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1 SUPPORTING INFORMATION Synthesis and Preliminary Pharmacological Evaluation of Aryl Dithiolethiones with Cyclooxygenase-2 Selective Inhibitory Activity and Hydrogen-Sulfide-Releasing Properties Shannon D. Zanatta, a,b Bevyn Jarrott, a,c Spencer J. Williams* b a School of Chemistry and Bio21 Institute of Molecular Science and Biotechnology, University of Melbourne, Parkville, Victoria 3010, Australia b Howard Florey Institute, Parkville, Victoria 3010, Australia c Department of Pharmacology, University of Melbourne, Parkville, Victoria 3010, Australia
2 Representative procedure for the MOM protection of phenols Acetyl chloride (5.00 mmol) was added dropwise to a solution of dimethoxymethane (5 mmol), and ZnCl 2 (0.02 mmol) in toluene (6 ml). The reaction was stirred at rt for 4 h, and then the phenol (1.00 mmol) was added followed by N-ethyl-N,N-diisopropylamine (1.50 mmol). The reaction was then stirred at rt overnight. Water was added and the mixture was stirred for 15 min. The aqueous layer was extracted with EtOAc ( 2) and the combined organic extracts washed with 1 M NaOH ( 3), sat. NaHCO 3 ( 1), water ( 2), brine ( 1), dried (Na 2 SO 4 ) and concentrated. 1-[4-(Methoxymethoxy)-3,5-dimethylphenyl]ethanone 5b The title compound was prepared by the representative procedure starting from 1-(4-hydroxy- 3,5-dimethylphenyl)ethanone [1] (4b). Flash chromatography (10% EtOAc/petrol) afforded 5b as a yellow oil (427 mg, 68%). δ H (500 MHz, CDCl 3 ) 2.25 (s, 6H, ArCH 3 2), 2.46 (s, 3H, COCH 3 ), 3.52 (s, 3H, CH 3 ), 4.92 (s, 2H, CH 2 ), 7.56 ppm (s, 2H, Ar); δ C (100 MHz, CDCl 3 ) 16.7 (ArCH 3 ), 26.1 (COCH 3 ), 57.1 (OCH 3 ), 98.8 (CH 2 ), 129.1, 131.1, 133.0, (6C, Ar), ppm (CO); IR ν 2925, 1677, 1596, 1155, 959, 769 cm -1 ; HRMS-ESI + m/z [M+Na] + Calc. for C 12 H 17 O 3 : , found: [3,5-Diethyl-4-(methoxymethoxy)phenyl]ethanone 5c The title compound was prepared the representative procedure starting from 1-(3,5-diethyl-4- hydroxyphenyl)ethanone [2] (4c). Flash chromatography (5% EtOAc/petrol) afforded 5c as a yellow oil (691 mg, 46%). δ H (400 MHz, CDCl 3 ) 1.25 (t, J = 7.5 Hz, 6H, CH 2 CH 3 2), 2.56 (s, 3H, COCH 3 ), 2.71 (q, J = 7.5 Hz, 4H, CH 2 CH 3 2), 3.60 (s, 3H, OCH 3 ), 4.97 (s, 2H, OCH 2 O), 7.68 ppm (s, 2H, Ar); δ C (100 MHz, CDCl 3 ) 14.5 (CH 2 CH 3 ), 23.3 (CH 2 CH 3 ), 26.5 (COCH 3 ), 57.3 (OCH 3 ), 99.7 (OCH 2 O), 127.5, 133.5, 137.4, (6C, Ar), ppm (CO); IR ν 2968, 1679, 1357, 1288, 1157, 1072, 882 cm -1 ; HRMS-ESI + m/z [M+H] + Calc. for C 14 H 21 O 3 : , found [3,5-Diisopropyl-4-(methoxymethoxy)phenyl]ethanone 5d The title compound was prepared by the representative procedure starting from 1-[4-hydroxy- 3,5-diisopropyl)phenyl]ethanone [3] (4d). Flash chromatography (5% EtOAc/petrol) afforded 5d as a yellow oil (206 mg, 37%). δ H (500 MHz, CDCl 3 ) 1.26 (d, J = 7 Hz, 12H, CH(CH 3 ) 2 2), 2.59 (s, 3H, COCH 3 ), 3.36 (septet, J = 7.0 Hz, 2H, (CH 3 ) 2 CH 2) 3.62 (s, 3H, OCH 3 ),
