Comparison of carbon-sulfur and carbon-amine bond in therapeutic drug: -S-aromatic heterocyclic podophyllum derivatives display antitumor activity
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- Ἀριστόβουλος Γιαννόπουλος
- 5 χρόνια πριν
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1 Comparison of carbon-sulfur and carbon-amine bond in therapeutic drug: -S-aromatic heterocyclic podophyllum derivatives display antitumor activity Jian-Long Li 1,a, Wei Zhao 1,a, Chen Zhou 1,a, Ya-Xuan Zhang a, Hong-Mei Li a, Ya-Ling Tang b, Xin-Hua Liang b, Tao Chen c, and Ya-Jie Tang a *, a Key Laboratory of Fermentation Engineering (Ministry of Education), Hubei Provincial Cooperative Innovation Center of Industrial Fermentation, Hubei University of Technology, Wuhan , China b State Key Laboratory of Oral Diseases West China Hospital of Stomatology (Sichuan University), Chengdu Sichuan ,People s Republic of China c Key Laboratory of Systems Bioengineering (Ministry of Education), School of Chemical Engineering and Technology, Tianjin University, Tianjin , China *Corresponding author. Tel. & Fax: yajietang@hotmail.com 1 Equally contributed to this work
2 Supporting Information Table S1. Calculated docking of the complex of podophyllum derivatives with tubulin/topo II. Energy Energy Compound H-bond packing Compound ( -kcal/mol) ( -kcal/mol) H-bond packing 1S Ser A178 1'S 6.51 Asp B479 Arg B503, DG D13 1N 4.03 Asn B258 Lys B352 1'N 3.04 Asp B479 Arg B503, DT F9, DA D12, DG D13 2S 4.99 Lys B254 Leu B248 2'S Asp B479 Arg B503, DT F9, DG D13 2N 5.72 Lys B352 Leu B255, Lys B352 2'N 6.15 Asp B479 Arg B503, DA D12, DG D13 3S 4.37 Ser A178 Ala B316 3'S 3.86 Asp B479 Arg B503, DT F9, DG D13 3N 3.87 Asn B258, Thr B353 Leu B248 3'N 5.58 Asp B479 Arg B503, DT F9, DG D13 4S 2.90 Thr A179 Lys B254 4'S 4.52 Asp B479 Arg B503, DT F9, DG D13 4N 2.45 Asn B258 Lys B352 4'N 2.69 Asp B479 Arg B503, DT F9, DG D13 5S 6.45 Lys B254 Lys B254 5'S 5.10 Asp B479 Arg B503, DT F9, DG D13 5N Leu B248 5'N 4.12 Asp B479 Arg B503, DA D12, DG D13 6S 6.28 Lys B352-6'S 8.42 Asp B479 Arg B503, DT F9, DG D13 6N 3.14 Leu B255-6'N 8.10 Asp B479, DG D13 Arg B503, DA D12, DG D13 7S 'S N Thr B353-7'N DC E8 DT F9, DA D12 8S 'S Lys B456 Arg B503 8N Leu B248 8'N Arg B503, DT F9 9S 'S Lys B456 Arg B503 9N Leu B255-9'N Arg B503 PTOX 4.11 Leu B248 Ala B316 VP Asp B479 Arg B503, DC E8, DG D13 2
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4 Figure S1. Effects of podophyllum derivatives on the HeLa cell cycle arrest and apoptosis induce. (A) Compound 4β-S-(1, 3, 4-trizole-2)-4-deoxy-podophyllotoxin (Compound 1S), Compound 4β-NH-(1, 3, 4-trizole-2)-4-deoxy-podophyllotoxin (Compound 1N), 4β-S-(1, 3, 4-trizole-2)-4-deoxy-4'-demethylepipodophyllotoxin (Compound 1'S) and Compound 4β-NH-(1, 3, 4-trizole-2)-4-deoxy-4'-demethylepipodophyllotoxin (Compound 1'N) arrested cell cycle in HeLa cells in a dose- and time-dependent manner at the concentration of 0, 0.1, 1, and 5 µm for 6, 12, 24, and 48 h, respectively. Compared with the cells incubated with no drug, the treatment of Compounds 1S and 1N did not induce the G 2 /M phase arrest at a lower concentration of 0.1 μm. However, the percentage of G 2 /M phase cells was accumulated significantly to about 80% at 48 h when the concentration was increased to 1 μm. And then the percentage of G 2 /M phase cells continuously increased to the maximum about 80-90% at the higher concentration of 5 μm after the incubation of 48 h. Corresponding to Compounds 1S and 1N, the comparison between Compound 1'S and 1'N showed the similar trend that Compound 1'S was superior than Compound 1'N to arrest the cell cycle. (B) Compound 1S, 1N, 1'S, and 1'N induced cell apoptosis in HeLa cells in a dose- and time-dependent manner at the concentration of 0, 0.1, 1, and 5 µm for 6, 12, 24, and 48 h, respectively. Symbols: the negative control without adding Compounds 1S, 1N, 1'S and 1'N (0 µm), Compound 1S (black triangle, ), Compound 1N (open Compound 1'N (open circle, ). triangle, ), Compound 1'S (black circle, ), and 4
5 Figure S2 Figure S3 5
6 1 Calculated docking of complexes 2 6
7 3 7
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12 Copies of 1 H, 13 C NMR and 2D NMR (1H-1H COSY, HMBC, HSQC) Spectra 1. NMR and MS spectrum of compound 3S H NMR spectrum of compound 3S C NMR spectrum of compound 3S H- 1 H COSY spectrums for compound 3S HMBC spectrums for compound 3S HSQC spectrums for compound 3S MS diagram for compound 3S NMR spectrum of compound 4S H NMR spectrum of compound 4S C NMR spectrum of compound 4S H- 1 H COSY spectrums for compound 4S HMBC spectrums for compound 4S HSQC spectrums for compound 4S MS diagram for compound 4S NMR and MS spectrum of compound 5S H NMR spectrum of compound 5S C NMR spectrum of compound 5S H- 1 H COSY spectrums for compound 5S HMBC spectrums for compound 5S HSQC spectrums for compound 5S MS diagram for compound 5S NMR and MS spectrum of compound 6S. 12
13 H NMR spectrum of compound 6S C NMR spectrum of compound 6S H- 1 H COSY spectrums for compound 6S HMBC spectrums for compound 6S HSQC spectrums for compound 6S MS diagram for compound 6S NMR and MS spectrum of compound 3'S H NMR spectrum of compound 3'S C NMR spectrum of compound 3'S H- 1 H COSY spectrums for compound 3'S HMBC spectrums for compound 3'S HSQC spectrums for compound 3'S MS diagram for compound 3'S NMR and MS spectrum of compound 4'S H NMR spectrum of compound 4'S C NMR spectrum of compound 4'S H- 1 H COSY spectrums for compound 4'S HMBC spectrums for compound 4'S HSQC spectrums for compound 4'S MS diagram for compound 4'S NMR and MS spectrum of compound 5'S H NMR spectrum of compound 5'S C NMR spectrum of compound 5'S. 13
