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115.3, 115.4, 127.4, 127.5, 137.6, 161.4, 163.3, 175.1. EI-MS: m/z
calcd for C22H36FNO2: 365.2730 [M]+; observed: 365.2726.
4.17. Compound KPB-200
Aminol used (0.30 g, 1.50 mmol); Yield: 0.28 g (45%) as light
yellow amorphous solid. Mp: 108–110 °C. 1H NMR (CDCl3,
300 MHz, ppm): d = 0.88 (t, J = 6.7 Hz, 3H), 1.26 (s, 18H), 1.30 (s,
10H), 1.57 (m, 2H), 2.14 (t, J = 7.5 Hz, 2H), 3.27–3.31 (m, 1H),
3.62–3.65 (m, 1H), 4.76 (d, J = 5.3 Hz,1H), 6.31 (br, 1H), 7.26 (d,
J = 8.1 Hz, 2H), 7.35 (d, J = 7.9 Hz, 2H). 13C NMR (CDCl3, 75 MHz,
ppm): 14.1, 22.7, 25.7, 29.3, 29.4, 29.6, 29.7, 31.3, 31.9, 34.5,
36.6, 47.3, 73.3, 125.3, 125.6, 138.8, 150.7, 174.8. ESI-MS: m/z calcd
for C26H45NO2: 426.3343 [M+Na]+; observed: 426.3342.
4.12. Compound KPB-46
Aminol used (0.12 g, 0.78 mmol); Yield: 0.16 g (57%) as white
solid. Mp: 104–106 °C. 1H NMR (MeOH-d4, 500 MHz, ppm):
d = 0.92 (t, J = 7.0 Hz, 3H), 1.31 (br, 20H), 1.55–1.61 (m, 2H), 2.18
(t, J = 7.5 Hz, 2H), 3.35–3.37 (m, 1H), 3.42 (dd, J1 = 5.3 Hz,
J2 = 13.5 Hz, 1H), 4.67 (dd, J1 = 5.3 Hz, J2 = 7.5 Hz, 1H), 6.77 (d,
J = 8.6 Hz, 2H), 7.21 (d, J = 8.5 Hz, 2H). 13C NMR (MeOH-d4,
125 MHz, ppm): 14.5, 23.8, 27.0, 30.3, 30.5, 30.6, 30.7, 30.8, 33.1,
37.1, 47.9, 73.3, 116.1, 128.5, 134.6, 158.1, 176.6. ESI-MS: m/z calcd
for C22H35NO3: 362.2701 [M+H]+; observed: 362.2701.
4.18. Synthesis of sulfonamide analogues
To a solution of amine (0.73 mmol) in the presence of triethyl-
amine (1.2 mL, 0.87 mmol) in CH2Cl2 (3.0 mL) was added dropwise
a solution of 1-dodecanesulfonyl chloride (0.19 mg, 0.73 mmol) in
CH2Cl2 (1.0 mL). The reaction mixture was stirred for 2–3 h at room
temperature and the completion of the reaction was monitored by
TLC. The mixture was diluted with CH2Cl2 and extracted with water
followed by brine solution. The combined organic layer was dried
over anhydrous sodium sulfate and the solvent was evaporated un-
der reduced pressure to obtain the crude product as semi-solid com-
pound. The product was purified by silica gel column
chromatography using cyclohexane and ethyl acetate as eluent.
