4584
A. K. Tiwari et al. / Bioorg. Med. Chem. Lett. 16 (2006) 4581–4585
and Benzoin (0.03 mol) in polyphosphoric acid (10 ml)
was heated at 100 ꢀC on oil bath for 5 h. The crude com-
pound was obtained by separating solvent at reduced
pressure and purified by column chromatography.
Calcd for C29H20N3O2Cl C 72.90, H 4.19, N 8.39,
O 6.70, Cl 7.43. Found: m/z [M+1] 478.5.
Compound 4(E): mp 220 ꢀC, IR (KBr pellets, cmꢀ1
)
1
1367, 3474, 1680, 1658. H NMR (200 MHz, CDCl3) d
ppm; 7.1–7.7 (m, 17H, –ArH), 6.03 (s, 1H, –NH). Anal.
Calcd for C29H21N3O2 C 78.60, H 4.24, N 9.48, O 7.22.
Found: m/z [M+1] 444.
Synthesis of N-Aryl-8,9-diphenyl-2-oxo-pyrido-[g]-4-ar-
yl-2-oxo-1,3-dihydro-quinazolones (D). A mixture of
compound C (0.01 mol) and para substituted Aniline
(0.02 mol) in anhydrous pyridine (30 ml) refluxed for
6 h. The solution was cooled to room temperature and
acidified with diluted HCl (50 ml). A solid separated
out which was filtered off and washed with water succes-
sively. It was dried at 100 ꢀC and recrystallized from gla-
cial acetic acid.
Various tricyclic pyrido-quinazolone derivatives have
been synthesized and evaluated for anti-fungal, antibac-
terial and anticancer analgesic activities. Similarly,
radiolabeling and biodistribution studies have confirmed
the respective receptor binding. These compounds have
shown promising results for future application.
Compound 2(X): mp 249 ꢀC, IR (KBr pellets, cmꢀ1
)
1
3032, 1665, 3465, 815. H NMR (200 MHz, CDCl3) d
ppm; 4.12 (d, 2H, CH2), 6.13 (s, 1H, –NH), 6.01 (t,
1H, –NH), 7.1–7.4 (m, 8H, ArH). Anal. Calcd for
C9H8N2O3 C 56.25, H 4.17, N 14.58, O 25.01. Found:
m/z [M+1] 193.
Acknowledgment
We thank Dr. R. P. Tripathi, director, INMAS, for pro-
viding all the facilities and his deep interest and constant
encouragement during the course of the studies.
Compound 2(Y): mp 284 ꢀC, IR (KBr pellets, cmꢀ1
)
1
3045, 1672, 865, 840. H NMR (200 MHz, CDCl3) d
ppm; 4.07 (d, 2H, CH2), 6.31 (s, 1H, –NH), 7.1–7.6
(m, 8H, ArH). Anal. Calcd for C15H12N2O3 C 60.23,
H 4.72, N 10.45, O 23.79. Found: m/z [M+1] 269.
Supplementary data
Supplementary data associated with this article can be
Compound 3(U): mp 136 ꢀC, IR (KBr pellets, 1742,
3036, 1125, 1670). 1H NMR (200 MHz, CDCl3) d
ppm; 6.0 (d, 1H, –CH), 6.11 (s, 1H, –NH), 6.29 (d,
1H, –NH), 7.09–7.90 (m, 17H, ArH). Anal. Calcd for
C23H16N2O3; C 72.21, H 4.51, N 7.31, O 14.32. Found:
m/z [M+1] 339.
References and notes
1. Kamed, K.; Ono, S.; Kayama, J.; Abiko, Y. Acta
Endocrinol. 1982, 99, 410.
2. Knaus, E. E.; Corleto, L. A.; Redda, S. Canadian Patent
1, 20 Mar 1982; 120; Chem. Abstr. 37, 1982, 37, 38859c.
3. Palameta, B.; Bogri, T.; Bagh, J. US Patent, 4,382,088, 03
Mar 1983; Chem. Abstr., 1983, 99, 282091.
4. Kossayama, M.; Ischikawa, F.; Watanable, Y.; Abiko, Y.;
Kameda, K. Ger. Often, 2, Jan 5 1976, 728; Chem.