14 H- 1 H COSY spectrums for compound 5'S HMBC spectrums for compound 5'S HSQC spectrums for compound 5'S MS diagram for compound 5'S NMR spectrum of compound 6'S H NMR spectrum of compound 6'S C NMR spectrum of compound 6'S H- 1 H COSY spectrums for compound 6'S HMBC spectrums for compound 6'S HSQC spectrums for compound 6'S MS diagram for compound 6'S NMR and MS spectrum of compound 1N H NMR spectrum of compound 1N C NMR spectrum of compound 1N H- 1 H COSY spectrums for compound 1N HMBC spectrums for compound 1N HSQC spectrums for compound 1N MS diagram for compound 1N NMR spectrum of compound 2N H NMR spectrum of compound 2N C NMR spectrum of compound 2N H- 1 H COSY spectrums for compound 2N HMBC spectrums for compound 2N. 14
15 HSQC spectrums for compound 2N MS diagram for compound 2N NMR spectrum of compound 3N H NMR spectrum of compound 3N C NMR spectrum of compound 3N H- 1 H COSY spectrums for compound 3N HMBC spectrums for compound 3N HSQC spectrums for compound 3N MS diagram for compound 3N NMR spectrum of compound 4N H NMR spectrum of compound 4N C NMR spectrum of compound 4N COSY spectrums for compound 4N HMBC spectrums for compound 4N HSQC spectrums for compound 4N MS diagram for compound 4N NMR and MS spectrum of compound 5N H NMR spectrum of compound 5N C NMR spectrum of compound 5N COSY spectrums for compound 5N HMBC spectrums for compound 5N HSQC spectrums for compound 5N MS diagram for compound 5N. 15
16 NMR and MS spectrum of compound 6N H NMR spectrum of compound 6N C NMR spectrum of compound 6N COSY spectrums for compound 6N HMBC spectrums for compound 6N HSQC spectrums for compound 6N MS diagram for compound 6N NMR and MS spectrum of compound 1'N H NMR spectrum of compound 1'N C NMR spectrum of compound 1'N H- 1 H COSY spectrums for compound 1'N HMBC spectrums for compound 1'N HSQC spectrums for compound 1'N MS diagram for compound 1'N NMR spectrum of compound 2'N H NMR spectrum of compound 2'N C NMR spectrum of compound 2'N H- 1 H COSY spectrums for compound 2'N HMBC spectrums for compound 2'N HSQC spectrums for compound 2'N MS diagram for compound 2'N NMR spectrum of compound 3'N H NMR spectrum of compound 3'N. 16
17 C NMR spectrum of compound 3'N H- 1 H COSY spectrums for compound 3'N HMBC spectrums for compound 3'N HSQC spectrums for compound 3'N MS diagram for compound 3'N NMR spectrum of compound 4'N H NMR spectrum of compound 4'N C NMR spectrum of compound 4'N COSY spectrums for compound 4'N HMBC spectrums for compound 4'N HSQC spectrums for compound 4'N MS diagram for compound 4'N NMR and MS spectrum of compound 5'N H NMR spectrum of compound 5'N C NMR spectrum of compound 5'N COSY spectrums for compound 5'N HMBC spectrums for compound 5'N HSQC spectrums for compound 5'N MS diagram for compound 5'N NMR and MS spectrum of compound 6'N H NMR spectrum of compound 6'N C NMR spectrum of compound 6'N COSY spectrums for compound 6'N. 17