3 4.96 (s, 2H, CH 2 ), 7.73 ppm (s, 2H, Ar); δ C (100 MHz, CDCl 3 ) 23.8 (CH(CH 3 ) 2 ) 26.5 (COCH 3 ), 26.6 (CH(CH 3 ) 2 ), 62.1 (OCH 3 ), 99.1 (CH 2 ), 124.7, 133.6, 142.0, (6C, Ar), ppm (CO); IR ν 2963, 1680, 1300, 1192, 1006, 798 cm -1 ; HRMS-ESI + m/z [M+H] + Calc. for C 16 H 25 O 3 : , found [3,5-di-(tert-Butyl)-4-(methoxymethoxy)phenyl]ethanone 5e The title compound was prepared by the representative procedure starting from 1-[3,5-di- (tert-butyl)-4-hydroxyphenyl]ethanone [4] (4e). Flash chromatography (10% EtOAc/petrol) and recrystallisation from EtOH/water afforded 5e as a colourless solid (1.67 g, 71%). mp C; δ H (500 MHz, CDCl 3 ) 0.88 (s, 18H, (C(CH 3 ) 3 ) 2), 1.98 (s, 3H, COCH 3 ), 3.06 (s, 3H, OCH 3 ), 4.33 (s, 2H, CH 2 ), 7.32 ppm (s, 2H, Ar); δ C (100 MHz, CDCl 3 ) 26.4 (COCH 3 ), 31.8 (C(CH 3 ) 3 ), 35.8 (C(CH 3 ) 3 ), 57.4 (CH 3 ), (CH 2 ), 127.0, 132.1, 144.7, (6C, Ar), ppm (CO); IR ν 2956, 2873, 1762, 1676, 1589, 1227, 881 cm -1 ; HRMS-ESI + m/z [M+Na] + Calc. for C 18 H 28 NaO 3 : , found ; Anal. Calc. for C 18 H 28 O 3 : C 73.93, H Found: C 73.92, H 9.70%. Representative procedure for the etherification of phenols Iodoalkane (2.50 mmol) was added to a mixture of anhydrous potassium carbonate (1.70 mmol) and the phenol (1.00 mmol). The mixture was heated at reflux for 18 h. Diethyl ether was then added to the cooled solution and the organic phase washed with water ( 2), brine ( 1), dried (Na 2 SO 4 ) and concentrated. 1-(4-Methoxy-3,5-dimethylphenyl)ethanone 9b2 [5] The title compound was prepared by the representative procedure starting from 1-(4-hydroxy- 3,5-dimethylphenyl)ethanone [1] (4b) and iodomethane. After flash chromatography (5% EtOAc/petrol), 9b2 was obtained as a yellow oil (1.19 g, 70%). δ H (400 MHz, CDCl 3 ) 2.21 (s, 6H, ArCH 3 2), 2.44 (s, 3H, COCH 3 ), 3.65 (s, 3H, OCH 3 ), 7.53 ppm (s, 2H, Ar); δ C (100 MHz, CDCl 3 ) 15.9 (ArCH 3 ), 26.1 (COCH 3 ), 59.2 (OCH 3 ), 129.0, 130.7, 132.5, (6C, Ar), ppm (CO); IR ν 2940, 1674, 1591, 1482, 1092, 874 cm -1 ; HRMS-ESI + m/z [M+H] + Calc. for C 11 H 15 O 2 : , found (4-Ethoxy-3,5-dimethylphenyl)ethanone 9b3 [6]
