206
ABBASI et al.
1149 (C–O–C stretching of ether); 1H NMR: 9.79 (s,
1H, –NHCO), 7.67 (d,
7.60 (d, = 8.8 Hz, 2H, Hꢀ3' & Hꢀ5'), 6.64 (d,
1H, Hꢀ8), 6.53 (d, = 2.4 Hz, 1H, Hꢀ5), 6.48 (dd,
= 2.4, 8.4 Hz, 1H, Hꢀ7), 4.25 (sex, = 7.2 Hz,
1H,CHꢀ1''), 4.13 (s, 4H, CH2ꢀ2 & CH2ꢀ3), 2.09 (s,
3H, –COCH3), 1.01 (d, = 6.8 Hz, 3H, CH3ꢀ1'''),
0.90–0.85 (m, 2H, CH2ꢀ2''), 0.74 (t, = 7.2 Hz, 3H,
CH3ꢀ3''); EIꢀMS ( ): 405 (2.18%), 404 (6.08%),
389 (47.81%), 376 (28.83%), 361 (12.33%), 346
(9.91%), 282 (32.11%), 207 (42.24%), 198 (2.88%),
135 (17.00%), 134 (6.91%), 107 (32.09%), 81
(12.98%), 57 (99.55%).
line solid; yield 89%; mp 212
°C; molecular formula
J
= 8.8 Hz, 2H, Hꢀ2' & Hꢀ6'), C23H22N2O5S; molecular weight 438 g mol–1; HRꢀMS:
[M]+ 438.4979 (calculated for C23H22N2O5S;
438.4974); IR: 3230 (N–H stretching), 3055 (C–H
stretching of aromatic ring), 2928 (–CH2 stretching),
1714 (C=O stretching), 1620 (C=C stretching of aroꢀ
matic ring), 1365 (–SO2 stretching), 1160 (C–O–C
J
J= 8.4 Hz,
J
J
J
J
J
stretching of ether); 1H NMR (Fig. 2): 10.36 (s, 1H,
m/z
–NHCO), 7.77 (d,
(d, = 8.8 Hz, 2H, Hꢀ3' & Hꢀ5'), 7.25–7.18 (m, 5H,
Hꢀ2'' to Hꢀ6''), 6.68 (d, = 8.4 Hz, 1H, Hꢀ8), 6.51 (d,
= 2.4 Hz, 1H, Hꢀ5), 6.44 (dd, = 2.4, 8.4 Hz, 1H,
Hꢀ7), 4.68 (s, 2H, CH2ꢀ7''), 4.15 (s, 4H, CH2ꢀ2 &
CH2ꢀ3), 2.09 (s, 3H, –COCH3); EIꢀMS ( ): 438
J = 8.8 Hz, 2H, Hꢀ2' & Hꢀ6'), 7.58
J
J
J
J
m/z
Nꢀ(1ꢀMethylbutyl)ꢀNꢀ(2,3ꢀdihydroꢀ[1,4]ꢀbenzodioxꢀ
(9.65%), 422 (4.91%), 409 (5.19%), 399 (47.06%),
394 (10.08%), 379 (10.61%), 315 (7.77%), 198
(2.84%), 135 (18.64%), 134 (5.98%), 107 (33.60%),
91 (100%), 81 (17.03%), 65 (18.21%).
inꢀ6ꢀyl)ꢀ4ꢀacetamidobenzenesulfonamide (Vh). Brownish
grey solid; yield 86%; mp 135°C; molecular formula
C21H26N2O5S; molecular weight 418 g mol–1; HRꢀMS:
[M]+ 418.5083 (calculated аor C21H26N2O5S; 418.5088);
IR: 3252 (N–H stretching), 3054 (C–H stretching of arꢀ
omatic ring), 2965 (–CH2 stretching), 1719 (C=O
stretching), 1628 (C=C stretching of aromatic ring),
1389 (–SO2 stretching), 1163 (C–O–C stretching of
N
ꢀ(2ꢀPhenylethyl)ꢀ
dioxinꢀ6ꢀyl)ꢀ4ꢀacetamidobenzenesulfonamide (Vk).
