S. Shaikh et al.
Bioorganic Chemistry 110 (2021) 104770
4
.22; N, 8.54.
4
.2.2.5. 2-amino-4-(p-tolyl)-7-tosyl-4,7-dihydropyrano[2,3-e]indole-3-
◦
carbonitrile (5e). White solid, Yield: 94%, M.P: 267–269 C. IR (
υ
max
/
¡
1
1
cm ): 3302 (NH
DMSO) δ ¼ 7.84 (t, J = 5.6 Hz, 3H, Ar-H), 7.61 (d, J = 8.6 Hz, 1H, Ar-H),
), 6.93
2 2
), 2200 (CN), 1190 (SO ). H NMR (300 MHz,
7
.36 (d, J = 8.2 Hz, 2H, Ar-H), 7.07 (s, 4H, Ar-H), 7.00 (s, 2H, NH
2
(
d, J = 8.6 Hz, 1H, Ar-H), 6.75 (d, J = 3.6 Hz, 1H, Ar-H), 4.75 (s, 1H,
13
3 3
CH), 2.30 (s, 3H, CH ), 2.23 (s, 3H, CH ). C NMR (75 MHz, DMSO) δ
=
159.83, 145.76, 142.99, 140.75, 135.89, 133.90, 133.81, 130.32,
1
1
29.19, 127.39, 127.29, 126.75, 125.60, 120.36, 118.90, 117.25,
09.47 (CN), 104.66, 56.48 (CH), 20.98 (CH
3
), 20.54 (CH
3
). MS (ESI)
+
Fig. 5. Lane 1-pBR322 (control), Lane 2-pBR322 + Fenton’s reagent, Lane 3-
pBR322 + Fenton’s reagent + 5o (10 µM), Lane 4-pBR322 + Fenton’s reagent
m/z: 456 (M+1) . Elemental analysis for C26
21 3 3
H N O
S: C, 68.55; H,
4.65; N, 9.22; found: C, 68.31; H, 4.23; N, 9.17.
+
5o (20 µM), Lane 5-pBR322 + Fenton’s reagent + 5o (40 µM).
4
.2.2.6. 2-amino-4-(3-chlorophenyl)-7-tosyl-4,7-dihydropyrano[2,3-e]
cm 1): 3324 (NH
DMSO) δ = 7.87 (t, J = 5.7 Hz, 3H, Ar-H), 7.72 (d, J = 8.5 Hz, 1H, Ar-H),
.38 (d, J = 8.1 Hz, 2H, Ar-H), 7.28–7.19 (m, 3H, NH , Ar-H), 6.75 (d, J
3.6 Hz, 1H, Ar-H), 4.52 (s, 1H, CH), 4.08 (q, J = 7.1 Hz, 2H, CH ), 2.31
). C NMR (75 MHz, DMSO) δ
171.82, 161.09, 145.84, 141.57, 134.60, 133.82, 130.32, 127.60,
¡
). H NMR (300 MHz,
1
indole-3-carbonitrile (5f). White solid, Yield: 94%, M.P: 247–249 C. IR
◦
2
), 2203 (CN), 1165, 1181 (SO
2
¡
1
1
( max/cm ): 3322 (NH ), 2199 (CN), 1170 (SO ). H NMR (300 MHz,
υ
2
2
7
2
DMSO) δ ¼ 7.98–7.78 (m, 3H, Ar-H), 7.64 (d, J = 8.6 Hz, 1H, Ar-H),
7.45–7.21 (m, 5H, Ar-H), 7.22–7.07 (m, 3H, Ar-H), 6.98 (d, J = 8.7 Hz,
1H, Ar-H), 6.77 (d, J = 3.5 Hz, 1H, Ar-H), 4.88 (s, 1H, CH), 2.29 (s, 3H,
=
2
1
3
(
s, 3H, CH
3
), 1.14 (t, J = 7.1 Hz, 3H, CH
3
1
3
=
CH
3
). C NMR (75 MHz, DMSO) δ = 160.07, 148.33, 145.79, 140.85,
1
26.77, 124.83, 119.75, 119.09, 111.74, 109.52 (CN), 104.56, 61.10
134.02, 133.89, 133.19, 130.67, 130.31, 127.43, 127.23, 126.88,
(
(
CH), 50.67 (CH
2
), 20.98 (CH
3
), 13.96 (CH
3
). MS (ESI) m/z: 438.4
S: C, 60.40; H, 4.38; N,
126.76, 126.32, 125.47, 120.17, 118.98, 116.34, 109.69 (CN), 104.68,
+
+
M+1) . Elemental analysis for C22
19
H N
3
O
5
55.75 (CH), 20.97 (CH
analysis for C25 18ClN
2.98; H, 3.51; N, 8.64.
3
). MS (ESI) m/z: 476.3 (M+1) . Elemental
9
.61; found: C, 60.24; H, 4.20; N, 9.42.
