M. Sherafati et al.
Bioorganic Chemistry 109 (2021) 104703
ꢀ
3
8
8
2
1
1
1
1
3
367, 3026, 2224, 1630 cm 1; 1H NMR (301 MHz, DMSO‑d
6
) δ 8.17 –
159.64, 156.37, 149.20, 147.35, 140.09, 136.87, 135.31, 132.92,
131.09, 130.10, 129.15, 128.26, 127.08, 126.63, 120.10, 119.54,
115.13, 114.76, 55.98, 51.69, 46.42, 32.85; EI-MS m/z: 596; Anal Calcd
.09 (m, 2H), 7.89 – 7.79 (m, 2H), 7.58 (d, J = 2.6 Hz, 2H), 7.45 (d, J =
.0 Hz, 1H), 7.21 (d, J = 1.8 Hz, 2H), 7.01 (d, J = 2.3 Hz, 2H), 6.76 (s,
H), 6.51 (s, 1H, C
–
H vinyl), 4.63 (s, 1H, CH), 4.16 (AB-quartet, J =
for C31
4 5
H21ClN O S, C, 62.36; H, 3.55; N, 9.38 found: C, 62.38; H, 3.52;
1
3
5.3 Hz, 2H, S-CH
2
6
). 3.73 (s, 3H, CH3); C NMR (76 MHz, DMSO‑d ) δ
N, 9.34.
69.84, 164.03, 161.34, 161.09, 159.62, 159.18, 155.64, 155.25,
50.07, 147.36, 146.93, 136.55, 135.91, 135.39, 132.99, 129.07,
27.94, 127.12, 120.13, 119.70, 119.27, 114.41, 56.30, 55.48, 47.22,
4.5.7. 2-amino-6-(((3-(4-chlorophenyl)-4-oxo-3,4-dihydroquinazolin-2-
yl)thio)methyl)-8-oxo-4-phenyl-4,8-dihydropyrano[3,2-b]pyran-3-
2.65; EI-MS m/z: 562; Anal Calcd for C31
H
22
N
4
O
5
S, C, 66.18; H, 3.94;
carbonitrile (10G)
◦
N, 9.96 found: C, 66.13; H, 3.95; N, 9.97.
White solid; isolated yield: 92%; mp 222–224 C; IR (KBr,
υ
): 3407,
ꢀ
1 1
3
369, 3022, 2220, 1635 cm ; H NMR (301 MHz, DMSO‑d
6
) δ 8.10 (d,
4
.5.3. 2-amino-4-(4-chlorophenyl)-8-oxo-6-(((4-oxo-3-phenyl-3,4-
J = 7.5 Hz, 1H), 7.86 (t, J = 7.2 Hz, 1H), 7.66 (d, J = 8.1 Hz, 2H), 7.52 (t,
J = 7.5 Hz, 1H), 7.42 (t, J = 8.5 Hz, 3H), 7.32 – 7.23 (m, 5H), 7.17 (d, J
dihydroquinazolin-2-yl)thio)methyl)-4,8-dihydropyrano[3,2-b]pyran-3-
carbonitrile (10C)
= 6.4 Hz, 2H), 6.57 (s, 1H, C H vinyl), 4.78 (s, 1H, CH), 4.30 (s, 2H, S-
–
13
◦
White solid; isolated yield: 92%; mp 188–190 C; IR (KBr,
υ
): 3404,
) δ 8.11 (dd,
J = 7.9, 1.2 Hz, 1H), 7.89 – 7.83 (m, 1H), 7.61 – 7.56 (m, 3H), 7.51 (d, J
2 6
CH ); C NMR (76 MHz, DMSO- d ) δ 169.88, 163.99, 161.06, 159.69,
ꢀ 1 1
3
367, 3020, 2225, 1638 cm ; H NMR (301 MHz, DMSO‑d
6
155.27, 149.81, 147.32, 141.13, 136.78, 135.49, 135.28, 134.81,
131.88, 130.11, 129.19, 128.11, 127.02, 126.76, 126.54, 120.11,
119.68, 114.72, 55.98, 45.79, 32.83; EI-MS m/z: 566; Anal Calcd for
=
8.2 Hz, 1H), 7.44 (d, J = 8.0 Hz, 1H), 7.38 – 7.34 (m, 2H), 7.31 – 7.26
H vinyl), 4.85 (s, 1H, CH),
(
m, 4H), 7.23 – 7.19 (m, 2H), 6.57 (s, 1H, C
–
C
30
4 4
H19ClN O S, C, 63.55; H, 3.38; N, 9.88 found: C, 63.47; H, 3.34; N,
1
3
4
.15 (AB-quartet, J = 16.2 Hz, 2H, S-CH
2 6
); C NMR (76 MHz, DMSO‑d )
9.90.
