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Table 2 Spectral characteristics of the synthesized compounds

From: Synthesis, molecular docking and biological potentials of new 2-(4-(2-chloroacetyl) piperazin-1-yl)-N-(2-(4-chlorophenyl)-4-oxoquinazolin-3(4H)-yl)acetamide derivatives

Compd. no. IUPAC nomenclature IR (KBr pellets, cm−1) 1H-NMR and 13C–NMR (DMSO δ, ppm) C, H, N analysis and MS
1. N-(2-(4-Chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-(4-(2-(p-tolyl-amino)acetyl)piperazin-1-yl)acetamide IR: 1669 (C=O str., CONH2), 3214 (N–H str., 2° NH2), 1469 (N–N str.), 1250 (C–N str.), 3067 (C–H str., Ar), 1590 (C=C str., Ar), 1634 (C= N str., Ar), 2920 (C–H str., R-CO–CH2), 725 (C–Cl str., Ar–Cl), 2853 (C–H sym str., Ar-CH3) 1H-NMR: 7.38–8.05 (m, 12H, ArH), 8.19 (s, 1H, N–NH), 4.15 (d, 2H, CH2), 2.38 (s, 3H CH3), 3.32 (t, 4H, CH2 of piperazine), 2.63 (t, 4H, CH2 of piperazine); 13C–NMR: 170.2, 164.6, 164.2, 161.4, 151.7, 149.3, 135.6, 135.4, 133.1, 131.2, 129.3, 129.5, 128.8, 127.4, 127.2, 126.6, 122.5, 120.5, 117.5, 113.6, 111.7, 58.5, 53.5, 52.7, 52.5, 46.9, 46.5 Anal cal. C, 63.91; H, 5.36; N, 15.42; Found: C, 63.94; H, 5.32; N, 15.40; MS ES+ (ToF): m/z 546 [M+ + 1]
2. N-(2-(4-Chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-(4-(2-((3-chloro-phenyl)amino)acetyl)- piperazin-1-yl)acetamide IR: 1668 (C=O str., CONH2), 3213 (N–H str., 2° NH2), 1468 (N–N str.), 1252 (C–N str.), 3067 (C–H str., Ar), 1591 (C=C str., Ar), 1632 (C= N str., Ar), 2957 (C–H str., R-CO–CH2), 1727 (C=O str., Ar-ketone), 726 (C–Cl str., Ar–Cl) 1H-NMR: 6.55–7.86 (m, 12H, ArH), 8.19 (s, 1H, N–NH), 4.15 (d, 2H, CH2), 3.33 (t, 4H, CH2 of piperazine), 2.64 (t, 4H, CH2 of piperazine); 13C–NMR: 170.0, 164.6, 164.3, 161.3, 151.0, 145.5, 135.5, 133.5, 129.9, 129.8, 129.6, 129.5, 128.7, 127.1, 127.2, 127.3, 126.2, 122.7, 122.4, 120.9, 114.6, 58.6, 53.4, 52.1, 52.0, 46.9, 46.7 Anal cal. C, 59.47; H, 4.63; N, 14.86; Found: C, 59.49; H, 4.67; N, 14.83; MS ES+ (ToF): m/z 566 [M+ + 1]
3. N-(2-(4-Chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-(4-(2-(m-tolyl-amino)acetyl)piperazin-1-yl)acetamide IR: 1669 (C=O str., CONH2), 3214 (N–H str., 2° NH2), 1467 (N–N str.), 1272 (C–N str.), 3068 (C–H str., Ar), 1592 (C=C str., Ar), 1632 (C= N str., Ar), 2958 (C–H str., R-CO–CH2), 1726 (C=O str., Ar-ketone), 727 (C–Cl str., Ar–Cl), 2863 (C–H sym str., Ar-CH3) 1H-NMR: 