3.1 Result of spectroscopic analyses
(E)-1-(4′-bromophenyl)-3-(4-(diphenylamino)phenyl)prop-2-en-1-one (1a) was obtained as deep yellow solid powder at 70% yield. Its melting point was determined to be 145–147 °C. The IR spectrum (Additional file 1: Appendix 1) showed the following prominent peaks (cm−1); 3041 (= C–H), 1684 (C=O), 1580 (C=C), 1267 (C–N) and 530 (C–Br). The GC–MS analysis showed the molecular ion peak of 454 m/z (Additional file 1: Appendix 2). The NMR spectral showed the following signals; 1H-NMR (400 MHz, CDCl3) δ 8.03 (d, 1H J = 15.3 Hz, 3-H), 7.68 (d, 2H, J = 3.0 Hz, 2′,6′-H), 7.57 (d, 1H, J = 12.1 Hz, 2-H), 7.43 (d, 2H, J = 4.4 Hz, 3′,5′-H), 7.38 (d, 2H, J = 7.8 Hz, 5,9-H), 7.35 (d, 2H, J = 6.5–2.1 Hz, 11,15,17, 21-H), 7.18 (d, 2H, J = 5.4–1.8 Hz, 12,14,18,20-H) 7.08 (d, 2H, J = 3.2–28 Hz,13,19-H) and 7.02 (d, 2H, J = 8.7 Hz, 6,8-H) (Additional file 1: Appendix 3), 13C-NMR (400 MHz, CDCl3) δ 190.29 (C-1), 149.68 (C-3,7), 145.95 (C-10,16), 130.73 (C-3′–5′), 130 (C-2′,6′), 129.90 (C-4,12,14,18,20), 128.51 (C-13,19), 126.02 (C-11,15,17,21), 125 (C-4′), 124 (C-6,8) and 119.29 (C-2) (Additional file 1: Appendix 4) (Fig. 1).
(E)-3-(4-(diphenylamino)phenyl)-1-(3′-nitrophenyl)prop-2-en-1-one (1b) was obtained as golden yellow solid powder at 92% yield. Its melting point was found to be 143–145 °C. The IR spectrum (Additional file 1: Appendix 5) showed the following prominent peaks (cm−1); 3037 (= C–H), 1684 (C=O), 1580 (C=C), 1390 (N=O) and 1285 (C–N). The GC–MS analysis showed the molecular ion peak of 420 m/z (Additional file 1: Appendix 6). The NMR spectral showed the following signals; 1H-NMR (400 MHz, CDCl3) δ 8.75 (s, 1H, 2′-H), 8.47 (d, J = 3.3 Hz, 4′-H), 8.26 (d, 1H, J = 4.3 Hz, 6′-H), 8.13 (d, 1H, J = 14.6 Hz, 2H), 8.02 (t, 1H, J = 5.6 Hz, 5′-H), 7.97 (d, 1H, J = 12.3 Hz, 3-H), 7.79 (d, 2H, J = 8.7 Hz, 6,8-H) and 7.60 (d, 2H, J = 3.2 Hz, 5,9-H), 7.18 (d, 2H, J = 5.4 2.4 Hz, 11,15,17,21-H), 7.13 (d, 2H, J = 6.4–2.8 Hz, 12,14,18,20-H) and 7.02 () (Additional file 1: Appendix 7), 13C-NMR (400 MHz, CDCl3) δ 190.46 (C-1), 149.23 (C-3′), 145.9 (C-10,16), 144.6 (C-7), 142.8 (C-3), 138.87 (C-1′), 133.82 (C-6′), 131.29 (C-5′), 129.73 (C-4′), 129.7 (C-5,9), 129.6 (C-12,14,18,20), 126.9 (C-13,19), 126.29 (C-6,8), 125.7 (C-11,15,17,21), 125.08 (C-4), 123.29 (C-2′) and 119.08 (C-2) (Additional file 1: Appendix 8) (Fig. 2).
