd), 2.07 (dm, 1 H, J = 12.7, CHabcd), 3.78 (dd, 1 H, J =
12.0, 2.8, CHabcd), 3.80 (s, 1 H, NH), 4.72 (m, 1 H, CHabcd), 6.63 (d, 1 H, J = 1.9, Ar-H), 6.77 (s,
1 H, NH), 6.89 (d, 1 H, J = 1.9, Ar-H), 7.59 (m, 3 H, Ar-H), 7.69 (s, 1 H, NH), 7.90 (m, 2 H, Ar-
H), [DMSO-d6, 400 MHz]
>260
dec.
3400 s (-NH), 3000 s
(-OH), 1720 s (-C=O),
1650 s (-NHCO)
trans 25
trans 26
data were consistent with
the literature
Lit. [3]
Arch. Pharm. Pharm. Med. Chem. 333, 267–274 (2000)