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Benzene Derivatives Bearing Electron-Withdrawing Substituents

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Benzene Derivatives Bearing Electron-Withdrawing Substituents Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is © The Royal Society of Chemistry 2016 Highly efficient anion transport mediated by 1,3-bis(benzimidazol-2- yl)benzene derivatives bearing electron-withdrawing substituents Chen-Chen Peng, Meng-Jia Zhang, Xiao-Xiao Sun, Xiong-Jie Cai, Yun Chen and Wen-Hua Chen* Guangdong Provincial Key Laboratory of New Drug Screening, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, P. R. China Supporting Information Experimental Generals. 1H NMR spectra were recorded using a Bruker Avance AV 400 spectrometer and the solvents as internal standards. LR and HR-ESI MS spectra were measured on Waters UPLC/Quattro Premier XE and Agilent 6210 LC/MSD TOF mass spectrometers, respectively. Silica gel 60 Å (reagent pure, Qingdao Haiyang Chemical Co. Ltd) was used for column chromatography. Analytical thin-layer chromatography (TLC) was performed on silica gel plates 60 GF254. Detection on TLC was made by use of iodine and UV (254 or 365 nm). UV-Vis and Fluorescence spectra were measured on a Perkin Elmer Lambda 25 spectrophotometer and LS55 spectrofluorimeter, respectively. EYPC, pyranine and lucigenin were purchased from Sigma Chemical Co. (St Louis, USA), whereas calcein was from J&K Chemical Co. (Beijing, China). All the other chemicals and reagents were obtained from commercial sources and used without further purification. Buffer solutions were prepared in triply distilled deionized water. S1 Chemistry 4 N (ii) NH N N 1 N N 4 2 (i) 1 3 R (3-, R1 = H) 2 H COOH + NH N N HOOC 3 R1 NH 2-, R1 = H (o-Bimbe) 1 2 2 1 Me bimbe R1 4-, R = H (p-Bimbe) 2 3-, R1 = Me (Me-Bimbe) 1 3-, R = F (F-Bimbe) N N 1 (iv) 3-, R = H (m-Bimbe) NH HN COOH NH2 (i) N Imbe + O N NO -Bimbe NO NH N 2 2 2 2 H R1 = Cl (Cl-Bimbe) NH2 (iii) N N 1 + NH HN R = Br (Br-Bimbe) OHC CHO R1 NH 1 2 R = CF3 (CF3-Bimbe) R1 R1 Scheme S1. Synthesis of 1,3-Bis(benzimidazol-2-yl)benzene and related derivatives used in this study. Reagents and conditions: (i) concentrated H3PO4, heat; (ii) MeI, NaH, TMU; (iii) o MeOH, room temperature; (iv) HNO3/H2SO4, 0 C then room temperature. m-Bimbe. This compound was prepared according to reported procedures. 1, 2 Specifically, a solution of isophthalic acid (200 mg, 1.72 mmol) and o-phenylenediamine (410 mg, 3.79 mmol) in concentrated phosphoric acid (2.4 mL) was heated at 220 ºC for 4 h. Then water (20 mL) was added and the resulting mixture was stirred vigorously and filtered. The obtained residue was suspended in hot aqueous sodium carbonate solution (10 %, 10 mL), stirred vigorously and filtered. The obtained residue was dissolved in methanol (10 mL) and filtered. The filtrate was concentrated under reduced pressure. Purification was achieved by chromatography on a silica-gel column, eluted with a mixture of CHCl3/CH3OH (100/1, v/v) 1 to give m-Bimbe (196 mg, 37%) having H NMR (DMSO-d6, 400 MHz) δ 13.11 (s, 2H), 9.06 (t, J = 1.6 Hz, 1H), 8.27 (dd, J = 8.0 Hz and 2 Hz, 2H), 7.76-7.71 (m, 3H), 7.57 (d, J = 8.0 Hz, – 2H) 7.28-7.21 (m, 4H); negative ESI-MS: m/z 310.03 ([M–H] ) and HRMS for C20H14N4 ([M+H]+) Calcd: 311.1291; Found: 311.1319. The 1H NMR data were in agreement with the reported ones.1 S2 o-Bimbe. This compound was prepared according to reported procedures. 3, 4 Specifically, a solution of phthalic acid (200 mg, 1.20 mmol) and o-phenylenediamine (260 mg, 2.40 mmol) in concentrated phosphoric acid (10 mL) was heated at 200 oC for 6 h. Then water (20 mL) was added. The resulting mixture was stirred vigorously and filtered. The obtained residue was suspended in hot aqueous sodium carbonate solution (10 %, 20 mL), stirred vigorously and filtered. The obtained residue was dried and recrystallized from DMF to give o-Bimbe 1 (152 mg, 41%) having H NMR (DMSO-d6, 400 MHz) δ 13.28 (s, 2H), 8.10 (dd, J = 3.6 Hz and 3.2 Hz, 2H), 7.72 (dd, J = 3.2 Hz and 3.6 Hz, 2H), 7.68 (br, 2H), 7.55 (br, 2H), 7.22-7.21 + + (m, 4H); ESI-MS: m/z 311.6 ([M+H] ) and HRMS for C20H14N4 ([M+H] ) Calcd: 311.1291; Found: 311.1311. The 1H NMR data were in agreement with the reported ones.3 p-Bimbe. This compound was prepared according to reported procedures. 