Ayhan-Kılcıgil et al.
Table 3: Continued
MS
Compd.
Formulas
M.P (ꢀC)
NMR
M + H (%)
8t
C25H21ClN4O3S-0.5HSCH2COOH-0.9H2O
159
178
3.76, 3.88 (2H, 2d, j = 14.40 Hz CH2-thiazolidine ring
C5), 3.81 (s, 3H, OCH3), 4.85 (2H, j = 17.20 Hz, AB
quartet, CH2), 5.76 (s, 1H, CH thiazolidine ring C2),
6.98–7.82 (m, 12H, Ar-H), 10.77 (s, 1H, NH)
3.80, 4.00 (2H, 2d, j = 16.0 Hz, CH2-thiazolidine ring
C5), 4.88 (2H, AB quartet, j = 18.8 Hz CH2), 6.02 (s,
1H, CH thiazolidine ring C2), 7.17–8.34 (m, 12H, Ar-H),
10.90 (s, 1H, NH)
3.73, 3.88 (2H, 2d, j = 16.0 Hz, CH2-thiazolidine ring
C5), 4.91 (2H, AB quartet, j = 20.4 Hz, CH2), 5.24 (s,
2H, OCH2-), 5.76 (s, 1H, CH thiazolidine ring C2),
6.98–7.70 (m, 19H, Ar-H)
3.77, 3.95 (2H, 2d, j = 15.6 Hz, CH2-thiazolidine ring
C5), 4.93 (2H, s, CH2), 5.96 (s, 1H, CH thiazolidine ring
C2), 7.20–7.74 (m, 11H, Ar-H), 10.87 (s, 1H, NH)
3.75, 3.98 (2H, 2d, j = 16.0 Hz CH2-thiazolidine ring C5),
4.89 (2H, s, CH2), 5.84 (s, 1H, CH thiazolidine ring C2),
7.22–7.86 (m, 11H, Ar-H), 10.84 (s, 1H, NH)
3.81, 3.97 (2H, 2d, j = 16.4 Hz CH2-thiazolidine ring C5),
4.93 (2H, AB quartet, j = 17.5 Hz , CH2), 6.19 (s, 1H,
CH thiazolidine ring C2), 7.18–8.25 (m, 11H, Ar-H),
11.04 (s, 1H, NH)
493 (78) 495 (22)
9t
C24H18ClN5O4S-1H2O
508 (73) 510 (27)
569 (64) 571 (36)
10t
C31H25ClN4O3S-0.6C2H5OH-1.5H2O
C24H17ClF2N4O2S-0.1H2O
220 decomp.
11t
12t
13t
307–310
128
499 (71) 501 (39)
559 (37) 561 (48) 563 (15)
542 (63) 544 (37)
C24H17BrClFN4O2S-0.5
HSCH2COOH-0.9C2H5OH
C24H17Cl2N5O4S-0.85HSCH2COOH
169
14t
15t
C24H17Cl3N4O2S-0.85H2O
297–299
287–289
3.77, 3.92 (2H, 2d, j = 15.6 Hz, CH2-thiazolidine ring
C5), 4.94 (2H, s, CH2), 6.06 (s, 1H, CH thiazolidine ring
C2), 7.19–7.74 (m, 11H, Ar-H), 10.96 (s, 1H, NH)
3.72–3.93 (m, 8H, OCH3, CH2-thiazolidine ring C5), 4.89
((2H, AB quartet, j = 16.0 Hz , CH2), 5.79 (s, 1H, CH
thiazolidine ring C2), 6.55–7.70 (m, 11H, Ar-H), 10.90
(s, 1H, NH)
531 (41) 533 (45) 535 (14)
523 (70) 525 (30)
C26H23ClN4O4S-0.9HSCH2COOH-1.3H2O
13C: 29.7, 46.2, 55.9, 62.0, 101.3, 105.9, 11.4, 119.8,
123.0, 123.4, 129.1, 129.5, 131.5, 135.4, 136.9, 141.4,
142.9, 152.9, 161.3, 166.9, 169.7
16t
17t
18t
C32H27ClN4O4S-0.3HSCH2COOH-0.45H2O
C32H27ClN4O4S-0.95HSCH2COOH
119
106–107
127
3.70–3.90 (m, 5H, OCH3,CH2-thiazolidine ring C5), 4.88
((2H, AB quartet, j = 17.2 Hz , CH2), 5.05 (s, 2H,
OCH2-), 5.81 (s, 1H, CH thiazolidine ring C2),
6.96–7.69 (m, 16H, Ar-H), 10.78 (s, 1H, NH)
3.71–3.88 (m, 5H, OCH3, CH2-thiazolidine ring C5), 4.84
((2H, AB quartet, j = 17.0 Hz, CH2), 5.11 (s, 2H,
OCH2-), 5.76 (s, 1H, CH thiazolidine ring C2),
6.87–7.67 (m, 16H, Ar-H), 10.75 (s, 1H, NH)
3.74, 3.86 (2H, 2d, j = 15.6 Hz CH2-thiazolidine ring C5),
4.86 (2H, AB quartet, j = 17.6 Hz, CH2), 5.06 (s, 2H,
OCH2-), 5.18 (s, 2H, OCH2-), 5.78 (s, 1H, CH
thiazolidine ring C2), 6.94–7.70 (m, 21H, Ar-H), 10.87
(s, 1H, NH)
599 (68) 601 (32)
599 (69) 601 (31)
675 (66) 677 (34)
C38H31ClN4O4S-0.25
HSCH2COOH-1.4H2O
compounds. A dose response curve was plotted to determine the IC50
values. IC50 is defined as the concentration sufficient to obtain 50%
of a maximum scavenging capacity. All tests and analyses were run in
triplicate and averaged. The standard used in this assay was BHT.
via oxidative condensation of o-phenylenediamine, p-chlorobenzalde-
hyde, and sodium metabisulfite. Treatment of compound A with
ethyl chloroacetate in KOH ⁄ DMSO gave the N-alkylated product B.
Hydrazine hydrate and the ester B in ethanol were refluxed for 4 h
to give the desired hydrazide compound, (2-(p-chlorophenyl)-benz-
imidazole-1-yl)-acetic acid hydrazide C. Compounds 1–18 were
obtained by condensing acyl hydrazide C with the corresponding
aldehyde derivatives in the presence of catalytic amounts of ceric
ammonium nitrate (CAN) in ethanol (36) Condensation of 1–18 with
thioglycolic acid in toluene yielded 2-[2-(4-chlorophenyl) benzimid-
azole-1-yl]-N-(4-oxo-2-aryl-thiazolidine-3-yl) acetamides (1t–18t).
Results and Discussion
Chemistry
The desired benzimidazole derivatives were synthesized according
to Scheme 1. Compound A having benzimidazole ring was prepared
874
Chem Biol Drug Des 2012; 79: 869–877