4 The title compound was prepared by the representative procedure starting from 1-(4-hydroxy- 3,5-dimethylphenyl)ethanone [1] (4b) and iodoethane. After flash chromatography (5% EtOAc/petrol), 9b3 was obtained as a yellow oil (94% 1.08 g). δ H (400 MHz, CDCl 3 ) 1.30 (t, J = 6.4 Hz, 3H, CH 2 CH 3 ), 2.27 (s, 6H, ArCH 3 2), 2.50 (s, 3H, COCH 3 ), 3.84 (q, J = 6.4 Hz, 2H, CH 2 ), 7.59 ppm (s, 2H, Ar); δ C (100 MHz, CDCl 3 ) 15.6, 16.3 (ArCH 3,CH 2 CH 3 ), 26.3 (COCH 3 ), 67.8 (CH 2 ), 129.1, 131.0, 132.5, (6C. Ar), ppm (CO); IR ν 2980, 2929, 1677, 1306, 1030, 900, 777 cm -1 ; HRMS-ESI + m/z [M+H] + Calc. for C 12 H 17 O 2 : , found (3,5-Diethyl-4-methoxyphenyl)ethanone 9c2 The title compound was prepared by the representative procedure starting from 1-(3,5-diethyl- 4-hydroxyphenyl)ethanone [2] (4c) and iodomethane. After flash chromatography (5% EtOAc/petrol), 9c2 was obtained as a yellow oil (59%, 505 mg). δ H (500 MHz, CDCl 3 ) 1.25 (t, J = 7.5 Hz, 6H, CH 2 CH 3 ), 2.56 (s, 3H, COCH 3 ), 2.70 (q, J = 7.5 Hz, 4H, CH 2 ), 3.76 (s, 3H, OCH 3 ), 7.62 ppm (s, 2H, Ar); δ C (125 MHz, CDCl 3 ) 14.7 (CH 2 CH 3 ), 22.8 (CH 2 ), 26.4 (COCH 3 ), 61.0 (OCH 3 ), 127.6, 133.3, 137.2, (6C, Ar), ppm (CO); IR ν 2968, 1679, 1595, 1356, 1191, 1164 cm -1 ; HRMS-ESI + m/z [M+Na] + Calc. for C 13 H 19 NaO 2 : , found [3,5-Diisopropyl-4-methoxyphenyl]ethanone 9d2 The title compound was prepared by the representative procedure starting from 1-(4-hydroxy- 3,5-diisopropylphenyl)ethanone [3] (4d) and iodomethane. After flash chromatography (5% EtOAc/petrol), 9d2 was obtained as a yellow oil (46%, 836 mg). δ H (500 MHz, CDCl 3 ) 1.30 (d, J = 6.5 Hz, 12H, (CH 3 ) 2 CH 2), 2.57 (s, 3H, COCH 3 ), 3.33 (septet, J = 6.5 Hz, 2H, (CH 3 ) 2 CH 2), 3.75 (s, 3H, OCH 3 ), 7.72 ppm (s, 2H, Ar); δ C (125 MHz, CDCl 3 ) 23.8 (CH(CH 3 ) 2 ), 26.4 (COCH 3 ), 26.5 (CH(CH 3 ) 2 ), 62.1 (OCH 3 ), 124.7, 133.6, 142.0, (6C, Ar), ppm (CO); IR ν 2963, 1680, 1300, 1192, 1006, 798 cm -1 ; HRMS-ESI + m/z [M+H] + Calc. for C 15 H 23 O 2 : , found [4-Ethoxy-3,5-diisopropylphenyl]ethanone 9d3 The title compound was prepared by the representative procedure starting from 1-(4-hydroxy- 3,5-diisopropylphenyl)ethanone (4d) and iodoethane. After flash chromatography (5% EtOAc/petrol) and recrystallisation from EtOH/water, 9d3 was obtained as a yellow oil (72%,
5 772 mg). mp C; δ H (500 MHz, CDCl 3 ) 1.26 (d, J = 7 Hz, 12H, CH(CH 3 ) 2 2), 1.47 (t, J = 7 Hz, CH 2 CH 3 ), 2.59 (s, 3H, COCH 3 ), 3.34 (septet, J = 7 Hz, CH(CH 3 ) 2 2), 3.84 (q, J = 7 Hz, 2H, CH 2 ), 7.73 ppm (s, 2H, Ar); δ C (125 MHz, CDCl 3 ) 15.8 (CH 2 CH 3 ), 24.0 (CH(CH 3 ) 2 ), 26.5 (COCH 3 ), 26.7 (CH(CH 3 ) 2 ), 70.6 (CH 2 ), 133.6, 142.3, 144.7, (6C, Ar), ppm (CO); IR ν 2963, 1680, 1462, 1192, 1007, 973, 816, 730 cm -1 ; HRMS-ESI + m/z [M+H] + Calc. for C 16 H 25 O 2 : , found [3,5-di-(tert-Butyl)-4-methoxyphenyl]ethanone 9e2 The title compound was prepared by the representative procedure starting from 1-[3,5-di- (tert-butyl)-4-hydroxyphenyl]ethanone [4] (4e) and iodomethane. After flash chromatography (10% EtOAc/petrol) and recrystallisation from EtOH/water, 9e3 was obtained as a colourless solid (2.68 g, 82%). mp C (lit. [7] mp C). δ H (400 MHz, CDCl 3 ) 1.45 (s, 18H, C(CH 3 ) 3 2), 2.57 (s, 3H, COCH 3 ), 3.71 (s, 1H, OCH 3 ), 7.88 ppm (s, 2H, Ar). 