2 Specifically, a solution of terephthalic acid (200 mg, 1.20 mmol) and o-phenylenediamine (260 mg, 2.40 mmol) in concentrated phosphoric acid (10 mL) was heated at 200 oC for 6 h. Then water (20 mL) was added. The resulting mixture was stirred vigorously and filtered. The obtained residue was suspended in hot aqueous sodium carbonate solution (10 %, 20 mL), stirred vigorously and filtered. The obtained residue was dried and recrystallized from DMF to give 1 p-Bimbe (74 mg, 20%) having H NMR (DMSO-d6, 400 MHz) δ 13.04 (s, 2H), 8.36 (s, 4H), 7.71 (d, J = 7.6 Hz, 2H), 7.58 (d, J = 8.0 Hz, 2H), 7.28-7.21 (m, 4H); ESI-MS: m/z 311.6 + + ([M+H] ) and HRMS for C20H14N4 ([M+H] ) Calcd: 311.1291; Found: 311.1324. Imbe. This compound was prepared according to reported procedures. 5 Specifically, a solution of benzoic acid (200 mg, 1.64 mmol) and o-phenylenediamine (177 mg, 1.64 mmol) in concentrated phosphoric acid (10 mL) was heated at 150 oC for 16 h. Then water (20 mL) was added. The resulting mixture was stirred vigorously and filtered. The obtained residue 1 was washed thoroughly with water to give Imbe (82 mg, 26%) having H NMR (DMSO-d6, 400 MHz) δ 8.19 (d, J = 7.6 Hz, 2H), 7.61 (dd, J = 5.6 Hz and 3.2 Hz, 2H), 7.57 (d, J = 7.6 S3 Hz, 2H), 7.51 (d, J = 7.2 Hz, 1H), 7.22 (dd, J = 3.2 Hz and 6.0 Hz, 2H) and ESI-MS: m/z 195.3 ([M+H]+). The 1H NMR data were in agreement with the reported ones. 5 6 Me2bimbe. Similar procedures as described in literature were taken. Specifically, NaH (oil dispersion 60%, 14 mg, 0.35 mmol) was washed with petroleum ether (3 mL×3) and then suspended in dry tetramethylurea (TMU, 0.4 mL). This suspension was added to a solution of m-Bimbe (50 mg, 0.16 mmol) in TMU (0.4 mL) at 0 ºC. The resulting mixture was stirred for 30 min and then warmed to room temperature and stirred for another 1h. After the mixture was cooled to 0 ºC, MeI (22 μL) was added. The resulting mixture was stirred for 10 min and heated at 40 ºC overnight. Water (5 mL) was added to quench the reaction and the resulting mixture was concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica-gel column, eluted with a mixture of CHCl3/MeOH (160/1, v/v) to 1 give Me2bimbe (29 mg, 53%) having H NMR (CDCl3, 400 MHz) δ 8.15 (s, 1H), 7.93 (dd, J = 1.6 Hz and 7.6 Hz, 2H), 7.85-7.83 (m, 2H), 7.71 (t, J = 7.6 Hz, 1H), 7.42 (dd, J = 5.6 Hz and 2.4 Hz, 2H) 7.37-7.31 (m, 4H) 3.91 (s, 6H); ESI-MS: m/z 339.37 ([M+H]+) and HRMS + 1 for C22H18N4 ([M+H] ) Calcd: 339.1604; Found: 339.1636. The H NMR data were in agreement with the reported ones. 7 Me-Bimbe. 8 A solution of isophthalic acid (150 mg, 0.90 mmol) and 4-methyl-o-phenylene diamine (221 mg, 1.81 mmol) in concentrated phosphoric acid (12 mL) was heated at 180 ºC for 6 h. The reaction mixture was poured into iced water (20 mL) and stirred vigorously. The resulting precipitates were collected by filtration, suspended in hot aqueous sodium carbonate solution (10 %, 20 mL), stirred vigorously and filtered. The obtained residue was purified by chromatography on a silica-gel column, eluted with a mixture of CHCl3/CH3OH (100/1, v/v) 1 to afford Me-Bimbe (220 mg, 72%) having H NMR (CD3OD, 400 MHz) δ 8.70 (s, 1H), 8.18 (d, J = 7.6 Hz, 2H), 7.73 (t, J = 7.6 Hz, 1H), 7.55 (d, J = 8.0 Hz, 2H), 7.45 (s, 2H), 7.15 (d, J S4 + + = 8.0 Hz, 2H), 2.51 (s, 6H); ESI-MS: m/z 339.6 ([M+H] ) and HRMS for C22H18N4 ([M+H] ) Calcd: 339.1604; Found: 339.1639. F-Bimbe. Similar procedures as described in literature were taken. 2 Specifically, a solution of isophthalic acid (100 mg, 0.60 mmol) and 4-fluoro-o-phenylenediamine (152 mg, 1.21 mmol) in concentrated phosphoric acid (10 mL) was heated at 200 ºC for 6 h. The reaction mixture was poured into iced water (20 mL) and stirred vigorously. The resulting precipitates were collected by filtration, suspended in hot aqueous sodium carbonate solution (10 %, 20 mL), stirred vigorously and filtered. The obtained residue was purified by chromatography on a silica-gel column, eluted with a mixture of CHCl3/CH3OH (70/1, v/v) to give F-Bimbe (13 1 mg, 6%) having H NMR (DMSO-d6, 400 MHz) δ 13.28 (s, 2H), 9.04 (s, 1H), 8.27 (d, J = 7.2 Hz, 2H), 7.78-7.72 (m, 1H), 7.72 (br, 1H), 7.57 (br, 1H), 7.51 (br, 1H), 7.37 (br, 1H), 7.11 (br, 13 2H); C NMR (DMSO-d6, 100 MHz) δ 131.2, 130.2, 128.1, 125.2; ESI-MS: m/z 347.6 + + + ([M+H] ), 369.5 ([M+Na] ) and HRMS for C20H12F2N4 ([M+H] ) Calcd: 347.11028; Found: 347.11003.
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