Phosphoramide Derivatives as Urease Inhibitors
J. Agric. Food Chem., Vol. 56, No. 10, 2008 3725
1
Table 2. Spectroscopic Data (IR, H NMR, and MS) for Synthesized Compounds
ref
IR (KBr, cm-1
)
1H NMR (DMSO-d6, 400 MHz) δ (J, Hz)
MS (m/z % abundance)
217 (M•+, 5), 95 (100)
172 (M•+, 87), 94 (100)
a
1a
1b
3420-3223, 1200
3366-3229, 1182
4.55 (bs, 4H, 2 NH2 ), 7.42 (d, 2H, H2, H6, J2-3 ) 5.8), 8.24 (d, 2H, H3, H5, J3-2 ) 6.5)
a
4.33 (d, 4H, 2 NH2 ), 7.09 (dt, 1H, H4), 7.18 (d, 2H, H2, H6, J2-3 ) 8.2), 7.30 (t, 2H,
H3, H5)
a
2.23 (s, 6H, 2 CH3), 4.28 (s, 4H, NH2 ), 6.72 (s, 1H, H4); 6.80 (s, 2H, H2, H6)
1c
1d
3435-3322, 1190
3428-3367, 1225
200 (M•+, 40), 122 (100)
278 (M•+, 7), 91 (100)
a
4.25 (bs, 4H, 2 NH2 ), 5.04 (s, 2H, CH2), 6.92 (d, 2H, H3, H5, J3-2 ) 9.0), 7.08 (d, 2H,
H2, H6, J2-3 ) 8.9), 7.32 (d, 2H, H2′ H6′), 7.38 (t, 1H, H4), 7.42 (t, 2H, H3′, H5′)
a
1e
2a
2b
3446-3298
2.28 (s, 3H, CH3), 7.30 (dd, 1H, H5, J5-6 ) 8.5), 7.33 (bs, 4H, 2 NH2 ), 7.53 (s, 1H, H3),
231 (M•+, 2), 77 (100)
7.62 (d, 1H, H6, J6-5 ) 8.5)
1.12 (t, 12H, CH2CH3, J ) 7.1), 3.16 (m, 8H, CH2CH3), 7.41 (d, 2H, H2, H6, J2-3 ) 9.3),
8.22 (dd, 2H, H3, H5, J3-2 ) 9.2)
(NaCl) 3178-3109, 1190
3095, 3083, 1222
0.87 (dt, 12H, H4′, H4′′, J4′-3′ ) 7.4), 1.28 (m, 8H, H3′, H3′′), 1.46 (m, 4H, H2′), 1.76 (m,
4H, H2′′), 2.77 (m, 4H, H1′), 3.11 (m, 4H, H1′′), 7.33 (d, 2H, H2, H6, J2-3 ) 9.3), 8.15 (d,
2H, H3, H5, J3-2 ) 9.2), 10.02 (bs, HCla)
441 (M•+, 5), 86 (100)
294 (M•+, 61), 91 (100)
a
3
3389-3246, 825
4.75 (s, 4H, 2 NH2 ), 5.06 (s, 2H, CH2), 6.96 (d, 2H, H3, H5, J3-2 ) 9.1), 7.11 (dd, 2H,
H2, H6, J2-3 ) 9.0), 7.34 (dt, 1H, H4′, J4′-3′ ) 7.2), 7.40 (t, 2H, H3′, H5′), 7.45 (d, 2H,
H2′, H6′, J2′-3′ ) 6.8)
4
3423, 1232
3377, 1216
3404, 1185
4.24 (bs, 2H, CH2), 7.99 (s, 1H, H5), 8.62 (s, 1H, H4), 8.88 (bs, 4H, H6, NH, 2 OHa), 9.04
(s, 1H, H2)
188 (M•+, 5), 69 (100)
216 (M•+, 5), 96 (100)
258 (M•+, 100)
5a
5b
2.12 (s, 3H, Ar-CH3), 3.45 (dd, 6H, 2 OCH3), 6.68 (t, 1H, H5), 7.62 (d, 1H, H4, J4-5
)
7.1), 7.75 (d, 1H, H6, J6-5 ) 6.0), 7.77 (bs, 1H, NHa)
3.64 (d, 6H, 2 OCH3), 7.18 (t, 1H, H6), 7.32 (d, 2H, H5, H4), 7.70 (d, 1H, H7, J7-6 ) 7.9),
12.2 (bs, 1H, NHa)
a
6a
6b
3416-3254, 1259
3420-3100, 1261
