Design, synthesis and anticancer activity evaluation of aziridine-1,2,3-triazole hybrid derivatives
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Hong-Ru Dong
und
Jian-Guo Wu
Abstract
New 1-aryl-4-[(aziridine-1-yl)diarylmethyl]-5-methyl-1H-1,2,3-triazole derivatives 7a–i were synthesized by a one-pot reaction of diaryl-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)methanols 6a–i derived from 1-aryl-5-methyl-1H-1,2,3-triazole-4-carboxylic acids 4a–c. Structures of compounds 7a–i were confirmed by analysis of proton nuclear magnetic resonance (1H NMR) and carbon-13 nuclear magnetic resonance (13C NMR), mass spectrometry (MS) and infrared (IR) data. The structure of compound 7f was studied by X-ray diffraction analysis. The anticancer activities of compounds 7a–i against human leukemia HL-60 cells and human hepatoma G2 cells were evaluated. Some of the compounds are highly active.
Introduction
A vast majority of biologically important molecules are heterocyclic compounds [1], [2], [3]. The biological properties of aziridine-containing compounds such as azicemicins [4], miraziridine [5], [6], azinomycins [7], ficellomycin [8], FR-900482 [9] and mitomycins [10] are of significant interest (Figure 1). In particular, mitomycin C has a broad activity against a range of tumors and has been applied clinically since the 1960s. 1,2,3-Triazoles are also pharmacologically important molecules that show anticancer [11], [12], [13], antibacterial [14], [15], antifungal [16], antiviral [17], anti-inflammatory and analgesic activities [18] (Figure 2). However, there is little information describing compounds containing aziridine and 1,2,3-triazole moieties in one molecule. Such compounds are the subject of this report.
Fused aziridine-containing natural products.
Anticancer compounds containing 1,2,3-triazole.
Results and discussion
1-Aryl-4-[(aziridin-1-yl)diaryl-methyl]-5-methyl-1H-1,2,3-triazoles 7a–i were synthesized from diaryl-1H-1,2,3-triazol-4-yl)methanols 6a–i. The synthetic route is shown in Scheme 1. Details of the synthesis of compounds 6a–i starting with anilines 1 through intermediaries 4 and 5 were described in our previous report [19]. Structures of products 7a–i were deduced by spectral methods. In particular, a strong absorption at 3320–3520 cm−1 for a hydroxy group, observed in the infrared (IR) spectra of substrates 6a–i, is absent in the IR spectra of products 7a–i. The proton nuclear magnetic resonance (1H NMR) spectra of compounds 7a–i show signals of the aziridine protons at δ 1.80–1.88 and δ 1.15–1.33, as expected. The structure of compound 7f was additionally determined by X-ray diffraction analysis (Figure 3). Compound 7f (CCDC deposit No 775599), C25H24N4, MW 380.48, crystallizes in the triclinic space group P1̅ with unit cell parameters a=9.3100(7), b=13.8263(11), c=17.4605(15) Å, α=107.402(4), β=92.607(4), γ=92.829(4)°, V=2137.8(3) Å3, Z=4, Dx=1.182 mg/cm3. The final R value was 0.0558.
View of the molecular structure of 7f (CCDC, 2005).
Conclusions
New 1-aryl-4-[(aziridin-1-yl)diaryl-methyl]-5-methyl-1H-1,2,3-triazoles 7a–i were synthesized and their anticancer activities were evaluated. The anticancer activity was investigated under our previously reported conditions [20], [21] using the MTT assay. Compounds 7b,c and 7i are highly active against human leukemia cells and compounds 7c,d, 7f,g inhibit human hepatoma G2 cells.
Experimental
1H NMR spectra were obtained in deuterated chloroform (CDCl3) at 300 MHz. Starting materials 4–6 were synthesized as previously reported [19].