Abstr.,1978, 89, 676.
5. Pathak, S. R.; Ph.D. Thesis, Lucknow University, Luc-
know, 1999, p. 15.
6. Pandey, V. K.; Jindal, S. Indian Drugs 1995, 32, 317.
7. Shukla, A. Ph.D. Thesis, Lucknow University, Lucknow,
2000, p. 236.
8. Katz, A. M.; Hager, W. D.; Messinco, F. C.; Pappano, A.
J. Am. J. Med. 1985, 79(Suppl. 4A), 2.
9. Swartz, A. J. Mol. Cell. Cardiol. 1987, 19(Suppl. 11), 49.
10. Mannschreck, A.; Koller, H.; Stunier, G.; Davies, M. A.;
Traber, J. Eur. J. Med. Chem. 1984, 19, 381.
11. Sharma, S. D.; Kaur, V. Synthesis 1989, 677.
12. Molamas, M. S.; Miller, J. J. Med. Chem. 1991, 34, 1492.
13. Baker, B. R.; Kochler, R.; Goodman, L.; Graw, J. D. J. Am.
Chem. Soc. 1958, 80, 5779; . Chem. Abstr. 1961, 26, 1156.
14. Hynes, J. B.; Buck, J. M.; D’Souza, L.; Freisheim, J. H.
J. Med. Chem. 1975, 18, 1191.
Compound 3(V): mp 145 ꢀC, IR (KBr pellets, 1740,
3032, 1125, 1665, 3465). H NMR (200 MHz, CDCl3)
1
d ppm; 4.40 (d, 2H, –CH2), 6.14 (s, 1H, –NH), 6.3 (d,
1H, NH), 7.10–7.9 (m, 11H, ArH). Anal. Calcd for
C29H20N2O3; C 77.32, H 4.11, N 5.99, O 11.21. Found:
m/z [M+1] 415.
Compound 4(A): mp 128 ꢀC, IR (KBr pellets, cmꢀ1
)
3470, 1565, 1695, 1640, 3020. 1H NMR (200 MHz,
CDCl3) d ppm; 6.1–7.2 (m, 22H, –ArH), 8.36 (s, 1H,
–NH). Anal. Calcd for C35H25N3O2 C 80.92, H 4.80,
N 8.09, O 6.17. Found: m/z [M+1] 520.
Compound 4(B): mp 140 ꢀC, IR (KBr pellets, cmꢀ1
)
1
1568, 1640, 3022. H NMR (200 MHz, CDCl3) d ppm;
7.0–8.4 (m, 21H, –ArH), 4.02 (s, 1H, –NH). Anal. Calcd
for C35H24N3O2Cl C 75.88, 1n, H 4.34, N 75.68, O 5.78,
Cl 6.41. Found: m/z [M+1] 354.5.
Compound 4(C): mp 170 ꢀC, IR (KBr pellets, cmꢀ1
)
1
1360, 3470, 3020. H NMR (200 MHz, CDCl3) d ppm;
6.9–7.9 (m, 21H, –ArH), 3.70 (s, 3H, OCH3). Anal.
Calcd for C36H27N3O3C 78.69, H 4.12, N 8.79, O 8.74.
Found: m/z [M+1] 550.
15. Hynes, J. B.; Easen, D. E.; Garreti, C. M.; Shares, K. E.;
Friesheim, J. H. J. Med. Chem. 1971, 20, 588.
16. Carroll, F. I.; Berrang, B.; Linn, C. P. Chem. Ind.
(London). 1975, 477.
17. Johns, D. G.; Capizzi, R. L.; Nahas, A.; Cashmore, A. R.;
Bertiono, J. R. Biochem. Pharmacol. 1970, 19, 1528.
18. Hutchison, D. J. Cancer Chemother. Rep. 1968, 52, 697.
Compound 4(D): mp 194 ꢀC, IR (KBr pellets, cmꢀ1
)
1
2930, 1660, 3465, 1635. H NMR (200 MHz, CDCl3) d
ppm; 7.1–7.8 (m, 16H, –ArH), 4.38 (d, 2H, –CH2). Anal.