18 HMBC spectrums for compound 6'N HSQC spectrums for compound 6'N MS diagram for compound 6'N
19 Copies of 1 H, 13 C NMR and 2D NMR ( 1 H- 1 H COSY, HMBC, HSQC) Spectra H NMR spectrum of compound 3S C NMR spectrum of compound 3S
20 H- 1 H COSY diagram of compound 3S HMBC diagram of compound 3S
21 HSQC diagram of compound 3S MS spectrum of compound 3S β-S-(pyridine-2)-4-deoxy-podophyllotoxin (3S). 1 H NMR (400 MHz, CDCl 3, δ): 8.40 (d, J = 4.0 Hz, 1H), 7.52 (t, J = 4.0 Hz, 1H), 7.18 (d, J = 8.0 Hz, 1H), 7.05 (t, J = 4.0 Hz, 1H), 6.95 (s, 1H), 6.46 (s, 1H), 6.33 (s, 2H), 5.95 (d, J = 8.0 Hz, 2H), 5.57 (d, J = 4.0 Hz, 1H), 4.60 (d, J = 4.0 Hz, 1H), 4.34 (t, J = 8.0 Hz, 1H), 3.86 (t, J = 8.0 Hz, 1H), 3.80 (s, 3H), 3.76 (s, 6H), (m, 2H); 13 C NMR (101 MHz, CDCl 3, δ): , , (2C), , , , , , , , , , , , , (2C), , 71.01, 60.76, (2C), 45.63, 43.77, 42.50, ESI-MS: calc d for C 27 H 25 NO 7 S [M+H] + : , found [M+H] +. 21
22 H NMR spectrum of compound 4S C NMR spectrum of compound 4S
23 H- 1 H COSY diagram of compound 4S HMBC diagram of compound 4S
24 HSQC diagram of compound 4S MS spectrum of compound 4S β-S-(pyrimidine-2)-4-deoxy-podophyllotoxin (4S) 1 H NMR (400 MHz, CDCl 3, δ): 8.57 (d, J = 4.0 Hz, 2H), 7.08 (t, J = 4.0 Hz, 1H), 6.97 (s, 1H), 6.48 (s, 1H), 6.34 (s, 2H), 5.97 (d, J = 8.0 Hz, 2H), 5.45 (d, J = 4.0 Hz, 1H), 4.62 (d, J = 4.0 Hz, 1H), 4.39 (t, J = 8.0 Hz, 1H), 3.88 (t, J = 8.0 Hz, 1H), 3.81 (s, 3H), 3.77 (s, 6H), (m, 2H); 13 C NMR (101 MHz, CDCl 3, δ): , , (2C), (2C), , , , , , , , , , (2C), , 70.68, 60.73, (2C), 47.13, 43.75, 42.40, ESI-MS: calc'd for C 26 H 24 N 2 O 7 S [M+H] + : , found [M+H] + ; calc'd for C 26 H 24 N 2 O 7 S [M+H] + : , found [M+2H] + ; calc'd for C 26 H 24 N 2 O 7 S [M+Na] + : , found [M+Na] + ; calc'd for C 26 H 24 N 2 O 7 S [M+2Na+2K-2H] + : , found [M+2Na+2K-2H]
25 H NMR spectrum of compound 5S C NMR spectrum of compound 5S
26 H- 1 H COSY spectrums for compound 5S HMBC spectrums for compound 5S
27 HSQC spectrums for compound 5S MS spectrum of compound 5S β-S-(benzothiazole-2)-4-deoxy-podophyllotoxin (5S) 1 H NMR (400 MHz, CDCl 3, δ): 7.86 (d, J = 8.0 Hz, 1H), 7.80 (d, J = 8.0 Hz, 1H), 7.45 (t, J = 8.0 Hz, 1H), 7.35 (t, J = 8.0 Hz, 1H), 7.01 (s, 1H), 6.50 (s, 1H), 6.33 (s, 2H), 6.99 (d, J = 8.0 Hz, 2H), 5.77 (d, J = 4.0 Hz, 1H), 4.63 (d, J = 4.0 Hz, 1H), 4.47 (t, J = 8.0 Hz, 1H), 3.99 (t, J = 8.0 Hz, 1H), 3.82 (s, 3H), 3.78 (s, 6H), (m, 1H), (m, 1H); 13 C NMR (101 MHz, CDCl 3, δ): , , (2C), (2C), , , , , , , (2C), , , , , (2C), , 70.79, 60.76, (2C), 49.64, 43.74, 42.58, ESI-MS: calc d for C 29 H 25 NO 7 S 2 [M+H] + : , found [M+H] +. 27
28 H NMR spectrum of compound 6S C NMR spectrum of compound 6S
29 H- 1 H COSY spectrums for compound 6S HMBC spectrums for compound 6S
