Synthesis and evaluation of novel aza-caged Garcinia xanthones
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- Μίδας Ἰωσίας Κουταλιανός
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1 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Synthesis and evaluation of novel aza-caged Garcinia xanthones Xiaojin Zhang, a,1 Xiang Li, a,1 Haopeng Sun, * b Zhengyu Jiang, b Lei Tao, c Yuan Gao, c Qinglong Guo * c and Qidong You* a,c Supplementary Information Pages Experimental procedure for 3, 4, MR spectra for compounds 11, 12, 13, 8, 7, 14, 17, 20a-e, 6a-e 6-25 Energy data for compounds 7, 15, 16, 17, 20a, 21a, 22a, 23a, 6a, 25, 26, 27, 4, Figures with each analogue (GA, 4, 6c) docked in the active site
2 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Experimental procedure Reagents and conditions: (a) Et 2, AlCl 3, 25 C, 12 h; then ah, MeH, H 2, 110 C, 24 h; (b) 40% HBr, HAc, reflux, 12 h; (c) allyl chloride, DMF, 45 C, 2 h; (d) decalin, 180 C, 3 h; (e) 2-chloro-2-methylbut-3-yne, DBU, K 2 C 3, CuI, Acetone, reflux, 6 h; (f) DMF, 120 C, 1 h. 3,4-Dihydroxy-9H-xanthen-9-one (24) To a solution of 2-methoxylbenzoyl chloride (1.72 g, 10.1 mmol) and 1,2,3-trimethoxybenzene (1.68 g, 10 mmol) in 20 ml H H anhydrous ether, aluminum trichloride (3.61 g, 27 mmol) was added at 0 C. The reaction mixture was stirred for 12 h at room temperature. Then a mixture of 15% hydrochloric acid and ethyl acetate (100 ml, V/V = 1:1) were added. The organic layer was partitioned, washed with brine (30 ml 3), dried over magnesium sulfate and concentrated under reduced pressure. The residue was suspended in a solution that contained methanol (22.4 ml), water (14.9 ml) and sodium hydrate (1.2 g, 30 mmol) at 25 C. Then the reaction mixture was heated to 110 C for next 24 h. After cooled to 0 C, the mixture was acidified with 2 mol/l HCl solution till ph=2~3. The precipitation was formed, filtered, washed with cold water and dried. Then the filter cake was dissolved in a mixture of 40% HBr and acetic acid (150 ml, V/V = 1:2), the reaction mixtre was refluxed for 12 h at 120 C under 2 protection. After cooled to 0 C, the reaction mixture as acidified till ph=3-4 with 10% ah solution, the precipitation was filtered, washed with ice water and dried to provide 24 as a yellow solid (1.19 g, 52% combined yield). 1 H MR (DMS-d 6, 300 MHz): δ 9.91 (br, 2H), 8.15 (d, J = 8.2 Hz,1H), 7.83 (t, J = 7.8 Hz,1H), 7.60 (d, J = 8.7 Hz,1H), 7.56 (d, J = 8.7 Hz,1H), 7.46 (t, J = 2
3 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 7.5 Hz,1H), 6.95 (d, J = 8.7 Hz,1H); EI-MS (m/z): 228 (M) + (100), 207(52), 169(54). 3,4-Bis(allyloxy)-9H-xanthen-9-one (25) To a solution of compound 14 (1.14 g, 5 mmol) in DMF (15 ml) was added potassium carbonate (1.518 g, 11 mmol) and allyl chloride (912 mg, 12 mmol). The mixture was stirred under nitrogen at 45 C for 2 h. The reaction mixture was allowed to cool to 25 C and then partitioned between EtAc (30 ml) and water (70 ml). The water layer was back-extrated with EtAc (30 ml 2) and the combined organic layers were dried over MgS 4, filtered and concentrated. The residue was purified by flash column chromatography (10-20% EtAc-PE) to provide compound 25 (1.53 g, 99%) as a white solid. 