S.K. Konidala, et al.
BioorganicChemistry104(2020)104207
(KBr, cm−1): v 3370(OeH), 3281(NeH), 2943(CeH Ar), 2870(CeH),
1735(C]O), 1613, 1474 (C]C); 1572, 1350 (NeO), 1257 (CeO),
751(p-sub); 1H NMR (400 MHz, DMSO‑d6, δ/ppm): 1.39 (t,3H, CH),
2.26 (s, 3H, CH), 4.02 (q, 2H, CH), 5.20 (s, H CHeAr), 6.87–7.52 (m,
9H, Ar), 8.20 (d, 2H, CH]CH), 9.48 (s, H, OH). 13C NMR (100 MHz,
DMSO‑d6) δ/ppm: 15.6 (CH3), 21.3 (CH3), 44.7 (CeH, Ar), 60.3 (CH2),
98.4,104.8, 117.6, 121.1, 124.5, 125.7, 126.5, 127.6, 128.4, 148.5
(AreC), 147.5 160.7 (CeN), 152.4 (C]C), 159.9 (C]O), 160.4 (CeN),
167.2 (C]O), 174.3 (C]S), 179.8 (CeOH), 183.8 (C]O). MS (m/z,
(relative abundance, %)): 536 (M+1, 10), 414 (52), 337 (100), 200
(37), 123 (46).
chromen-8-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-
carboxylate (DPCT 11). Greenish white solid; yield 59.45%; m.p.
236–238 °C; IR (KBr, cm−1): v 3458(OeH), 3128(NeH), 2929 (CeH
Ar), 2863(CeH), 1746(C]O), 1602, 1475 (C]C); 1568, 1347 (NeO),
1257 (CeO), 765 (m-sub); 1H NMR (400 MHz, DMSO‑d6, δ/ppm): 1.31
(t, 3H, CH), 2.30 (s, 3H, CH), 4.22 (q, 2H, CH), 5.25 (s, H, CH, Ar),
6.79–7.68 (m, 9H, Ar), 8.30 (d, 2H, CH]CH), 9.45 (s, H, OH). 13C NMR
(100 MHz, DMSO‑d6) δ/ppm: 14.9 (CH3), 19.6 (CH3), 45.2 (CeH, Ar),
60.9 (CH2), 98.7, 104.8, 117.6, 120.3, 121.7, 124.8, 125.2, 126.2,
128.8, 129.4, 132.7, 136.6, (AreC), 148.7 (C-NO2), 152.9 (C]C),
159.1 (C]O), 160.8 (CeN), 167.5 (C]O), 174.7 (C]S), 179.1 (CeO),
183.7 (C]O). MS (m/z, (relative abundance, %)): 536 (M+1, 12), 414
(55), 337 (100), 184 (67), 123 (28).
Ethyl 4-(3-(3-(4-chlorophenyl) acryloyl)-4-hydroxy-2-oxo-2H-
chromen-8-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-
carboxylate (DPCT 7). Golden yellow solid; yield 56.75%; m.p.
170–172 °C; IR (KBr, cm−1): v 3394(OeH), 3010(NeH), 2938 (CeH
Ar), 2841(CeH), 1738(C]O), 1601, 1474 (C]C); 1286 (CeO), 755 (p-
sub); 1H NMR (400 MHz, DMSO‑d6, δ/ppm): 1.06 (t, 3H, CH), 2.39 (s,
3H, CH), 4.37 (q, 2H, CH), 5.41 (s, H, CH, Ar), 6.83–7.37 (m, 9H, Ar),
7.85 (d, 2H, CH]CH), 9.44 (s, H, OH). 13C NMR (100 MHz, DMSO‑d6)
δ/ppm: 14.7 (CH3), 19.6 (CH3), 44.3 (CeH, Ar), 61.7 (CH2), 98.6,104.5,
117.9, 124.4, 125.7, 126.3, 127.4, 128.7, 148.1 (AreC), 133.7 (CeCl),
152.7 (C]C), 159.6 (C]O), 160.8 (CeN), 167.8 (C]O), 174.8 (C]S),
179.2 (CeOH), 183.7 (C]O). MS (m/z, (relative abundance, %)): 525
(M+1, 6), 414 (33), 326 (100), 200 (58), 112 (27).
Ethyl 4-(3-(3-(2-chlorophenyl) acryloyl)-4-hydroxy-2-oxo-2H-
chromen-8-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-
carboxylate (DPCT 12). Brown crystals; yield 58.72%; m.p.
