Synthesis and in vitro inhibitory potential towards urease of 9-anilinoacridines and aciridinyl hydrazides

Letters in Drug Design and Discovery

Volumn 4, Issue 2, 2007, Pages 114-121

  Khan, Khalid Mohammed ^a   Rao, Nosheen Akbar ^a   Lodhi, M Arif ^a   Perveen, Shahnaz ^b   Choudhary, M Iqbal ^a   Voelter, Wolfgang ^c  

^a UNIVERSITY OF KARACHI   (Pakistan)

^b PCSIR LABORATORIES COMPLEX   (Pakistan)

^c UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

9 anilinoacridines; Acridinyl hydrazides; Urease inhibition

Indexed keywords

3,4 DIMETHYL 9 (2 METHOXY 4 NITRO)ANILINOACRIDINE; 3,4 DIMETHYL 9 (2' METHOXY 5' NITRO)ANILINOACRIDINE; 3,4 DIMETHYL 9 (2',3' DIMETHYL)ANILINOACRIDINE; 3,4 DIMETHYL 9 (2',4' DICHLORO)ANILINOACRIDINE; 3,4 DIMETHYL 9 (2',4' DIMETHYL)ANILINOACRIDINE; 3,4 DIMETHYL 9 (2',5' DIMETHYL)ANILINOACRIDINE; 3,4 DIMETHYL 9 (2',6' DICHLORO)ANILINOACRIDINE; 3,4 DIMETHYL 9 (3' METHOXY 4' METHYL)ANILINOACRIDINE; 3,4 DIMETHYL 9 (3',4' DICHLORO)ANILINOACRIDINE; 3,4 DIMETHYL 9 (3',4' DIMETHYL)ANILINOACRIDINE; 3,4 DIMETHYL 9 (3',5' DIMETHYL)ANILINOACRIDINE; 3,4 DIMETHYL 9 (4' NITRO)ANILINOACRIDINE; 3,4 DIMETHYL 9 (6 METHYL 2 NITRO)ANILINOACRIDINE; 3,4 DIMETHYL 9 ANILINOACRIDINE; 4 DIMETHYL 9 PYRIMIDINOACRIDINE; 9 ANILINOACRIDINE DERIVATIVE; ACRIDINYLHYDRAZIDE DERIVATIVE; HYDRAZIDE DERIVATIVE; N (3,4 DIMETHYL 9 ACRIDINYL) 2 METHYLBENZOHYDRAZIDE; N (3,4 DIMETHYL 9 ACRIDINYL) 3 METHYLBENZOHYDRAZIDE; N (3,4 DIMETHYL 9 ACRIDINYL) 4 HYDROXYBENZOHYDRAZIDE; N (3,4 DIMETHYL 9 ACRIDINYL) 4 METHYLBENZENESULFONOHYDRAZIDE; N (3,4 DIMETHYL 9 ACRIDINYL)ACRYLOHYDRAZIDE; N (3,4 DIMETHYL 9 ACRIDINYL)BUTANOHYDRAZIDE; N (3,4 DIMETHYL 9 ACRIDINYL)ETHANOHYDRAZIDE; N (3,4 DIMETHYL 9 ACRIDINYL)NICOTINOHYDRAZIDE; N (3,4 DIMETHYL 9 ACRIDINYL)PROPANOHYDRAZIDE; THIOUREA; UNCLASSIFIED DRUG; UNINDEXED DRUG; UREASE INHIBITOR;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; IN VITRO STUDY; PRIORITY JOURNAL;

EID: 33846299168     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/157018007779422523     Document Type: Article

References (37)