Grayish brown crystalline solid; yield 81%; mp 242 C;
Nꢀ(2,3ꢀdihydroꢀ[1,4]ꢀbenzoꢀ
°
molecular formula C24H24O5N2S; molecular weight
1
452 g mol–1; HRꢀMS: [M]+ 452.5248 (calculated for
C24H24O5N2S; 452.5244); IR: 3240 (N–H stretching),
3065 (C–H stretching of aromatic ring), 2918 (–CH2
stretching), 1710 (C=O stretching), 1630 (C=C
stretching of aromatic ring), 1385 (–SO2 stretching),
ether); H NMR: 9.82 (s, 1H, –NHCO), 7.66 (d,
J
= 8.8 Hz, 2H, Hꢀ2' & Hꢀ6'), 7.63 (d,
Hꢀ3' & Hꢀ5'), 6.66 (d, = 8.4 Hz, 1H, Hꢀ8), 6.56 (d,
= 2.4 Hz, 1H, Hꢀ5), 6.46 (dd, = 2.4, 8.4 Hz, 1H,
Hꢀ7), 4.84 (sex., = 7.6 Hz, 1H, CHꢀ1"), 4.12 (s, 4H,
CH2ꢀ2 & CH2ꢀ3), 2.09 (s, 3H, –COCH3), 1.35–1.30
(m, 4H, CH2ꢀ2" & CH2ꢀ3"), 1.02 (d, = 6.8 Hz, 3H,
CH3ꢀ1'''), 0.88 (t, = 8.4 Hz, 3H, CH3ꢀ4"); EIꢀMS
): 419 (6.98%), 418 (10.11%), 403 (8.39%), 390
J = 8.8 Hz, 2H,
J
J
J
J
1161 (C–O–C stretching of ether); 1H NMR: 9.83 (s,
J
1H, –NHCO), 7.71 (d,
7.58 (d, = 8.8 Hz, 2H, Hꢀ3' & Hꢀ5'), 7.22 (br.t,
J = 7.6 Hz, 2H, Hꢀ3'' & Hꢀ5''), 7.17 (br.t, J = 6.8 Hz,
1H, Hꢀ4''), 7.06 (d, = 7.8 Hz, 2H, Hꢀ2'' & Hꢀ6''),
6.71 (d, = 8.4 Hz, 1H, Hꢀ8), 6.58 (d, = 2.4 Hz, 1H,
Hꢀ5), 6.45 (dd, = 2.4, 8.4 Hz, 1H, Hꢀ7), 4.17 (s, 4H,
J = 8.8 Hz, 2H, Hꢀ2' & Hꢀ6'),
J
J
(m/z
(40.08%), 375 (8.98%), 360 (11.13%), 296 (13.08%),
207 (32.98%), 198 (2.98%), 135 (12.88%), 134
(4.14%), 107 (23.11%), 81 (19.00%), 71 (100.0%).
J
J
J
J
CH2ꢀ2 & CH2ꢀ3), 2.85 (t, J = 6.8 Hz, 2H, CH2ꢀ8''), 2.64
(t, J = 6.8 Hz, 2H, CH2ꢀ7''), 2.08 (s, 3H, –COCH3);
N
ꢀ(1ꢀPentyl)ꢀ
Nꢀ(2,3ꢀdihydroꢀ[1,4]ꢀbenzodioxinꢀ6ꢀ
yl)ꢀ4ꢀacetamidobenzenesulfonamide (Vi). Dark brown
crystalline solid; yield 70%; mp 238°C; molecular forꢀ
EIꢀMS (m/z): 453 (3.18%), 452 (5.98%), 437
mula C21H26O5N2S; molecular weight 418 g mol–1;
(9.91%), 424 (14.72%), 413 (46.12%), 409 (15.03%),
394 (42.98%), 330 (12.01%), 255 (27.47%), 198
(2.84%), 135 (16.19%), 134 (9.98%), 107 (33.08%),
105 (100.0%), 81 (17.03%).
