Indole-3-carbinol and 1,3,4-Oxadiazole Hybrids
I
C19H16N4O4S: C 57.57, H 4.07, N 14.13, S 8.09. Found: C 57.55,
H 4.05, N 14.10, S 8.07 %.
135.56, 133.32, 131.67, 131.59, 131.53, 126.95, 116.01,
115.80, 113.80, 113.53, 112.65, 112.55, 54.34, 35.70, 32.76.
m/z (ESI) 369.9 ([M ꢀ 17]þ). Anal. Calc. for C19H15F2N3O2S:
C 58.91, H 3.90, N 10.85, S 8.28. Found: C 58.89, H 3.87 N
10.82, S 8.27 %.
4-((5-(5-Fluoro-3-(hydroxymethyl)-1-methyl-1H-indol-2-yl)-
1,3,4-oxadiazo-2-ylthio)methyl)benzonitrile (10m): dH ([D6]
DMSO, 400 MHz) 7.85–7.10 (7H, m, Ar–H), 4.91 (1H, s, J 5.2,
–OH), 4.85 (2H, d, J 5.2, O–CH2), 4.34 (2H, s, S–CH2), 3.98 (3H,
s, N–CH3). dC ([D6]DMSO, 100 MHz) 162.42, 161.53, 159.87,
145.41, 132.26, 132.23, 131.91, 131.50, 129.61, 129.59, 128.82,
120.54, 115.61, 113.89, 112.84, 112.57, 111.04, 55.53, 34.59,
32.73. m/z (ESI) 376.6 ([M ꢀ 17]þ). Anal. Calc. for
C20H15FN4O2S: C 60.90, H 3.83, N 14.20, S 8.13. Found: C
60.87, H 3.81, N 14.18, S 8.10%.
(2-(5-(2-Fluorobenzylthio)-1,3,4-oxadiazol-2-yl)-5-fluoro-
1-methyl-1H-indol-3-yl)methanol (10n): dH ([D6]DMSO,
400 MHz) 7.66–7.18 (7H, m, Ar–H), 5.01 (1H, s, –OH), 4.84
(2H, s, O–CH2), 4.63 (2H, s, S–CH2), 3.99 (3H, s, N–CH3). dC
([D6]DMSO, 100 MHz) 162.38, 160.92; 159.87, 158.53,
132.54, 130.31, 129.47, 128.30, 127.39, 126.77, 124.96,
115.39, 113.98, 113.54, 112.99, 111.24, 55.45, 34.68, 33.51.
m/z (ESI) 369.9 ([M ꢀ 17]þ). Anal. Calc. for C19H15F2N3O2S:
C 58.91, H 3.90, N 10.85, S 8.28. Found: C 58.89, H 3.87,
N 10.82, S 8.27 %.
(2-(5-(4-Nitrobenzylthio)-1,3,4-oxadiazol-2-yl)-5-fluoro-
1-methyl-1H-indol-3-yl)methanol (10o): dH ([D6]DMSO,
400 MHz) 8.24–7.14 (7H, m, Ar–H), 4.96 (1H, s br, –OH),
4.84 (2H, s, O–CH2), 4.71 (2H, s, S–CH2), 3.99 (3H, s, N–
CH3). dC ([D6]DMSO, 100 MHz) 160.91, 158.87, 159.87,
147.66, 146.46, 132.20, 131.09, 129.66, 129.49, 128.15,
122.63, 122.09, 113.98, 113.54, 112.64, 111.18, 54.67,
35.36, 33.41. m/z (ESI) 397.9 ([M ꢀ 17]þ). Anal. Calc. for
C19H15FN4O4S: C 55.07, H 3.65, N 13.52, S 7.74. Found: C
55.04, H 3.61, N 13.50, S 7.71 %.
(5-Fluoro-2-(5-(isopropylthio)-1,3,4-oxadiazol-2-yl)-1-methyl-
1H-indol-3-yl)methanol (10p): dH ([D6]DMSO, 400 MHz) 7.66–
7.20 (3H, m, Ar–H), 5.00 (1H, s, –OH), 4.86 (2H, s, O–CH2), 4.03
(3H, s, N–CH3), 3.94 (1H, sept, J 7.2, –CH), 1.49 (6H, d, J 7.2,
aliphatic). dC ([D6]DMSO, 100 MHz) 162.78, 160.66, 159.86,
132.23, 131.91, 127.37, 113.98, 113.56, 112.64, 111.23, 55.32,
35.89, 33.48, 23.55, 20.45. m/z (ESI) 303.6 ([M ꢀ 17]þ). Anal.
