Microwave-assisted one-step synthesis of fenamic acid hydrazides from the corresponding acids

Molecules

Volumn 16, Issue 5, 2011, Pages 3544-3551

  Aboul Fadl, Tarek ^a   Abdel Aziz, Hatem A ^a   Kadi, Adnan ^a   Bari, Ahmed ^a   Ahmad, Pervez ^a   Al Samani, Tilal ^a   Ng, Seik Weng ^b  

^a KING SAUD UNIVERSITY   (Saudi Arabia)

^b UNIVERSITY OF MALAYA   (Malaysia)

Author keywords

Fenamic acid hydrazides; Fenamic acids; Microwave irradiation; Solvent free reaction

Indexed keywords

ANTHRANILIC ACID DERIVATIVE; FENAMIC ACID; HYDRAZINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MICROWAVE RADIATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ANTHRANILIC ACIDS; HYDRAZINES; MAGNETIC RESONANCE SPECTROSCOPY; MICROWAVES; MOLECULAR STRUCTURE;

EID: 79957593203     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16053544     Document Type: Article

References (30)

1. Syed, M.M.; Parekh, A.B.; Tomita, T. Receptors involved in mechanical responses to catecholamines in the circular muscle of guinea-pig stomach treated with meclofenamate. Brit. J. Pharm. 1990, 101, 809-814.
2. Belsole, S.C. Meclofenamic acid topical pharmaceutical composition. US Patent 4602040, 1986.
3. Martindale, J.E.F. The extra pharmacopoeia, 31st ed.; Reynolds Ed.; The Pharmaceutical Press: London, UK, 1996.
4. Metz, G. Method of producing 2-(2-hydroxyethoxy)-ethanol ester of flufenamic acid. US Patent 4980498, 1990.
5. Insel, P.A.; Gilman, A.G.; Rall, T.W.; Nies, A.S.; Taylor, P. Goodman and Gilman's: The Pharmacological Basis of Therapeutics, 8th ed.; McGraw-Hill: New York, NY, USA, 1990.
6. Sriram, D.; Yogeeswari, P.; Devakaram, R.V. Synthesis, in vitro and in vivo antimycobacterial activities of diclofenac acid hydrazones and amides. Bioorg. Med. Chem. 2006, 14, 3113-3118.
7. Koz'minykh, V.O. Synthesis and biological activity of substituted amides and hydrazides of 1,4-dicarboxylic acids. Pharm. Chem. J. 2006, 40, 8-17. (Pubitemid 44043060)
8. Kidawi, M.; Misra, P.; Kumma, R.; Saxena, R.K.; Gupta, R.; Bardoo, S. Microwave assisted synthesis and antibacterial activity of new quinolone derivatives. Monatsh. Chem. 1998, 129, 961-965. (Pubitemid 128355037)
9. Fuquang, L.I.U.; Palmer, D.C.; Sorgi, K.L. Diethoxyphosphinyl acetic acid hydrazide: A uniquely versatile reagent for the preparation of fused [5,5]-, [5,6]-, and [5,7]-3-[(E)-2-(arylvinyl)]-1,2,4- triazoles. Tetrahedron Lett. 2004, 45, 1877-1880. (Pubitemid 38228346)
10. Demirbas, N.; Ugurluoglu, R.; Demirbas, A. Synthesis of 3-alkyl(aryl)-4-alkylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones and 3-alkyl-4-alkylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones as antitumor agents. Bioorg. Med. Chem. 2002, 10, 3717-3723. (Pubitemid 36164675)
11. Holla, B.S.; Akberali, P.M.; Shivananda, M.K. Studies on nitrophenylfuran derivatives-Part XII. Synthesis, characterization, antibacterial and antiviral activities of some nitrophenylfurfurylidene-1,2,4-triazolo[3,4-b]-1,3,4- thiadiazines. Farmaco 2001, 56, 919-927. (Pubitemid 34017398)
12. Aboul-Fadl, T.; Mohammed, F.A.; Hassan, E.A. Synthesis, antitubercular activity and pharmacokinetic studies of some Schiff Bases derived from 1-alkylisatin and isonicotinic acid hydrazide (INH). Arch. Pharm. Res. 2003, 26, 778-784. (Pubitemid 43073762)
13. Hussein, M.A.; Aboul-Fadl, T.; Hussein, A. Synthesis and antitubercular activity of some Mannich bases derived from isatin isonicotinic acid hydrazone. Bull. Pharm. Sci. Assiut Univ. 2005, 28, 131-136.
14. Abdel-Aziz, H.A.; Hamdy, N.A.; Farag, A.M.; Fakhr, I.M.I. Synthesis and reactions of 3-methylthiazolo[3,2-a]benzimidazole-2-carboxylic acid hydrazide: Synthesis of some new pyrazole, 1,3-thiazoline, 1,2,4-triazole and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives pendant to thiazolo[3,2-a]benzimidazole moiety. J. Chin. Chem. Soc. 2007, 54, 1573-1582.
