J. Acharya et al. / European Journal of Medicinal Chemistry 46 (2011) 3926e3933
3931
Table 2
Spectral data of carbamoyl bis-pyridinium oximes.
Oxime
I.R. (KBr) gmax(cmꢀ1
)
1H NMR(400 MHz)
, ppm, DMSO-d6)
13C NMR (100 MHz)
d, ppm, DMSO-d6)
d
5a
3279, 3143, 3028, 2946,
1703, 1646, 1505, 1434,
1396, 1278, 1262, 1004,
775, 667
5.87 (s, 2H, NCH2), 5.95 (s, 2H, NCH2), 7.61e7.69(m, 4H, -Ph),
8.20 (s, 1H, NH2), 8.24e8.25 (d, 2H, -Py), 8.27e8.31 (t, 1H, -Py),
8.41 (s, 1H, CH]N), 8.64 (s,1H, NH2), 8.97e8.99 (d,1H),
9.17e9.18 (d, 2H, -Py), 9.34e9.35 (d, 1H, -Py), 9.69 (s, 1H, -Py),
12.87 (s, 1H, OH)
62.12, 62.95, 124.41, 128.29, 128.41, 129.71,
129.97, 134.15, 135.03, 135.45, 144.09, 145.33,
146.11, 148.89
5b
5c
3361, 3169, 3118, 3038,
2997, 1669, 1623, 1570,
1454, 1430, 1399, 1279,
1129, 995, 777, 754
3270, 3148, 3025, 2955,
1696, 1638, 1514, 1441,
1403, 1282, 1275, 1011,
768, 671
5.85 (s, 2H, NCH2), 5.93 (s, 2H, NCH2), 7.60e7.63 (m, 4H, -Ph)
8.24e8.25 (d, 2H, -Py), 8.29 (s, 1H, NH2), 8.40 (s, 1H, CH]N),
8.44e8.46 (d,2H), 8.67 (s,1H, NH2), 9.15e9.16 (d, 2H, -Py),
9.38e9.39 (d, 2H, -Py), 12.87 (s, 1H, OH)
5.95 (s, 2H, NCH2), 5.98 (s, 2H, NCH2), 7.66e7.71 (m, 4H, -Ph),
8.17e8.22 (t, 1H, -Py), 8.28e8.32 (m, 2H, -Py), 8.36 (s, 1H,
CH]N),
8.66 (s, 1H, NH2), 8.73e8.75 (d, 1H, -Py), 8.99e9.01 (d, 1H, -Py),
9.23e9.24 (d, 1H, -Py), 9.38e9.39 (d, 1H, -Py), 9.47 (s, 1H, eNH2),
9.72 (s, 1H, -Py), 12.27 (s, 1H, OH)
61.18, 62.82, 123.11, 126.22, 128.98, 129.61,
134.77, 135.85, 144.37, 145.42, 148.07, 148.93
64.31, 64.55, 128.63, 129.96, 130.19, 130.51,
133.95, 134.22, 134.33, 142.99, 144.46,
144.73, 144.85
5d
5e
3355, 3144, 3108, 3037,
2988, 1657, 1631, 1560,
1459, 1404, 1260, 1123, 631
5.93 (s, 2H, NCH2), 5.95 (s, 2H, NCH2), 7.66 (s, 4H, -Ph), 8.17e8.21
(t, 1H, -Py), 8.30 (s, 1H, NH2), 8.35 (s, 1H, CH]N), 8.45e8.47
(d, 1H), 8.70 (s, 1H, NH2), 8.73e8.75 (d, 1H, -Py), 9.19e9.21
(d, 2H, -Py), 9.41 (s, 1H, -Py), 9.43e9.45 (d, 2H, -Py), 12.28
(s, 1H, OH)
5.95 (s, 2H, NCH2), 6.12 (s, 2H, NCH2), 7.65 (s, 4H, -Ph),
8.20e8.22 (m, 2H, -Py), 8.25 (s, 1H, NH2), 8.44e8.46
(d, 1H, -Py), 8.67e8.71 (m, 3H, -Py), 8.98e9.01 (d, 1H, -Py),
9.23e9.24 (d, 1H, -Py), 9.39e9.41 (d, 1H, -Py), 9.65 (s,1H, NH2),
13.10 (s, 1H, OH).