Calc. for C15H16FN3O2S: C 56.06, H 5.02, N 13.08, S 9.98. Found:
C 56.04, H 4.99, N 13.05, S 9.96 %.
(2-(5-(Cyclopentylthio)-1,3,4-oxadiazol-2-yl)-5-fluoro-1-
methyl-1H-indol-3-yl)methanol (10q): dH ([D6]DMSO,
400 MHz) 7.66–7.58 (2H, m, Ar–H), 7.24–7.20 (1H, m,
Ar–H), 4.99 (1H, s, –OH), 4.86 (2H, s, O–CH2), 4.06 (1H,
m, S–CH), 4.02 (3H, s, N–CH3), 2.23–1.65 (8H, m, aliphatic).
dC ([D6]DMSO, 100 MHz) 162.77, 160.58, 159.78, 133.33,
129.59, 127.32, 113.70, 113.51, 112.62, 111.20, 55.78,
44.23, 35.28, 35.31, 32.49, 26.35, 26.29. m/z (ESI) 329.9
([M ꢀ 17]þ). Anal. Calc. for C17H18FN3O2S: C 58.77, H
5.22, N 12.10, S 9.23. Found: C 58.75, H 5.19, N 12.08,
S 9.20 %.
(2-(5-(4-(Trifluoromethoxy)benzylthio)-1,3,4-oxadiazol-2-
yl)-5-fluoro-1-methyl-1H-indol-3-yl)methanol (10r): dH ([D6]
DMSO, 400 MHz) 7.64–7.22 (7H, m, Ar–H), 5.00 (1H, s br, –
OH), 4.83 (2H, s, O–CH2), 4.64 (2H, s, S–CH2), 3.99 (3H, s, N–
CH3). dC ([D6]DMSO, 100 MHz) 163.58, 160.34, 158.95,
156.62, 135.55, 131.49, 126.93, 126.83, 121.79, 121.60,
121.37, 121.09, 113.80, 113.54, 112.64, 112.55, 105.71,
54.31, 35.52, 32.69. m/z (ESI) 435.9 ([M ꢀ 17]þ). Anal. Calc.
(2-(5-(Isopropylthio)-1,3,4-oxadiazol-2-yl)-1-methyl-1H-
indol-3-yl)methanol (10f): dH ([D6]DMSO, 400 MHz) 7.86–
7.14 (4H, m, Ar–H), 4.95 (1H, s, –OH), 4.89 (2H, s, O–CH2),
4.03 (3H, s, N–CH3), 3.94 (1H, sept, J 6.8, –CH), 1.49 (6H, d,
J 7.2, –(CH3)2). dC ([D6]DMSO, 100 MHz) 163.15, 160.50,
138.80, 127.48, 126.80, 121.21, 121.16, 120.03, 119.92,
111.02, 110.94, 54.28, 32.41, 23.64, 20.46. m/z (ESI) 285.6
([M ꢀ 17]þ). Anal. Calc. for C15H17N3O2S: C 59.38, H 5.65,
N 13.85, S 10.57. Found: C 59.37, H 5.62, N 13.82, S 10.55 %.
(2-(5-(Cyclopentylthio)-1,3,4-oxadiazol-2-yl)-1-methyl-1H-
indol-3-yl)methanol (10g): dH ([D6]DMSO, 400 MHz) 7.85–
7.14 (4H, m, Ar–H), 4.90 (3H, s br, –CH2–OH), 4.07 (1H, m,
S–CH), 4.02 (3H, s, N–CH3), 2.26–1.65 (8H, m, aliphatic). dC
([D6]DMSO, 100 MHz) 163.09, 160.59, 139.71, 129.59,
127.75, 121.92, 121.24, 121.10, 111.23, 109.92, 44.19, 35.28,
35.34, 32.40, 26.35, 26.18. m/z (ESI) 312.9 ([M ꢀ 17]þ). Anal.
Calc. for C17H19N3O2S: C 61.98, H 5.81, N 12.76, S 9.73.
Found: C 61.96, H 5.78, N 12.73, S 9.70 %.
