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254–257 ꢀC. 1H NMR (DMSO-d6, 400 MHz) d (ppm): 7.97 (d, 2H, J SO2NH), 7.82 (d, 2H, J ¼ 8.3 Hz, ArH), 7.53–7.49 (m, 4H, ArH),
¼ 8.4 Hz, ArH), 7.88 (t, 1H, J ¼ 7.5 Hz, ArH), 7.72 (t, 2H, J ¼ 7.9 7.33–7.27 (m, 3H, ArH), 7.20 (t, 1H, J ¼ 5.9 Hz, ArH), 7.13–7.10
Hz, ArH), 7.40 (d, 2H, J ¼ 8.8 Hz, ArH), 7.34–7.28 (m, 3H, ArH), (m, 1H, NH), 6.39 (d, 2H, J ¼ 8.3 Hz, ArH), 4.10 (d, 2H, J ¼ 5.8
7.11–7.08 (m, 1H, NH), 6.82 (s, 1H, ArH), 6.57 (s, 4H, NH2 and Hz, CH2), 2.43 (s, 3H, CH3), 1.86 (s, 3H, CH3). MS (ESI):
NH), 6.36 (d, 2H, J ¼ 8.7 Hz, ArH), 4.10 (s, 2H, CH2). MS (ESI): 475.1 ([M + H]+).
461.1 ([M + H]+).
4.3.16 2-((4-(N-Acetylsulfamoyl)phenylamino)methyl)phenyl
4.3.9 2-((4-(N-Carbamimidoylsulfamoyl)phenylamino)methyl)- 4-nitrobenzenesulfonate (25). Yellow crystal, yield 66.3%, m.p.
phenyl 4-methylbenzenesulfonate (18). White crystal, yield 160–162 ꢀC. 1H NMR (DMSO-d6, 400 MHz) d (ppm): 11.71 (s, 1H,
59.9%, m.p. 182–184 ꢀC. 1H NMR (DMSO-d6, 300 MHz) d (ppm): SO2NH), 8.47 (d, 2H, J ¼ 8.9 Hz, ArH), 8.24 (d, 2H, J ¼ 8.9 Hz,
7.82 (d, 2H, J ¼ 8.3 Hz, ArH), 7.51 (d, 2H, J ¼ 8.2 Hz, ArH), 7.38 ArH), 7.54 (d, 2H, J ¼ 8.9 Hz, ArH), 7.35–7.32 (m, 3H, ArH), 7.19
(d, 2H, J ¼ 8.7 Hz, ArH), 7.31–7.26 (m, 3H, ArH), 7.12–7.09 (m, (t, 1H, J ¼ 5.9 Hz, ArH), 7.09–7.07 (m, 1H, NH), 6.51 (d, 2H, J ¼
1H, NH), 6.78 (t, 1H, J ¼ 5.9 Hz, ArH), 6.54 (s, 4H, NH2 and NH), 8.8 Hz, ArH), 4.19 (d, 2H, J ¼ 5.8 Hz, CH2), 1.86 (s, 3H, CH3). MS
6.32 (d, 2H, J ¼ 8.7 Hz, ArH), 4.07 (d, 2H, J ¼ 6.0 Hz, CH2), 2.43 (ESI): 506.1 ([M + H]+).
(s, 3H, CH3). MS (ESI): 475.1 ([M + H]+).
4.3.17 2-((4-(N-Acetylsulfamoyl)phenylamino)methyl)phenyl
4.3.10 2-((4-(N-Carbamimidoylsulfamoyl)phenylamino)- 4-bromobenzenesulfonate (26). White crystal, yield 59.2%, m.p.
methyl)phenyl 4-nitrobenzenesulfonate (19). Yellow crystal, 190–193 ꢀC. 1H NMR (DMSO-d6, 400 MHz) d (ppm): 11.70 (s, 1H,
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yield 58.5%, m.p. 132–134 C. H NMR (DMSO-d6, 300 MHz) d SO2NH), 7.93–7.86 (m, 4H, ArH), 7.55 (d, 2H, J ¼ 9.0 Hz, ArH),
(ppm): 8.49 (d, 2H, J ¼ 8.8 Hz, ArH), 8.25 (d, 2H, J ¼ 8.8 Hz, ArH), 7.36–7.30 (m, 3H, ArH), 7.22 (t, 1H, J ¼ 5.9 Hz, ArH), 7.12–7.10
7.40 (d, 2H, J ¼ 8.6 Hz, ArH), 7.33–7.29 (m, 3H, ArH), 7.08–7.05 (m, 1H, NH), 6.45 (d, 2H, J ¼ 9.0 Hz, ArH), 4.14 (d, 2H, J ¼ 5.9
(m, 1H, NH), 6.80 (t, 1H, J ¼ 5.7 Hz, ArH), 6.55 (s, 4H, NH2 and Hz, CH2). MS (ESI): 538.0 ([M + H]+).
