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Design, Synthesis and in Silico Studies of New Quinazolinone Derivatives As Antitumor PARP-1 Inhibitors

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Design, Synthesis and in Silico Studies of New Quinazolinone Derivatives As Antitumor PARP-1 Inhibitors Electronic Supplementary Material (ESI) for RSC Advances. This journal is © The Royal Society of Chemistry 2020 Design, Synthesis and In Silico Studies of New Quinazolinone Derivatives as Antitumor PARP-1 Inhibitors Sayed K. Ramadana, Eman Z. Elrazazb, Khaled A. M. Abouzid b,c *, Abeer M. El-Naggar a, * a Department of Chemistry, Faculty of Science, Ain Shams University, Abbassia, 11566 Cairo, Egypt b Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ain Shams University, Abbassia, 11566 Cairo, Egypt c Department of Organic and Medicinal Chemistry, Faculty of Pharmacy, University of Sadat City, Sadat City, Egypt Supporting information * Corresponding authors: Khaled A. M. Abouzid Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ain Shams University, Abbassia, 11566 Cairo, Egypt Email: [email protected] Abeer M. El-Naggar Chemistry Department, Faculty of Science, Ain Shams University, Abbassia, Cairo-11566, Egypt. E-mail: [email protected] 1 3-Phenyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one (3). IR O Ph N N S H 2 HNMR O Ph N N S H 3 HNMR-D2O O Ph N N S H 4 Methyl 4-(2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetamido)benzoate (5a). IR O Ph N N S O CH2 C HN COOCH3 5 1H NMR O Ph N N S O CH2 C HN COOCH3 6 O Ph N N S O CH2 C HN COOCH3 7 Dr_AbeerElngar-Q1_PROTON_01 Dr_AbeerElngar-Q18.06 8.06 8.04 8.04 7.91 7.89 7.81 7.80 7.79 7.78 7.77 7.76 7.73 7.71 7.59 7.58 7.58 7.57 7.50 7.49 7.48 7.47 7.46 7.42 7.42 900 800 700 O Ph N 600 N S 500 O CH2 C 400 HN 300 COOCH3 200 100 0 1.00 2.02 1.10 2.00 2.81 3.79 8.05 7.95 7.85 7.75 7.70 7.65 7.55 7.45 7.35 7.25 7.15 7.05 6.95 6.85 f1 (ppm) 8 D2O O Ph N N S O CH2 C HN COOCH3 9 Mass O Ph N N S O CH2 C HN COOCH3 10 IR N-(4-acetylphenyl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetamide %T 1 - - - 0 1 3 2 8 9 1 2 3 4 5 6 7 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Q 0 1 A C 2 3 5 0 0 3461.26 N O N 3245.06 3181.61 S Ph 3 3102.37 0 0 0 3040.44 3006.80 O N H 2 5 0 W 0 11 a v e n O u m b CH e r s 3 ( 2 c 0 m 0 - 0 1 ) 1961.86 1925.29 (5b). 1686.97 1671.38 1 5 1595.59 0 1546.17 0 1492.21 1471.58 1410.04 1393.89 1359.55 1324.10 1305.23 1270.97 1204.73 1186.04 1155.50 1 1133.89 1116.90 0 1075.85 0 0 1022.41 968.25 895.85 876.03 837.07 775.78 758.48 694.00 643.91 669.64 5 616.84 0 592.50 0 530.72 500.19 472.02 414.26 HNMR O Ph N H N N S O CH3 O 12 13 Mass O Ph N H N N S O CH3 O 14 I.R 2-((4-Oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)-N-(4-sulfamoylphenyl)acetamide %T 1 - - 0 2 1 1 2 3 4 5 6 7 8 9 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Q 0 1 S U 2 3 5 0 0 3311.94 3245.52 3220.16 3 3133.03 0 0 3070.50 0 3040.16 O N O 2 HN 5 N 0 15 W 0 a CH S Ph v e n 2 u m b e r s SO ( 2 c 0 m 2 0 - NH 0 1 ) 1954.52 2 1845.01 (5c). 