(E)-1-(4′-chlorophenyl)-3-(4-diphenylamino)phenyl)prop-2-en-1-one (1c) was obtained as yellow solid powder at 57% yield. Its melting point was determined to be 137–139 °C. The IR spectrum (Additional file 1: Appendix 9) showed the following prominent peaks (cm−1); 3036 (= C–H), 1684 (C=O), 1580 (C=C), 1285 (C–N) and 620 (C–Cl). The GC–MS analysis showed the molecular ion peak of 409 m/z (Additional file 1: Appendix 10). The NMR spectral showed the following signals; 1H-NMR (400 MHz, CDCl3) δ 8.51 (d, 1H, J = 13.3 Hz, 3-H), 8.15 (d, 2H, J = 4.3 Hz, 2′,6′-H), 7.68 (d, 1H, J = 12.5 Hz, 2-H), 7.46 (d, 2H, J = 8.4 Hz, 3′,5′-H), 7.33 (d, 2H, J = 2.7 Hz, 6,8-H) 7.22 (d, 2H, J = 7.3–3.4 Hz, 12,14,18,20-H) 7.17 (d, 2H, J = 2.7 Hz, 5, 9-H), 7.15 (d, 2H, J = 3.3–1.8 Hz, 11,14,17,21-H) and 6.97 (d, 2H, J = 4.3–2.1 Hz, 13,19-H) (Additional file 1: Appendix 11). 13C-NMR (400 MHz, CDCl3) δ 190.46 (C-1), 149.48 (C-3,7), 145.88 (C-10,16), 142.74 (C-4′), 136.50 (C-1′), 131.30 (C-3′,5′), 129.70 (C-2′,6′,5,9), 129.60 (C-12,14,18,20), 128.40 (C-4), 126.8 (C-13,19), 126.29 (C-6,8), 125.09 (C-11,15,17,21) and 119.30 (C-2) (Additional file 1: Appendix 12) (Fig. 3).
(E)-3-(4-diphenylamino)phenyl)-1-(4′-fluorophenyl)prop-2-en-1-one (1d) was obtained as lemon green solid powder at 60% yield. Its melting point was found to be 136–138 °C. The IR spectrum (Additional file 1: Appendix 13) showed the following prominent peaks (cm−1); 3037 (= C–H), 1684 (C=O), 1580 (C=C), 1286 (C–N) and 1073 (C–F). The GC–MS analysis showed the molecular ion peak of 393 m/z (Additional file 1: Appendix 14). The NMR spectral showed the following signals; 1H-NMR (400 MHz, CDCl3) δ 8.44 (d, 1H, J = 12.8 Hz, 3-H), 8.29 (d, 2H, J = 7.8 Hz, 2′, 6′-H), 7.68 (d, 1H, J = 11.3 Hz, 2-H), 7.42 (d, 2H, J = 6.3–3.1 Hz, 12,14,18,20-H), 7.35 (d, 2H, J = 6.2 Hz, 3′,5′-H), 7.16 (d, 2H, J = 5.0 Hz, 5,9-H), 7.15 (d, 2H, J = 7.0 Hz, 6,8-H), 7.09 (d, 2H, J = 4.5–1.2 Hz, 11,15,17,21-H) and 6.98 (d, 2H, J = 3.6–1.2, 13,19-H) (Additional file 1: Appendix 15), 13C-NMR (400 MHz, CDCl3) δ 190.49 (C-1), 168.14 (C-4′), 149.7 (C-10,16), 146.10 (C-3,7), 136.36 (C-1′), 131.28 (C-2′,6′), 129.69 (C-5,9), 129.6 (C-4), 128.37 (C-12,14,18,20), 126.28 (C-13,19), 125.08 (C-11,15,17,21), 120.08 (C-6,8), 119.29 (C-2), and 116 (C-3′,5′) (Additional file 1: Appendix 16) (Fig. 4).