30 HSQC spectrums for compound 6S MS spectrum of compound 6S β-S-(purine-6)-4-deoxy-podophyllotoxin (6S) 1 H NMR (300 MHz, CDCl 3, δ): 6.87 (s, 1H), 6.54 (s, 1H), 6.27 (s, 2H), 5.99 (d, J = 9.0 Hz, 2H), 5.29 (s, 1H), 4.86 (d, J = 9.0 Hz, 1H), 4.59 (d, J = 9.0 Hz, 1H), (m, 1H), 3.79 (s, 3H), 3.73 (s, 6H), 3.28 (dd, J 1 = 16.0 Hz, J 2 = 6.0 Hz, 1H), (m, 1H); 13 C NMR (75 MHz, CDCl 3, δ): (2C), (2C), , (2C), , (2C), , , (2C), , (2C), 67.61, 66.72, 60.74, (2C), 53.42, , 43.89, 40.47, ESI-MS: calc d for C 27 H 24 N 4 O 7 S [M+H] + : , found [M+H] +. 30
31 H NMR spectrum of compound 3'S C NMR spectrum of compound 3'S
32 H- 1 H COSY spectrums for compound 3'S HMBC spectrums for compound 3'S
33 HSQC spectrums for compound 3'S MS spectrum of compound 3'S β-S-(pyridine-2)-4-deoxy-4'-demethyl-podophyllotoxin (3'S) 1 H NMR (400 MHz, CDCl 3, δ): 8.40 (d, J = 4.0 Hz, 1H), 7.52 (t, J = 8.0 Hz, 1H), 7.18 (d, J = 8.0 Hz, 1H), 7.05 (t, J = 8.0 Hz, 1H), 6.94 (s, 1H), 6.46 (s, 1H), 6.34 (s, 2H), 5.96 (d, J = 12.0 Hz, 2H), 5.56 (d, J = 4.0 Hz, 1H), 5.35 (s, 1H), 4.59 (d, J = 4.0 Hz, 1H), 4.33 (t, J = 8.0 Hz, 1H), 3.85 (t, J = 8.0 Hz, 1H), 3.79 (s, 6H), (m, 2H); 13 C NMR (101 MHz, CDCl 3, δ): , , , , , (2C), , , , , , , , , , (2C), , 70.98, (2C), 45.64, 43.61, 42.61, ESI-MS: calc d for C 26 H 23 NO 7 S [M+H] + : , found [M+H] +. 33
34 H NMR spectrum of compound 4'S C NMR spectrum of compound 4'S
35 H- 1 H COSY spectrums for compound 4'S HMBC spectrums for compound 4'S
36 HSQC spectrums for compound 4'S MS spectrum of compound 4'S β-S-(pyrimidine-2)-4-deoxy-4'-demethyl-podophyllotoxin (4'S) 1 H NMR (300 MHz, CDCl 3, δ): (d, J = 7.2 Hz, 1H), (t, J = 6.9 Hz, 1H), (d, J = 7.8 Hz, 1H), (t, J = 6.0 Hz, 1H), (s, 1H), (s, 1H), (s, 2H), (d, J = 7.2 Hz, 2H), (t, J = 6.0 Hz, 1H), (d, J = 4.2 Hz, 1H), (t, J = 8.1 Hz, 1H), (t, J = 9.0 Hz, 1H), (s, 6H), (m, 2H); 13 C NMR (75 MHz, CDCl 3, δ): , , , , , , , , , , , , , , , (2C), , , (2C), , , , ESI-MS: calc'd for C 25 H 22 N 2 O 7 S [M+H] + : , found [M+H] +. 36
37 H NMR spectrum of compound 5'S C NMR spectrum of compound 5'S
38 H- 1 H COSY spectrums for compound 5'S HMBC spectrums for compound 5'S
39 HSQC spectrums for compound 5'S MS spectrum of compound 5'S. Intens. x MS, 5.9min # m/z 4β-S-(benzothiazole-2)-4-deoxy-4'-demethyl-podophyllotoxin (5'S) 1 H NMR (400 MHz, CDCl 3, δ): 7.88 (d, J = 8.0 Hz, 1H), 7.80 (d, J = 8.0 Hz, 1H), 7.46 (t, J = 8.0 Hz, 1H), 7.35 (t, J = 8.0 Hz, 1H), 7.27 (s, 1H), 6.56 (s, 1H), 6.40 (s, 2H), 6.00 (d, J = 8.0 Hz, 2H), 5.59 (d, J = 4.0 Hz, 1H), 4.65 (d, J = 4.0 Hz, 1H), (m, 2H), 3.80 (s, 6H), (m, 1H), (m, 1H); 13 C NMR(101 MHz, CDCl 3, δ): , , , , , (2C), , , , , , , , , , , , (2C), , 71.55, (2C), 49.75, 47.69, 43.90, ESI-MS: calc d for C 28 H 23 NO 7 S 2 [M+H] + : , found [M+H] +. 39
40 H NMR spectrum of compound 6'S C NMR spectrum of compound 6'S