171–173 °C; IR (KBr, cm−1): v 3369(OeH), 3249(NeH), 2939(CeH
Ar), 2865(CeH), 1732(C]O), 1600, 1474 (C]C); 1281 (CeO), 765(o-
sub); 1H NMR (400 MHz, DMSO‑d6, δ/ppm): 1.42 (t, 3H, CH), 2.27 (s,
3H, CH), 4.33 (q, 2H, CH), 5.03 (s, H, CH, Ar), 6.88–7.39 (m, 9H, Ar),
7.63 (d, 2H, CH]CH), 9.41 (s, H, OH). 13C NMR (100 MHz, DMSO‑d6)
δ/ppm: 15.8 (CH3), 19.4 (CH3), 45.2 (CeH, Ar), 61.9 (CH2), 98.3,
104.8, 117.2, 124.1, 125.4, 126.7, 127.1, 128.8, 129.7, 131.2, 133.9,
148.5 (AreC), 152.3 (C]C), 159.3 (C]O), 160.7 (CeN), 167.8 (C]O),
174.7 (C]S), 179.8 (CeO), 183.7 (C]O). MS (m/z, (relative abun-
dance, %)): 526 (M+2, 13), 414 (38), 326 (100), 200 (69), 112 (48).
Ethyl 4-(3-(3-(4-(dimethylamino) phenyl)acryloyl)-4-hydroxy-2-
oxo-2H-chromen-8-yl)-6-methyl-2-thioxo-1,2,3,4-tetra-
hydropyrimidine-5-carboxylate (DPCT 8). Dark brown solid; yield
71.37%; m.p. 191–193 °C; IR (KBr, cm−1): v 3400(OeH), 3281(NeH),
3003 (CeH Ar), 2927(CeH), 1739(C]O), 1615, 1475 (C]C); 1281
(CeO), 1167 (CeN), 764 (p-sub); 1H NMR (400 MHz, DMSO‑d6, δ/
ppm): 1.22 (t, 3H, CH), 2.21 (s, 3H, CH), 2.88 (s, 6H, CH), 4.21 (q, 2H,
CH), 5.17 (s, H, CH), 6.50–7.28 (m, 9H, Ar), 7.88 (d, 2H, CH]CH),
9.51 (s, H, OH). 13C NMR (100 MHz, DMSO‑d6) δ/ppm: 15.6 (CH3),
20.3 (CH3), 40.7 (NeCH3), 45.7 (CeH, Ar), 61.6 (CH2), 98.2,104.1,
114.6, 117.2, 124.6, 125.4, 126.5, 127.8, 128.3, (AreC), 148.4, 160.4
(CeN), 152.3 (C]C), 159.8 (C]C), 167.5 (C]O), 174.3 (C]S), 179.1
Ethyl
4-(4-hydroxy-2-oxo-3-(3-(3,4,5-trimethoxyphenyl)acry-
loyl)-2H-chromen-8-yl)-6-methyl-2-thioxo-1,2,3,4-tetra-
hydropyrimidine-5-carboxylate (DPCT 13). Brick red solid; yield
70.33%; m.p. 263–265 °C; IR (KBr, cm−1): v 3356(OeH), 3216(NeH),
2939 (CeH Ar), 2839(CeH), 1735(C]O), 1610, 1474 (C]C); 1281
(CeO), 755 (3,4,5-sub); 1H NMR (400 MHz, DMSO‑d6, δ/ppm): 1.36 (t,
3H, CH), 2.32 (s, 3H, CH),3.88 (s, 9H, CH), 4.34 (q, 2H, CH), 4.91 (s, H,
CH), 6.15–7.10 (m, 7H, Ar), 7.68 (d, 2H, CH]CH), 9.72 (s, H, OH). 13
C
NMR (100 MHz, DMSO‑d6) δ/ppm: 16.4 (CH3), 20.3 (CH3), 44.8 (CeH,
Ar), 56.9 (OeCH3), 61.6 (CH2), 98.7, 103.1, 104.3, 106.5, 117.2, 124.5,
125.8, 126.2, 128.2, 138.1, 148.6, 149.9 (AreC), 150.5 (C-OCH3),
152.3 (C]C), 159.9 (C]O), 160.3 (CeN), 167.5 (C]O), 174.9 (C]S),
179.7 (CeO), 183.1 (C]O). MS (m/z, (relative abundance, %)): 581
(M + 1, 9), 414 (48), 382 (100), 200 (23), 168 (15).
(CeOH), 183.8 (C]O). MS (m/z, (relative abundance, %)): 534 (M+1
,
11), 414 (54), 335 (100), 200 (19), 121 (61).
Ethyl 4-(4-hydroxy-3-(3-(2-hydroxyphenyl) acryloyl)-2-oxo-2H-
chromen-8-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-
carboxylate (DPCT 9). Orange solid; yield 58.56%; m.p. 208–210 °C;
5-cinnamoyl-4-(4-hydroxy-2-oxo-2H-chromen-8-yl)-6-methyl-
3,4,dihydropyrimidin2(1H)-one (DCCU 1). The was found to be
Yellow solid; yield 65.41%; m.p. 153–155 °C; IR (KBr, cm−1): v
3479(NeH), 3370(OeH), 3060 (CeH Ar), 2925(CeH), 1734(C]O),
1671(C]O), 1601, 1471 (C]C), 1282, 1056 (CeOeC); 1H NMR
(400 MHz, DMSO‑d6, δ/ppm): 2.50(s, 3H, CH), 4.95(s, H, CH), 6.9 (s,
2H, NH) 7.42–7.65 (m, 9H, aromatic), 8.32 (d, 2H, HC]CH), 9.11(s, H,
OH). 13C NMR (100 MHz, DMSO‑d6) δ/ppm: 17.7 (CH3), 42.5(CeCH),
117.4, 121.3, 125.2, 126.5, 127.9, 128.4, 128.5, 128.6, 135.2, 148.3,
154.8 (AreC), 193.3 (C]O), 150.2 (C]O), 162.2 (C]O), 166.1(CeO),
142.2 (C]C). MS (m/z, (relative abundance, %)): 403 (M+1, 25.6), 271
(47), 243 (100), 162 (54), 132 (36).
