S. K. Murari et al. / Bioorg. Med. Chem. Lett. 14 (2004) 2423–2425
2425
12. Dey, B. B.; Sitaraman, M. V. Laboratory Manual of
Organic Chemistry, 3rd ed.; 1957; p 145.
at 3 mM concentration. Compounds 4c and 4d were not
much effective compared to 4a and 4b in both in vivo
anti-inflammatory activity and in vitro PLA2 enzyme
inhibition.
13. 3a: mp 149–150 ꢁC (lit. mp 150–151 ꢁC); IR (Nujol):
1600 cmꢀ1 (aromatic C@C), 1640 (C@O), 1660 (C@N)
1
cmꢀ1; H NMR (CDCl3): d 3.73 (s, 6H, 2OCH3), 6.9–7.9
(m, 8H, Ar-H). Anal. Calcd for C17H17NO3 (283): C,
72.08; H, 6.01; N, 4.95. Found: C, 72.06; H, 6.04; N, 4.93.
3b: mp 165–166 ꢁC; (lit. mp 150–151 ꢁC); IR (Nujol):
1608 cmꢀ1 (aromatic C@C), 1652 (C@O), 1662 (C@N)
cmꢀ1; 1H NMR (CDCl3): d 2.35 (s, 3H, 2CH3), 7.0–7.9 (m,
8H, Ar-H). Anal. Calcd for C17H17NO3 (283): C, 72.08; H,
6.01; N, 4.95. Found: C, 72.06; H, 6.04; N, 4.93.
The synthetic route of compounds 3a–e and 4a–e is as
depicted in Scheme 1. Intermolecular Fridel Crafts
reaction of substituted hydrocarbons with substituted
aromatic acids in the presence of PPA (polyphosphoric
acid) as catalyst afforded compounds 3a–e.11 Conden-
sation of 3a–e with hydroxylamine hydrochloride gave
corresponding oximes 4a–e in excellent yield.12 The IR
3c: mp 155–160 ꢁC (lit. mp 150–151 ꢁC); IR (Nujol):
1600 cmꢀ1 (aromatic C@C), 1640 (C@O), 1663 (C@N)
cmꢀ1; 1H NMR (CDCl3): d 3.73 (s, 6H, 2OCH3), 6.9–7.65
(m, 8H, Ar-H). Anal. Calcd for C17H17NO3 (283): C,
72.08; H, 6.01; N, 4.95. Found: C, 72.06; H, 6.04; N, 4.93.
3d: mp 145–150 ꢁC (lit. mp 150–151 ꢁC); IR (Nujol):
1600 cmꢀ1 (aromatic C@C), 1642 (C@O), 1660 (C@N)
1
and H NMR data of compounds 3a–e and 4a–e are in
complete agreement.13;14
1
cmꢀ1; H NMR (CDCl3): d 3.73 (s, 6H, 2OCH3), 6.9–7.9
Acknowledgements
(m, 8H, Ar-H). Anal. Calcd for C17H17NO3 (283): C,
72.08; H, 6.01; N, 4.95. Found: C, 72.06; H, 6.04; N, 4.93.
3e: mp 165–170 ꢁC (lit. mp 150–151 ꢁC); IR (Nujol):
1600 cmꢀ1 (aromatic C@C), 1640 (C@O), 1660 (C@N)
Department of Science and Technology, Government of
India, New Delhi supports this research. S.K.M. and
S.N.S. thank Council of Scientific and Industrial
Research, Government of India, New Delhi for Senior
Research Fellowship.
cmꢀ1 1H NMR (CDCl3): d 2.73 (s, H, 2OCH3), 6.9–7.9
;
(m, 8H, Ar-H). Anal. Calcd for C17H17NO3 (283): C,
72.08; H, 6.01; N, 4.95. Found: C, 72.06; H, 6.04; N, 4.93.
14. 4a: mp 149–150 ꢁC (lit. mp 150–151 ꢁC); IR (Nujol):
1600 cmꢀ1 (aromatic C@C), 1650 (–N–OH), 1660 (C@N)
1
cmꢀ1; H NMR (CDCl3): d 3.73 (s, 6H, 2OCH3), 6.9–7.9
References and notes
(m, 8H, Ar-H). Anal. Calcd for C17H17NO3 (283): C,
72.08; H, 6.01; N, 4.95. Found: C, 72.06; H, 6.04; N, 4.93.
4b: mp 165–166 ꢁC; (lit. mp 150–151 ꢁC); IR (Nujol):
1608 cmꢀ1 (aromatic C@C), 1652 (–N–OH), 1662 (C@N)
cmꢀ1; 1H NMR (CDCl3): d 2.35 (s, 3H, 2CH3), 7.0–7.9 (m,
8H, Ar-H). Anal. Calcd for C17H17NO3 (283): C, 72.08; H,
6.01; N, 4.95. Found: C, 72.06; H, 6.04; N, 4.93.
1. Dennis, D. A. Trends Biochem. Sci. 1997, 22, 1.
2. Fox, N.; Song, M.; Schermenti, J.; Sharp, J. D.; White, D.
L.; Snyder, D. W.; Hartley, L. W.; Carlson, D. G.; Bach,
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4. Glaser, K. B. Adv. Pharmacol. 1995, 32, 31.
5. Mayer, R. J.; Marshall, L. A. FASEB J. 1993, 7, 339.
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Inflammation 1988, 12, 549.
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1991, 146, 3904.
8. Albert, P.; Juan, P. J.; Susana, N.; Oriol, L. L. J. Med.
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9. Yamakawa, M.; Nozaki, M.; Hokoma, Z. In Animal,
Plant and Microbial Toxins; Ohsaka, A., Ed.; Plenum:
New York, 1976; Vol. 1, pp 97–118.
10. Vishwanath, B. S.; Frey, F. J.; Bradbury, M. J.; Dallman,
M. F.; Frey, B. M. J. Clin. Invest. 1993, 92, 1974.
11. Shargi, H.; Shagi, E. Bull. Chem. Soc. Jpn. 1993, 66, 135.
4c: mp 155–160 ꢁC (lit. mp 150–151 ꢁC); IR (Nujol):
1600 cmꢀ1 (aromatic C@C), 1650 (–N–OH), 1663 (C@N)
cmꢀ1; 1H NMR (CDCl3): d 3.73 (s, 6H, 2OCH3), 6.9–7.65
(m, 8H, Ar-H). Anal. Calcd for C17H17NO3 (283): C,
72.08; H, 6.01; N, 4.95. Found: C, 72.06; H, 6.04; N, 4.93.
4d: mp 145–150 ꢁC (lit. mp 150–151 ꢁC); IR (Nujol):
1600 cmꢀ1 (aromatic C@C), 1650 (–N–OH), 1660 (C@N)
1
cmꢀ1; H NMR (CDCl3): d 3.73 (s, 6H, 2OCH3), 6.9–7.9
(m, 8H, Ar-H). Anal. Calcd for C17H17NO3 (283): C,
72.08; H, 6.01; N, 4.95. Found: C, 72.06; H, 6.04; N, 4.93.
4e: mp 165–170 ꢁC (lit. mp 150–151 ꢁC); IR (Nujol):
1600 cmꢀ1 (aromatic C@C), 1650 (–N–OH), 1660 (C@N)
cmꢀ1 1H NMR (CDCl3): d 2.73 (s, H, 2OCH3), 6.9–7.9
;
(m, 8H, Ar-H). Anal. Calcd for C17H17NO3 (283): C,
72.08; H, 6.01; N, 4.95. Found: C, 72.06; H, 6.04; N, 4.93.