62.51, 63.32, 125.11, 128.28, 129.49, 133.25,
134.89, 141.66, 142. 69, 143.55, 145.35,
146.10, 148.88
3350, 3291,3148, 3025,
2937, 1696, 1646, 1583,
1508, 1442, 1393, 1188, 672
60.32, 62.14, 125.63, 128.52, 129.11, 129.96,
130.36, 130.89, 134.02, 134.57, 142.01,
143.40, 144.08, 146.11, 146.53, 147.38,
147.74, 148.58
5f
3357, 3150,3115, 3031, 2994,
1678, 1622, 1568, 1455, 1399,
1264, 1131, 621
5.92 (s, 2H, NCH2), 6.10 (s, 2H, NCH2), 7.67 (s, 4H, -Ph), 7.98
(s, 1H, NH2), 8.18e8.21 (t, 1H, -Py), 8.34 (s, 1H, NH2), 8.38
(s, 1H, CH]N), 8.43e8.47 (m, 2H, -Py), 8.63e8.69 (m, 3H),
9.20e9.21 (d, 1H, -Py), 9.33e9.35 (m, 1H, -Py), 13.07 (s, 1H, OH).
5.86 (s, 2H, NCH2), 5.95 (s, 2H, NCH2), 7.52e7.59 (m, 3H, -Ph),
7.76 (s, 1H, -Ph), 8.21 (s, 1H, NH2), 8.25e8.30 (m, 3H, -Py), 8.44
(s, 1H, CH]N), 8.64 (s, 1H, NH2), 8.99e9.01 (d, 1H, -Py),
9.14e9.16 (d, 2H, -Py), 9.31e9.32 (d, 1H, -Py), 9.64 (s,1H, -Py),
12.89 (s, 1H, OH)
59.82, 61.21, 126.43, 127.51, 128.17,
129.36, 130.09, 133.91, 135.27, 135.84,
141.08, 145.50, 146.18, 146.72, 147. 53,
148.10
62.05, 62.76, 123.84, 127.63, 129.14,
129.75, 130.41, 130.93, 134.16, 134.88,
135.79, 144.14, 145. 21, 145.79, 146.20,
147.01, 148.94
5g
3266, 3135, 3034, 2943, 1697,
1649, 1500, 1441, 1390, 1282,
1266, 1001, 776, 661
5h
5i
3246, 3124, 3049, 2955, 1705,
1641, 1507, 1435, 1388, 1298,
1279, 998, 772, 669
5.86 (s, 2H, NCH2), 5.94 (s, 2H, NCH2), 7.52e7.59 (m, 3H, -Ph),
7.75 (s, 1H, -Ph), 8.26e8.27 (d, 2H, -Py), 8.31 (s, 1H, NH2), 8.44
(s, 1H, CH]N), 8.47e8.48 (d, 2H, -Py), 8.71 (s,1H, NH2),
9.15e9.17 (d, 2H, -Py), 9.38e9.40 (d, 2H, -Py), 12.89
(s, 1H, OH)
5.97 (s, 2H, NCH2), 6.00 (s, 2H, NCH2), 7.50e7.54 (m, 2H, -Ph),
7.71 (s, 1H, -Ph), 8.19 (s, 1H, -Ph), 8.22e8.24 (t, 1H, -Py),
8.28e8.32 (m, 2H, -Py), 8.39 (s, 1H, CH]N), 8.66 (s, 1H, NH2),
8.76e8.78 (d, 1H, -Py), 9.01e9.03 (d, 1H, -Py), 9.24e9.25
(d, 1H, -Py), 9.40e9.41 (d, 1H, -Py), 9.49 (s, 1H, eNH2), 9.73
(s, 1H, -Py), 12.24 (s, 1H, OH)
62.25, 62.77, 124.35, 126.21, 128.95,
129.88, 130.69, 135.70, 136.42, 144.91,
146.65, 147.90, 148.33
3231, 3130, 3029, 2948, 1699,
1652, 1505, 1448, 1397, 1287,
1268, 1006, 770, 667
62.91, 63.17, 127.89, 128.55, 129.17,
129.54, 130.61, 134.58, 135.00, 135.88,
142.65, 143.25, 143.96, 144.46, 144.98,
146.27, 147.11
5j
3228, 3137, 3065, 2943, 1709,
1654, 1496, 1450, 1392, 1280,
1263, 1005, 772, 669
5.92 (s, 2H, NCH2), 5.94 (s, 2H, NCH2), 7.51e7.59 (m, 3H, -Ph),