1789.72 1669.15 1619.85 1608.31 1 5 1595.77 0 1578.10 0 1552.43 1489.98 1533.86 1472.62 1402.26 1335.26 1268.59 1229.05 1197.40 1150.38 1 1122.21 0 1096.49 0 0 1028.10 988.01 969.84 891.27 837.06 799.20 766.56 691.01 645.04 5 602.64 0 569.03 0 541.76 504.13 453.53 411.09 O Ph N N S O CH2 HN SO2NH2 16 HNMR Dr_AbeerElnagar-q1su2_PROTON_01 Dr_AbeerElnagar-q1su2 13.03 10.79 8.06 8.00 7.94 7.93 7.90 7.75 7.57 7.49 7.46 7.35 7.31 7.29 7.27 7.25 7.24 4.11 3.37 3.32 2.49 2.48 650 600 O 550 Ph N 500 450 N S 400 O CH2 HN 350 300 SO2NH2 250 200 150 100 50 0 -50 1.00 2.06 2.19 1.65 4.45 5.91 12.89 3.59 7.46 4.32 9.80 18.92 16 15 14 13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 f1 (ppm) 17 Dr_AbeerElnagar-q1su2_PROTON_01 Dr_AbeerElnagar-q1su2 8.06 8.04 7.94 7.93 7.75 7.59 7.58 7.57 7.51 7.49 7.47 7.46 7.44 7.42 7.40 7.38 7.35 7.33 7.31 7.27 7.25 7.24 650 600 550 500 O 450 Ph N 400 N S 350 O CH2 300 HN 250 SO2NH2 200 150 100 50 0 -50 2.13 1.51 3.59 4.36 16.09 6.79 8.5 8.4 8.3 8.2 8.1 8.0 7.9 7.8 7.7 7.6 7.5 7.4 7.3 7.2 7.1 7.0 6.9 6.8 f1 (ppm) 18 IR Methyl %T 1 0 4-(2-(4-oxo-3-phenyl-2-thioxo-3,4-dihydroquinazolin-1(2H)-yl)acetamido)benzoate 2 2 3 3 4 4 5 5 6 6 7 7 8 8 9 9 4 0 0 5 0 5 0 5 0 5 0 5 0 5 0 5 0 5 0 0 Q 0 1 p 3 5 0 3549.83 0 3474.07 3414.58 3 0 0 0 O 2926.92 HN C O N 2 N 5 0 W 0 S Ph a 19 v e COOCH n u m b e 3 r s ( 2 c 0 m 0 - 2044.43 0 1 ) 1664.63 1637.83 (6a). 1 1618.33 5 0 1553.28 0 1491.07 1470.25 1434.45 1410.38 1385.11 1281.78 1 1115.82 0 0 0 969.61 858.25 769.44 694.49 5 619.41 0 0 478.02 HNMR O Ph N N S O C HN COOCH3 20 Dr_AbeerElngar-Q1P_PROTON_01 Dr_AbeerElngar-Q1P 11.09 8.03 7.92 7.87 7.83 7.82 7.77 7.73 7.51 7.43 4.10 3.75 3.43 3.35 3.27 2.49 45 O 40 Ph N 35 N S 30 O C 25 HN 20 COOCH3 15 10 5 0 1.00 2.96 15.69 1.37 6.26 4.62 8.79 1787.95 606.45 -0.75 16 15 14 13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 f1 (ppm) 21 abeer-najar-Q1P 11.21 8.05 7.97 7.92 7.90 7.86 7.83 7.76 7.61 7.56 7.52 7.50 7.41 4.19 3.81 3.67 2.51 1.76 8000 7500 7000 6500 6000 O 5500 Ph 5000 N 4500 N S 4000 O 3500 C 3000 HN 2500 2000 COOCH3 1500 1000 500 0 -500 1.00 1.24 5.70 8.26 2.18 3.53 2.39 0.55 16 15 14 13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 -3 f1 (ppm) 22 abeer-najar-Q1P 8.07 8.05 7.97 7.92 7.90 7.86 7.83 7.81 7.78 7.76 7.61 7.59 7.56 7.54 7.52 7.50 7.48 7.46 7.44 7.42 7.41 8000 7500 7000 6500 6000 O 5500 Ph 5000 N 4500 N S 4000 O 3500 C 3000 HN 2500 2000 COOCH3 1500 1000 500 0 -500 1.24 5.70 8.26 8.8 8.7 8.6 8.5 8.4 8.3 8.2 8.1 8.0 7.9 7.8 7.7 7.6 7.5 7.4 7.3 7.2 7.1 7.0 6.9 f1 (ppm) 23 13C NMR 24 abeer-najar-Q1P 1400 166.67 166.44 161.23 157.49 147.46 144.16 136.03 135.50 130.90 130.37 130.04 126.83 126.30 124.67 119.75 119.01 52.33 41.46 40.59 39.75 37.91 1300 1200 1100 O Ph 1000 N 900 N S 800 O 700 C 600 HN 500 400 COOCH3 300 200 100 0 -100 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10 f1 (ppm) N-(4-acetylphenyl)-2-(4-oxo-3-phenyl-2-thioxo-3,4-dihydroquinazolin-1(2H)-yl)acetamide (6b).
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