1-[3,5-di-(tert-Butyl)-4-ethoxyphenyl]ethanone 9e3 The title compound was prepared by the representative procedure starting from 1-[3,5-di- (tert-butyl)-4-hydroxyphenyl]ethanone (4e) and iodoethane. After flash chromatography (5% EtOAc/petrol), 9e3 was obtained as a yellow oil (171 mg, 65%). δ H (400 MHz, CDCl 3 ) 1.43 (t, 3H, J = 7 Hz, CH 2 CH 3 ), 1.44 (s, 18H, C(CH 3 ) 3 2), 2.57 (s, 3H, COCH 3 ), 3.77 (t, 2H, J = 7 Hz, CH 2 ), 7.78 ppm (s, 2H, Ar); δ C (100 MHz, CDCl 3 ) 14.8 (CH 2 CH 3 ), 26.4 (COCH 3 ), 31.8 (C(CH 3 ) 3 ), 35.9 (C(CH 3 ) 3 ), 72.0 (CH 2 ), 127.1, 131.7, 144.0, (6C, Ar), ppm (CO); IR ν 2963, 1682, 1590, 1298, 1105, 971, 887 cm -1 ; HRMS-ESI + m/z [M+H] + Calc. for C 18 H 29 O 2 : , found ; Anal. Calc. for C 18 H 28 O 2 : C 78.21, H Found C 78.24, H 10.20%. References [1] S. L. Goldstein, E. McNelis, J. Org. Chem. 1984, 49, [2] R. Breslow, K. Groves, M. U. Mayer, J. Am. Chem. Soc. 2002, 124, [3] P.-e. Chabrier De Lassauniere, J. Harnett, D. Bigg, A.-M. Liberatore, J. Pommier, J. Lannoy, C. Thurieau, Z. X. Dong, Patent US 2005/ [4] A. Nishinaga, T. Shimizu, Y. Toyoda, T. Matsuura, K. Hirotsu, J. Org. Chem. 1982, 47, [5] F. Benington, R. D. Morin, L. C. Clark, Jr., R. P. Fox, J. Org. Chem. 1958, 23, [6] B. J. Armitage, G. W. Kenner, M. J. T. Robinson, Tetrahedron Lett. 1964, 20, 723. [7] D. Braun, B. Maier, Makromol. Chem. 1973, 167, 119.
6 1 H NMR spectrum of compound (5b)
7 1 H NMR spectrum of compound (5c)
8 1 H NMR spectrum of compound (5d)
9 1 H NMR spectrum of compound (6a)
10 1 H NMR spectrum of compound (6b)
11 1 H NMR spectrum of compound (6c)
12 1 H NMR spectrum of compound (7b1)
13 1 H NMR spectrum of compound (7c1)
14 1 H NMR spectrum of compound (7c2)
15 1 H NMR spectrum of compound (7e3)
16 1 H NMR spectrum of compound (9c2)
17 1 H NMR spectrum of compound (9d2)
18 1 H NMR spectrum of compound (9d3)
19 1 H NMR spectrum of compound (10b2)
20 1 H NMR spectrum of compound (10b3)
21 1 H NMR spectrum of compound (10c3)
22 1 H NMR spectrum of compound (10d2)
23 1 H NMR spectrum of compound (10d3)
24 1 H NMR spectrum of compound (10e2)
25 1 H NMR spectrum of compound (10e3)
26 1 H NMR spectrum of compound (11)
27 1 H NMR spectrum of compound (12e2)
28 1 H NMR spectrum of compound (12e2)
29 1 H NMR spectrum of compound (12e3)
30 1 H NMR spectrum of compound (14e2)
31 1 H NMR spectrum of compound (15e2)
32 1 H NMR spectrum of compound (15e3)
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