1 H MR (CDCl 3, 300 MHz): δ 8.32 (dd, J = 8.4, 1.5 Hz,1H), 8.07 (d, J = 9.0 Hz,1H), 7.72 (dt, J = 8.4, 1.5 Hz,1H), 7.56 (d, J = 7.8 Hz,1H), (m,1h), 6.99 (d, J = 9.0 Hz,1H), (m,2h), (m, 4H), (m, 4H); EI-MS (m/z): 308 (M) + (42), 267(100). Caged compounds 4 and 5 A solution of 25 (100 mg, 0.32 mmol) in decalin was stirred under + nitrogen at 180 C for 3 h. The reaction mixture was then cooled to 25 C and the residue was purified by flash column chromatography (5-10% EtAc-PE) to 4 5 yield caged compounds 4 (32mg, 32%) and 5 (29mg, 29%) as white solids. For compound 4, 1 H MR (CDCl 3, 300 MHz): δ 7.94 (dd, J = 7.8, 1.5 Hz, 1H), (m, 1H), 7.33 (d, J = 6.9 Hz, 1H), (m, 2H), (m, 1H), 4.68 (d, J = 10.2 Hz, 1H), (m, 2H), 3.90 (d, J = 7.8 Hz, 1H), (m, 1H), (m, 1H), 2.62 (dd, J = 7.8, 3.3 Hz, 1H), (m, 1H), (m, 2H); EI-MS (m/z): 308 (M) + (18), 169(100); HRMS (ESI) calc. For C 19 H 16 4 (M + H) , found For compound 5, 1 H MR (CDCl 3, 300 MHz): δ 7.91 (dd, J = 7.8, 1.5 Hz, 1H), (m, 1H), 7.30 (d, J = 6.9 Hz, 1H), 7.18 (d, J = 8.4 Hz, 1H), (m, 1H), (m, 1H), (m, 2H), 4.08 (dd, J = 8.1, 3.6 Hz, 1H), 3.97 (d, J = 8.1 Hz, 1H), 3.48 (dd, J = 6.9, 4.2 Hz, 1H), (m, 2H), (m, 3H); EI-MS (m/z): 308 (M) + (21), 169(100); HRMS (ESI) calc. For C 19 H 16 4 (M + H) , found
4 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 3,4-Bis((2-methylbut-3-yn-2-yl)oxy)-9H-xanthen-9-one (28) To a solution of 24 (388 mg, 1.7 mmol) in acetone (10 ml), potassium iodide (288 mg, 1.7 mmol), DBU (1.2 ml, 8.16 mmol) and CuI (5 mg, mmol) were added. The reaction mixture was stirred at room temperature for 10min, then 2-chloro-2-methylbut-3-yne (1.4 ml, 13.6 mmol) was added and the resulted mixture was refluxed for 6 more hours. Water (50 ml) and EtAc (20 ml) was added to the mixture and stirred for 30min. The organic layer was separated, dried over sodium sulfate, and evaporated. The residue was purified by flash column chromatography (10-20% EtAc-PE) to afford 28 (413 mg, 55%) as a white solid. 1 H MR (CDCl 3, 300 MHz): δ 8.26 (d, J = 7.5 Hz, 1H), 7.80 (d, J = 9.0 Hz, 1H), 7.62 (dd, J = 7.5, 8.4 Hz, 1H), 7.58 (d, J = 9.0 Hz, 1H), 7.45 (d, J = 8.4 Hz, 1H), 7.30 (t, J = 7.5 Hz, 1H), 2.50 (s, 1H), 2.22 (s, 1H), 1.77 (s, 6H), 1.70 (s, 6H). EI-MS (m/z): 360 (M) + (40). 3,4-Bis((2-methylbut-3-en-2-yl)oxy)-9H-xanthen-9-one (29) To a solution of 28 (221 mg, 0.50 mmol) in ethanol (10 ml) was added 10% Pd/BaS 4 (22 mg). The mixture was stirred under an atmosphere of hydrogen for 2 h at room temperature and filtered through a plug of silica gel, the filtration was concentrated and purified by flash column chromatography (10-20% EtAc-PE) to afford 29 (188 mg, 85%) as a yellow oil. 1 H MR (CDCl 3, 300 MHz): δ 8.32 (d, J = 9 Hz, 1H), 7.93 (d, J = 9 Hz, 1H), 7.71 (t, J = 9 Hz, 1H), 7.50 (d, J = 5.1Hz, 1H), 7.36 (t, J = 7.5 Hz, 1H), 7.12 (d, J = 9 Hz, 1H), 6.30 (dd, J = 17.7, 11.1 Hz, 1H), 6.20 (dd, J = 17.7, 11.1 Hz, 1H), (m, 3H), 5.03 (d, J = 12.1Hz, 1H), 1.61 (s, 6H), 1.58 (s, 6H). EI-MS (m/z) = 364 (M) + (34). Caged compounds 3 and 3a To a solution of 29 (200 mg, 0.55 mmol) in DMF (4.0 ml) was heated at 120 C under 2 protection for 1 h. The yellow reaction mixture was cooled to 25 C and the + 3 3a mixture was purified by flash column chromatography (5-10% EtAc-PE) to yield the caged compounds 3 (114mg, 57%) and 3a (56 mg, 28%) as pale-yellow solids. For compound 3, 4