(E)-4-(3-(diphenylamino)phenyl)-1-(4′-hydroxyphenyl)-2-methylbut-3-en-1-one (2a) was obtained as pale yellow solid powder at 55% yield. Its melting point was determined to be 146–148 °C. The IR spectrum (Additional file 1: Appendix 17) showed the following prominent peaks (cm-1); 3243 (O–H), 3037 (= C–H), 1684 (C=O), 1580 (C=C), 1282 (C–N). The GC–MS analysis showed the molecular ion peak of 419 m/z (Additional file 1: Appendix 18). The NMR spectral showed the following signals; 1H-NMR (400 MHz, CDCl3) δ 9.80 (s, 1H, 12-H), 7.96 (d, 2H, J = 6.5 Hz, 2′,6′-H), 7.68 (d, 2H, J = 4.4 Hz, 6,10-H), 7.32 (d, 2H, J = 8.6 Hz, 7,9-H), 7.14 (d, 2H, J = 7.2–1.2 Hz, 12,16,18,22-H), 7.08 (d, 2H, J = 4.3–1.2 Hz, 13,15,19,21-H), 7.02 (d, 2H, J = 3.8–1.3 Hz, 14,20-H), 6.63 (d, 2H, J = 11.2 Hz, 3′,5′-H), 6.58 (d, 1H, J = 14.3 Hz, 4-H), 6.31 (d, 1H, J = 12.7 Hz, 3-H), 3.81 (dd,1H, J = 15.0, 7.5 Hz, 2-H) and 0.90 (d, 3H, J = 12.3 Hz, 11′-H) (Additional file 1: Appendix 19). 13C-NMR (400 MHz, CDCl3) δ 190.44 (C-1), 162.92 (C-4′), 145.1 (C-8), 145.9 (11,17), 132.66 (C-2′,6′), 131.32 (C-5), 129.8 (C-14,20), 129.45 (C-4,6,10,13,19,21), 125.94 (C-12,16,18,22), 123.2 (C-7,9), 124.30 (C-1′), 118.92 (C-3), 114.43 (C-3′,5′), 47.10 (C-2) and 17.73 C-(11′) (Additional file 1: Appendix 20) (Fig. 5).
(E)-1-(2′-bromophenyl)-4-(3-(diphenylamino)phenyl)-2-methylbut-3-en-1-one (2b) was obtained as brownish yellow solid powder at 30% yield. Its melting point was found to be 147–148 °C. The IR spectrum (Additional file 1: Appendix 21) showed the following prominent peaks (cm−1); 3037 (= C–H), 1684 (C=O), 1580 (C=C) 1285 (C–N) and 580 (C–Br). The GC–MS analysis showed the molecular ion peak of 482 m/z (Additional file 1: Appendix 22). The NMR spectral showed the following signals; 1H-NMR (400 MHz, CDCl3) δ 7.92 (d, 1H, J = 9.5 Hz, 6′-H), 7.81 (d, 2H, J = 5.7 Hz, 6,10-H), 7.42 (d, 1H, J = 8.9 Hz, 3′-H), 7.39 (t, 1H, J = 12.4 Hz, 5′-H), 7.32 (t, 1H, J = 12.4 Hz, 4′-H), 7.24 (d, 2H, J = 9.6–5.7 Hz, 13,15,21,19-H), 7.16 (d, 2H, J = 10.3 Hz, 7,9-H), 7.08 (d, 2H, J = 10.3–7.4 Hz, 12,16,18,22-H), 6.60 (d, 1H, J = 15.4 Hz, 4-H), 7.0 (d, 2H, J = 6.3–4.1 Hz, 14,20-H), 6.33 (d, 1H, J = 14.0 Hz, 3-H), 3.75 (q, 1H, J = 30.2, 12.1 Hz, 2-H) and 0.89 (d, 3H, J = 15.6 Hz, 11′H) (Additional file 1: Appendix 23). 13C-NMR (400 MHz, CDCl3) δ 190.47 (C-1), 146.81 (C-11,17), 146.07 (C-8), 140.99 (C-1′), 133.62 (C-3′), 132.70 (C-4′), 131.29 (C-5), 129.7 (C-4,6,10), 129.69 (C-13,15,19,21), 126.8 (C-14,20), 126.29 (C-6′), 125.7 (C-12,16,18,22), 125.2 (C-5′), 125.09 (C-7,9), 119.30 (C-2′), 116 (C-3), 46.46 (C-2) and 17.59 (C-11′) (Additional file 1: Appendix 24) (Fig. 6).
