KANKATE et al., Orient. J. Chem., Vol. 30(4), 1855-1863 (2014)
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132(arom. CH), 133(quat. C), 134.5(quat. C), 150.6
(quat. C), 171.2 (carbonyl C); ESI-MS m/z:
362,347,333,319,257,145.Anal. Calcd. For
C22H26N4O (362): C, 72.90; H, 7.23; N, 15.46; O, 4.41
Found: C, 72.92; H, 7.20; N, 15.49; O, 4.39.
1557(C=C), 1235 (C-N) cm -1; H NMR (300 MHz,
CDCl3) ppm:1.22(d,1H,-CH-), 3.24-3.29(m,
4H,PIP-H), 4.09(q, 3H,-CH3), 5.14(s, 1H, N-H), 7.25-
7.48 (m, 4H, Ar -H of Benzim) 7.89-8.20 (4H, Ar -H
of benzoyl) ; 13C-NMR (400 MHz, CDCl3, TMS):
18.9 (CH3), 50 (CH2), 52.4(CH2), 63.4 (CH),
118(arom. CH), 121.6 (arom. CH), 127.5 (arom. CH),
133.5 (quat. C), 136.2 (quat. C), 143.2 (quat. C),
174.5 (carbonyl C); ESI-MS m/z:368,319,257,
145,117. Anal. Calcd. For C20H22N4O (368): C, 65.12;
H, 5.74; Cl, 9.61; N, 15.19; O, 4.34.Found: C, 65.09;
H, 5.72; Cl, 9.59; N, 15.17; O, 4.30.
(4-((1-ethyl-1H-benzo[d]imidazol-2-yl) (phenyl)
methyl) piperazin-1-yl)(Phenyl) methanone (11i)
Compound 11i was obtained as a white
solid (yield: 67%; MP:258-260; IR (KBr): 3219 (N-
H), 2359 (C-H), 1671(C=O),1605(C=N),
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1548(C=C), 1236 (C-N) cm-1; H NMR (300 MHz,
CDCl3) ppm:1.24(t,2H,N-CH2-),3.12-3.16(m,
4H,PIP-H), 3.81(q, 3H,C-CH3), 4.98(s, 1H, C-H),
7.49-8.11 ( Complex m, 4H, Ar -H); 13C-NMR (400
MHz, CDCl3, TMS): ´ 16.1 (CH3), 39.10 (CH2), 52.09
(CH2), 53.2(CH2), 68.2 (CH), 116(arom. CH), 124
(arom. CH), 131 (arom. CH), 133.1 (arom. CH), 134.5
(quat. C), 138.6(quat. C), 147. (quat. C), 142.6 (quat.
C), 165.5; (carbonyl C); 13C-NMR (400 MHz, CDCl3,
TMS): 49.05 (CH2), 53.2(CH2), 63.1 (CH2),
115(arom. CH), 125.8 (arom. CH), 130.4 (arom. CH),
128.3 (quat. C), 135.9 (quat. C), 141.5 (quat. C),
147.3 (quat. C), 175.3 (carbonyl C) ; ESI-MS m/
z:424,395,319,235,181.Anal. Calcd. For C27H28N4O
(424): C, 76.39; H, 6.65; N, 13.20; O, 3.77 Found: C,
76.39; H, 6.65; N, 13.20; O, 3.77.
(4-((5-chloro-1H-benzo[d]imidazol-2-yl) (phenyl)
methyl) piperazin-1-yl)(Phenyl) methanone (11l)
Compound (11l) was obtained as a white
solid (yield: 54%; MP:214-216; IR (KBr): 3214 (N-
H), 2352 (C-H), 1668(C=O),1613(C=N),
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1539(C=C), 1236 (C-N) cm-1; H NMR (300 MHz,
CDCl3) ppm:3.19-3.28(m, 4H,PIP-H), 4.78(s,
1H,N-H), 5.94(s, 1H, C-H), 7.25-8.12 ( Complex m,
4H, Ar -H);13C-NMR (400 MHz, CDCl3,TMS) : 48.05
(CH2), 51.4(CH2), 74(CH), 116(arom. CH), 127
(arom. CH),131.5 (arom. CH), 134.3 (arom. CH),
134.8 (quat. C), 139 (quat. C), 145.5 (quat. C), 147.2
(quat. C),170(carbonyl C); ESI-MS m/z:430,395,325,
245. Anal. Calcd. For C25H23ClN4O (430): C, 69.68;
H, 5.38; Cl, 8.23; N, 13.00; O, 3.71Found: C, 69.71;
H, 5.40; Cl, 8.21; N, 13.11; O, 3.69.
(4-((5-chloro-1H-benzo[d]imidazol-2-yl) methyl)
piperazin-1-yl)(Phenyl) methanone (11j)
Compound 11j was obtained as a white
Invitro Antifungal Activity
solid (yield: 52%; MP:293-295; IR (KBr): 3224 (N-H),
2361 (C-H), 1672(C=O),1607(C=N), 1553(C=C),
1235 (C-N) cm-1; 1H NMR (300 MHz, CDCl3) ppm:
3.39-3.41(m, 4H,PIP-H), 4.28(s, 2H, -CH2-), 4.82(s,
1H, N-H), 7.25-7.85 (m, 3H, Ar -H of Benzim) 7.98-
8.12 (4H, Ar -H of benzoyl) ; 13C-NMR (400 MHz,
CDCl3, TMS): 54.8 (CH2), 56(CH2), 65.2 (CH2),
119(arom. CH), 121.3 (arom. CH),127.5 (arom. CH),
138.5 (quat. C), 140.8 (quat. C), 147.1 (quat. C),172.4
(carbonyl C).ESI-MS m/z : 354,319,203,151.Anal.
Calcd. For C19H19ClN4O (354): C, 64.31; H, 5.40; Cl,
9.99; N, 15.79; O, 4.51Found: C, 64.28; H, 5.42; Cl,
9.95; N, 15.74; O, 4.48.
The stock solution of (1m mole/ml)
compounds (equimolar mixture) was prepared in
DMSO and water. To each tube containing sterilized
sabouraud’s liquid medium (2 ml), 2 ml of drug
solution were added. Each tube was inoculated with
the microorganism and was kept at 300C for 14 days.
The solutions were first tested at the
concentration of 0.5 mmole/ml. The sets, which are
found active at this concentration, were again tested
at concentration of 0.25 mmole/ml. The groups,
which were found active, were subjected to serial
dilutions. The serial dilutions were made to obtain
concentrations 0.5, 0.25, 0.125, 0.0625,
0.0314,0.0152 and 0.0076 m mole/ml. Positive
control tubes (organism + broth + DMSO) and
negative control tubes (broth + drug) were also
prepared. Each tube was inoculated with the
microorganism.
(4-(1-(5-chloro-1H-benzo[d]imidazol-2-
yl)ethyl)piperazin-1-yl)(Phenyl) methanone (11k)
Compound (11k) was obtained as a white
solid (yield: 56%; MP:245-246; IR (KBr): 3209 (N-
H), 2358 (C-H), 1667(C=O),1611(C=N),