41 H- 1 H COSY spectrums for compound 6'S HMBC spectrums for compound 6'S
42 HSQC spectrums for compound 6'S MS spectrum of compound 6'S β-S-(purine-6)-4-deoxy-4'-demethyl-podophyllotoxin (6'S) 1 H NMR (400 MHz, DMSO): δ 8.24 (s, 1H), 6.91 (s, 1H), 6.48 (s, 1H), 6.19 (s, 2H), 5.98 (d, J = 8.0 Hz, 2H), 5.42 (d, J = 8.0 Hz, 1H), 4.71 (dd, J = 4.0 Hz, 1H), 4.47 (d, J = 8.0 Hz, 1H), 4.31 (t, J = 8.0 Hz, 1H), 4.15 (t, J = 8.0 Hz, 1H), 3.59 (s, 6H), (m, 1H), (m, 1H); 13 C NMR (101 MHz, DMSO): δ (2C), , (2C), (2C), , (2C), , (2C), , , (2C), , 68.11, 65.41, (2C), 55.36, 43.41, ESI-MS: calc d for C 27 H 25 NO 7 S [M+H] + : , found [M+H] +. 42
43 H NMR spectrum of compound 1N C NMR spectrum of compound 1N
44 H- 1 H COSY spectrums for compound 1N HMBC spectrums for compound 1N
45 HSQC spectrums for compound 1N MS spectrum of compound 1N β-N-(1,2,4-trizole-3)-4-deoxy-podophyllotoxin (1N). 1 H NMR (400 MHz, CDCl 3 ): δ 6.83 (s, 1H), 6.52 (s, 1H), 6.27 (s, 2H), 5.99 (d, J = 16 Hz, 2H), 4.60 (dd, J = 4.0 Hz, 2H), 4.37 (t, J = 4.0 Hz, 1H), 4.24 (t, J = 4.0 Hz, 1H), 3.80 (s, 3H), 3.74 (s, 6H), 3.71 (t, J = 4.0 Hz, 1H), (dd, J = 8.0 Hz, 1H), (m, 1H); 13 C NMR (101 MHz, CDCl 3 ): δ , , (3C), , , , , , , , , (2C), , , , (2C), , , , ; ESI-MS: calc d for C 24 H 24 N 4 O 7 [M+H] + : , found [M+H]
46 H NMR spectrum of compound 2N C NMR spectrum of compound 2N
47 H- 1 H COSY spectrums for compound 2N HMBC spectrums for compound 2N
48 HSQC spectrums for compound 2N MS spectrum of compound 2N β-N-(1,3,4-thiodiazole-2)-4-deoxy-podophyllotoxin (2N). 1 H NMR (400 MHz, CDCl 3 ): δ 6.82 (s, 1H), 6.52 (s, 1H), 6.27 (s, 2H), 5.98 (d, J = 3.6 Hz, 2H), 5.30 (s, 1H), 5.46 (dd, 2H, J = 4.0 Hz), 4.36 (t, 1H, J = 8.0 Hz), 4.24 (t, 1H, J = 8.0 Hz), 3.80 (s, 3H), 3.74 (s, 6H), 3.72 (t, J = 8.0 Hz, 1H), 3.38 (m, J = 4.0 Hz, 1H), (m, 1H); 13 C NMR(101 MHz, CDCl 3 ): δ , (2C), , , , , , , , , (2C), , , 71.31, 71.25, 67.76, 60.73, (2C), 43.86, 41.19, 38.43; ESI-MS: calc d for C 24 H 23 N 3 O 7 S: , found [M+H] +. 48
49 H NMR spectrum of compound 3N C NMR spectrum of compound 3N
50 H- 1 H COSY diagram of compound 3N HMBC diagram of compound 3N
51 HSQC diagram of compound 3N MS spectrum of compound 3N 4β-N-(pyridine-2)-4-deoxy-podophyllotoxin (3N). 1 H NMR (300 MHz, CD 3 OD): δ (d, J = 6.3 Hz, 2H), (m, 2H), (t, J = 7.8 Hz,1H), (s, 2H), (s, 2H), (s, 2H), (s, 1H), (d, J = 4.5 Hz, 3H), (s, 6H), (s, 3H), (m, 2H); 13 C NMR(75 MHz, CD 3 OD): δ , , , , , (2C), , , , , , , , (2C), , , (2C), , , , , ESI-MS: calc d for C 27 H 26 N 2 O 7 [M+H] + : , found [M+H] H NMR spectrum of compound 4N
52 C NMR spectrum of compound 4N H- 1 H COSY diagram of compound 4N
53 HMBC diagram of compound 4N HSQC diagram of compound 4N