IR (KBr, cm−1):
v 3426(OeH), 3104(NeH), 2934 (CeH Ar),
2867(CeH), 1737(C]O), 1611, 1474 (C]C); 1287 (CeO), 751(o-
sub);1H NMR (400 MHz, DMSO‑d6, δ/ppm): 1.24 (t, 3H, CH), 2.18 (s,
3H, CH), 4.22 (q, 2H, CH), 5.08 (s, H, CH, Ar), 5.52 (s, H, OH),
6.55–7.31 (m, 9H, Ar), 8.02 (d, 2H, CH]CH), 10.13 (s, H, OH). 13C
NMR (100 MHz, DMSO‑d6) δ/ppm: 16.3 (CH3), 20.9 (CH3), 45.2 (CeH,
Ar), 61.3 (CH2), 98.3, 104.7, 115.3, 116.9, 117.7, 121.8, 124.2, 125.1,
126.9, 128.8, 148.2 (AreC), 152.7 (C]C), 159.7 (C]O), 167.4 (C]O),
178.8 (CeO), 183.1 (C]O). MS (m/z, (relative abundance, %)): 507
(M+1, 7), 414 (59), 308 (100), 200 (20), 94 (35).
Ethyl 4-(4-hydroxy-3-(3-(3-hydroxyphenyl) acryloyl)-2-oxo-2H-
chromen-8-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-
carboxylate (DPCT 10). Yellow solid; yield 62.37%; m.p. 206–208 °C;
4-(4-hydroxy-2-oxo-2H-chromen-8-yl)-5-(3-(4-methoxyphenyl)
acryloyl)-6-methyl-3,4-dihydropyrimidin2(1H)-one (DCCU 2). Dark
red solid; yield 62.76%; m.p. 168–170 °C; IR (KBr, cm−1): v
3436(NeH), 3362(OeH), 2928 (CeH Ar), 2840(CeH), 1732(C]O),
1665(C]O), 1611, 1474 (C]C), 1252, 1054 (CeOeC), 830 (o-sub); 1H
NMR (400 MHz, DMSO‑d6, δ/ppm): 2.54(s, 3H, CH), 3.78 (s, 3H, CH),
4.91(s, H, CH), 6.9 (s, 2H, NH), 7.34–7.84 (m, 8H, aromatic), 8.37 (d,
2H, HC]CH), 9.11(s, H, OH). 13C NMR (100 MHz, DMSO‑d6) δ/ppm:
17.9 (CH3), 42.2(CeCH), 54.3(CH), 91.4, 114.4, 117.6, 118.2, 121.1,
123.7, 125.6, 126.1, 127.3, 128.7, 130.4, 154.3, 159.2 (AreC), 193.5
(C]O), 150.4 (C]O), 162.6 (C]O), 166.5(CeO), 142.6 (C]C). MS
(m/z, (relative abundance, %): 433 (M+1, 26.4), 327 (100), 272 (36),
162 (28), 108 (57).
IR (KBr, cm−1):
v 3346(OeH), 3219(NeH), 2939 (CeH Ar),
2885(CeH), 1731(C]O), 1611, 1474 (C]C); 1251 (CeO), 757(o-sub);
1H NMR (400 MHz, DMSO‑d6, δ/ppm): 1.28 (t, 3H, CH), 2.20 (s, 3H,
CH), 4.27 (q, 2H, CH), 4.69 (s, H, OH), 5.37 (s, H, CH, Ar), 6.51–7.10
(m, 9H, Ar), 7.86 (d, 2H, CH]CH), 9.69 (s, H, OH). 13C NMR
(100 MHz, DMSO‑d6) δ/ppm: 16.5 (CH3), 20.6 (CH3), 44.8 (CeH, Ar),
60.7 (CH2), 98.1, 104.2, 112.9, 115.8, 117.1, 119.2, 124.2, 125.8,
126.9, 128.2, 148.8 (AreC), 152.3 (C]C), 158.2 (CeO), 159.8 (C]O),
160.7 (CeN), 167.8 (C]O), 174.8 (C]S), 179.1 (CeO), 183.7 (C]O).
MS (m/z, (relative abundance, %)): 507 (M+1, 6), 414 (63), 308 (100),
200 (26), 94 (44).
Ethyl 4-(4-hydroxy-3-(3-(3-nitrophenyl) acryloyl)-2-oxo-2H-
4-(4-hydroxy-2-oxo-2H-chromen-8-yl)-6-methyl-5-(5-
7