4.13. Compound KPB-53
Aminol used (0.2 g, 1.31 mmol); Yield: 0.23 g (48%) as yellowish
crystalline solid. Mp: 68–70 °C. 1H NMR (MeOH-d4, 500 MHz,
ppm): d = 0.92 (t, J = 7.0 Hz, 3H), 1.31 (br, 20H), 1.57–1.62 (m,
2H), 2.19 (t, J = 7.5 Hz, 2H), 3.33 (dd, J1 = 8.4 Hz, J2 = 12.9 Hz, 2H),
3.45 (dd, J1 = 4.8 Hz, J2 = 13.6 Hz, 1H), 4.70 (dd, J1 = 5.0 Hz,
J2 = 7.6 Hz, 1H), 6.71 (dd, J1 = 1.6 Hz, J2 = 7.6 Hz, 1H), 6.85 (d,
J = 6.6 Hz, 2H), 7.16 (t, J = 8.0 Hz, 1H). 13C NMR (MeOH-d4,
125 MHz, ppm): 14.5, 23.8, 27.1, 30.3, 30.5, 30.7, 30.8, 33.1, 37.1,
48.1, 73.6, 114.1, 115.5, 118.4, 130.4, 145.5, 158.6, 176.7. EI-MS:
m/z calcd for C22H37NO3: 363.2773 [M]+; observed: 363.2773.
4.19. Compound KPB-70
Aminol used (50 mg, 0.23 mmol); Yield: 51 mg (49%) as white
amorphous solid. Mp: 94–96 °C. 1H NMR (CDCl3, 500 MHz, ppm):
d = 0.90 (t, J = 6.7 Hz, 3H), 1.28 (br, 16H), 1.37–1.44 (m, 2H),
1.84–1.94 (m, 2H), 2.49 (d, J = 4.5 Hz, 1H), 2.61 (d, J = 3.6 Hz, 1H),
2.70 (d, J = 3.6 Hz, 1H), 3.05–3.13 (m, 2H), 4.73 (t, J = 4.6 Hz, 1H),
7.64 (d, J = 8.4 Hz, 2H), 8.28 (d, J = 8.8 Hz, 2H). 13C NMR (CDCl3,
125 MHz, ppm): 14.1, 22.7, 22.9, 28.3, 29.0, 29.3, 29.4, 29.5, 29.6,
31.9, 42.4, 52.4, 71.8, 124.0, 127.0, 147.0, 147.9. ESI-MS: m/z calcd
for C21H36N2O6S: 443.2221 [M-H]-; observed: 443.2221.
4.14. Compound KPB-185
Aminol used (0.30 g, 1.81 mmol); Yield: 0.41 g (62%) as yellow-
ish amorphous solid. Mp: 86–88 °C. 1H NMR (CDCl3, 300 MHz,
ppm): d = 0.89 (t, J = 6.6 Hz, 3H), 1.19–1.26 (br, 25H), 1.53 (br,
2H), 2.09 (t, J = 7.5 Hz, 2H), 2.61 (q, J = 7.5 Hz, 2H), 3.21–3.27 (m,
1H), 3.55–3.58 (m, 1H), 4.71 (d, J = 5.4 Hz, 1H), 6.58 (br, 1H), 7.12
(d, J = 7.6 Hz, 2H), 7.22 (d, J = 7.8 Hz, 2H). 13C NMR (CDCl3,
75 MHz, ppm): 14.1, 14.6, 22.7, 25.8, 29.3, 29.4, 29.5, 29.7, 31.9,
36.7, 51.0, 76.6, 126.3, 127.4, 128.1, 140.8, 174.2. ESI-MS: m/z calcd
for C24H39NO2: 362.3054 [M+H]+; observed: 362.3054.