NH), 6.43 (d, 2H, J ¼ 8.7 Hz, ArH), 4.18 (d, 2H, J ¼ 5.6 Hz, CH2).
4.3.18 2-((4-(N-Acetylsulfamoyl)phenylamino)methyl)phenyl
4-chlorobenzenesulfonate (27). White crystal, yield 54.2%, m.p.
MS (ESI): 506.1 ([M + H]+).
4.3.11 2-((4-(N-Carbamimidoylsulfamoyl)phenylamino)- 184–186 ꢀC. 1H NMR (DMSO-d6, 400 MHz) d (ppm): 11.70 (s, 1H,
methyl)phenyl 4-bromobenzenesulfonate (20). White crystal, SO2NH), 7.96 (d, 2H, J ¼ 8.7 Hz, ArH), 7.78 (d, 2H, J ¼ 8.7 Hz,
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yield 41.9%, m.p. 108–110 C. H NMR (DMSO-d6, 400 MHz) d ArH), 7.55 (d, 2H, J ¼ 9.0 Hz, ArH), 7.34–7.28 (m, 3H, ArH), 7.22
(ppm): 7.94 (d, 2H, J ¼ 8.7 Hz, ArH), 7.87 (d, 2H, J ¼ 8.8 Hz, ArH), (t, 1H, J ¼ 6.0 Hz, ArH), 7.13–7.11 (m, 1H, NH), 6.45 (d, 2H, J ¼
7.40 (d, 2H, J ¼ 8.6 Hz, ArH), 7.34–7.26 (s, 3H, ArH), 7.12–7.10 8.8 Hz, ArH), 4.15 (d, 2H, J ¼ 5.9 Hz, CH2), 1.86 (s, 3H, CH3). MS
(m, 1H, NH), 6.85 (t, 1H, J ¼ 6.1 Hz, ArH), 6.56 (s, 4H, NH2 and (ESI): 495.0 ([M + H]+).
NH), 6.34 (d, 2H, J ¼ 8.7 Hz, ArH), 4.10 (d, 2H, J ¼ 6.0 Hz, CH2).
4.3.19 2-((4-(N-Acetylsulfamoyl)phenylamino)methyl)phenyl
4-uorobenzenesulfonate (28). White crystal, yield 51.7%, m.p.
MS (ESI): 539.1 ([M + H]+).
4.3.12 2-((4-(N-Carbamimidoylsulfamoyl)phenylamino)- 140–141 ꢀC. 1H NMR (DMSO-d6, 400 MHz) d (ppm): 11.70 (s, 1H,
methyl)phenyl 4-chlorobenzenesulfonate (21). White crystal, SO2NH), 8.07–8.03 (m, 2H, ArH), 7.58–7.54 (m, 4H, ArH), 7.35–
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yield 48.3%, m.p. 98–100 ꢀC. H NMR (DMSO-d6, 400 MHz) d 7.31 (m, 3H, ArH), 7.22 (t, 1H, J ¼ 6.0 Hz, ArH), 7.11–7.10 (m, 1H,
(ppm): 7.96 (d, 2H, J ¼ 8.6 Hz, ArH), 7.79 (d, 2H, J ¼ 8.7 Hz, ArH), NH), 6.48 (d, 2H, J ¼ 8.7 Hz, ArH), 4.17 (d, 2H, J ¼ 5.9 Hz, CH2),
7.40 (d, 2H, J ¼ 8.6 Hz, ArH), 7.33–7.28 (m, 3H, ArH), 7.12–7.09 1.87 (s, 3H, CH3). MS (ESI): 479.1 ([M + H]+).
(m, 1H, NH), 6.85 (t, 1H, J ¼ 6.0 Hz, ArH), 6.56 (s, 4H, NH2 and
4.3.20 2-((4-(N-Acetylsulfamoyl)phenylamino)methyl)phenyl
NH), 6.43 (d, 2H, J ¼ 8.7 Hz, ArH), 4.11 (d, 2H, J ¼ 6.0 Hz, CH2). 3-nitrobenzenesulfonate (29). Yellow crystal, yield 58.9%, m.p.