H
3 3
O S: C, 63.09; H, 3.81; N, 8.83; found: C,
6
4
.2.2.2. 2-amino-4-(2-methoxyphenyl)-7-tosyl-4,7-dihydropyrano[2,3-e]
◦
indole-3-carbonitrile (5b). White solid, Yield: 94%, M.P: 266–268 C. IR
4.2.2.7. 2-amino-4-(4-chlorophenyl)-7-tosyl-4,7-dihydropyrano[2,3-e]
¡
1
1
◦
(
υ
max/cm ): 3319 (NH
2
), 2197 (CN), 1185 (SO
2
). H NMR (300 MHz,
indole-3-carbonitrile (5 g). White solid, Yield: 94%, M.P: 283–285 C. IR
¡
1
1
DMSO) δ = 7.83 (t, J = 6.4 Hz, 3H, Ar-H), 7.58 (d, J = 8.6 Hz, 1H, Ar-H),
( max/cm ): 3321 (NH ), 2199 (CN), 1173 (SO ). H NMR (300 MHz,
υ
2
2
7
.34 (d, J = 8.1 Hz, 2H, Ar-H), 7.17 (t, J = 7.2 Hz, 1H, Ar-H), 7.09–6.93
DMSO) δ = 7.96–7.79 (m, 3H, Ar-H), 7.63 (d, J = 8.6 Hz, 1H, Ar-H),
7.48–7.31 (m, 4H, Ar-H), 7.22 (d, J = 8.4 Hz, 2H, Ar-H), 7.08 (s, 2H,
(
m, 5H, NH
2
, Ar-H), 6.88–6.74 (m, 2H, Ar-H), 5.15 (s, 1H, CH), 3.76 (s,
13
3
1
1
1
H, OCH
3
), 2.27 (s, 3H, CH
3
). C NMR (75 MHz, DMSO) δ = 160.59,
NH
2
), 6.94 (d, J = 8.6 Hz, 1H, Ar-H), 6.76 (d, J = 3.6 Hz, 1H, Ar-H), 4.86
56.23, 145.71, 141.13, 133.89, 133.80, 133.57, 130.27, 128.75,
28.12, 127.18, 126.72, 124.99, 120.81, 120.46, 118.86, 117.28,
3
(s, 1H, CH), 2.31 (s, 3H, CH ).
1
3
C NMR (75 MHz, DMSO) δ = 159.93, 145.81, 144.86, 140.82,
11.64, 109.41 (CN), 104.74, 55.67 (CH), 55.43 (OCH
3
), 20.96 (CH
3
).
133.94, 133.88, 131.41, 130.34, 129.40, 128.64, 127.39, 126.77,
125.50, 120.20, 118.95, 116.56, 109.62 (CN), 104.66, 55.95 (CH),
+
MS (ESI) m/z: 472.3 (M+1) . Elemental analysis for C26
21 3 4
H N O
S: C,
+
.
6
6.23; H, 4.49; N, 8.91; found: C, 66.07; H, 4.27; N, 8.23.
20.99 (CH ). MS (ESI) m/z: 475 (M) Elemental analysis for
3 3
18ClN O S: C, 63.09; H, 3.81; N, 8.83; found: C, 63.00; H, 3.04; N,
3
C
25
H
4
.2.2.3. 2-amino-4-(3-methoxyphenyl)-7-tosyl-4,7-dihydropyrano[2,3-e]
8.43.
◦
indole-3-carbonitrile (5c). White solid, Yield: 95%, M.P: 222–224 C. IR
¡
1
1
(
υ
max/cm ): 3301 (NH
2
), 2198 (CN), 1181 (SO
2
). H NMR (300 MHz,
4.2.2.8. 2-amino-4-(3-fluorophenyl)-7-tosyl-4,7-dihydropyrano[2,3-e]
◦
DMSO) δ ¼ 7.84 (dd, J = 5.9, 3.8 Hz, 3H, Ar-H), 7.62 (d, J = 8.6 Hz, 1H,
Ar-H), 7.35 (d, J = 8.2 Hz, 2H, Ar-H), 7.19 (dd, J = 8.8, 7.6 Hz, 1H, Ar-
indole-3-carbonitrile (5 h). White solid, Yield: 95%, M.P: 284–286 C. IR
¡
1
1
( max/cm ): 3321 (NH ), 2205 (CN), 1178 (SO ). H NMR (300 MHz,
υ
2
2
H), 7.07–6.98 (m, 3H, NH
CH), 3.69 (s, 3H, OCH
2
, Ar-H), 6.80–6.72 (m, 4H, Ar-H), 4.78 (s, 1H,
DMSO) δ ¼ 7.98–7.79 (m, 3H, Ar-H), 7.64 (d, J = 8.6 Hz, 1H, Ar-H),
7.34 (dd, J = 11.3, 4.9 Hz, 3H, Ar-H), 7.11 (s, 2H, NH ), 7.07–6.93 (m,
4H, Ar-H), 6.77 (d, J = 3.6 Hz, 1H, Ar-H), 4.88 (s, 1H, CH), 2.29 (s, 3H,
1
3
3
), 2.28 (s, 3H, CH
3
). C NMR (75 MHz, DMSO)
2
δ = 160.01, 159.33, 147.45, 145.76, 140.78, 133.89, 130.30, 129.81,
1
3
1
1
1
27.32, 126.74, 125.53, 120.34, 119.68, 118.93, 116.98, 113.59,
CH
3
). C NMR (75 MHz, DMSO) δ ¼ 162.20 (d,
J
FC = 244.4 Hz),
11.64, 109.51 (CN), 104.70, 56.21 (CH), 54.91 (OCH
3
), 20.96 (CH
3
).