3.24 (m, 4H, CH2N), 3.66 (t, 4H, CH2Cl, J2-1 ) 7.6), 3.77 (bs, 4H, NH2 )
1.55 (s, 6H, 2 H4, 2 H7, 2 H9), 1.64 (s, 2H, H10), 1.82 (s, 4H, 2H2, 2H6), 1.96 (s, 2H, H3,
H5), 2.09 (s, 1H, H8), 3.09 (bs, 1H, NHa), 3.35 (s, 4H, 2NH2 )
4.06 (s, 4H, 2 NH2), 6.71 (d, 1H, NH), 7.36 (m, 2H, H3, H4), 7.46 (s, 2H, H6, H7), 7.56 (d,
220 (M•+, 10), 92 (100)
229 (M•+, 15), 94 (100)
a
6c
6d
6e
3433-3225, 1199
3423-3335, 1202
3445-3293, 1202
221 (M•+, 15), 191 (100)
201 (M•+, 48), 79 (100)
253 (M•+, 93),132 (100)
1H, H2, J2-3 ) 6.9), 7.82 (s, 1H, H8), 8.22 (s, 1H, H5)
a
3.67 (s, 3H, CH3), 3.93 (bs, 4H, 2 NH2 ), 6.31 (dd, 1H, H4, J4-5 ) 8.1), 6.68 (d, 1H, H6,
J6-5 ) 8.1), 6.75 (t, 1H, H2), 6.86 (d, 1H, NHa), 7.00 (t, 1H, H5)
1.22 (t, 1H, H4′a), 1.33 (m, 4H, H3′e, H2′a, H5′e, H6′a), 1.71 (m, 5H, H4’e, H3′a, H5′a, H2′e
,
a
H
6′e), 2.34 (H1′a), 3.88 (bs, 4H, 2 NH2 ), 6.71 (d, 1H, NHa), 6.94 (d, 2H, H3, H5, J3-2
)
8.5), 7.01 (d, 2H, H2, H6, J2-3 ) 8.5)
a
6f
3378-3261, 1229
3393-3245, 1145
2.28 (s, 3H, CH3), 4.48 (d, 4H, 2 NH2 ), 7.44 (dd, 1H, H5, J5-6 ) 8.8, J5-3 ) 1.7), 7.83
230 (M•+, 27), 184 (100)
277 (M•+, 5), 108 (100)
(d, 1H, H6, J6-5 ) 8.7), 7.92 (s, 1H, H3), 8.24 (d, 1H, NHa)
a
6g
3.86 (bs, 4H, 2 NH2 ), 4.99 (s, 2H, CH2), 6.63 (d, 1H, NHa), 6.80 (d, 2H, H3, H5, J3-2
)
8.8), 7.04 (d, 2H, H2, H6, J2-3 ) 8.8), 7.32 (d, 2H, H2′, H6′, J2′-3′ ) 7.0), 7.38 (t, 1H,
H4′, J4′-5′ ) J4′-3′ ) 7.4), 7.41 (t, 2H, H3′, H5′)
a
6h
6i
3407-3249, 1221
3374-3233, 1148
3394-3251, 1244
3401-3262, 1207
3415, 1175
3.66-3.74 (s, 6H, 2 CH3), 4.10 (s, 4H, 2 NH2 ), 5.45 (d, 1H, NHa), 6.29 (dd, 1H, H4, J4-3
231 (M•+, 58), 138 (100)
263 (M•+, 36), 185 (100)
217 (M•+, 5), 109 (100)
228 (M•+, 25), 150 (100)
222 (M•+, 5), 100 (100)
222 (M•+, 10), 144 (100)
171 (M•+, 63), 93 (100)
216 (M•+, 63), 108 (100)
216 (M•+, 25), 170 (100)
199 (M•+, 8), 108 (100)
255 (M•+, 100), 177 (100)
) 8.7, J4-6 ) 3.2), 6.79 (d, 1H, H3, J3-4 ) 8.8), 7.09 (d, 1H, H6, J6-4 ) 2.8)
a
3.96 (bs, 4H, 2 NH2 ), 6.86 (t, 4H, H3, H5, H2′, H6′), 6.93 (d, 1H, NHa), 7.02 (t, 1H, H4′,
J4′-3′ ) 6.7), 7.15 (d, 2H, H2, H6, J2-3 ) 7.9), 7.31 (t, 2H, H3′, H5′)
2.70 (t, 2H, CH2Ph, J2-1 ) 7.5), 2.94 (m, 2H, CH2NH), 3.36-3.43 (bs, 5H, 2H2, NHa),
7.10 (t, 2H, H3′, H5′), 7.24 (m, 2H, H2′, H6′)
6j
a
6k
6l
