D. Vargas-Oviedo et al.
J=7.5 Hz, 1H), 7.20 (t, J=7.6 Hz, 1H), 7.32 (d, J=8.1 Hz,
1H), 7.35 (br s, 4H), 7.40 (d, J=7.9 Hz, 1H), 7.63 (s, 1H)
ppm; 13C{1H} NMR (CDCl3, 100 MHz): δ = 51.8 (CH2),
70.6 (CH), 109.4 (CH), 119.3 (CH), 121.2 (CH), 122.1
(CH), 126.8 (CH), 127.9 (CH), 132.7 (C), 133.5 (C), 140.0
(C–Cl), 142.8 (C), 143.5 (CH) ppm; HRMS: m/z calcd. for
C15H1435ClN2O+ 273.0789 ([M+H]+), found 273.0788.
J = 4.40 Hz), 128.3, 128.4 (C, d, J = 13.20 Hz), 129.6,
129.7 (CH, d, J = 8.07 Hz), 133.5 (C), 142.8 (C), 143.7
(CH), 158.5, 160.9 (C–F, d, J = 244.30 Hz) ppm; HRMS:
m/z calcd. for C15H14FN2O+ 257.1085 ([M + H]+), found
257.1091.
2‑(1‑Benzimidazolyl)‑1‑(2,4‑dichlorophenyl)ethanol (7e,
C15H12Cl2N2O) By following the Method B in the reaction
with 122 × 10–3 g N-(2,4-dichlorophenacyl)benzimida-
zole (6e, 0.4 × 10–3 mol), the alcohol 7e was obtained as
a yellow solid (117× 10–3 g, 95%). M.p.: 185–187 °C; 1H
NMR (DMSO-d6, 400 MHz): δ = 4.28 (m, 1H), 4.45 (d,
J=14.3 Hz, 1H), 5.20 (br s, 1H), 6.05 (d, J=3.6 Hz, 1H),
7.20 (m, 2H), 7.44 (d, J=8.0 Hz, 1H), 7.50 (d, J=7.7 Hz,
1H), 7.55 (d, J=8.3 Hz, 1H), 7.64 (br m, 2H), 8.08 (s, 1H)
ppm; 13C{1H} NMR (DMSO-d6, 100 MHz): δ=49.8 (CH2),
67.6 (CH), 110.2 (CH), 119.4 (CH), 121.4 (CH), 122.2 (CH),
127.6 (CH), 128.5 (CH), 129.5 (CH), 131.8 (C), 132.9 (C),
134.0 (C), 138.8 (C), 143.2 (C), 144.8 (CH) ppm; HRMS:
m/z calcd. for C15H1335Cl2N2O+ 307.0400 ([M+H]+), found
307.0399.
2‑(1‑Benzimidazolyl)‑1‑(4‑fluorophenyl)ethanol (7b,
C15H13FN2O) By following the Method B in the reaction
with 102×10–3 g N-(4-fuorophenacyl)benzimidazole (6b,
0.4×10–3 mol), the alcohol 7b was obtained as a white solid
1
(93 × 10–3 g, 91%). M.p.: 153–155 °C; H NMR (DMSO-
d6, 400 MHz): δ = 4.30–4.42 (m, 2H), 4.97 (br m, 1H),
5.94 (d, J=4.4 Hz, 1H), 7.10 (t, J=8.8 Hz, 2H), 7.16–7.23
(m, 2H), 7.38 (m, 2H), 7.52 (d, J = 7.2 Hz, 1H), 7.60 (d,
J=7.1 Hz, 1H), 8.04 (s, 1H) ppm; 13C{1H} NMR (DMSO-
d6, 100 MHz): δ=51.9 (CH2), 70.9 (CH), 111.2 (CH), 115.2,
115.4 (CH, d, J=21.3 Hz), 119.5 (CH), 122.0 (CH), 122.8
(CH), 128.5 (CH, d, J = 8.1 Hz), 134.4 (C), 138.8 (C, d,
J = 2.9 Hz), 143.0 (C), 145.0 (CH), 160.7, 163.2 (CF, d,
J = 242.8 Hz) ppm; HRMS: m/z calcd. for C15H14FN2O+
257.1085 ([M+H]+), found 257.1090.