Synthesis of compounds 7a–i
Dry hydrogen chloride was bubbled through a hot solution of compounds 6a–i (0.04 mol) in benzene (20 mL) in a 50-mL flask equipped with an automatic water separator, a reflux condenser and a calcium chloride guard-tube. After 1 h, the solution was concentrated to 10 mL and treated with aziridine (0.06 mol) with rapid stirring followed by the addition of triethylamine (0.08 mol). After the mixture was stirred at 45°C for an additional 1 h, the solvent was evaporated and the residue was crystallized from ethyl acetate or purified by column chromatography on silica gel and eluted with ethyl acetate/petroleum ether.
4-[(Aziridin-1-yl)-bis(4-chlorophenyl)methyl]-5-methyl-1-(4-chlorophenyl)-1H-1,2,3-triazole (7a)
White flakes; yield 86%; mp 90–92°C; 1H NMR: δ 7.52 (d, 1H, J=3 Hz), 7.50 (d, 1H, J=3 Hz), 7.48 (d, 2H, J=3 Hz), 7.45 (d, 2H, J=3 Hz), 7.40 (d, 1H, J=3.6 Hz), 7.37 (d, 1H, J=3Hz), 7.29 (d, 2H, J=3 Hz), 7.26 (d, 2H, J=3.6 Hz), 2.10 (s, 3H), 1.81 (s, 2H), 1.15 (s, 2H); 13C NMR (CDCl3-d1), δ 145.7, 141.6, 135.6, 134.7, 133.1, 132.9, 130.4, 129.6, 127.8, 126.8, 69.3, 21.7, 10.6; MS: m/z 468 (M+, 0.39), 428 (6), 426 (6), 154 (32), 152 (100); IR: 3425, 3061, 2987, 2926, 2844, 1734, 1496, 1442, 1422, 1400, 1264, 1117, 1092, 1010, 922, 867, 829, 818 cm−1. HRMS (ESI). Calcd for C24H19Cl3N4, [M+H]+: m/z 469.0748. Found: m/z 469.0755.
4-[(Aziridin-1-yl)-bis(3-chlorophenyl)methyl]-5-methyl-1-(4-chlorophenyl)-1H-1,2,3-triazole (7b)
White flakes; yield 65%; mp 96–98°C; 1H NMR: δ 7.61 (s, 2H), 7.52 (q, 2H, J=2.4 Hz), 7.38 (m, 4H), 7.23 (m, 4H), 2.04 (s, 3H), 1.84 (d, 2H, J=2Hz), 1.17 (d, 2H, J=2 Hz); 13C NMR (CDCl3-d1), δ 145.3, 144.8, 135.6, 134.7, 133.7, 133.2, 129.6, 128.9, 128.8, 127.4, 127.3, 126.8, 69.5, 21.8, 10.6; MS: m/z 468 (M+, 0.71), 428 (5), 154 (27), 152 (100), 111 (29), 75 (12); IR: 3449, 3088, 3063, 2990, 2931, 2869, 1734, 1590, 1572, 1496, 1469, 1422, 1368, 1256, 1202, 1148, 1120, 1091, 1049, 1006, 978, 940, 893, 875, 845, 785, 753, 728, 699, 681 cm−1; HRMS (ESI). Calcd for C24H19Cl3N4, [M+H]+: m/z 469.0748. Found: m/z 469.0751.
4-[(Aziridin-1-yl)diphenylmethyl]-5-methyl-1-(4-chlorophenyl)-1H-1,2,3-triazole (7c)
White needles; yield 90%; mp 92–94°C; 1H NMR: δ 7.50 (m, 6H), 7.50 (m, 2H ), 7.26 (m, 6H), 2.08 (s, 3H), 1.80 (s, 2H), 1.19 (d, 2H, J=2 Hz); 13C NMR (CDCl3-d1), δ 146.6, 143.3, 135.3, 134.9, 132.8, 129.5, 129.2, 127.4, 126.8, 126.7, 69.9, 21.7, 10.5; MS: m/z 400 (M+, 1.2), 358 (11), 178 (5), 154 (32) 152 (100), 11 (26), 77 (8), 75 (11), 51 (5), 43 (7); IR: 3459, 3088, 3059, 2987, 2928, 1738, 1594, 1495, 1445, 1422, 1402, 1371, 1262, 1235, 1202, 1177, 1120, 1090, 1042, 1004, 938, 902, 848, 821, 765, 744, 700, 639 cm−1. HRMS (ESI). Calcd for C24H21ClN4, [M+H]+: m/z 401.1528. Found: m/z 401.1532.
