ANTIBACTERIAL AND ANTIFUNGAL PROPERTIES
963
CH2), 1.31–1.36 (m, 4H, CH2), 1.52–1.57 (m, 4H, CH2), 3.19 (t, J = 7.32 Hz, 4H, SCH2),
7.58–7.60 (m, 2H, CHarom), 7.95–7.97 (m, 2H, CHarom). 13C NMR (CDCl3): 13.1, 21.6,
27.7, 28.1, 28.2, 28.4, 29.5, 30.8 (CH2, CH3), 33.9 (SCH2), 125.8, 132.1, 132.3 (CHarom
,
Carom), 146.8 (S C C O), 177.9 ppm (C=O). MS [-ESI] m/z = 474 [M]−. Anal. Calcd.
for C28H42O2S2 (474.76): C, 70.84; H, 8.92; S, 13.51. Found C, 70.90; H, 8.27; S, 12.76.
17: Red oil. Yield: 0.16 g (32%). Rf: 0.43 (CHCl3). IR 3369 (OH), 3069 (CHarom),
2923, 2853 (CHaliph), 1658 (C O), 1591 (C C). 1H NMR (CDCl3): 0.77 (t, J = 6.8 Hz,
3H, CH3), 1.15–1.19 (m, 10H, CH2), 1.28–1.37 (m, 6H, CH2), 1.38–1.49 (m, 2H, CH2),
1.50–1.59 (m, 4H, CH2), 1.95 (s, 1H, OH), 3.18 (t, 4H, SCH2), 3.53 (t, 2H, OCH2),
7.58–7.59 (m, 2H, CHarom), 7.93–7.94 (m, 2H, CHarom). 13C NMR (CDCl3): 14.3, 22.8,
25.5, 28.7, 28.9, 29.3, 29.4, 29.6, 30.5, 30.6, 32.0, 32.7 (CH2, CH3), 35.0, 35.2 (SCH2), 62.9
(OCH2), 126.9, 133.2, 133.6 (CHarom, Carom), 147.7, 148.2 (S C C O), 179.1 (C=O).
MS [+ESI] m/z = 471 [M+Na]+. Anal. Calcd. for C25H36O3S2 (448.69): C, 66.92; H,
8.09; S, 14.29. Found C, 66.35; H, 7.90; S, 14.20.
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1812: Red solid. Yield: 0.11 g (22%). M.p. 70.3–70.6 C. Rf: 0.3 (CH2Cl2/EtAc
3:1). IR: 3382, 3304 (OH), 2922, 2854 (CHaliph), 1654 (C O), 1589 (C C). Anal.
Calcd. for C22H30O4S2 (422.61): C, 62.53; H, 7.16; S, 15.17. Found C, 62.79; H, 7.05;
S, 15.57.
2,3-Bis[(6-hydroxyhexyl)thio]-1,4-naphthoquinone (18)12, 2-[(6-hydroxyhexyl)
thio]-3-[(3-hydroxypropyl)thio]-1,4-naphthoquinone (20), 2,3-bis[(3-hydroxypropyl)
thio]-1,4-naphthoquinone (21), and 8,9,19,20-tetrahydrodinaphtho[2,3-b:2ꢁ,3ꢁ-i]
[1,4,8,11]dioxadithia-cyclotetradecine-5,11,16,22(7H,18H)-tetraone (22) were synthe-
sized from 1 (0.5 g, 2.19 mmol), 14 (0.3 mL, 2.19 mmol), and 19 (0.38 mL, 2.19 mmol)
by use of the general procedure 3.
1812: Red solid. Yield: 0.11 g (22%). M.p. 70.3–70.6 ◦C. Rf: 0.3 (CH2Cl2/EtAc 3:1).
IR: 3382, 3304 (OH), 2922, 2854 (CHaliph), 1654 (C O), 1589 (C C). Anal. Calcd. for
C22H30O4S2 (422.61): C, 62.53; H, 7.16; S, 15.17. Found C, 62.79; H, 7.05; S, 15.57.
20: Red oil. Yield: 0.13 g (16%). Rf: 0.17 (CHCl3/EtAc 2:1). IR: 3349 (OH), 3065
1
(CHarom), 2930, 2856 (C–Haliph), 1657 (C O), 1591 (C C). H NMR (CDCl3): 1.19 (s,
1H, OH), 1.29–1.33 (m, 2H, CH2), 1.37–1.43 (m, 2H, CH2), 1.45–1.51 (m, 2H, CH2),
1.54–1.61 (m, 2H, CH2), 1.79–1.84 (m, 2H, CH2), 1.93 (s, 1H, OH), 3.22 (t, J = 7.3 Hz,
2H, SCH2), 3.29 (t, 2H, SCH2), 3.53–3.56 (m, 2H, OCH2), 3.71 (t, 2H, OCH2), 7.59–7.63
(m, 2H, CHarom), 7.94–7.97 (m, 2H, CHarom). 13C NMR (CDCl3): 24.3, 27.3, 29.3, 30.5,
31.5 (CH2), 31.9, 33.9 (SCH2), 59.9, 61.6 (OCH2), 125.9, 131.9, 132.5 (CHarom, Carom),
146.1, 147.8 (S C C O), 177.9, 178.0 (C=O). MS [+ESI] m/z = 404 [M+Na]+. Anal.
Calcd. for C19H24O4S2 (380.53): C, 59.97; H, 6.36; S, 16.85. Found C, 60.77; H, 7.19; S,
15.92.
21: Orange solid. Yield: 0.11 g (15%). Rf: 0.10 (CHCl3/EtAc 2:1). IR: 3357 (OH),
2967, 2924, 2853 (CHaliph), 1658 (C O), 1590 (C C). 1H NMR (CDCl3): 1.81–1.90 (m,
4H, CH2), 2.75 (t, 2H, SCH2), 3.32 (t, J = 6.8 Hz, 2H, SCH2), 3.70 (t, 2H, OCH2),
3.74 (t, J = 5.9 Hz, 2H, OCH2), 7.62–7.64 (m, 2H, CHarom), 7.97–7.99 (m, 2H, CHarom).
13C NMR (CDCl3): 31.9 (CH2), 35.4 (SCH2), 61.3 (OCH2), 127.2, 133.2, 133.9 (CHarom
,
Carom), 148.3 (S C C O), 179.2 (C=O). MS [–ESI] m/z = 338 [M]−. Anal. Calcd. for
C16H18O4S2 (338.45): C, 56.78; H, 5.36; S, 18.95. Found C, 56.83; H, 6.16; S, 17.42.
◦
22: Orange solid. Yield: 0.6 g (47%). M.p. 165.2–165.6 C. Rf: 0.71 (CHCl3/EtAc
2:1). IR: 3076 (CHarom), 2966, 2942, 2925, 2845 (CHaliph), 1666, 1643 (C O), 1589, 1546
(C C). 1H NMR (CDCl3): 2.17–2.22 (m, 4H, CH2), 3.24 (t, 4H, SCH2), 4.77 (t, J = 5.9 Hz,
4H, OCH2), 7.58–7.61 (m, 2H, CHarom), 7.93–7.98 (m, 2H, CHarom). 13C NMR (CDCl3):