δ 169.84, 164.12, 161.03, 159.65, 155.66, 149.21, 147.34, 140.07,
1
36.86, 135.91, 135.39, 132.94, 130.51, 130.09, 129.86, 129.14,
4.5.8. 2-amino-6-(((3-(4-chlorophenyl)-4-oxo-3,4-dihydroquinazolin-2-
yl)thio)methyl)-4-(4-methoxyphenyl)-8-oxo-4,8-dihydropyrano[3,2-b]
1
27.13, 126.71, 126.45, 120.10, 119.53, 114.77, 55.63, 47.22, 32.82;
EI-MS m/z: 566; Anal Calcd for C30
H
19ClN
4
O
4
S, C, 63.55; H, 3.38; N,
pyran-3-carbonitrile (10H)
◦
9
.88 found: C, 63.51; H, 3.34; N, 9.86.
White solid; isolated yield: 90%; mp 176–178 C; IR (KBr,
υ
): 3401,
ꢀ 1 1
3
365, 3023, 2224, 1630 cm ; H NMR (301 MHz, DMSO‑d
6
) δ 8.11 (dd,
4
2
.5.4. 2-amino-6-(((3-(4-methoxyphenyl)-4-oxo-3,4-dihydroquinazolin-
-yl)thio)methyl)-8-oxo-4-phenyl-4,8-dihydropyrano[3,2-b]pyran-3-
J = 7.9, 1.2 Hz, 1H), 7.91 – 7.81 (m, 1H), 7.67 – 7.61 (m, 2H), 7.57 –
7.50 (m, 1H), 7.47 – 7.34 (m, 3H), 7.21 – 7.15 (m, 2H), 7.04 (d, J = 8.7
carbonitrile (10D)
White solid; isolated yield: 93%; mp 174–176 C; IR (KBr,
3
8
8
8
Hz, 2H), 6.79 (d, J = 8.7 Hz, 2H), 6.54 (s, 1H, C H vinyl), 4.70 (s, 1H,
–
◦
13
υ
): 3408,
CH), 4.30 (AB-quarted, J = 15.5 Hz, 2H, S-CH
2
), 3.75 (s, 3H, CH3);
C
ꢀ
1 1
362, 3029, 2223, 1630 cm ; H NMR (301 MHz, DMSO‑d
6
) δ 8.13 –
NMR (76 MHz, DMSO- d ) δ 169.88, 164.01, 161.05, 159.51, 159.17,
6
.05 (m, 1H), 7.88 – 7.79 (m, 1H), 7.51 (t, J = 7.6 Hz, 1H), 7.43 (d, J =
.1 Hz, 1H), 7.34 – 7.20 (m, 7H), 7.16 (d, J = 6.4 Hz, 2H), 7.09 (d, J =
155.26, 150.05, 147.32, 136.58, 135.46, 135.27, 134.83, 133.19,
131.80, 130.07, 129.25, 127.03, 126.78, 126.51, 120.09, 119.70,
114.45, 56.32, 55.50, 46.72, 32.74; EI-MS m/z: 596; Anal Calcd for
.9 Hz, 2H), 6.56 (s, 1H, C H vinyl), 4.77 (s, 1H, CH), 4.27 (AB-quartet,
–
1
3
J = 15.2 Hz, 2H, S-CH
2
), 3.86 (s, 3H, CH
3
); C NMR (76 MHz, DMSO‑d
6
)
C
31
4 5
H21ClN O S, C, 62.36; H, 3.55; N, 9.38 found: C, 62.33; H, 3.52; N,
δ 169.88, 164.23, 161.28, 160.62, 159.70, 156.35, 149.79, 147.37,
9.32.
1
1
3
41.14, 136.77, 135.34, 131.03, 129.18, 128.25, 128.10, 127.03,
26.62, 126.48, 120.13, 119.69, 115.12, 114.65, 62.28, 55.99, 45.08,
4.5.9. 2-amino-4-(4-chlorophenyl)-6-(((3-(4-chlorophenyl)-4-oxo-3,4-
dihydroquinazolin-2-yl)thio)methyl)-8-oxo-4,8-dihydropyrano[3,2-b]
22 4 5
2.86; EI-MS m/z: 562; Anal Calcd for C31H N O S, C, 66.18; H, 3.94;
N, 9.96 found: C, 66.12; H, 3.96; N, 9.90.
