Electronic Supplementary Material (ESI) for RSC Advances. This journal is © The Royal Society of Chemistry 2020 Supporting information Synthesis and biological evaluation of dehydroabietic acid- pyrimidine hybrids as antitumor agents Lin Huanga, Rong Huanga，Fuhua Panga, Anke Lia, Guobao Huangb, Xiaoqun Zhoua*, Qian Lia*, Fangyao Lia,b,c*, Xianli Maa a School of Pharmacy, Guilin Medical University, Guilin, Guangxi 541004, PR China b Guangxi Key Lab of Agricultural Resources Chemistry and Biotechnology, College of Chemistry and Food Science, Yulin Normal University, Yulin, Guangxi 537000, PR China cState Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University, Guilin, Gungxi 541006, PR China. 2 1 90 . 6 3 7 3 8 %T 4 0 9 . 1 8 2 5 6 75 3 2 0 3 7 1 8 4 . 5 . 8 . 6 . 7 6 5 7 5 0 2 7 0 5 0 5 . 7 4 4 1 5 4 . 60 3 6 0 9 0 7 . 1 9 7 6 8 3 . 0 9 4 45 3 1 9 8 5 4 . 0 3 8 5 3 1 . 2 9 1 8 7 7 . 9 8 1 1 2 1 1 5 . 7 1 5 . 30 6 0 . 2 1 6 9 . 7 4 2 2 1 1 5 4 1 7 1 2 8 1 6 . 3 9 . 2 4 9 8 2 15 2 2 7 . 1 2 7 6 1 0 4000 3500 3000 2500 2000 1750 1500 1250 1000 750 500 1/cm Figure S1. FTIR spectrum of the target compound (3a) 8 . 0 230 0.76 7.82 7.81 220 7 . 5 0.84 7.28 210 7.19 1.19 7.17 7 . 200 0 Figure 0.97 7.01 Figure 0.94 6.90 190 6 . 5 S3. 180 S2. 6.22 178.43 0.77 6.21 13 1 6 170 . H-NMR 0 C-NMR 164.93 160 161.23 5 . 155.03 5 150 spectrum spectrum 146.93 145.89 140 5 . 0 134.77 130 127.05 4.38 4 of of 124.31 . 4.37 f f 5 120 1 124.07 1 4.33 ( ( the the ppm ppm 2.19 4.31 110 ) ) 4.14 111.22 target 4 target . 4.13 0 100 compound compound 3 . 90 5 3.47 2.01 3.44 80 77.37 3 77.16 . 76.95 0 1.02 2.90 70 2.84 0.79 ( ( 3a 3a 2 2.32 60 62.62 . 5 ) ) 2.30 in in 1.13 2.25 50 0.85 2.23 CDCl CDCl 47.85 2 2.06 . 0.52 44.82 0 40 10.8465 1.78 3 3 37.05 1.76 33.58 1.22 30 1.66 1 . 29.44 5 1.28 25.30 1.06 20 24.12 0.72 1.24 24.10 3.11 1.23 1 1.22 21.94 . 6.23 0 10 18.68 3.00 0.90 16.60 0 % - 1 4 6 7 9 1 3 T 5 5 0 5 0 5 0 0 4 0 0 0 3 5 0 3550.95 0 3414.00 Figure Figure 3230.77 3 0 0 0 2956.87 S4. 2870.08 S5. 2 2671.41 HR-MS 5 FTIR 0 0 spectrum 2 spectrum 0 0 0 1 of 7 of 5 the 0 1728.22 the 1660.71 target target 1 1577.77 5 0 1539.20 0 compound 1458.18 1386.82 compound 1 2 5 0 1230.58 1170.79 ( 1124.50 3b 1 ( 3a 0 ) 1037.70 0 ) 0 966.34 883.40 7 821.68 5 0 752.24 628.79 5 1 559.36 0 / 0 c 482.20 m 7 230 . 5 7.28 220 7.19 1.29 7.17 7 . 1.15 0 7.01 210 1.30 6.89 200 Figure Figure 6 . 5 190 6 S7. S6. 180 . 6.02 0 178.45 13 1 170 H-NMR C-NMR 169.35 5 166.08 . 5 160 160.15 150 5 spectrum spectrum . 146.93 0 145.85 140 134.76 4 130 . 127.06 5 1.15 4.35 of of 124.29 f f 4.29 120 1.23 1 1 124.06 ( ( the the ppm ppm 4 . 0 110 ) ) target target 107.94 100 3 . 5 compound compound 0.92 3.39 90 3 . 