4.20. Compound KPB-73
Aminol used (0.09 g, 0.64 mmol); Yield: 0.14 g (58%) as light
yellow semi-solid. 1H NMR (CDCl3, 500 MHz, ppm): d = 0.90 (t,
J = 7.0 Hz, 3H), 1.26 (br, 16H), 1.36–1.41 (m, 2H), 1.74–1.81 (m,
2H), 3.00–3.03 (m, 2H), 3.20 (dd, J1 = 7.9 Hz, J2 = 13.6 Hz, 1H),
3.44 (d, J = 13.0 Hz, 1H), 4.90 (dd, J1 = 3.2 Hz, J2 = 7.8 Hz, 1H),
5.50 (br, 1H), 7.33 (d, J = 4.2 Hz, 2H), 8.49 (s, 2H). 13C NMR (CDCl3,
125 MHz, ppm): 14.1, 22.7, 23.6, 28.3, 29.1, 29.3, 29.5, 29.6, 31.9,
49.9, 53.0, 71.8, 121.2, 149.5, 150.8. EI-MS: m/z calcd for
4.15. Compound KPB-196
Aminol used (0.20 g, 1.12 mmol); Yield: 0.38 g (70%) as white
amorphous solid. Mp: 100–102 °C. 1H NMR (CDCl3, 300 MHz,
ppm): d = 0.86–0.95 (m, 6H), 1.27 (br, 18H), 1.48–1.64 (m, 4H),
2.06 (t, J = 8.1 Hz, 2H), 2.54 (t, J = 7.8 Hz, 2H), 3.21 (m, 1H), 3.53
(m, 1H), 4.69 (d, J = 7.7 Hz, 1H), 4.90 (s, 1H), 6.84 (t, J = 4.36 Hz,
1H), 7.07 (d, J = 8.1 Hz, 2H), 7.19 (d, J = 8.1 Hz, 2H). 13C NMR (CDCl3,
75 MHz, ppm): 13.8, 14.1, 22.7, 24.5, 25.8, 29.3, 29.4, 29.5, 29.6,
29.8, 31.9, 36.5, 47.5, 73.0, 125.7, 128.4, 139.3, 141.9, 174.9. ESI-
C
19H34N2O3S: 370.2290 [M]+; observed: 370.2290.
4.21. Compound KPB-77
MS: m/z calcd for
C
25H43NO2: 412.3186 [M+Na]+; observed:
412.3186.
Aminol used (0.1 g, 0.73 mmol); Yield: 0.14 g (52%) white amor-
phous solid. Mp: 76–78 °C. 1H NMR1H NMR (CDCl3, 500 MHz,
ppm): d = 0.90 (t, J = 11.0 Hz, 3H), 1.27 (br, 18H), 1.71–1.82 (m,
2H), 2.95–3.00 (m, 2H), 3.21–3.28 (m, 1H), 3.39–3.44 (m, 1H),
4.88–4.91 (m, 1H), 7.30–7.40 (m, 5H). 13C NMR (CDCl3, 125 MHz,
ppm): 14.1, 22.7, 23.6, 26.9, 28.3, 29.1, 29.3, 29.5, 29.6, 31.9,
50.3, 53.0, 73.3, 125.9, 128.3, 128.7, 140.9. ESI-MS: m/z calcd for
4.16. Compound KPB-199
Aminol used (0.29 g, 1.50 mmol); Yield: 0.31 g (52%) as light
yellow solid. Mp: 78–80 °C. 1H NMR (CDCl3, 300 MHz, ppm):
d = 0.86–0.95 (m, 6H), 1.26 (br, 18H), 1.31–1.38 (m, 2H), 1.52–
1.62 (m, 2H), 2.11 (t, J = 7.6 Hz, 2H), 2.58 (t, J = 8.1 Hz, 2H), 3.23–
3.30 (m, 1H), 3.57–3.63 (m, 1H), 4.74 (d, J = 5.2 Hz, 1H), 6.41 (br,
1H), 7.12 (d, J = 7.8 Hz, 2H), 7.22 (d, J = 7.9 Hz, 2H). 13C NMR (CDCl3,
75 MHz, ppm): 14.0, 14.1, 22.4, 22.7, 25.7, 29.3, 29.4, 29.6, 29.7,
31.9, 33.6, 35.4, 36.6, 47.4, 73.3, 125.7, 128.4, 139.1, 142.4, 174.8.
ESI-MS: m/z calcd for C26H45NO2: 426.3343 [M+Na]+; observed:
426.3343.
C
20H35NO3S: 368.9760 [MꢁH]ꢁ; observed: 368.9674.
4.22. Compound KPB-79
Aminol used (65 mg, 0.47 mmol); Yield: 75 mg (43%) as white
amorphous solid. Mp: 74–76 °C. 1H NMR (CDCl3, 500 MHz, ppm):
d = 0.87 (t, J = 11.0 Hz, 3H), 1.25 (br, 18H), 1.70–1.80 (m, 2H), 2.96–