7.00–7.74 (m, 11H, ArH), 8.19 (s, 1H, N–NH), 4.15 (d, 2H, CH2), 3.34 (t, 4H, CH2 of piperazine), 2.63 (t, 4H, CH2 of piperazine), 2.36 (s, 3H, CH3); 13C–NMR: 170.2, 164.7, 164.6, 161.0, 151.1, 136.7, 136.6, 135.3, 133.4, 129.6, 129.2, 128.6, 127.4, 127.2, 127.1, 127.0, 126.1, 122.0, 120.7, 116.5, 114.4, 114.0, 58.8, 53.6, 52.4, 52.3, 46.8, 46.7, 15.6 Anal cal. C, 63.91; H, 5.36; N, 15.42; Found: C, 63.95; H, 5.40; N, 15.48; MS ES+ (ToF): m/z 545 [M+ + 1]
4. N-(2-(4-Chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-(4-(2-((3,5-dimethylphenyl)amino)-acetyl)piperazin-1-yl)acetamide IR: 1669 (C=O str., CONH2), 3213 (N–H str., 2° NH2), 1467 (N–N str.), 1253 (C–N str.), 3066 (C–H str., Ar), 1588 (C=C str., Ar), 1634 (C= N str., Ar), 2957 (C–H str., R-CO–CH2), 1726 (C=O str., Ar-ketone), 725 (C–Cl str., Ar–Cl), 2862 (C–H sym str., Ar-CH3) 1H-NMR: 7.55–7.86 (m, 11H, ArH), 8.19 (s, 1H, N–NH), 4.16 (d, 2H, CH2), 3.30 (t, 4H, CH2 of piperazine), 2.65 (t, 4H, CH2 of piperazine), 2.37 (s, 3H, CH3); 13C–NMR: 170.3, 164.9, 164.7, 161.2, 151.4, 143.4, 135.4, 133.3, 131.5, 129.7, 129.3, 128.3, 127.3, 127.0, 126.8, 126.6, 126.4, 126.3, 122.2, 120.4, 113.5, 58.9, 53.8, 52.1, 52.0, 46.9, 46.4, 24.7, 15.6 Anal cal. C, 64.45; H, 5.59; N, 15.03; Found: C, 64.47; H, 5.56; N, 15.05; MS ES+ (ToF): m/z 560 [M+ + 1]
5. N-(2-(4-Chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-(4-(2-((3,4-dichlorophenyl)-amino)acetyl)piperazin-1-yl)acetamide IR: 1665 (C=O str., CONH2), 3216 (N–H str., 2° NH2), 1463 (N–N str.), 1252 (C–N str.), 3056 (C–H str., Ar), 1591 (C=C str., Ar), 1611 (C= N str., Ar), 2923 (C–H str., R-CO–CH2), 1709 (C=O str., Ar-ketone), 724 (C–Cl str., Ar–Cl) 1H-NMR: 6.72–7.86 (m, 11H, ArH), 8.19 (s, 1H, N–NH), 4.15 (d, 2H, CH2), 3.32 (t, 4H, CH2 of piperazine), 2.64 (t, 4H, CH2 of piperazine); 13C–NMR: 170.5, 164.9, 164.7, 161.5, 151.3, 145.6, 135.0, 134.3, 133.2, 129.8, 129.4, 129.2, 128.5, 127.5, 127.1, 126.6, 123.2, 122.5, 120.7, 118.9, 113.1, 58.8, 52.8, 52.4, 46.3, 46.8 Anal cal. C, 56.06; H, 4.20; N, 14.01; Found: C, 56.06; H, 4.20; N, 14.01; MS ES+ (ToF): m/z 600 [M+ + 1]