MS (ESI): 495.1 ([M + H]+). 186–188 ꢀC. 1H NMR (DMSO-d6, 400 MHz) d (ppm): 11.70 (s, 1H,
4.3.13 2-((4-(N-Carbamimidoylsulfamoyl)phenylamino)- SO2NH), 8.64–8.62 (m, 1H, ArH), 8.56 (t, 1H, J ¼ 1.9 Hz, ArH),
methyl)phenyl 4-uorobenzenesulfonate (22). White crystal, 8.40 (d, 1H, J ¼ 7.9 Hz, ArH), 7.97 (t, 1H, J ¼ 8.1 Hz, ArH), 7.54 (d,
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yield 46.4%, m.p. 112–114 C. H NMR (DMSO-d6, 400 MHz) d 2H, J ¼ 9.0 Hz, ArH), 7.38–7.31 (m, 3H, ArH), 7.18 (t, 1H, J ¼ 5.8
(ppm): 8.06–8.02 (m, 2H, ArH), 7.59–7.54 (m, 2H, ArH), 7.39 (d, Hz, ArH), 7.13–7.11 (m, 1H, NH), 6.51 (d, 2H, J ¼ 8.8 Hz, ArH),
2H, J ¼ 8.8 Hz, ArH), 7.33–7.28 (m, 3H, ArH), 7.09–7.07 (m, 1H, 4.21 (d, 2H, J ¼ 5.8 Hz, CH2), 1.87 (s, 3H, CH3). MS (ESI): 506.1
NH), 6.85 (t, 1H, J ¼ 6.0 Hz, ArH), 6.56 (s, 4H, NH2 and NH), 6.36 ([M + H]+).
(d, 2H, J ¼ 8.7 Hz, ArH), 4.11 (d, 2H, J ¼ 5.9 Hz, CH2). MS (ESI):
4.3.21 2-((4-(N-(4-Methylpyrimidin-2-yl)sulfamoyl)phenyl-
amino)methyl)phenyl benzenesulfonate (30). White crystal,
479.1 ([M + H]+).
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4.3.14 2-((4-(N-Carbamimidoylsulfamoyl)phenylamino)- yield 43.4%, m.p. 203–205 C. H NMR (DMSO-d6, 400 MHz) d
methyl)phenyl 3-nitrobenzenesulfonate (23). Yellow crystal, (ppm): 11.18 (s, 1H, SO2NH), 8.32 (d, 1H, J ¼ 5.1 Hz, ArH), 7.95
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yield 61.1%, m.p. 214–216 C. H NMR (DMSO-d6, 400 MHz) d (d, 2H, J ¼ 7.3 Hz, ArH), 7.85 (t, 1H, J ¼ 7.5 Hz, ArH), 7.72–7.64
(ppm): 8.68–8.65 (m, 1H, ArH), 8.56 (t, 1H, J ¼ 2.0 Hz, ArH), 8.41– (m, 4H, ArH), 7.34–7.27 (m, 3H, ArH), 7.09–7.04 (m, 2H, ArH),
8.39 (m, 1H, ArH), 7.98 (t, 1H, J ¼ 8.0 Hz, ArH), 7.39 (d, 2H, J ¼ 8.8 6.90 (d, 1H, J ¼ 5.1 Hz, NH), 6.42 (d, 2H, J ¼ 5.1 Hz, ArH), 4.10
Hz, ArH), 7.35–7.29 (m, 3H, ArH), 7.13–7.08 (m, 1H, NH), 6.82 (t, (d, 2H, J ¼ 5.8 Hz, CH2), 2.31 (s, 3H, CH3). MS (ESI):
1H, J ¼ 5.8 Hz, ArH), 6.56 (s, 4H, NH2), 6.42 (d, 2H, J ¼ 8.8 Hz, 511.1 ([M + H]+).
ArH), 4.19 (d, 2H, J ¼ 5.5 Hz, CH2). MS (ESI): 506.1 ([M + H]+).
4.3.22 2-((4-(N-(4-Methylpyrimidin-2-yl)sulfamoyl)phenyl-
4.3.15 2-((4-(N-Acetylsulfamoyl)phenylamino)methyl)phenyl amino)methyl)phenyl 4-methylbenzenesulfonate (31). White
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4-methylbenzenesulfonate (24). White crystal, yield 55.7%, m.p. crystal, yield 48.5%, m.p. 184–186 C. H NMR (DMSO-d6, 400
120–122 ꢀC. 1H NMR (DMSO-d6, 400 MHz) d (ppm): 11.70 (s, 1H, MHz) d (ppm): 11.21 (s, 1H, SO2NH), 8.30 (d, 1H, J ¼ 5.0 Hz,
39222 | RSC Adv., 2014, 4, 39214–39225
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