4-[(Aziridin-1-yl)-bis(4-chlorophenyl)methyl]-5-methyl-1-p-tolyl-1H-1,2,3-triazole (7d)
White flakes; yield 89%; mp 86–88°C; 1H NMR: δ 7.48 (m, 4H), 7.28 (m, 8H), 2.43 (s, 3H), 2.00 (s, 3H), 1.80 (d, 2H, J=2 Hz), 1.15 (d, 2H, J=2 Hz); 13C NMR (CDCl3-d1), δ 144.8, 142.1, 139.6, 133.7, 133.1, 132.8, 130.3, 129.9, 127.8, 125.4, 69.2, 21.7, 21.1, 10.5; MS: m/z 448 (M+, 0.52), 406 (8), 152 (22), 133 (11), 132 (100), 125 (7), 111 (12), 97 (8), 91 (11), 83 (12), 74 (11), 55 (15); IR: 3429, 3060, 2987, 2923, 2856, 1517, 1486, 1443, 1421, 1400, 1264, 1205, 1180, 1094, 1011, 923, 867, 819, 559 cm−1. HRMS (ESI). Calcd for C25H22Cl2N4, [M+H]+: m/z 449.1294. Found: m/z 449.1299.
4-[(Aziridin-1-yl)-bis(3-chlorophenyl)methyl]-5-methyl-1-p-tolyl-1H-1,2,3-triazole (7e)
White needles; yield 82%; mp 103–105°C; 1H NMR: δ 7.65 (s, 2H), 7.42 (m, 2H), 7.30 (s, 4H), 7.22 (m, 4H), 2.42 (s, 3H), 1.95 (s, 3H), 1.85 (d, 2H, J=2 Hz), 1.18 (d, 2H, J=2 Hz); 13C NMR (CDCl3-d1), δ 145.8, 143.8, 139.7, 133.8, 133.7, 133.3, 129.9, 128.9, 128.7, 127.3, 127.2, 125.4, 69.4, 21.8, 21.2, 10.6; MS: m/z 448 (M+, 0.54), 406 (5), 133 (10), 132 (100), 91 (30), 65 (13); IR: 3449, 3062, 2990, 2923, 2865, 1735, 1590, 1571, 1515, 1469, 1420, 1368, 1256, 1235, 1203, 1179, 1147, 1121, 1102, 1078, 1048, 1010, 939, 883, 826, 785, 754, 729, 698, 682 cm−1; HRMS (ESI). Calcd for C25H22Cl2N4, [M+H]+: m/z 449.1294. Found: m/z 449.1301.
4-[(Aziridin-1-yl)-diphenylmethyl]-5-methyl-1-p-tolyl-1H-1,2,3-triazole (7f)
White needles; yield 91%; mp 151–152°C; 1H NMR: δ 7.57 (m, 4H), 7.37 (m, 10H), 2.42 (s, 3H), 1.98(s, 3H), 1.82 (d, 2H, J=2 Hz), 1.22 (d, 2H, J=2 Hz); 13C NMR (CDCl3-d1), δ 145.7, 143.8, 139.4, 133.9, 132.9, 129.8, 129.1, 127.4, 126.8, 125.5, 69.9, 21.8, 21.2, 10.5; MS: m/z 380 (M+, 1.0), 33 (13), 178 (6), 133 (10), 132 (100), 91 (34), 77 (6), 65 (14); IR: 3430, 3055, 3021, 2983, 2926, 2864, 1594, 1516, 1488, 1444, 1420, 1387, 1259, 1208, 1181, 1120, 1104, 1031, 1006, 987, 935, 898, 859, 838, 818, 798, 767, 748, 700, 662, 640, 553, 529 cm−1. HRMS (ESI). Calcd for C24H24N4, [M+H]+: m/z 381.2074. Found: m/z 381.2079.