6. N-(2-(4-Chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-(4-(2-((3-methyl-4-nitrophenyl)-amino)acetyl)piperazin-1-yl)acetamide IR: 1669 (C=O str., CONH2), 3211 (N–H str., 2° NH2), 1474 (N–N str.), 1251 (C–N str.), 1590 (C=C str., Ar), 1634 (C= N str., Ar), 2928 (C–H str., R-CO–CH2), 1729 (C=O str., Ar-ketone), 725 (C–Cl str., Ar–Cl), 2862 (C–H sym str., Ar-CH3), 1559 (NO2 asym str.) 1H-NMR: 6.45–8.05 (m, 11H, ArH), 8.19 (s, 1H, N–NH), 4.15 (d, 2H, CH2), 3.33 (t, 4H, CH2 of piperazine), 2.63 (t, 4H, CH2 of piperazine), 3.54 (s, 3H, OCH3); 13C–NMR: 170.6, 164.6, 164.4, 161.1, 152.7, 151.5, 136.8, 135.2, 133.4, 129.6, 129.4, 128.3, 127.4, 127.3, 126.3, 125.2, 122.7, 120.9, 118.6, 114.5, 58.5, 53.5, 52.5, 46.9, 46.0, 52.5, 14.3 Anal cal. C, 57.47; H, 4.66; N, 16.18; Found: C, 57.46; H, 4.68; N, 16.19; MS ES+ (ToF): m/z 591 [M+ + 1]
7. N-(2-(4-Chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-(4-(2-((3-nitrophenyl)amino)-acetyl)piperazin-1-yl)acetamide IR: 1668 (C=O str., CONH2), 3213 (N–H str., 2° NH2), 1467 (N–N str.), 1253 (C–N str.), 3066 (C–H str., Ar), 1588 (C=C str., Ar), 1632 (C= N str., Ar), 2958 (C–H str., R-CO–CH2), 1727 (C=O str., Ar-ketone), 725 (C–Cl str., Ar–Cl), 1558 (NO2 asym str.) 1H-NMR: 6.73–7.85 (m, 12H, ArH), 8.19 (s, 1H, N–NH), 4.16(d, 2H, CH2), 3.32 (t, 4H, CH2 of piperazine), 2.63 (t, 4H, CH2 of piperazine); 13C–NMR: 170.5, 164.5, 164.2, 161.0, 151.6, 149.4, 148.3, 135.5, 133.5, 130.8, 129.3, 129.0, 128.5, 127.6, 127.2, 127.1, 126.3, 122.8, 120.7, 119.4, 107.6, 109.7, 58.3, 53.0, 52.6, 52.3, 46.8, 46.2 Anal cal. C, 58.39; H, 4.55; N, 17.02; Found: C, 58.42; H, 4.56; N, 17.01; MS ES+ (ToF): m/z 577 [M+ + 1]
8. N-(2-(4-Chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-(4-(2-((4-chlorophenyl)amino)- acetyl)-piperazin-1-yl)acetamide IR: 1667 (C=O str., CONH2), 3214 (N–H str., 2° NH2), 1469 (N–N str.), 1250 (C–N str.), 3067 (C–H str., Ar), 1592 (C=C str., Ar), 1630 (C= N str., Ar), 2958 (C–H str., R-CO–CH2), 1720 (C=O str., Ar-ketone), 725 (C–Cl str., Ar–Cl), 2862 (C–H sym str., Ar-CH3) 1H-NMR: 6.09–8.03 (m, 12H, ArH), 8.19 (s, 1H, N–NH), 4.15 (d, 2H, CH2), 3.31 (t, 4H, CH2 of piperazine), 2.66 (t, 4H, CH2 of piperazine); 13C–NMR: 170.2, 164.6, 164.2, 161.4, 151.7, 149.3, 135.6, 135.4, 131.2, 133.1, 129.5, 129.3, 128.8, 127.4, 127.2, 126.6, 122.5, 120.5, 117.5, 113.6, 111.7, 58.5, 52.7, 52.5, 53.5, 46.9, 46.5 Anal cal. C, 59.47; H, 4.63; N, 14.86; Found: C, 59.43; H, 4.68; N, 14.88; MS ES+ (ToF): m/z 565 [M+ + 1]