HRꢀMS: [M]+ 418.5094 (calculated for C21H26O5N2S;
418.5089); IR: 3232 (N–H stretching), 3049 (C–H
stretching of aromatic ring), 2915 (–CH2 stretching),
1705 (C=O stretching), 1638 (C=C stretching of aroꢀ
matic ring), 1384 (–SO2 stretching), 1151 (C–O–C
Nꢀ(4ꢀFlourobenzyl)ꢀ
Nꢀ(2,3ꢀdihydroꢀ[1,4]ꢀbenꢀ
zodioxinꢀ6ꢀyl)ꢀ4ꢀacetamidobenzenesulfonamide (Vl).
stretching of ether); 1H NMR: 9.78 (s, 1H, –NHCO), Light brown solid; yield 76%; mp 93
°C; molecular forꢀ
mula C23H21FN2O5S; molecular weight 456 g mol–1;
7.66 (d,
Hz, 2H, Hꢀ3' & Hꢀ5'), 6.66 (d,
6.58 (d, = 2.4 Hz, 1H, Hꢀ5), 6.47 (dd,
J
= 8.4 Hz, 2H, Hꢀ2' & Hꢀ6'), 7.58 (d,
= 8.4 Hz, 1H, Hꢀ8),
= 2.2, 8.2 Hz,
J = 8.4
HRꢀMS: [M]+ 456.4893 (calculated for C23H21FN2O5S;
456.4889); IR: 3247 (N–H stretching), 3045 (C–H
stretching of aromatic ring), 2977 (–CH2 stretching),
1713 (C=O stretching), 1634 (C=C stretching of aroꢀ
matic ring), 1384 (–SO2 stretching), 1151 (C–O–C
J
J
J
1H, Hꢀ7), 4.11 (s, 4H, CH2ꢀ2 & CH2ꢀ3), 3.65 (t, J =
7.6 Hz, 2H, CH2ꢀ1''), 2.07 (s, 3H, –COCH3), 1.34–
1.16 (m, 6H, CH2ꢀ2''–CH2ꢀ4''), 0.80 (t,
J = 6.8 Hz,
3H, CH3ꢀ5''); EIꢀMS ( z): 419, 418 (5.15%), 403
m
/
stretching of ether); 1H NMR: 9.83 (s, 1H, –NHCO),
(9.35%), 390 (17.35%), 375 (42.05%), 360 (7.45%), 296
(13.15%), 221 (37.22%), 198 (3.55%), 135 (7.79%), 134
(7.15%), 107 (31.33%), 81 (17.02%), 71 (100.0%).
7.72 (d,
Hz, 2H, Hꢀ3' & Hꢀ5'), 7.21 (d,
&Hꢀ5''), 7.02 (d, = 8.4 Hz, 2H, Hꢀ2'' & Hꢀ6''), 6.69
(d, = 8.4 Hz, 1H, Hꢀ8), 6.57 (d, = 2.4 Hz, 1H, Hꢀ5),
6.50 (dd, = 2.4, 8.4 Hz, 1H, Hꢀ7), 4.29 (s, 2H, CH2ꢀ7''),
J
= 8.8 Hz, 2H, Hꢀ2' & Hꢀ6'), 7.64 (d,
J = 8.8
J
= 8.4 Hz, 2H, Hꢀ3''
J
J
J
Nꢀ(Benzyl)ꢀNꢀ(2,3ꢀdihydroꢀ[1,4]ꢀbenzodioxinꢀ6ꢀ
J
yl)ꢀ4ꢀacetamidobenzenesulfonamide (Vj). Brown crystalꢀ
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY Vol. 42
No. 2
2016