(2-(5-(4-(Trifluoromethoxy)benzylthio)-1,3,4-oxadiazol-2-
yl)-1-methyl-1H-indol-3-yl)methanol (10h): dH ([D6]DMSO,
400 MHz) 7.85–7.12 (8H, m, Ar–H), 4.93 (1H, s br, –OH), 4.86
(2H, s, O–CH2), 4.63 (2H, s, S–CH2), 3.98 (3H, s, N–CH3). dC
([D6]DMSO, 100 MHz) 161.70, 160.58, 159.63, 139.62,
133.30, 129.97, 129.89, 128.47, 128.16, 126.98, 121.24,
121.10, 120.28, 115.68, 115.38, 111.23, 110.67, 55.02,
35.58, 32.41. m/z (ESI) 417.9 ([M ꢀ 17]þ). Anal. Calc. for
C20H16F3N3O3S: C 55.17, H 3.70, N 9.65, S 7.36. Found: C
55.14, H 3.67, N 9.63, S 7.33 %.
(2-(5-(4-(Trifluoromethyl)benzylthio)-1,3,4-oxadiazol-2-yl)-
1-methyl-1H-indol-3-yl)methanol (10i): dH ([D6]DMSO,
400 MHz) 7.85–7.14 (8H, m, Ar–H), 4.96 (1H, s br, –OH),
4.85 (2H, s, O–CH2), 4.69 (2H, s, S–CH2), 3.98 (3H, s, N–CH3).
dC ([D6]DMSO, 100 MHz) 160.43, 158.62, 139.75, 135.21,
129.49, 129.18, 128.51, 126.55, 125.54, 122.43, 122.12,
122.01, 120.94, 120.11, 119.91, 113.04, 110.45, 54.35, 35.29,
32.69. m/z (ESI) 401.9 ([M ꢀ 17]þ). Anal. Calc. for
C20H16F3N3O2S: C 57.27, H 3.85, N 10.02, S 7.65. Found: C
57.25, H 3.81, N 9.98, S 7.62 %.
(2-(5-(Benzylthio)-1,3,4-oxadiazol-2-yl)-1-methyl-1H-indol-
3-yl)methanol (10j): dH ([D6]DMSO, 400 MHz) 7.85–7.14 (9H,
m, Ar–H), 4.97 (1H, s br, –OH), 4.88 (2H, s, O–CH2), 4.61 (2H,
s, S–CH2), 3.99 (3H, s, N–CH3). dC ([D6]DMSO, 100 MHz)
163.50, 160.56, 138.80, 136.94, 129.51, 129.45, 129.11, 128.29,
126.79, 125.19, 121.22, 120.64, 120.44, 119.91, 111.03, 110.94,
54.26, 36.52, 32.39. m/z (ESI) 333.9 ([M ꢀ 17]þ). Anal. Calc. for
C19H17N3O2S: C 64.94, H 4.88, N 11.96, S 9.12. Found: C 64.91,
H 4.86, N 11.94, S 9.09 %.
(2-(5-(Ethylthio)-1,3,4-oxadiazol-2-yl)-1-methyl-1H-indol-
3-yl)methanol (10k): dH ([D6]DMSO, 400 MHz) 7.85–7.01
(4H, m, Ar–H), 4.97 (1H, s br, –OH), 4.87 (2H, s, O–CH2),
4.02 (3H, s, N–CH3), 3.34 (2H, q, J 7.2, S–CH2), 1.46 (3H, t J
7.2, –CH3). dC ([D6]DMSO, 100 MHz) 163.10, 160.17, 139.55,
131.28, 126.59, 122.20, 121.73, 121.19, 111.17, 110.72, 54.44,
33.18, 30.05, 15.86. m/z (ESI) 271.6 ([M ꢀ 17]þ). Anal. Calc.
for C14H15N3O2S: C 58.11, H 5.23, N 14.52, S 11.08. Found: C
58.09, H 5.21, N 14.48, S 11.06 %.
(2-(5-(4-Fluorobenzylthio)-1,3,4-oxadiazol-2-yl)-5-fluoro-
1-methyl-1H-indol-3-yl)methanol (10l): dH ([D6]DMSO,
400 MHz) 7.65–7.17 (7H, m, Ar–H), 5.00 (1H, s, –OH), 4.83
(2H, s, O–CH2), 4.60 (2H, s, S–CH2), 3.99 (3H, s, N–CH3).
dC ([D6]DMSO, 100 MHz) 160.80, 160.29, 158.95, 156.63,