9. N-(2-(4-Chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-(4-(2-((2-methyl-5-nitrophenyl) amino)-acetyl)piperazin-1-yl)acetamide IR: 1668 (C=O str., CONH2), 3213 (N–H str., 2° NH2), 1468 (N–N str.), 3068 (C–H str., Ar), 1589 (C=C str., Ar), 1631 (C= N str., Ar), 2957 (C–H str., R-CO–CH2), 1726 (C=O str., Ar-ketone), 725 (C–Cl str., Ar–Cl), 1252 (C–N str., piperazine), 1558 (NO2 asym str.) 1H-NMR: 7.16–7.74 (m, 11H, ArH), 8.19 (s, 1H, N–NH), 4.15(d, 2H, CH2), 3.33 (t, 4H, CH2 of piperazine), 2.63 (t, 4H, CH2 of piperazine), 2.38 (s, 3H, CH3); 13C–NMR: 170.5, 164.4, 164.0, 161.2, 151.6, 147.5, 146.5, 135.7, 133.0, 132.6, 130.9, 129.6, 129.5, 128.5, 127.6, 127.5, 127.1, 126.9, 122.4, 120.3, 109.7, 107.5, 58.7, 53.4, 52.9, 52.6, 46.8, 46.6, 15.7 Anal cal. C, 59.03; H, 4.78; N, 16.62; Found: C, 59.01; H, 4.74; N, 16.60; MS ES+ (ToF): m/z 591 [M+ + 1]
10. N-(2-(4-Chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-(4-(2-((4-methoxyphenyl) amino)acetyl)-piperazin-1-yl)-acetamide IR: 1670 (C=O str., CONH2), 3215 (N–H str., 2° NH2), 1470 (N–N str.), 1250 (C–N str.), 3065 (C–H str., Ar), 1591 (C=C str., Ar), 1635 (C= N str., Ar), 1776 (C=O str., Ar-ketone), 725 (C–Cl str., Ar–Cl), 2892 (C–H str., R-CO–CH2), 1195 (C–O–C str., Ar–O–CH3) 1H-NMR: 7.55–7.88 (m, 12H, ArH), 8.19 (s, 1H, N–NH), 4.15(d, 2H, CH2), 3.33 (t, 4H, CH2 of piperazine), 2.64 (t, 4H, CH2 of piperazine), 3.71 (s, 3H, OCH3); 13C–NMR: 170.5, 164.3, 161.2, 151.5, 149.4, 139.7, 135.9, 133.4, 129.4, 129.3, 128.7, 127.8, 127.7, 127.6, 126.6, 122.7, 120.8, 115.3, 115.2, 114.7, 114.6, 58.9, 55.4, 53.6, 52.7, 52.5, 46.7, 46.6 Anal cal. C, 62.08; H, 5.21; N, 14.98; Found: C, 62.09; H, 5.25; N, 14.99; MS ES+ (ToF): m/z 562 [M+ + 1]
11. N-(2-(4-Chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-(4-(2-((2-chlorophenyl)amino)-acetyl)piperazin-1-yl)acetamide IR: 3177 (N–H str., 2° NH2), 1500 (N–N str.), 1247 (C–N str.), 3096 (C–H str., Ar), 1598 (C=C str., Ar), 1634 (C= N str., Ar), 2958 (C–H str., R-CO–CH2), 1725 (C=O str., Ar-ketone), 722 (C–Cl str., Ar–Cl) 1H-NMR: 7.22–7.71 (m, 11H, ArH), 8.19 (s, 1H, N–NH), 4.15(d, 2H, CH2), 3.31 (t, 4H, CH2 of piperazine), 2.65 (t, 4H, CH2 of piperazine); 13C–NMR: 170.5, 164.8, 164.2, 161.0, 151.3, 150.1, 138.4, 135.5, 133.2, 129.3, 129.1, 128.4, 127.7, 127.4, 127.3, 126.9, 122.6, 124.7, 123.5, 120.3, 120.1, 115.6, 58.6, 52.9, 52.7, 52.5, 46.6, 46.2 Anal cal. C, 55.09; H, 4.13; N, 16.06; Found: C, 55.06; H, 4.17; N, 16.09; MS ES+ (ToF): m/z 566 [M+ + 1]
