One pot synthesis of pyrimidine and bispyrimidine derivatives and their evaluation for anti-inflammatory and analgesic activities

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 10, 2007, Pages 3334-3344

  Sondhi, Sham M ^a   Jain, Shubhi ^a   Dinodia, Monica ^a   Shukla, Rakesh ^b   Raghubir, Ram ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY ROORKEE   (India)

^b CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Analgesic; Anti inflammatory; Bispyrimidine; Ketoisothiocynate; Pyrimidine

Indexed keywords

1 (FURAN 2 YLMETHYL) 4,4,6 TRIMETHYL 3,4 DIHYDROPYRIMIDINE 2(1H) THIONE; 1 [3 (1H IMIDAZOL 1 YL)PROPYL] 4,4,6 TRIMETHYL 3,4 DIHYDROPYRIMIDINE 2(1H) THIONE; 1 [3 (1H IMIDAZOL 1 YL)PROPYL] 6 HYDROXY 4,4,6 TRIMETHYLTETRAHYDROPYRIMIDINE 2(1H) THIONE; 1 [3 (4,4,6 TRIMETHYL 2 THIOXO 3,4 DIHYDROPYRIMIDINE 1(2H) PROPYL)PYRROLIDIN] 2 ONE; 1 [3 (6 HYDROXY 4 METHYL 2 THIOXOTETRAHYDROPYRIMIDIN 1(2H) YLPROPYL)PYRROLIDIN] 2 ONE; 1 [3 (6 HYDROXY 4,4,6 TRIMETHYL 2 THIOXOTETRAHYDROPYRIMIDIN 1(2H) YLPROPYL)PYRROLIDIN] 2 ONE; 1 [3 [9 [3 (4 HYDROXO 6 METHYLTETRAHYDROPYRIMIDINE 2(1H) THION 3 YL)PROPYL] 2,4,8,10 TETRAOXASPIRO[5.5]UNDECAN 3 YL]PROPYL] 6 HYDROXO 4 METHYLTETRAHYDROPYRIMIDINE 2(1H) THIONE; 1 [3 [9 [3 (4,6,6 TRIMETHYLDIHYDROPYRIMIDINE 2(1H) THION 4 EN 3 YL)PROPYL] 2,4,8,10 TETRAOXASPIRO[5.5]UNDECAN 3 YL]PROPYL] 4,4,6 TRIMETHYLDIHYDROPYRIMIDINE 2(1H) THIONE; 2 (4,6,6 TRIMETHYL 2 THIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL)BENZONITRILE; 3 (FURAN 2 YLMETHYL) 4 HYDROXY 4,6,6 TRIMETHYLTETRAHYDROPYRIMIDINE 2(1H) THIONE; 4 HYDROXO 3 [3 [4 [3 (6 HYDROXY 4 METHYL 2 THIOXOTETRAHYDROPYRIMIDIN 1(2H) YL)PROPYL]PIPERAZIN 1 YL]PROPYL] 6 METHYLTETRAHYDROPYRIMIDINE 2(1H) THIONE; 4 HYDROXO 3 [3 [4 [3 (6 HYDROXY 4,4,6 TRIMETHYL 2 THIOXOTETRAHYDROPYRIMIDIN 1(2H) YL)PROPYL]PIPERAZIN 1 YL]PROPYL] 4,6,6 TRIMETHYLTETRAHYDROPYRIMIDINE 2(1H) THIONE; 4 HYDROXY 6 METHYL 3 (PYRIDIN 2 YLAMINO)PYRIMIDINE 2(1H) THIONE; 4,4,6 TRIMETHYL 1 [5 (4,4,6 TRIMETHYL 2 THIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL) 2H 1,2,4 TRIAZOL 3 YL] 3,4 DIHYDROPYRIMIDINE 2(1H) THIONE; 6 HYDROXY 1 [2 (1H IMIDAZOL 4 YL)ETHYL] 4 HYDROXY 4,6,6 TRIMETHYLTETRAHYDROPYRIMIDINE 2 THIONE; ANALGESIC AGENT; ANTIINFLAMMATORY AGENT; BISPYRIMIDINE DERIVATIVE; IBUPROFEN; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CHEMICAL ANALYSIS; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DOSE COMPARISON; DRUG SYNTHESIS; FEMALE; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MOUSE; NONHUMAN; ONE POT SYNTHESIS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; RAT;

ANALGESICS, NON-NARCOTIC; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BENZOQUINONES; CARRAGEENAN; DOSE-RESPONSE RELATIONSHIP, DRUG; EDEMA; FEMALE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; PAIN MEASUREMENT; PYRIMIDINES; RATS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 34047132283     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.03.028     Document Type: Article

References (29)