160.08, 148.73, 148.64, 145.82, 140.82, 133.91 (d, 3JFC = 11.0 Hz),
+
130.70 (d, 3
MS (ESI) m/z: 472.0 (M+1) . Elemental analysis for C26
H
21
N
3
O
4
S: C,
J
FC = 8.2 Hz), 130.30, 127.36, 126.74, 125.44, 123.55,
2
2
6
6.23; H, 4.49; N, 8.91; found: C, 66.19; H, 4.21; N, 8.64.
120.22, 119.00, 116.40, 114.14 (d,
J
FC = 21.5 Hz), 113.68 (d, JFC
=
2
1.2 Hz), 109.62 (CN), 104.81, 55.80 (CH), 20.95 (CH
3
). MS (ESI) m/z:
+
4
.2.2.4. 2-amino-4-(4-methoxyphenyl)-7-tosyl-4,7-dihydropyrano[2,3-e]
460.3 (M+1) . Elemental analysis for C25
3 3
H18FN O S: C, 65.35; H,
◦
indole-3-carbonitrile (5d). White solid, Yield: 94%, M.P: 221–223 C. IR
3.95; N, 9.14; found: C, 65.20; H, 3.74; N, 9.09.
¡
1
1
(
υ
max/cm ): 3324 (NH
2 2
), 2200 (CN), 1173 (SO ). H NMR (300 MHz,
DMSO) δ ¼ 7.84 (t, J = 6.3 Hz, 3H, Ar-H), 7.60 (d, J = 8.6 Hz, 1H, Ar-H),
4.2.2.9. 2-amino-4-(4-fluorophenyl)-7-tosyl-4,7-dihydropyrano[2,3-e]
◦
7
.37 (d, J = 8.1 Hz, 2H, Ar-H), 7.10 (d, J = 8.5 Hz, 2H, Ar-H), 7.04–6.90
indole-3-carbonitrile (5i). White solid, Yield: 93%, M.P: 280–282 C. IR
¡
1
1
(
m, 3H, NH
2
, Ar-H), 6.84 (d, J = 8.5 Hz, 2H, Ar-H), 6.76 (d, J = 3.5 Hz,
( max/cm ): 3324 (NH ), 2200 (CN), 1176 (SO ). H NMR (300 MHz,
υ
2
2
1
3
1
H, Ar-H), 4.74 (s, 1H, CH), 3.70 (s, 3H, CH
3
), 2.30 (s, 3H, CH
3
).
C
DMSO) δ = 7.85 (dd, J = 5.6, 4.8 Hz, 3H, Ar-H), 7.62 (d, J = 8.6 Hz, 1H,
Ar-H), 7.37 (d, J = 8.2 Hz, 2H, Ar-H), 7.23 (dd, J = 8.5, 5.6 Hz, 2H, Ar-
NMR (75 MHz, DMSO) δ = 159.76, 158.04, 145.77, 140.71, 138.04,
1
1
33.90, 133.78, 130.32, 128.53, 127.26, 126.75, 125.61, 120.39,
H), 7.12 (d, J = 8.8 Hz, 2H, Ar-H), 7.07 (d, J = 7.8 Hz, 2H, NH
2
), 6.94 (d,
18.90, 117.41, 113.98, 109.46 (CN), 104.70, 56.67 (CH), 54.97
J = 8.6 Hz, 1H, Ar-H), 6.77 (d, J = 3.6 Hz, 1H, Ar-H), 4.85 (s, 1H, CH),
+
1
3
1
(
OCH
3
), 20.99 (CH
3
). MS (ESI) m/z: 472.3 (M+1) . Elemental anal-
2.30 (s, 3H, CH
3
). C NMR (75 MHz, DMSO) δ = 160.99 (d,
J
FC
=
3
ysis for C26
H
21
N
3
O
4
S: C, 66.23; H, 4.49; N, 8.91; found: C, 66.10; H,
246.7 Hz), 159.88, 145.79, 142.11 (d, JFC = 3.0 Hz), 140.80, 133.89,
7