12. 2-(4-(2-((2-Chloro-4-nitrophenyl)amino)acetyl)piperazin-1-yl)-N-(2-(4-chloro-phenyl)-4-oxoquinazolin-3(4H)-yl)acetamide IR: 1669 (C=O str., CONH2), 3214 (N–H str., 2° NH2), 1479 (N–N str.), 1251 (C–N str.), 3071 (C–H str., Ar), 1591 (C=C str., Ar), 1636 (C= N str., Ar.), 2958 (C–H str., R-CO–CH2), 1726 (C=O str., Ar-ketone), 724 (C–Cl str., Ar–Cl) 1H-NMR: 6.60–7.85 (m, 11H, ArH), 8.19 (s, 1H, N–NH), 4.16(d, 2H, CH2), 3.31 (t, 4H, CH2 of piperazine), 2.65 (t, 4H, CH2 of piperazine); 13C–NMR: 170.6, 164.5, 164.3, 161.4, 151.5, 149.7, 146.7, 135.6, 133.4, 130.7, 129.6, 129.3, 128.5, 127.9, 127.5, 127.1, 126.7, 122.7, 121.2, 120.3, 117.5, 108.9, 58.8, 53.6, 52.9, 52.8, 46.7, 46.4 Anal cal. C, 55.09; H, 4.13; N, 16.06; Found: C, 55.07; H, 4.17; N, 16.03; MS ES+ (ToF): m/z 611 [M+ + 1]
13. N-(2-(4-Chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-(4-(2-(phenylamino)acetyl) piperazin-1-yl)acetamide IR: 1668 (C=O str., CONH2), 3214 (N–H str., 2° NH2), 1468 (N–N str.), 1251 (C–N str.), 3067 (C–H str., Ar), 1590 (C=C str., Ar), 1631 (C= N str., Ar), 2928 (C–H str., R-CO–CH2), 1725 (C=O str., Ar-ketone), 725 (C–Cl str., Ar–Cl) 1H-NMR: 6.50–7.73 (m, 13H, ArH), 8.19 (s, 1H, N–NH), 4.19 (d, 2H, CH2), 3.31 (t, 4H, CH2 of piperazine), 2.65 (t, 4H, CH2 of piperazine); 13C–NMR: 170.9, 164.7, 164.0, 161.5, 151.7, 147.8, 135.9, 133.1, 129.9, 129.6, 129.4, 129.2, 128.3, 127.6, 127.5, 127.2, 126.4, 122.9, 120.6, 117.5, 113.6, 113.3, 58.9, 53.4, 52.8, 52.4, 46.9, 46.6 Anal cal. C, 63.33; H, 5.13; N, 15.83; Found: C, 63.38; H, 5.17; N, 15.81; MS ES+ (ToF): m/z 632 [M+ + 1]
14. N-(2-(4-Chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-(4-(2-((2,4-dichlorophenyl)amino)-acetyl)piperazin-1-yl)acetamide IR: 1668 (C=O str., CONH2), 3213 (N–H str., 2° NH2), 1467 (N–N str.), 1274 (C–N str.), 3066 (C–H str., Ar), 1592 (C=C str., Ar), 1632 (C= N str., Ar), 2928 (C–H str., R-CO–CH2), 1726 (C=O str., Ar-ketone), 726 (C–Cl str., Ar–Cl) 1H-NMR: 6.35–7.69 (m, 11H, ArH), 8.19 (s, 1H, N–NH), 4.15 (d, 2H, CH2), 3.32 (t, 4H, CH2 of piperazine), 2.65 (t, 4H, CH2 of piperazine); 13C–NMR: 170.6, 164.8, 164.1, 161.8, 151.4, 147.4, 135.8, 134.3, 133.0, 131.4, 129.2, 129.0, 128.7, 127.5, 127.4, 127.3, 126.7, 122.6, 121.7, 120.7, 115.5, 113.2, 58.5, 53.5, 52.5, 52.2, 46.8, 46.5 Anal cal. C, 56.06; H, 4.20; N, 14.01; Found: C, 56.08; H, 4.22; N, 14.04; MS ES+ (ToF): m/z 601 [M+ + 1]