1. Hill, M. R.; Holland, S. J.; Pearson, S. L.; Yeates, K. T. PCT Int. Appl. WO 2004048344 Chem. Abstr. 2004, 141, 38626.
2. Carter, M. C.; Naylor, A.; Payne, J. J.; Pegg, N. A. PCT Int. Appl. WO 2003014091 Chem. Abstr. 2003, 138, 187783.
3. Agarwal, S. K.; Tadiparthi, R.; Aggarwal, P; Shivakumar, S. PCT Int. Appl. WO 2003084936, Chem. Abstr. 2003, 139, 323529.
4. Bahekar S.S., and Shinde D.B. Bioorg. Med. Chem. Lett. 14 (2004) 1733
5. Liu, L.; Lopez, P.; Bajpai, M.; Siegmund, A. C. U.S. Pat. Appl. Publ. US 2004-923067 Chem. Abstr. 2005, 142, 261550.
6. Clare, M.; Hagen, T. J.; Houdek, S. C.; Lennon, P. J.; Weier, R. M.; Xu, X., PCT Int. Appl. WO 2005040133 Chem. Abstr. 2005, 142, 463736.
7. Eatherton, A. J.; Giblin, G. M. P.; Mitchell, W. L.; Naylor, A.; Rawlings, D. A.; Wall, I. D. PCT Int. Appl. WO 2005075440 Chem. Abstr. 2005, 143, 211924.
8. Gangjee A., Jain H.D., Phan J., Lin X., Song X., McGuire J.J., and Kisliuk R.L. J. Med. Chem. 49 (2006) 1055
9. Alam O., Imran M., and Khan S.A. Indian J. Heterocycl. Chem. 14 (2005) 293
10. Hazarika J., and Kataky J.C.S. Indian J. Chem., Sect B 40B (2001) 255
11. Buurman E.T., Blodgett A.E., Hull K.G., and Carcanague D. Antimicrob. Agents Chemother. 48 (2004) 313
12. Kidwai M., Saxena S., Rastogi S., and Venkataramanan R. Curr. Med. Chem.: Anti-Infect. Agents 2 (2003) 269
13. Sondhi S.M., Singhal N., Verma R.P., Raghubir R., Goel A.K., and Patnaik G.K. Indian J. Chem., Sect B 36B (1997) 620
14. Sondhi S.M., Sharma V.K., Singhal N., Verma R.P., Shukla R., Raghubir R., and Dubey M.P. Phosphorus, Sulfur Silicon Relat. Elem. 156 (2000) 21
15. Sondhi S.M., Johar M., Singhal N., Dastidar S.G., Shukla R., and Raghubir R. Monatshefte fuer Chemie 131 (2000) 511
16. Sondhi S.M., Johar M., Singh N., Shukla R., Raghubir R., and Dastidar S.G. Indian J. Chem., Sect B 41B (2002) 2659
17. Sondhi S.M., Bhattacharjee G., Jameel R.K., Shukla R., Lozach O., and Meijer L. Cent. Eur. J. Chem. 2 (2004) 1
18. Sondhi S.M., Bhattacharjee G., Jameel R.K., Kumar A., and Bajaj K. Indian J. Chem., Sect A 44A (2005) 232
19. Sondhi S.M., Singh N., Lahoti A.M., Bajaj K., Kumar A., Lozach O., and Meijer L. Bioorg. Med. Chem. 13 (2005) 4291
20. Sondhi S.M., Verma R.P., Singhal N., Shukla R., Raghubir R., and Dubey M.P. Indian Drugs 36 (1999) 50
21. Sondhi S.M., Singhal N., Johar M., Reddy B.S.N., and Lown J.W. Curr. Med. Chem. 9 (2002) 1045
22. Sondhi S.M., Rajvanshi S., Singh N., Jain S., and Lahoti A.M. Cent. Eur. J. Chem. 2 (2004) 141
23. Sondhi, S.M.; Dinodia, M.; Singh, J.; Rani, R., Curr. Bioactive Compounds, in press.
24. Mathes R.A., Stewart F.D., and Frank Jr. S. J. Am. Chem. Soc. 70 (1948) 1452
25. Peretokin A.V., Shutalev A.D., Chupin V.V., Mergenova A.M., Ignatova L.A., Malina Y.F., and Unkovskii B.V. Zhurnal Organicheskoi Khimii 21 (1985) 1004
26. Chem. Abstr. 104 (1986) 108981
27. Winter C.A., Risley E.A., and Nuss G.W. Proc. Soc. Exp. Biol. Med. 111 (1962) 544
28. Singh P.P., Junnarkar A.V., Seshagiri Rao C., Verma R.K., and Shridhar D.R. Methods Find. Exp. Clin. Pharmacol. 5 (1983) 601
29. 1H FT NMR spectra, 1993, 3, 81B.