Synthesis of novel quinoline analogues of nimesulide: An unusual observation

Journal of Heterocyclic Chemistry

Volumn 48, Issue 3, 2011, Pages 555-562

  Reddy, Lingam Venkata ^a   Nakka, Mamatha ^a   Suman, Alishetty ^a   Ghosh, Soumen ^b   Helliwell, Madeleine ^c   Mukkanti, Khagga ^a   Mukherjee, Alok Kumar ^b   Pal, Sarbani ^d  

^a INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^b JADAVPUR UNIVERSITY   (India)

^c UNIVERSITY OF MANCHESTER   (United Kingdom)

^d MNR Degree and PG College   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 CHLORO 3 FORMYLQUINOLINE DERIVATIVE; AROMATIC AMINE; FORMAMIDE DERIVATIVE; N (2 CHLORO 3 FORMYL 7 PHENOXY QUINOLIN 6 YL)FORMAMIDE; N (2 CHLORO 3 FORMYL 7 PHENOXYQUINOLIN 6 YL)METHANESULFONAMIDE; N [2 CHLORO 3 ((2 (2 (2,3 DIMETHYLPHENYLAMINO)BENZOYL)HYDRAZONO)METHYL) 7 PHENOXYQUINOLIN 6 YL]METHANESULFONAMIDE; N [2 CHLORO 3 ((2 (2 HYDROXYBENZOYL)HYDRAZONO)METHYL) 7 PHENOXYQUINOLIN 6 YL)METHANESULFONAMIDE; N [2 CHLORO 3 ((2 (2 METHYLBENZOYL)HYDRAZONO)METHYL) 7 PHENOXYQUINOLIN 6 YL]FORMAMIDE; N [2 CHLORO 3 ((2 (2,4 DINITROPHENYL)HYDRAZONO)METHYL) 7 PHENOXYQUINOLIN 6 YL]FORMAMIDE; N [2 CHLORO 3 ((2 (2,4 DINITROPHENYL)HYDRAZONO)METHYL) 7 PHENOXYQUINOLIN 6 YL]METHANESULFONAMIDE; N [2 CHLORO 3 ((2 (3 NITROBENZOYL)HYDRAZONO)METHYL) 7 PHENOXYQUINOLIN 6 YL]FORMAMIDE; N [2 CHLORO 3 ((2 (4 CHLOROBENZOYL)HYDRAZONO)METHYL) 7 PHENOXYQUINOLIN 6 YL]FORMAMIDE; N [3 ((2 BENZOYLHYDRAZONO)METHYL) 2 CHLORO 7 PHENOXYQUINOLIN 6 YL]FORMAMIDE; NIMESULIDE; NITROGEN; QUINOLINE DERIVATIVE; SCHIFF BASE; SULFUR; UNCLASSIFIED DRUG; [(2 CHLORO 6 FORMAMIDO 7 PHENOXYQUINOLIN 3 YL)METHYLENE]N (4 METHOXYPHENYL)HYDRAZINECARBOTHIOAMIDE;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; SYNTHESIS; VILSMEIER HAACK REACTION; X RAY ANALYSIS;

EID: 79957490882     PISSN: 0022152X     EISSN: 19435193     Source Type: Journal    
DOI: 10.1002/jhet.618     Document Type: Article

References (25)

1. Roberts, L. J.; Morrow, J. D., Analgesic-antipyretic and anti-inflammatory agents and drugs employed in the treatment of gout, in Goodman & Gilman's the pharmacological basis of therapeutics;, Hardman, J. G.; Limbird, L. E., Eds.; McGraw-Hill, New York, 2001; pp 687-731.
2. Karakuş, S.; Küçükgüzel, S. G.; Küçükgüzel, I.; Clercq, E. D.; Pannecouque, C.; Andrei, G.; Snoeck, R.; Şahin, F.; Bayrak, O. F., Eur J Med Chem 2009, 44, 3591.
3. Michaux, C.; Charlier, C.; Julémont, F.; Leval, X. de,;, Dogné, J.-M.; Pirotte, B.; Durant, F., Eur J Med Chem 2005, 40, 1316.
4. Kidwai, M.; Negi, N., Monatshefte ffir Chemie 1997, 128, 85.
5. Nagaraja, G. K.; Prakash, G. K.; Kumaraswamy, M. N.; Vaidya, V. P.; Mahadevan, K. M., ARKIVOC 2006, xv, 160.
6. Pericherla, S.; Mareddy, J.; Geetha, R. D. P.; Gollapudi, P. V.; Pal, S., J Braz Chem Soc 2007, 18, 384.
7. Kouznetsov, V. V.; Méndez, L. Y. V.; Gómez, C. M. M., Curr Org Chem 2005, 9, 141.
8. Marson, C. M.; Giles, P. R., Synthesis using Vilsmeier Reagents; CRC: Boca Raton, 1994.
9. Meth-Cohn, O.; Taylor, D. L., Tetrahedron 1995, 51, 12869.
10. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 734903. Copies of available material can be obtained, free of charge via, by e-mailing data-request@ccdc. cam.ac.uk, or contacting the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: Φ44 1223 336033.
11. Sheldrick, G. M., CELL-NOW, 2002; University of Göttingen, Germany.
12. Sheldrick, G. M., SHELXS 97 and SHELXL 97, 1997; University of Göttingen, Germany.
13. Farrugia, L. J., J Appl Cryst 1997, 30, 565.
14. Palani, K.; Ambalavanan, P.; Ponnuswamy, N. N. G.; Yathirajan, H. S.; Prabhuswamy, B.; Raju, C. R.; Nagaraja, P.; Shashikanth, S., Anal Sci 2004, 20, 403.
15. Somvanshi, R. K.; Subashini, R.; Dhanasekaran, V.; Arulprakash, G.; Das, S.; Dey, S. J., Chem Crystallogr 2008, 38, 381.
16. Kalkhambkar, R. G.; Kulkarni, G. M.; Hwang, W.-S.; Lee, C.-S., Acta Cryst 2008, E64, 0258.
17. Rajendran, P.; Karavembu, R., Ind J Chem 2002, 41B, 222.
18. Dutta, N. J.; Khunt, R. C.; Parikh, A. R., Ind J Chem 2002, 41B, 433.
19. Bürgi, H.-B.; Dunitz, J. D., Eds. Structure Correlation, Vol. 2.; Weinheim, Verlag VCH: New York, 1994, p 771.
20. Cheng, H.-M.; Zhu, D.-R.; Lu, W.; Xu, R.-H.; Shen, X. J., Heterocyclic Chem 2010, 47, 210.
21. Blackburn, A. C.; Dobson, A. J.; Gerkin, R. E., Acta Cryst 1996, C52, 409.
22. Chiang, L. Y.; Swirczewski, J. W.; Kastrup, R.; Hsu, C. S.; Upasani, R. B., J Am Chem Soc 1991, 113, 6574.
23. Gdaniec, M.; Jaskolski, M.; Kosturkiewicz, Z., Polym J Chem 1980, 54, 1539.
24. Gdaniec, M.; Dziembowska, T., Polym J Chem 1980, 54, 87.
25. Ahmet, M. T.; Miller, J. R.; Osborne, A. G.; Warmsley, J. F., Acta Cryst 1995, C51, 2105.