15. N-(2-(4-Chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-(4-(2-((3,5-dichlorophenyl)amino)-acetyl)piperazin-1-yl)acetamide IR: 1668 (C=O str., CONH2), 3214 (N–H str., 2° NH2), 1468 (N–N str.), 1251 (C–N str.), 3072 (C–H str., Ar), 1591 (C=C str., Ar), 1632 (C=N str., Ar), 2956 (C–H str., R-CO–CH2), 1725 (C=O str., Ar-ketone), 725 (C–Cl str., Ar–Cl) 1H-NMR: 7.55–7.86 (m, 12H, ArH), 8.19 (s, 1H, N–NH), 4.14 (d, 2H, CH2), 3.31 (t, 4H, CH2 of piperazine), 2.64 (t, 4H, CH2 of piperazine); 13C–NMR: 170.4, 164.6, 164.0, 161.5, 151.1, 143.7, 135.5, 133.2, 129.8, 129.2, 129.0, 128.4, 127.7, 127.6, 127.5, 127.3, 126.9, 122.3, 122.5, 120.8, 118.4, 114.5, 58.3, 52.7, 52.4, 52.3, 46.9, 46.7 Anal cal. C, 59.47; H, 4.63; N, 14.86; Found: C, 59.49; H, 4.61; N, 14.87; MS ES+ (ToF): m/z 601 [M+ + 1]
16. N-(2-(4-Chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-(4-(2-((4-nitrophenyl)amino)acetyl)-piperazin-1-yl)acetamide IR: 1669 (C=O str., CONH2), 3217 (N–H str., 2° NH2), 1469 (N–N str.), 1254 (C–N str.), 3077 (C–H str., Ar), 1561 (C=C str., Ar), 1629 (C= N str., Ar), 2958 (C–H str., R-CO–CH2), 1726 (C=O str., Ar-ketone), 725 (C–Cl str., Ar–Cl), 1561 (NO2 asym str.) 1H-NMR: 6.43–7.76 (m, 12H, ArH), 8.19 (s, 1H, N–NH), 4.14 (d, 2H, CH2), 3.31 (t, 4H, CH2 of piperazine), 2.63 (t, 4H, CH2 of piperazine); 13C–NMR: 170.7, 164.8, 164.3, 161.6, 153.8, 151.5, 136.6, 135.6, 133.0, 129.3, 129.1, 128.2, 127.8, 127.5, 127.4, 126.8, 122.1, 121.7, 120.9, 114.6, 114.5, 58.4, 53.2, 52.4, 52.2, 46.9, 46.6 Anal cal. C, 58.39; H, 4.55; N, 17.02; Found: C, 58.40; H, 4.57; N, 17.04; MS ES+ (ToF): m/z 577 [M+ + 1]
17. N-(2-(4-Chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-(4-(2-((2-nitrophenyl)amino)acetyl)-piperazin-1-yl)acetamide IR: 1668 (C=O str., CONH2), 3213 (N–H str., 2° NH2), 1467 (N–N str.), 1253 (C–N str.), 3067 (C–H str., Ar), 1590 (C=C str., Ar), 1632 (C= N str., Ar), 2957 (C–H str., R-CO–CH2), 1726 (C=O str., Ar-ketone), 726 (C–Cl str., Ar–Cl), 1559 (NO2 asym str.) 1H-NMR: 6.63–7.76 (m, 12H, ArH), 8.19 (s, 1H, N–NH), 4.17 (d, 2H, CH2), 3.32 (t, 4H, CH2 of piperazine), 2.51 (t, 4H, CH2 of piperazine); 13C–NMR: 170.9, 164.9, 164.6, 161.3, 151.9, 138.4, 135.8, 135.5, 133.5, 132.3, 129.5, 129.4, 128.0, 127.9, 127.6, 127.4, 126.9, 122.4, 121.7, 120.6, 118.3, 114.6, 58.7, 52.5, 52.4, 52.3, 46.8, 46.7 Anal cal. C, 58.39; H, 4.55; N, 17.02; Found: C, 58.37; H, 4.51; N, 17.01; MS ES+ (ToF): m/z 577 [M+ + 1]