5 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 1 H MR (CDCl 3, 300 MHz): δ 7.87 (d, J = 8.4 Hz, 1H), 7.45 (dd, J = 8.4, 7.2 Hz, 1H), (d, J = 6.9 Hz, 1H), (m, 2H), 4.35 (t, 1H), (m, 1H), 2.55 (d, J = 9.3Hz, 2H), 2.39 (d, J = 9.6Hz, 1H), 2.27 (dd, J = 13.5, 4.5Hz, 1H), 1.66 (s, 3H), (m, 7H), 0.84 (s, 3H). HRMS (ESI) calc. For C 23 H 24 4 (M + H) , found For compound 3a, 1 H MR (CDCl 3, 300 MHz): δ 7.85 (dd, J = 8.1, 1,5 Hz, 1H), 7.49 (m, 1H), 7.20 (d, J = 7.1 Hz, 1H), 7.12 (d, J = 8.5 Hz, 1H) 6.99 (t, J = 7.5 Hz, 1H), 4.95 (m, 1H), (m, 1H), (m, 2H), (m, 2H), (m, 1H), 1.65 (s, 3H), 1.53 (s, 1H), 1.31 (s, 1H), 1.28 (s, 3H); MS (EI): m/z 364(M) + (17); Anal. calcd for C 23 H 24 4 : C 75.80, H Found: C 75.78, H The MR data of caged compounds 3-5, 3a were coordinate with the following references: 1 A. Batova, T. Lam, V. Wascholowski, A. L. Yu, A. Giannis and E. A. Theodorakis, rg. Biomol. Chem., 2007, 5, X. Wang,. Lu, Q. Yang, D. Gong, C. Lin, S. Zhang, M. Xi, Y. Gao, L. Wei, Q. Guo and Q. You, Eur. J. Med. Chem., 2011, 46,
6 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry MR spectra 11: 1 H MR, 300 MHz in DMS-d6 H H 11 H 11: 13 C MR, 300 MHz in DMS-d6 H H 11 H 6
7 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 12: 1 H MR, 300 MHz in DMS-d6 12 H 12: 13 C MR, 500 MHz in DMS-d6 12 H 7
8 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 13: 1 H MR, 300 MHz in DMS-d H 13: 13 C MR, 300 MHz in DMS-d H 8
9 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 8: 1 H MR, 300 MHz in DMS-d6 H 8 H 2 8: 13 C MR, 300 MHz in DMS-d6 H 8 H 2 9
10 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 7: 1 H MR, 300 MHz in CDCl 3 7 H 7: 1 H MR, 300 MHz in CDCl 3 7 H 10
11 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 14: 1 H MR, 300 MHz in CDCl 3 14 H 2 14: 13 C MR, 300 MHz in CDCl 3 14 H 2 11
12 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 17: 1 H MR, 300 MHz in CDCl 3 17 H 17: 13 C MR, 300 MHz in CDCl 3 17 H 12
13 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 17: 1 H- 1 H CSY, 300 MHz in CDCl 3 17 H 17: HSQC, 300 MHz in CDCl 3 17 H 13
14 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 17: HMBC, 300 MHz in CDCl 3 17 H 20a: 1 H MR, 300 MHz in CDCl 3 20a 14
15 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 20a: 13 C MR, 300 MHz in CDCl 3 20a 20b: 1 H MR, 300 MHz in CDCl 3 20b 15
16 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 20b: 13 C MR, 300 MHz in CDCl 3 20b 20c: 1 H MR, 300 MHz in CDCl 3 20c 16
17 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 20c: 13 C MR, 300 MHz in CDCl 3 20c 20d: 1 H MR, 300 MHz in CDCl 3 20d F 17
18 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 20d: 13 C MR, 300 MHz in CDCl 3 20d F 20e: 1 H MR, 300 MHz in CDCl 3 20e Cl 18
19 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 20e: 13 C MR, 300 MHz in CDCl 3 20e Cl 6a: 1 H MR, 300 MHz in CDCl 3 6a CH 3 19
20 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 6a: 13 C MR, 300 MHz in CDCl 3 6a CH 3 6a: 1 H- 1 H CSY, 300 MHz in CDCl 3 6a CH 3 20
21 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 6a: HSQC, 300 MHz in CDCl 3 6a CH 3 6a: HMBC, 300 MHz in CDCl 3 6a CH 3 21