2‑(1‑Benzimidazolyl)‑1‑(2,4‑difluorophenyl)ethanol (7f,
C15H12F2N2O) By following the Method B in the reaction
with 109 × 10–3 g N-(2,4-difuorophenacyl)benzimidazole
(6f, 0.4×10–3 mol), the alcohol 7f was obtained as a white
2‑(1‑Benzimidazolyl)‑1‑(2‑chlorophenyl)ethanol (7c,
C15H13ClN2O) By following the Method B in the reaction
with 108×10–3 g N-(2-chlorophenacyl)benzimidazole (6c,
0.4×10–3 mol), the alcohol 7c was obtained as a white solid
1
solid (106 × 10–3 g, 97%). M.p.: 169–171 °C; H NMR
(DMSO-d6, 400 MHz): δ = 4.33–4.45 (m, 2H), 5.16 (br s,
1H), 5.95 (d, J=4.4 Hz, 1H), 7.08 (t, J=7.7 Hz, 1H), 7.15–
7.25 (m, 3H), 7.45–7.54 (m, 2H), 7.63 (d, J=7.6 Hz, 1H),
8.07 (s, 1H) ppm; 13C{1H} NMR (DMSO-d6, 100 MHz):
δ=50.4 (CH2), 64.9 (CH), 103.6 (CH, t, J=26.0 Hz), 110.2
(CH), 111.5 (CH, dd, J=3.7, 20.9 Hz), 119.4 (CH), 121.4
(CH), 122.2 (CH), 125.7 (C, dd, J= 3.7, 13.9 Hz), 129.2
(CH, m), 134.0 (C), 143.2 (C), 144.6 (CH), 157.8, 160.3
(CF, dd, J=12.1, 246.1 Hz), 160.4, 162.9 (CF, dd, J=12.0,
246.1 Hz) ppm; HRMS: m/z calcd. for C15H13F2N2O+
275.0990 ([M+H]+), found 275.0992.
1
(98 × 10–3 g, 90%). M.p.: 187–189 °C; H NMR (DMSO-
d6, 400 MHz): δ=4.26 (m, 1H), 4.44 (d, J=13.2 Hz, 1H),
5.23 (br s, 1H), 5.96 (d, J=4.2 Hz, 1H), 7.21 (m, 2H), 7.35
(m, 2H), 7.45 (d, J=7.2 Hz, 1H), 7.53 (d, J=7.7 Hz, 1H),
7.59 (d, J=6.9 Hz, 1H), 7.64 (d, J=7.7 Hz, 1H), 8.10 (s,
1H) ppm; 13C{1H} NMR (DMSO-d6, 100 MHz): δ = 50.1
(CH2), 67.8 (CH), 110.2 (CH), 119.4 (CH), 121.4 (CH),
122.2 (CH), 127.4 (CH), 128.0 (CH), 129.1 (CH), 129.3
(CH), 130.9 (C), 134.0 (C), 139.6 (C), 143.3 (C), 144.8
(CH) ppm; HRMS: m/z calcd. for C15H1435ClN2O+ 273.0789
([M+H]+), found 273.0792.
2‑(1‑Benzimidazolyl)‑1‑phenylethanol (7g) By following the
Method B in the reaction with 95×10–3 g N-phenacylbenzi-
midazole (6g, 0.4×10–3 mol), the alcohol 7g was obtained
2‑(1‑Benzimidazolyl)‑1‑(2‑fluorophenyl)ethanol (7d,
C15H13FN2O) By following the Method B in the reaction
with 102×10–3 g N-(2-fuorophenacyl)benzimidazole (6d,
0.4×10–3 mol), the alcohol 7d was obtained as a white solid
1
(91 × 10–3 g, 89%). M.p.: 142–144 °C; H NMR (CDCl3,
400 MHz): δ = 4.12–4.15 (m, 1H), 4.42 (d, J = 14.43 Hz,
1H), 5.45 (d, J=8.56 Hz, 1H), 7.02 (t, J=7.52 Hz, 1H), 7.09
(t, J=9.36 Hz, 1H), 7.16–7.23 (m, 2H), 7.31 (d, J=6.23 Hz,
2H), 7.41 (d, J = 8.07 Hz, 1H), 7.67 (t, J = 7.46 Hz, 1H),
7.74 (s, 1H) ppm; 13C{1H} NMR (CDCl3, 100 MHz):
δ=52.2 (CH2), 66.3 (CH), 109.8 (CH), 115.2, 115.5 (CH,
d, J = 22.01 Hz), 119.6 (CH), 122.4 (CH), 123.2 (CH),
124.8, 124.9 (CH, d, J = 3.67 Hz), 127.6, 127.7 (CH, d,
In vitro antifungal activity
Microorganisms and media
For the antifungal evaluation, standardized strains from
the American Type Culture Collection (ATCC; Rockville,
MD, USA), C. albicans ATCC 10231 and C. neoformans
1 3