3512
T. D. Venu et al. / Bioorg. Med. Chem. 15 (2007) 3505–3514
C13H7Cl3O2: C, 51.78; H, 2.34; Cl, 35.27. Found: C,
51.77; H, 2.33; Cl, 35.26.
Compound 4g: Yield 79%, mp 122–124 ꢁC; IR (Nujol)
1
m (cmꢀ1): 1662 (C@O), 1743 (ester, C@O); H NMR
(CDCl3) d: 7.37–8.08 (m, 11H, Ar-H); EI-MS: m/z
(86%) M+ 405.5. Anal. Calcd for C20H11Cl3O3: C,
59.22; H, 2.73; Cl, 26.22. Found: C, 59.20; H, 2.71; F,
26.20.
Compound 2j: Yield 90%, mp 71–73 ꢁC; IR (Nujol)
m (cmꢀ1): 1665 (C@O), 3515–3645 (OH); 1H NMR
(CDCl3) d: 2.25–2.3 (2s, 6H, 2CH3), 6.9–7.7 (m, 7H,
Ar-H), 12.05 (br s, 1H, OH); EI-MS: m/z (83%) M+
226. Anal. Calcd for C15H14O2: C, 79.64; H, 6.19.
Found: C, 79.62; H, 6.18.
Compound 4h: Yield 72%, mp 114–116 ꢁC; IR (Nujol)
1
m (cmꢀ1): 1663 (C@O), 1745 (ester, C@O); H NMR
(CDCl3) d: 2.35 (s, 3H, CH3), 7.16–8.08 (m, 11H, Ar-
H); EI-MS: m/z (86%) M+ 368. Anal. Calcd for
C21H14ClFO3: C, 68.39; H, 3.83; Cl, 9.61; F, 5.15.
Found: C, 68.38; H, 3.82; Cl, 9.60; F, 5.14.
4.3. 2-(4-Methylbenzoyloxy-5-methylphenyl)phenyl
methanone (4a)
To a well-stirred ice-cold solution of 2a (3 g, 0.014 mol)
in 10% sodium hydroxide (20 mL), 4-methylbenzoyl
chloride (3a, 1.96 g, 0.014 mol) was added dropwise
and stirring was continued for about 15 min. The mix-
ture was made alkaline by adding 10% sodium hydrox-
ide. A white solid was separated, which was filtered,
washed with water and on recrystallization with alcohol
gave 4a.
Compound 4i: Yield 75%, mp 89–91 ꢁC; IR (Nujol):
1670 cmꢀ1 (C@O1760), (ester, C@O); 1H NMR (CDCl3)
d: 2.2 (s, 3H, CH3), 6.9–7.7 (m, 13H, Ar-H); MS: m/z
(76%) M+ 316. Anal. Calcd for C21H16O3: C, 79.73; H,
5.10. Found: C, 79.75; H, 5.12%.
Compound 4j: Yield 78%, mp 95–97 ꢁC; IR (Nujol)
1
m (cmꢀ1): 1675 (C@O), 1760 (ester, C@O); H NMR
Compound 4a: Yield 85%, mp 88–90 ꢁC; IR (Nujol)
(CDCl3) d: 2.35 (s, 3H, CH3), 7.13–8.14 (m, 12H, Ar-
H); EI-MS: m/z (81%) M+ 350. Anal. Calcd for
C21H15ClO3: C, 71.90; H, 4.31; Cl, 10.11. Found: C,
72.93; H, 4.30; Cl, 10.13.
1
m (cmꢀ1): 1670 (C@O), 1760 (ester, C@O); H NMR
(CDCl3) d: 2.2–2.3 (2s, 6H, 2CH3), 7.13–8.02 (m, 12H,
Ar-H); EI-MS: m/z (87%) M+ 330. Anal. Calcd
for C22H18O3: C, 79.98; H, 5.49. Found: C, 79.97; H,
5.47.
Compound 4k: Yield 72%, mp 126–128 ꢁC; IR (Nujol):
1665 cmꢀ1 (C@O), 1750 (ester, C@O); 1H NMR
(CDCl3) d: 7.14–8.08 (m, 11H, Ar-H); MS: m/z (77%)
M+ 449. Anal. Calcd for C20H11Br Cl2O3: C, 53.37; H,
2.46; Br, 17.75; Cl, 15.75. Found: C, 53.40; H, 2.44;
Br, 17.73; Cl, 15.77.