(E)-4-(3-(diphenylamino)phenyl)-1-(4′-methoxyphenyl)-2-methylbut-3-en-1-one (2c) was obtained as orange yellow solid powder at 52% yield. Its melting point was determined to be 142–144 °C. The IR spectrum (Additional file 1: Appendix 25) showed the following prominent peaks (cm−1); 3037 (= C–H), 1684 (C=O), 1580 (C=C), 1320 (C–O) and 1285 (C–N). The GC–MS analysis showed the molecular ion peak of 433 m/z (Additional file 1: Appendix 26). The NMR spectral showed the following signals; 1H-NMR (400 MHz, CDCl3) δ 8.00 (d, 2H, J = 13.2 Hz, 2′,6′-H), 7.73 (d, 2H J = 13.2 Hz, 6,10-H), 7.24 (d, 2H, J = 9.8–3.6 Hz, 13,15,21,19-H), 7.18 (d, 2H, J = 14.0 Hz, 3′,5′-H), 7.13 (d, 2H, J = 7.3–1.3 Hz, 7,9-H), 7.08 (d, 2H, J = 12.5–7.6 Hz, 12,16,18,22-H), 7.00 (d, 1H, J = 12.6 Hz, 4-H), 6.98 (d, 2H, J = 6.3–3,2 Hz, 14,20-H), 6.30 (d, 1H, J = 11.5 Hz, 3-H), 3.90 (s, 3H, 12′-H), 3.70 (q, 1H, J = 13.32, 15.23 Hz, 2-H) and 0.87 (d, 3H J = 6.8 Hz, 11′-H) (Additional file 1: Appendix 27). 13C-NMR (400 MHz, CDCl3) δ 190.64 (C-1), 165.20 (C-4′), 145.8 (C-11,17), 145.1 (C-8), 131.23 (C-5), 129.7 (C-4,6,10), 129.6 (C-13,15,21,19), 129.28 (C-2′,6′), 127 (C-1′), 126.8 (C-14,20), 126.46 (C-), 125.7 (C-12,16,18,22), 124.52 (C-7,9), 115.99 (C-3), 113.4 (C-3′,5′), 55.29 (12′), 47.04 (C-2) and 17.80 (C-11′) (Additional file 1: Appendix 28) (Fig. 7).
(E)-4-(3-(diphenylamino)phenyl)-1-(4-fluorophenyl)-2-methylbut-3-en-1-one (2d) was obtained as cotton brown solid powder at 54% yield. Its melting point was found to be 146–148 °C. The IR spectrum (Additional file 1: Appendix 29) showed the following prominent peaks (cm−1); 3037 (= C–H), 1684 (C=O), 1580 (C=C), 1287 (C–N) and 1028 (C–F). The GC–MS analysis showed the molecular ion peak of 421 m/z (Additional file 1: Appendix 30). The NMR spectral showed the following signals; 1H-NMR (400 MHz, cdcl3) δ 8.23 (d, 2H, J = 6.5 Hz, 2′,6′-H), 7.70 (d, 2H, J = 13.6 Hz, 6,10-H), 7.37 (d, 2H, J = 13.7 Hz, 3′,5′-H), 7.24 (d, 2H, J = 8.5–3.6 Hz, 13,15,21,19-H), 7.14 (d, 2H, J = 6.2–3.2 Hz, 7,9-H), 7.08 (d, 2H, J = 12.5–7.6 Hz, 12,16,18,22-H), 6.8 (d, 2H, J = 3.6–3.2 Hz, 14,20-H), 6.60 (d, 1H, J = 13.2 Hz, 4-H), 6.31 (d, 1H, J = 12.7 Hz, 3-H), 3.71 (q, 1H, J = 13.1, 6.7 Hz, 2-H) and 0.85 (d, 1H, J = 6.7 Hz, 11′-H) (Additional file 1: Appendix 31). 13C-NMR (400 MHz, CDCl3) δ 190.37 (C-1), 168.01 (C-4′), 146.8 (C-11,17), 146.4 (C-8), 133.89 (C-5), 131.29 (C-1′), 129.75 (C-2′,6′), 126.6 (C-13,15,19,21), 129.18 (C-4,6,10) 126.09 (C-14,20), 125.2 (C-12,16,18,22), 123.37 (C-7,9), 119.07 (C-3), 114.48 (C-3′,5′), 48.06 (C-2) and 17.74 (C-11′) (Additional file 1: Appendix 32) (Fig. 8).
3.2 Results of the biological studies
See Tables 2, 3 and 4.