7.76 (s, 1H, -Ph), 8.18e8.21 (m, 1H, -Py), 8.28 (s, 1H, NH2), 8.38
(s, 1H, CH]N), 8.46e8.48 (d, 2H, -Py), 8.69 s,1H, NH2),
8.75e8.77 (d, 1H, -Py), 9.14e9.16 (d, 1H, -Py), 9.37e9.41
(m, 3H, -Py), 12.26 (s, 1H, OH)
62.75, 63.01, 125.56, 128.88, 129.31,
129.62, 130.20, 133.48, 134.85, 142.08,
142.82, 143. 59, 144.61, 146.04, 148.92
5k
3223, 3110, 3071, 3005, 2940,
1682, 1633, 1573, 1513, 1458,
1257, 1182, 1135, 1006, 771, 676
5.92 (s, 2H, NCH2), 6.10 (s, 2H, NCH2), 7.29e7.31 (d, 1H, -Ph),
7.48e7.52 (m, 2H, -Ph), 7.57e7.59 (d, 1H, -Ph), 8.19e8.22
(m, 2H, -Py), 8.27 (s,1H, NH2), 8.41e8.43 (d, 1H, -Py),
8.61e8.66 (m, 3H), 8.98e9.01 (d, 1H, -Py), 9.20e9.21
(d, 1H, -Py), 9.26e9.28 (d, 1H, -Py), 9.65 (s,1H, NH2), 13.04
(s, 1H, OH).
62.11, 62.93, 125.81, 127.55, 127.90,
129.17, 129.45, 129.73, 130.04, 134.28,
135.16, 141.11, 144.02, 144.86, 145.44,
146.37, 146.91, 147.48
5l
3298, 3137, 3039, 2969, 1685,
1658, 1573, 1515, 1459, 1385,
1311, 1170, 998, 780, 727
5.91 (s, 2H, NCH2), 6.09 (s, 2H, NCH2), 7.27e7.28 (d, 1H, -Ph),
7.48e7.57 (m, 3H, -Ph), 7.94 (s, 1H, NH2), 8.19e8.23 (t, 1H, -Py),
8.30 (s, 1H, NH2), 8.42e8.47 (m, 3H), 8.63e8.69 (m, 3H),
9.20e9.21 (d, 1H, -Py), 9.33e9.35 (m, 1H, -Py), 13.07
(s, 1H, OH).
61.91, 63.08, 125.82, 127.45, 127.66,
128.71, 129.55, 130.50, 135.17, 142.03,
145.46, 145.83, 146.19, 146.72, 147.87,
148.26
5m
5n
3404, 3379, 3141, 3104, 3058,
2981, 1691, 1618, 1565, 1458,
1393, 1275, 1129, 875, 729
6.09 (s, 2H, NCH2), 6.17 (s, 2H, NCH2), 7.25e7.26 (d, 2H, -Ph),
7.51e7.53 (d, 2H, -Ph), 8.23 (s, 1H, NH2), 8.28e8.29 (d, 1H, -Py),
8.32e8.35 (m, 2H, -Py), 8.48 (s, 1H, NH2), 8.65 (s, 1H, CH]N),
9.04e9.05 (m, 3H, -Py), 9.18e9.20 (d, 1H, -Py), 9.53 (s, 1H, -Py),
12.93 (s, 1H, OH).
6.08 (s, 2H, NCH2), 6.15 (s, 2H, NCH2), 7.23e7.27 (m, 2H, -Ph),
7.51e7.53 (m, 2H, -Ph), 7.94 (s, 1H, NH2), 8.28e8.31 (m, 2H, -Py),
8.47 (s, 1H, CH]N), 8.48e8.50 (d, 2H, -Py), 8.73 (s, 1H, NH2),
9.02e9.03 (d, 2H, -Py), 9.24e9.26 (d, 2H, -Py), 12.92 (s, 1H, OH)
59.34, 59.79, 125.08, 128.43, 129.31,
129.78, 132.17, 132.76, 134.25, 144.01,
145. 19, 145.34, 145.70, 146.50, 148.85
3398, 3366, 3154, 3109, 3034,
2983, 1690, 1634, 1571, 1455,
1411, 1286, 1137, 874, 724
59.75, 60.27, 124.421, 126.29, 129.12,
129.65, 130.12, 132.50, 132.87, 145.08,
145.20, 145.64, 146.13, 148.77, 149.14
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