Compound 4b: Yield 88%, mp 97–99 ꢁC; IR (Nujol)
m
(cmꢀ1): 1668 (C@O), 1750 (ester, C@O); 1H
NMR (CDCl3) d: 2.3–2.5 (3s, 9H, 3CH3), 6.8–7.6
(m, 11H, Ar-H); EI-MS: m/z (87%) M+ 334. Anal.
Calcd for C23H20O3: C, 80.21; H, 5.85. Found: C,
80.20; H, 5.7.
Compound 4l: Yield 77%, mp 90–92 ꢁC; IR (Nujol)
1
m (cmꢀ1): 1660 (C@O), 1740 (ester, C@O); H NMR
Compound 4c: Yield 81%, mp 101–103 ꢁC; IR (Nujol)
(CDCl3) d: 6.9–7.65 (m, 11H, Ar-H); EI-MS: m/z
(86%) M+ 405.5. Anal. Calcd for C20H11Cl3O3: C,
59.22; H, 2.73; Cl, 26.22. Found: C, 59.23; H, 2.74; F,
26.23.
1
m (cmꢀ1): 1670 (C@O), 1755 (ester, C@O); H NMR
(CDCl3) d: 2.3–2.4 (3s, 9H, 3CH3), 6.75–7.7 (m, 11H,
Ar-H); EI-MS: m/z (87%) M+ 364. Anal. Calcd for
C22H17ClO3: C, 72.43; H, 4.70; Cl, 9.75. Found: C,
72.45; H, 4.71; Cl, 9.73.
Compound 4m: Yield 77%, mp 93–95 ꢁC; IR (Nujol):
1670 cmꢀ1 (C@O), 1755 (ester, C@O); 1H NMR
(CDCl3) d: 2.3 (s, 3H, CH3), 6.75–7.7 (m, 11H, Ar-H);
MS: m/z (77%) M+ 385. Anal. Calcd for C21H14
Cl2O3: C, 65.47; H, 3.66; Cl, 18.41. Found: C, 65.45;
H, 3.65; Cl, 18.40%.
Compound 4d: Yield 78%, mp 138–140 ꢁC; IR (Nujol)
1
m (cmꢀ1): 1665 (C@O), 1737 (ester, C@O); H NMR
(CDCl3) d: 2.3 (s, 3H, CH3), 7.19–8.02 (m, 11H, Ar-
H); EI-MS: m/z (87%) M+ 385. Anal. Calcd for
C21H14Cl2O3: C, 65.47; H, 3.66; Cl, 18.41. Found: C,
65.46; H, 3.65; Cl, 18.40.
Compound 4n: Yield 79%, mp 96–98 ꢁC; IR (Nujol):
1655 cmꢀ1 (C@O), 1735 (ester, C@O); 1H NMR
(CDCl3) d: 2.3–2.5 (3s, 9H, 3CH3), 6.92–7.7 (m,
11H, Ar-H); MS: m/z (74%) M+ 344. Anal. Calcd
for C23H20O3: C, 80.21; H, 5.85. Found: C, 80.22;
H, 5.84%.
Compound 4e: Yield 81%, mp 90–92 ꢁC; IR (Nujol)
1
m (cmꢀ1): 1665 (C@O), 1760 (ester, C@O); H NMR
(CDCl3) d: 2.3–2.4 (2s, 6H, 2CH3), 7.16–8.02 (m, 11H,
Ar-H); EI-MS: m/z (86%) M+ 348. Anal. Calcd for
C22H17FO3: C, 75.85; H, 4.92; F, 5.45. Found: C,
75.84; H, 4.91; F, 5.44.
4.4. Pharmacological evaluation
Compound 4f: Yield 74%, mp 65–67 ꢁC; IR (Nujol)
4.4.1. Anti-inflammatory activity. Adopting Winter
et al.’s19 method and using Albino rats paw oedema
inhibition test was performed on compounds 4a–n. To
groups of five rats (body weight 125–160 g), a dose of
test compounds 4a–n was given. After 30 min, 0.2 mL
of 1% carrageenan suspension in 0.9% sodium chloride
1
m (cmꢀ1): 1672 (C@O), 1765 (ester, C@O); H NMR
(CDCl3) d: 2.3 (s, 3H, CH3), 7.13–8.14 (m, 12H, Ar-
H); EI-MS: m/z (86%) M+ 334. Anal. Calcd for
C22H15FO3: C, 75.44; H, 4.52; F, 5.68. Found: C,
75.43; H, 4.51; F, 5.67.