80 77.36 0 1.04 2.89 77.15 0.84 2.83 76.94 70 ( 2 ( 0.60 3b . 3b 5 0.96 2.44 60 62.81 ) 0.55 ) 2.27 in in 1.18 0.96 2.25 50 1.12 2 CDCl CDCl . 47.83 0 0.56 44.89 0.85 1.78 40 10.2794 1.77 1.67 3 0.57 3 37.07 1 1.66 . 5 30 33.58 0.55 29.24 31.0426 1.28 25.32 1.23 63.3400 20 1.13 1.19 24.10 0.65 21.93 1 0.96 . 21.11 0 1.03 0.95 10 18.69 1.50 0.94 16.60 0.92 13.82 0 0 . 5 1 1 1 1 % - 2 2 5 7 0 2 5 7 T 5 5 0 5 0 5 0 5 0 4 0 0 0 3743.83 3 5 0 Figure 0 3429.43 3 0 S8. 0 0 2929.87 2870.08 HR-MS 2 5 2590.40 0 0 2378.23 spectrum 2 2142.91 0 0 0 of 1 7 the 5 0 1724.36 target 1645.28 1 1579.70 5 1537.27 0 compound 0 1498.69 1440.83 1386.82 1 1340.53 2 5 1265.30 0 1240.23 1172.72 ( 1124.50 3b 1 ) 0 1033.85 0 0 972.12 887.26 7 823.60 5 761.88 0 717.52 628.79 594.08 5 1 0 547.78 / 0 c m 478.35 230 7 . 5 220 7.28 7.19 1.04 7.17 210 7.03 7 . 0 1.03 1.02 6.90 Figure 200 Figure 1.03 6.69 6 . 190 5 Figure S11. S10. 180 178.54 6 . 0 170 13 1 170.30 H-NMR C-NMR 167.23 S9. 160 5 . 5 FTIR 150 spectrum spectrum 147.00 5 . 145.80 0 140 spectrum 134.89 130 4 127.08 . 5 124.30 1.09 4.40 of of f f 120 1 1 124.04 1.06 4.34 ( ( ppm ppm of the the 115.96 4 110 . ) ) the 0 target target target 100 3 . 5 compound compound 2.14 3.42 90 compound 3 80 77.38 . 77.17 0 0.72 2.85 76.96 1.27 70 ( ( 2 3c . 3c 6.06 63.39 5 60 1.04 2.39 ( ) 3c ) in in 1.04 2.26 ) 50 2 CDCl CDCl 47.84 . 0.84 0 1.79 44.86 1.59 1.71 40 1.21 1.67 37.08 1.04 1.65 3 3 33.59 1 . 30 29.57 5 2.11 1.47 25.36 3.10 1.29 20 24.11 6.00 1.25 23.96 1 1.24 . 0 3.05 21.93 1.22 10 18.74 16.63 0 0 . 5 1 1 % 8 9 3 4 5 6 7 0 1 T 0 0 0 0 0 0 0 0 0 4 0 0 0 3743.83 3 Figure 5 0 0 3441.01 S12. 3 0 0 0 2922.16 2852.72 HR-MS 2 5 0 0 2362.80 spectrum 2 0 0 0 of 1 the 7 5 0 1724.36 target 1649.14 1 1583.56 5 1544.98 compound 0 0 1462.04 1 2 1305.81 5 1246.02 0 ( 1172.72 3c 1128.36 ) 1 0 1031.92 0 0 954.76 848.68 7 817.82 5 0 748.38 628.79 5 1 561.29 0 / 0 c 518.85 m 443.63 8 . 0 230 220 7 . 5 7.28 210 7.19 1.10 7.18 7 . 0 1.09 7.01 Figure Figure 200 1.09 6.89 190 6 . 5 Figure S15. S14. 180 178.42 6 1.15 6.07 . 0 13 170 1 H-NMR C-NMR 166.05 S13. 165.44 160 5 . 159.66 5 FTIR 150 spectrum spectrum 146.94 5 . 145.85 0 140 spectrum 134.79 130 4 . 127.06 5 1.16 4.37 124.30 of of f f 120 1 124.06 1 1.19 4.33 ( ( ppm ppm the the of 4 . 0 110 ) ) the target target 108.59 100 target 3 . 5 3.46 1.26 3.45 compound compound 90 2.91 compound 3 . 2.89 0 80 77.37 0.99 2.85 77.16 0.55 2.84 76.95 2.82 70 2 . 2.33 5 ( ( 2.31 3d 1.14 3d 60 62.71 2.28 0.97 ( ) 2.27 ) 2.05 3.48 3d 2 in 2.25 in . 0.72 0 50 ) 0.97 1.79 CDCl CDCl 47.85 0.50 1.77 44.87 0.61 1.67 40 0.50 1 . 5 0.55 37.07 1.24 1.29 3 3 33.58 30 3.16 1.24 29.36 6.34 1.23 25.33 1 1.23 . 0 3.00 20 24.26 24.12 24.09 10 21.94 0 .