1. Mobley, H. L. T.; Island, M. D.; Hausinger, R. P. Microbiol. Rev. 1995, 59, 451.
2. Zonia, L. E.; Stebbins, N. E.; Polacco, J. C. Plant Physiol. 1995, 107, 1097.
3. Mulvaney, R. L.; Bremner, J. M.; Paul, E. A.; Ladd J. N. Soil Biochemistry, Ed.; Marcel Dekker Inc., New York, 1981, p.153.
4. Mobley, H. L. T.; Hausinger, R. P. Microbiol. Rev. 1989, 53, 85.
5. Suzuki, M.; Miura, S.; Suematsu, M.; Fukumura, D.; Kurose, I.; Suzuki, H.; Kai, A.; Kudoh, Y.; Ohashi, M.; Tsuchiya, M. Am. J. Physiol. 1992, 263, 719.
6. Grisham, M. B.; Jefferson, M. M.; Thomas, E. L. J. Biol. Chem. 1984, 259, 6766.
7. Thomas, E.L.; Grisham, M.B.; Jefferson, M.M. J. Clin. Invest. 1983, 72, 441.
8. Bayerdorffer, E.; Ottenjhan, R.; Scand. J. Gastroenterol. 1988, 23, 93.
9. Amtul, Z.; Atta-ur-Rahman, Siddiqui, R. A.; Choudhary, M. I. Curr. Med. Chem. 2002, 9, 1323.
10. Uesato, S.; Hashimoto, Y.; Nishino, M.; Nagaoka, Y.; Kuwajima, H.; Chem. Pharm. Bull. 2002, 50, 1280.
11. Morris, N. S.; Stickler, D. J.; Urol. Res. 1998, 26, 275.
12. Furr, P. M.; Taylor-Robinson, D.; Hetherington, C. M.; J. Antimicrob. Chemother. 1984, 14, 613.
13. Ligon, J.V.; Kenny, G.E. Infect. Immun. 1991, 59, 1170.
14. Ohta, T.; Shibata, H.; Kawamori, T.; Iimuro, M.; Sugimura, T.; Wakabayashi, K.; Biochem. Biophys. Res. Commun. 2001, 285, 728.
15. Lorente, A.; Fernández-Saiz, M.; Espinosa, J.-F.; Jaime, C.; Lehn, J.-M.; Vigneron, J. -P. Tetrahedron Lett. 1995, 36, 5261.
16. Bonse, S.; Santelli-Rouvier, C.; Barbe, J.; Krauth-Siegel, R. L. J. Med. Chem. 1999, 42, 5448.
17. Nguyen, T. M.; Sittisombut, C.; Boutefnouchet, S.; Lallemand, M.-C.; Michel, S.; Koch, M.; Tillequin, F.; Mazinghien, R.; Lansiaux, A.; David-Cordonnier, M.-H.; Pfeiffer, B.; Kraus-Berthier, L.; Léonce, S.; Pierré, A. J. Med. Chem. 2006, 49, 3383.
18. Berthet, N.; Constant, J. -F.; Demeunynck, M.; Michon, P.; Lhomme, J. J. Med. Chem. 1997, 40, 3346.
19. Lee, H. H.; Wilson, W. R.; Ferry, D. M.; Van Zijl, P.; Pullen, S. M.; Denny, W. A.; J. Med. Chem. 1996, 39, 2508.
20. Kirk, S. R.; Luedtke, N. W.; Tor, Y. J. Am. Chem. Soc. 2000, 122, 980.
21. Tabarrini, O.; Cecchetti, V.; Fravolini, A.; Nocentini, G.; Berzi, A.; Sabatini, S.; Miao, H.; Sissi, C. J. Med. Chem. 1999, 42, 2136.
22. Magiatis, P.; Mitaku, S.; Skaltsounis, A.-L.; Tillequin, F.; Koch, M.; Pierré, A.; Atassi, G. Chem. Pharm. Bull. 1999, 47, 611-614.
23. Lin, T. -P.; Chang, C. -P.; Tseng, R. -T.; Wang, J. -P. Chin. Pharm. J. 2002, 54, 115.
24. Ju-Ichi, M.; Inoue, M.; Aoki, K.; Furukawa, H. Heterocycles 1986, 24, 1595.
25. Dzierzbicka, K.; Kolodziejczyk, A. M. J. Med. Chem. 2001, 44, 3606.
26. Mehta, G.; Sambaiah, T;. Maiya, B. G.; Sirish, M.; Chatterjee, D. J. Chem. Soc. Perkin Trans. 1, 1993, 2667.
27. Tringali, C.; Spatafora, C.; Calì, V.; Simmonds, M. S. J. Fitoterapia 2001, 72, 538.
28. Wainwright, M. J. Antimicrob. Chemother. 2001, 47, 1.
29. (a) Khan, K. M.; Iqbal, S.; Lodhi, M. A.; Maharvi, G. M.; Perveen, S.; Choudhary, M. I.; Atta-ur-Rahman, Chohan, Z. H.; Supuran, C.T. J. Enz. Inhib. Med. Chem. 2004, 19, 367;
30. (b) Mesaik, M. A.; Rahat, S.; Khan, K.M.; Choudhary, M.I.; Shahnaz, M.; Ismaeil, Z.; Atta-ur-Rahman, Ahmad, A.; Zia-Ullah, Bioorg. Med. Chem. 2004, 12, 2049;
31. (c) Khan, K. M.; Iqbal, S.; Lodhi, M. A.; Maharvi, G. M.; Zia-Ullah, Choudhary, M. I.; Atta-ur-Rahman, Perveen, S. Bioorg. Med. Chem. 2004, 12, 1963;
32. (d) Khan, K. M.; Saify, Z. S.; Khan, M. Z.; Zia-Ullah, Choudhary, M. I.; Atta-ur-Rahman, Perveen, S.; Chohan, Z. H.; Supuran, C. T. J. Enz. Inhib. Med. Chem. 2004, 19, 373;
33. (e) Khan, K. M.; Saify, Z. S.; Khan, M. T. H.; Butt, N.; Maharvi, G. M.; Parveen, S.; Ambreen, N.; Choudhary, M. I.; Atta-ur-Rahman, J. Enz. Inhib. Med. Chem. 2005, 20, 401;
34. (f) Khan, K. M.; Maharvi, G. M.; Khan, M. T. H.; Perveen, S.; Choudhary M. I.; Atta-ur-Rahman, Mol. Diver. 2005, 9, 15;
35. (g) Khan, K. M.; Maharvi, G. M.; Khan, M. T. H.; Shaikh, A. J.; Parveen, S.; Begum, S.; Choudhary, M. I. Bioorg. Med. Chem. 2006, 14, 344.
36. Weatherburn, M. W. Anal. Chem. 1967, 39, 971.
37. Skonieczny, S. Heterocycles 1980, 14, 985.