pyran-3-carbonitrile (10I)
◦
White solid; isolated yield: 96%; mp 201–203 C; IR (KBr,
3368, 3027, 2220, 1637 cm ; H NMR (301 MHz, DMSO‑d
υ
): 3408,
ꢀ 1 1
4
3
.5.5. 2-amino-4-(4-methoxyphenyl)-6-(((3-(4-methoxyphenyl)-4-oxo-
,4-dihydroquinazolin-2-yl)thio)methyl)-8-oxo-4,8-dihydropyrano[3,2-b]
6
) δ 8.11 (dd,
J = 7.9, 1.2 Hz, 1H), 7.91 – 7.83 (m, 1H), 7.70 – 7.63 (m, 2H), 7.57 –
7.50 (m, 1H), 7.48 – 7.41 (m, 3H), 7.35 – 7.25 (m, 4H), 7.22 (d, J = 8.5
pyran-3-carbonitrile (10E)
White solid; isolated yield: 89%; mp 181–183 C; IR (KBr,
◦
υ
): 3404,
) δ 8.11 (dd,
J = 7.9, 1.1 Hz, 1H), 7.89 – 7.80 (m, 1H), 7.57 – 7.49 (m, 1H), 7.45 (d, J
8.1 Hz, 1H), 7.27 – 7.15 (m, 4H), 7.11 – 7.00 (m, 4H), 6.77 (d, J = 8.7
Hz, 2H), 6.53 (s, 1H, C H vinyl), 4.69 (s, 1H, CH), 4.28 (AB-quartet, J
15.4 Hz, 2H, , S-CH ), 3.86 (s, 3H, CH3), 3.74 (s, 3H, CH3); C NMR
76 MHz, DMSO- d ) δ 169.88, 164.24, 161.28, 160.63, 159.52, 159.17,
Hz, 2H), 6.57 (s, 1H, C H vinyl), 4.86 (s, 1H, CH), 4.29 (AB-quartet, J
–
13
ꢀ 1
1
3
367, 3025, 2229, 1639 cm ; H NMR (301 MHz, DMSO‑d
6
= 15.4 Hz, 2H, S-CH
2 6
); C NMR (76 MHz, DMSO‑d ) δ 169.84, 163.99,
161.01, 159.64, 155.29, 149.22, 147.30, 140.09, 136.88, 135.46,
135.29, 134.84, 132.92, 131.91, 130.12, 129.16, 127.07, 126.77,
126.48, 120.07, 119.53, 114.82, 55.64, 46.47, 32.81; EI-MS m/z: 600;
=
–
1
3
=
2
Anal Calcd for C30
2 4 4
H18Cl N O S, C, 59.91; H, 3.02; N, 9.32 found: C,
(
6
59.98; H, 3.01; N, 9.32.
1
1
5
56.34, 150.03, 147.38, 136.56, 135.31, 133.17, 131.08, 130.97,
29.23, 128.26, 127.04, 126.46, 120.13, 119.71, 115.07, 114.43, 55.96,
5.47, 51.09, 46.74, 32.78; EI-MS m/z: 592; Anal Calcd for
4.5.10. 2-amino-6-(((3-benzyl-4-oxo-3,4-dihydroquinazolin-2-yl)thio)
methyl)-8-oxo-4-phenyl-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile
C
32
H
24
4
N O
6
S, C, 64.85; H, 4.08; N, 9.45 found: C, 64.78; H, 4.12; N,
(10J)
◦
9
.44.
White solid; isolated yield: 91%; mp 198–200 C; IR (KBr,
υ
): 3407,
ꢀ 1 1
3
367, 3026, 2229, 1639 cm ; H NMR (301 MHz, DMSO‑d
6
) δ 8.11 (dd,
4
.5.6. 2-amino-4-(4-chlorophenyl)-6-(((3-(4-methoxyphenyl)-4-oxo-3,4-
J = 7.9, 1.2 Hz, 1H), 7.86 (td, J = 8.5, 8.0, 1.5 Hz, 1H), 7.59 – 7.55 (m,
3H), 7.51 (d, J = 8.0 Hz, 1H), 7.44 (d, J = 8.1 Hz, 1H), 7.34 – 7.22 (m,
dihydroquinazolin-2-yl)thio)methyl)-8-oxo-4,8-dihydropyrano[3,2-b]
pyran-3-carbonitrile (10F)
7H), 7.15 (dd, J = 7.9, 1.5 Hz, 2H), 6.56 (s, 1H, C H vinyl), 5.40 (AB-
–
◦
White solid; isolated yield: 90%; mp 170–172 C; IR (KBr,
υ
): 3407,
quartet, J = 12.5 Hz, 2H, N-CH2-Ph), 4.78 (s, 1H, CH), 4.28 (AB-quartet,
13
ꢀ 1
1
3
365, 3026, 2228, 1639 cm ; H NMR (301 MHz, DMSO‑d
6
) δ 8.11 (d,
J = 15.4 Hz, 2H, S-CH
2 6
); C NMR (76 MHz, DMSO‑d ) δ 169.86, 164.16,
J = 7.9 Hz, 1H), 7.85 (t, J = 7.7 Hz, 1H), 7.52 (t, J = 7.5 Hz, 1H), 7.43 (d,
J = 8.2 Hz, 1H), 7.36 – 7.18 (m, 8H), 7.10 (d, J = 8.8 Hz, 2H), 6.57 (s,
161.08, 159.68, 155.64, 149.80, 147.35, 141.13, 136.77, 135.89,
135.43, 130.48, 129.98, 129.81, 129.17, 128.09, 127.02, 126.71,
126.51, 120.14, 119.67, 114.67, 55.98, 48.12, 45.39, 32.79; EI-MS m/z:
1
2 3
H, C H vinyl), 4.86 (s, 1H, CH), 4.27 (s, 2H, S-CH ), 3.87 (s, 3H, CH );
–
1
3
C NMR (76 MHz, DMSO- d
6
) δ 169.84, 164.20, 161.22, 160.64,
22 4 4
546; Anal Calcd for C31H N O S, C, 68.12; H, 4.06; N, 10.25 found: C,
8