4-[(Aziridin-1-yl)-bis(4-chlorophenyl)methyl]-5-methyl-1-phenyl-1H-1,2,3-triazole (7g)
White flakes; yield 90%; mp 83–85°C; 1H NMR: δ 7.52 (m, 5H), 7.47 (m, 2H), 7.42 (m, 2H), 7.29 (m, 2H), 7.26 (s, 2H), 2.05 (s, 3H), 1.82 (d, 2H, J=3 Hz), 1.16 (d, 2H, J=3 Hz); 13C NMR (CDCl3-d1), δ 145.1, 141.9, 136.2, 133.0, 132.9, 130.4, 129.5, 129.4, 127.8, 125.6, 69.3, 21.7, 10.6; MS: m/z 434 (M+, 0.7), 394 (5), 392 (9), 332 (11), 129 (11), 119 (11), 118 (100), 104 (10), 91 (13), 77 (21), 57 (11); IR: 3429, 3060, 2987, 2955, 2924, 2854, 1595, 1485, 1416, 1398, 1264, 1113, 1092, 1072, 1011, 921, 867, 817, 763, 694, 565, 531 cm−1. HRMS (ESI). Calcd for C24H20Cl2N4, [M+H]+: m/z 435.1138. Found: m/z 435.1144.
4-[(Aziridin-1-yl)-bis(3-chlorophenyl)methyl]-5-methyl-1-phenyl-1H-1,2,3-triazole (7h)
White flakes; yield 40%; mp 141–143°C; 1H NMR: δ 7.65 (s, 2H), 7.52 (m, 3H), 7.40 (m, 4H), 7.23 (m, 4H), 1.99 (s, 3H), 1.85 (t, 2H, J=2 Hz), 1.19 (t, 2H, J=2 Hz); 13C NMR (CDCl3-d1), δ 145.7, 144.1, 136.2, 133.8, 133.3, 129.5, 129.4, 128.9, 128.7, 127.3, 127.2, 125.6, 69.4, 21.8, 10.5; MS: m/z 434 (M+, 0.3), 176 (5), 118 (100), 77 (69), 5 1 (16); IR: 3429, 3058, 2985, 2926, 2844, 1592, 1571, 1501, 1471, 1265, 1119, 1144, 1120, 1100, 1015, 976, 940, 893, 813, 784, 761, 747, 713, 695 cm−1. HRMS (ESI). Calcd for C24H20Cl2N4, [M+H]+: m/z 435.1138. Found: m/z 435.1145.
4-[(Aziridin-1-yl)-diphenylmethyl]-5-methyl-1-phenyl-1H-1,2,3-triazole (7i)
White needles; yield 89%; mp 203–206°C; 1H NMR: δ 7.56 (m, 4H), 7.51 (m, 3H), 7.43 (m, 2H), 7.26 (m, 6H), 2.03 (s, 3H), 1.81 (s, 2H), 1.21 (s, 2H); 13C NMR (CDCl3-d1), δ 145.9, 143.6, 136.4, 132.9, 129.3, 129.1, 127.4, 126.8, 125.6, 69.9, 21.7, 10.5; MS: m/z 366 (M+, 0.4), 324 (8), 178 (5), 119 (8), 118 (100), 77 (46); IR: 3424, 3070, 3051, 3022, 2988, 2925, 2890, 1594, 1496, 1444, 1416, 1387, 1261, 1207, 1077, 1033, 993, 937, 903, 854, 767, 747, 697, 646, 561 cm−1. HRMS (ESI). Calcd for C24H22N4, [M+H]+: m/z 367.1917. Found: m/z 367.1924.