4.30 (bs, 4H, 2 NH2 ), 7.11 (t, 1H, H6), 7.27 (t, 1H, H5), 7.50 (d, 1H, H4, J4-5 ) 7.8), 7.74
(d, 1H, H7, J7-6 ) 7.4), 9.13 (bs, 1H, NHa)
1.55 (q, 2H, 2 H2), 2.30 (m, 6H, 2 H1, 2 H3′, 2 H5′), 2.77 (q, 2H, 2 H3), 3.38 (bs, 5H, NH,
a
2 NH2 ), 3.56 (t, 4H, 2 H2′, 2 H6′)
4.20 (bs, 4H, 2 NH2 ), 7.46 (m, 3H, H6, H7, NH), 7.70 (m, 1H, H5), 7.84 (m, 1H, H8), 7.87
a
6m
6n
6o
6p
6q
6r
3427-3226, 1184
3391-3248, 1147
3480-3363, 1182
3430-3232, 1241
3388-3252, 1145
3441-3252, 1220
(d, 1H, H4), 8.74 (d, 1H, H2)
a
3.94 (bs, 4H, 2 NH2 ), 6.72 (dt, 1H, H4, J4-3 ) 8.5, J4-2 ) 4.2), 6.87 (d, 1H, NHa), 7.10
(d, 4H, H2, H3, H5, H6, J ) 4.1)
a
4.28 (bs, 4H, 2 NH2 ), 7.27 (d, 2H, H2, H6, J2-3 ) 9.2), 8.04 (d, 2H, H3, H5, J3-2 ) 9.2),
8.08 (d, 1H, NHa)
a
4.53 (s, 4H, 2NH2 ), 6.96 (t, 1H, H4), 7.60 (t, 1H, H5), 7.92 (d, 1H, H6, J6-5 ) 8.5), 8.11
(d, 1H, H3, J3-4 ) 8.5), 8.33 (d, 1H, NHa)
2.72 (t, 2H, CH2Ph), 2.96 (dd, 2H, CH2NH, J1-2 ) 16.3, 8.9), 3.40 (bs, 5H, 2H2, NHa),
7.19 (dd, 3H, H2′, H6′, H5′, J ) 12.4, 7.1), 7.29 (t, 2H, H3′, H5′)
a
4.20 (bs, 4H, 2 NH2 ), 5.86 (d, 1H, NH, J ) 7.1), 6.85 (dt, 1H, H5, J ) 8.2), 7.19 (t, 1H,
H4, J ) 7.3), 7.23 (dd, 1H, H3, J3-4 ) 8.2, J3-5 ) 1.4), 7.69 (dd, 1H, H6, J6-5 ) 8.3,
J6-4 ) 1.3)
6s
6t
3404-3329, 1248
3380-3265, 1228
3.20-3.53 (bs, 4H, 2 NH2), 3.79 (s, 3H, OCH3), 7.34 (d, 1H, H4, J4-5 ) 5.5), 7.38-7.43
235 (M•+, 5), 125 (100)
272 (M•+, 30), 165 (100)
(bs, 1H, NH·HCla), 7.55 (d, 1H, H5, J5-4 ) 5.5)
a
1.33 (t, 3H, CH3, J ) 6.9), 4.02 (q, 2H, CH2, J ) 6.9), 4.24 (bs, 4H, 2 NH2 ), 6.86 (dd,
1H, H5, J5-4 ) 8.7, J5-7 ) 2.5), 7.36 (ds, 1H, H7, J7-5 ) 2.4), 7.39 (d, 1H, H4, J4-5
)
8.7), 8.90 (bs, 1H, NHa)
a
6u
6v
6w
3398-3224, 1194
3382-3360, 1155
3378-3246, 1184
4.30 (bs, 4H, 2 NH2 ), 7.11 (dt, 1H, H7, J ) 9.2), 7.49 (dd, 1H, H5, J5-4 ) 8.7), 7.68 (dd,
246 (M•+, 75), 168 (100)
258 (M•+, 84), 79 (100)
242 (M•+, 70), 79 (100)
1H, H4, J4-5 ) 8.8), 9.12 (bs, 1H, NHa)
a
3.86 (s, 3H, CH3), 4.28 (bs, 4H, 2 NH2 ), 6.87 (d, 1H, H5, J5-6 ) 7.9), 7.07 (t, 1H, H6,
J6-5 ) J6-7 ) 8.0), 7.33 (d, 1H, H7, J7-6 ) 7.8), 8.90 (bs, 1H, NHa)
a
2.50 (s, 3H, CH3), 4.27 (bs, 4H, 2 NH2 ), 7.01 (t, 1H, H6, J6-5 ) J6-7 ) 7.6), 7.10 (d, 1H,
H5, J5-6 ) 7.2), 7.57 (d, 1H, H7, J7-6 ) 7.7), 9.08 (bs, 1H, NHa)