54 MS spectrum of compound 4N β-N-(pyrimidine-2)-4-deoxy-podophyllotoxin (4N) 1 H NMR (300 MHz, CDCl 3, δ): (s, 2H), (s, 1H), (s, 1H), (s, 1H), (s, 1H), (s, 2H), (d, J = 8.4 Hz, 2H), (s, 1H), (s, 1H), (t, J = 0.6 Hz, 1H), (s, 3H), (s, 6H), (s, 3H); 13 C NMR(75 MHz, CDCl 3, δ): , , (2C), (2C), , , , , , , , , , (2C), , , , (2C), , , , ESI-MS: calc d for C 26 H 25 N 3 O 7 [M+H] + : , found [M+H] H NMR spectrum of compound 5N
55 H- 1 H COSY diagram of compound 5N HMBC diagram of compound 5N
56 HSQC diagram of compound 5N MS spectrum of compound 5N β-N-(pyrimidine-2)-4-deoxy-podophyllotoxin (5N) 1 H NMR (400 MHz, CDCl 3, δ): 7.62 (d, J = 8.0 Hz, 1H), 7.57 (d, J = 8.0 Hz, 1H), 7.36 (t, J = 8.0 Hz, 1H), 7.19 (t, J = 4.0 Hz, 1H), 6.88 (s, 1H), 6.51 (s, 1H), 6.30 (s, 2H), 5.97 (d, J = 8.0 Hz, 2H), 5.39 (s, 1H), 4.61 (d, J = 4.0 Hz, 1H), 4.50 (t, J = 4.0 Hz, 1H), 4.02 (t, J = 8.0 Hz, H), 3.80 (s, 3H), 3.75 (s, 6H), (m, 2H); 13 C NMR(101 MHz, CDCl 3, δ): , , (2C), , (2C), , , , , , , , (2C), , , (2C), , 69.00, 60.75, (2C), 53.91, 43.69, 41.92, ESI-MS: calc d for C 29 H 26 N 2 O 7 S [M+H] + : , found [M+H] +. 56
57 H NMR spectrum of compound 6N C NMR spectrum of compound 6N
58 H- 1 H COSY diagram of compound 6N HMBC diagram of compound 6N
59 HSQC diagram of compound 6N MS spectrum of compound 6N β-N-(pyrimidine-2)-4-deoxy-podophyllotoxin (6N) 1 H NMR (400 MHz, CDCl 3, δ): 6.87 (s, 1H), 6.54 (s, 1H), 6.27 (s, 2H), 5.99 (d, J = 12.0 Hz, 2H), 5.29 (s, 1H), 4.86 (d, J = 4.0 Hz, 1H), 4.60 (d, J = 4.0 Hz, 1H), (m, 2H), 3.79 (s, 3H), 3.73 (s, 6H), (m, 1H), (m, 1H); 13 C NMR (101 MHz, CDCl 3, δ): (2C), (2C), (2C), , , (2C), , , (2C), , (2C), , 67.61, 66.72, 60.74, (2C), 53.42, 43.89, 40.47, ESI-MS: calc d for C 27 H 25 N 5 O 7 [M+H] + : , found [M+H] +. 59
60 H NMR spectrum of compound 1'N C NMR spectrum of compound 1'N
61 H- 1 H COSY diagram of compound 1'N HMBC diagram of compound 1'N 61
62 HSQC diagram of compound 1'N MS spectrum of compound 1'N β-N-(1,2,4-trizole-3)-4-deoxy-4'-demethyl-podophyllotoxin (1'N) 1 H NMR(400 MHz, CD 3 OD, CD 3 Cl): δ 6.87 (s, 1H), 6.50 (s, 1H), 6.28 (s, 2H), 5.98 (d, 2H, J = 8.0 Hz), (d, 1H, J = 1.8 Hz), (s, 1H), (d, 1H), (d, 1H, J = 2.4 Hz, (t, 1H J = 4.5 Hz,), (t, 1H, J = 4.8 Hz), (s, 6H), (t, 1H, J = 2.1Hz), (dd, 1H, J = 2.4Hz); 13 C NMR (101 MHz, CD 3 OD, CD 3 Cl): δ , , , , , , , , , , , , , 75.14, 75.04, 72.12, 67.42, (2C), 57.26, 47.52, 45.18, ESI-MS: calc d for C 23 H 22 N 4 O 7 [M+H] + : , found [M+H] +. 62
63 H NMR spectrum of compound 2'N C NMR spectrum of compound 2'N
64 H- 1 H COSY diagram of compound 2'N HMBC diagram of compound 2'N
65 HSQC diagram of compound 2'N MS spectrum of compound 2'N β-N-(1,3,4-thiodizole-2)-4-deoxy-4'-demethyl-podophyllotoxin (2'N) 1 H NMR(400 MHz, CDCl 3 ): δ 6.82 (s, 1H), 6.51 (s, 1H), 6.27 (s, 2H), 5.98 (d, J = 16.0 Hz, 2H), 5.38 (s, 1H), 4.59 (dd, J = 4.0 Hz, 2H), 4.34 (t, J = 4.0 Hz, 1H), 4.23 (t, J = 8.0 Hz, 1H), 3.76(s, 6H), 3.71 (t, J = 8.0 Hz, 1H), (m, 1H), (m, 1H); 13 C NMR (101 MHz, CDCl 3 ): δ , , (2C), , , , , , , , (2C), , 71.32, 71.24, 67.76, (2C), 43.69, 41.29, 38.37, ESI-MS: calc d for C 23 H 21 N 3 O 7 S [M+H] + : , found [M+H] +. 65