Biological evaluation
The effects of the synthesized compounds on cell viability were investigated under previously reported conditions with human leukemia cells and human hepatoma G2 cells [20], [21] using the MTT assay.
Acknowledgments
The authors wish to acknowledge the funding support by the Education Department of Gansu Province (grant 2016B-124) and by the Lanzhou University of Arts and Science (grant 2015GSP05).
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Artikel in diesem Heft
- Frontmatter
- Preliminary Communications
- A novel molecular probe for the detection of phosphorylated proteins
- Highly efficient [3+3] cycloaddition reactions of in situ generated aza-oxyallyl cation with nitrones
- Efficient three-component synthesis of 5-(6-hydroxy-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-5,12-dihydrobenzo[b]pyrimido[5,4-g][1,8]naphthyridine-2,4(1H,3H)-dione
- Research Articles
- A fast and efficient ‘on-solvent’ cascade assembling of salicylaldehydes and dimethylbarbituric acid into 5-(1,3-dimethyl-2,4-dioxo-1,3,4,5-tetrahydro-2H-chromeno[2,3-d]pyrimidin-5-yl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-triones
- Synthesis of novel push-pull fluorescent dyes – 7-(diethylamino)furo[3,2-c]coumarin and 7-(diethylamino)thieno[3,2-c]coumarin derivatives
- A fluorescent pH probe for an aqueous solution composed of 7-hydroxycoumarin, Schiff base and phenanthro[9,10-d]imidazole moieties (PICO)
- Synthesis of 2,3-dicyanopyrazine and ethyl 5-amino-4,6-dicyanobiphenyl-3-carboxylate derivatives from ethyl aroylpyruvates
- Baker’s yeast catalyzed one-pot synthesis of bioactive 2-[benzylidene(or pyrazol-4-ylmethylene)hydrazono]-1,3-thiazolidin-4-one-5-yl-acetic acids
- Design, synthesis and anticancer activity evaluation of aziridine-1,2,3-triazole hybrid derivatives
- Synthesis and antimicrobial activity of 3,4-dihydropyrimidin-2(1H)-one derivatives containing a hydrazone moiety
- Synthesis and antiproliferative activity of flavonoid triazolyl glycosides
Artikel in diesem Heft
- Frontmatter
- Preliminary Communications
- A novel molecular probe for the detection of phosphorylated proteins
- Highly efficient [3+3] cycloaddition reactions of in situ generated aza-oxyallyl cation with nitrones
- Efficient three-component synthesis of 5-(6-hydroxy-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-5,12-dihydrobenzo[b]pyrimido[5,4-g][1,8]naphthyridine-2,4(1H,3H)-dione
- Research Articles
- A fast and efficient ‘on-solvent’ cascade assembling of salicylaldehydes and dimethylbarbituric acid into 5-(1,3-dimethyl-2,4-dioxo-1,3,4,5-tetrahydro-2H-chromeno[2,3-d]pyrimidin-5-yl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-triones
- Synthesis of novel push-pull fluorescent dyes – 7-(diethylamino)furo[3,2-c]coumarin and 7-(diethylamino)thieno[3,2-c]coumarin derivatives
- A fluorescent pH probe for an aqueous solution composed of 7-hydroxycoumarin, Schiff base and phenanthro[9,10-d]imidazole moieties (PICO)
- Synthesis of 2,3-dicyanopyrazine and ethyl 5-amino-4,6-dicyanobiphenyl-3-carboxylate derivatives from ethyl aroylpyruvates
- Baker’s yeast catalyzed one-pot synthesis of bioactive 2-[benzylidene(or pyrazol-4-ylmethylene)hydrazono]-1,3-thiazolidin-4-one-5-yl-acetic acids
- Design, synthesis and anticancer activity evaluation of aziridine-1,2,3-triazole hybrid derivatives
- Synthesis and antimicrobial activity of 3,4-dihydropyrimidin-2(1H)-one derivatives containing a hydrazone moiety
- Synthesis and antiproliferative activity of flavonoid triazolyl glycosides