15. Abdel-Aziz, H.A.; Gamal-Eldeen, A.M.; Hamdy, N.A.; Fakhr, I.M.I. Immunomodulatory and anti-cancer activity of some novel 2-substituted-6-bromo-3- methylthiazolo[3,2-a]benzimidazole derivatives. Arch. Pharm. 2009, 342, 230-237.
16. Abdel-Aziz, H.A.; Abdel-Wahab, B.F.; Badria, F.A. Stereoselective synthesis and antiviral activity of (1E,2Z,3E)-1-(piperidin-1-yl)-1- (arylhydrazono)-2-[(benzoyl/benzothiazol-2-oyl)-hydrazono]-4-(aryl1)but-3-enes. Arch. Pharm. 2010, 343, 152-159.
17. Abdel-Aziz, H.A.; Mekawey, A.A.I. Stereoselective synthesis and antimicrobial activity of benzofuran-based (1E)-1-(piperidin-1-yl)-N2- arylamidrazones. Eur. J. Med. Chem. 2009, 44, 3985-4997.
18. Abdel-Aziz, H.A.; Mekawey, A.A.I.; Dawood, K.M. Convenient synthesis and antimicrobial evaluation of some novel 2-substituted-3-methylbenzofuran derivatives. Eur. J. Med. Chem. 2009, 44, 3637-3644.
19. Abdel-Wahab, B.F.; Abdel-Aziz, H.A.; Ahmed, E.M. Synthesis and antimicrobial evaluation of some new 1,3-thiazole, 1,3,4-thiadiazole, 1,2,4-triazole and [1,2,4]triazolo[3,4-b]-[1,3,4]thiadiazine derivatives including 5-(benzofuran-2-yl)-1-phenyl-pyrazole moiety. Monatsh. Chem. 2009, 140, 601-605.
20. Abdel-Wahab, B.F.; Abdel-Aziz, H.A.; Ahmed, E.M. Convenient synthesis and antimicrobial activity of some new 3-substituted-5-(benzofuran-2-yl)-pyrazole derivatives. Arch. Pharm. 2008, 341, 734-739.
21. Aboul-Fadl, T.; Abdel-Aziz, H.A.; Khadi, A.; Darwish, I.; Al-Samani, T.; Ahmad, P.; Bari, A.; Al-Hajoj, S. Design and Synthesis of a Combinatorial Library of Indoline-2,3-dione Schiff Bases with Potential Anti-tubercular Activity. In Proceedings of The 46th International Conference on Medicinal Chemistry, Interfacing Chemistry, Biology and Drug Discovery, Reims, France, June 30-July 2, 2010; Abstract No. P009.
22. Suman, A.; Poonam, R.; Ambati, N.R.; Kumaran, G.; Ramesh, C.M. Synthesis, characterization and spectral studies of various newer long chain aliphatic acid (2-hydroxy benzylidene and 1H-indol-3-ylmethylene) hydrazides as mosquito para-pheromones. J. Kor. Chem. Soc. 2007, 51, 506-512.
23. Saha, A.; Kumar, R.; Kumar, R.; Devakumar, C. Development and assessment of green synthesis of hydrazides. Indian J. Chem. 2010, 49B, 526-531.
24. Bose, A.K.; Manhas, M.S.; Banik, B.K.; Robb, E.W. Microwave-induced organic reaction enhancement (more) chemistry: Techniques for rapid, safe and inexpensive synthesis. Res. Chem. Intermed. 1994, 20, 1-11.
25. Lehmann, J.; Kraft, G. Amphiphile Verbindungen, 1. Mitt. Zur Synthese von 1-Aryl-, 1-Aroylund 1-benzyl-2,3,4-5-tetrahydro-1H-1,4-benzodiazepinen. Arch. Pharm. 1984, 317, 595-606. (Pubitemid 14077635)
26. Narsinghani, T.; Chaturvedi, S.C. QSAR analysis of meclofenamic acid analogues as selective COX-2 inhibitors. Bioorg. Med. Chem. Lett. 2006, 16, 461-468. (Pubitemid 41680647)
27. Reddy, L.V.; Suman, A.; Beevi, S.S.; Mangamoori, L.N.; Mukkanti, K.; Pal, S. Design and synthesis of 1-aroyl-2-ylidene hydrazines under conventional and microwave irradiation conditions and their cytotoxic activities. J. Braz. Chem. Soc. 2010, 21, 98-104.
28. Onnis, V.; Cocco, M.T.; Fadda, R.; Congiu, C. Synthesis and evaluation of anticancer activity of 2-arylamino-6-trifluoromethyl-3-(hydrazonocarbonyl) pyridines. Bioorg. Med. Chem. 2009, 17, 6158-6165.
29. Boschelli, D.H.; Connor, D.T.; Flynn, D.L.; Sircar, J.C.; Hoefle, M.L. Triazole derivatives of fenamates as antiinflammatory agents. US Patent 4962119, 1990.
30. A white single crystal of hydrazide 3c was crystallized from ethanol by slow evaporation at room temperature. Crystallographic data for the structure 3c has been deposited with the Cambridge Crystallographic Data Center (CCDC) under the deposition number 813246. Copies of the data can be obtained, free of charge, on application to CCDC 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44-1223-336033; e-mail: deposit@ccdc.cam.ac.uk or http://www.ccdc.cam.ac.uk].