22 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 6b: 1 H MR, 300 MHz in CDCl 3 6b 6b: 13 C MR, 300 MHz in CDCl 3 6b 22
23 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 6c: 1 H MR, 300 MHz in CDCl 3 6c 6c: 13 C MR, 300 MHz in CDCl 3 6c 23
24 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 6d: 1 H MR, 300 MHz in CDCl 3 6d F 6d: 13 C MR, 300 MHz in CDCl 3 6d F 24
25 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 6e: 1 H MR, 300 MHz in CDCl 3 6e Cl 6e: 13 C MR, 300 MHz in CDCl 3 6e Cl 25
26 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Energy data All structures were fully optimized at the B3LYP/6-31G(d) level of theory, with Gaussian 03. All structures were validated as minima or first-degree saddle points using frequency analysis. Minima structure geometries and energies. Energies are in Hartrees, distances and coordinates. Model System 7 C C C C C C C C C C C C C C C C C C C H H H H H H H H H H H H
27 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry H H H H H Sum of Energies = C C C C C C C C C C C C C C C C C C C H H H H H H H H H H H
28 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry H H H H H H Sum of Energies = C C C C C C C C C C C C C C C C H C C C H H H H H H H H H
29 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry H H H H H H H Sum of Energies = C C C C C C C C C C C C C C C C C C C H H H H H H H H H
30 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry H H H H H H H H Sum of Energies = a C C C C C C C C C C C C C C C C C C C C H H H H H H H
31 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry H H H H H H H H H H H H Sum of Energies = a C C C C C C C C C C C C C C C C C C C H H H H
32 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry H H H H H H H H H H H H C H H H Sum of Energies = a C C C C C C C C C C C C C C C C C C C
33 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry C H H H H H H H H H H H H H H H H H H H Sum of Energies = a C C C C C C C C C C C C C C C C C
34 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry C C H H H H H H H H H H H H H H H H C H H H Sum of Energies = a C C C C C C C C C C C C C
35 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry C C C C C C H H H H H H H H H H H H H H H H C H H H Sum of Energies = C C C C C C C C C C
36 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry C C C C C C C C C H H H H H H H H H H H H H H H H Sum of Energies = C C C C C C C C C
37 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry C C C C C C C C C C H H H H H H H H H H H H H H H H Sum of Energies = C C C C C C C C C C C
38 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry C C C C C C C C H H H H H H H H H H H H H H H H Sum of Energies = C C C C C C C C C C C C C
39 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry C C C C C C H H H H H H H H H H H H H H H H Sum of Energies = C C C C C C C C C C C C C
40 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry C C C C C C H H H H H H H H H H H H H H H H Sum of Energies = Fig. 3A-1 Molecular docking simulations for GA (1). 40
41 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Fig. 3A-2 Molecular docking simulations for 4. Fig. 3A-3 Molecular docking simulations for 6c. 41
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