66 H NMR spectrum of compound 3'N C NMR spectrum of compound 3'N
67 H- 1 H COSY diagram of compound 3'N HMBC diagram of compound 3'N
68 HSQC diagram of compound 3'N MS spectrum of compound 3'N β-N-(pyridine-2)-4-deoxy-4'-demethyl-podophyllotoxin (3'N) 1 H NMR (300 MHz, CD 3 OD): δ (d, J = 6.3 Hz, 2H), (s, 2H), (t, J = 6.6 Hz, 1H), (s, 1H), (s, 2H), (s, 2H), (d, J = 3.0 Hz, 3H), (t, J = 9.0 Hz, 1H), (s, 6H), (s, 2H); 13 C NMR (75 MHz, CD 3 OD): δ , , , (2C), , , , , , , , , , , , (2C), , , (2C), , , , ESI-MS: calc d for C 26 H 24 N 2 O 7 [M+H] + : , found [M+H] +. 68
69 H NMR spectrum of compound 4'N C NMR spectrum of compound 4'N
70 H- 1 H COSY diagram of compound 4'N HMBC diagram of compound 4'N
71 HSQC spectrums for compound 4'N MS spectrum of compound 4'N β-N-(pyrimidine-2)-4-deoxy-4'-demethyl-podophyllotoxin (4'N) 1 H NMR (300 MHz, CDCl 3 ): δ (s, 2H), (s, 1H), (s, 1H), (s, 1H), (s, 2H), (d, J = 9.6 Hz, 2H), (d, J = 2.7 Hz, 1H), (s, 1H), (t, J = 7.8 Hz, 1H), (s, 1H), (s, 1H), (t, J = 5.4 Hz, 1H), (s, 6H), (s, 2H); 13 C NMR (75 MHz, CDCl 3 ): δ , , , , , (2C), , , , , , , , (2C), , , (2C), , , , , ESI-MS: calc d for C 25 H 23 N 3 O 7 [M+H] + : , found [M+H] +. 71
72 H NMR spectrum of compound 5'N C NMR spectrum of compound 5'N
73 H- 1 H COSY diagram of compound 5'N HMBC diagram of compound 5'N
74 HSQC diagram of compound 5'N MS spectrum of compound 5'N β-N-(benzothiazole-2)-4-deoxy-4'-demethyl-podophyllotoxin (5'N) 1 H NMR (400 MHz, CDCl 3 ): δ 7.61 (d, J = 8.0 Hz, 1H), 7.56 (d, J = 8.0 Hz, 1H), 7.34 (t, J = 8.0 Hz, 1H), 7.15 (t, J = 8.0 Hz, 1H), 6.88 (s, 1H), 6.51 (s, 1H), 6.31 (s, 2H), 5.9 7(d, J = 12.0 Hz, 2H), 5.42 (d, J = 4.0 Hz, 1H), 4.58 (d, J = 4.0 Hz, 1H), 4.49 (t, J = 8.0 Hz, 1H), 4.00 (t, J = 8.0 Hz, 1H), 3.77 (s, 6H), (m, 2H); 13 C NMR (101 MHz, CDCl 3 ): δ (2C), , , , , (2C), , , , , , (2C), , , , , (2C), , 69.25, (2C), 53.40, 43.52, 42.02, ESI-MS: calc d for C 28 H 24 N 2 O 7 S [M+H] + : , found [M+H] +. 74
75 H NMR spectrum of compound 6'N C NMR spectrum of compound 6'N
76 H- 1 H COSY diagram of compound 6'N HMBC diagram of compound 6'N
77 HSQC diagram of compound 6'N MS spectrum of compound 6'N H NMR (400 MHz, DMSO): δ 8.24 (s, 1H), 6.91 (s, 1H), 6.48 (s, 1H), 6.19 (s, 2H), 5.98 (d, J = 8.0 Hz, 2H), 5.42 (d, J = 8.0 Hz, 1H), 4.71 (dd, J = 4.0 Hz, 1H), 4.47 (d, J = 8.0 Hz, 1H), 4.31 (t, J = 8.0 Hz, 1H), 4.15 (t, J = 8.0 Hz, 1H), 3.59 (s, 6H), (m, 1H), (m, 1H); 13 C NMR (101 MHz, DMSO): δ (2C), , (2C), (2C), , (2C), , (2C), , , (2C), , 68.11, 65.41, (2C), 55.36, 43.41, ESI-MS: calc d for C 26 H 23 N 5 O 7 [M+H] + : , found [M+H] + 77
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