Facile One-Pot Synthesis of Aryl, Heteryl Substituted Hydrazono Thiazolyl-Pyrazolone Derivatives via Three-Component Reaction

REFERENCES

• Lewis , J. R. Muscarine, imidazole, oxazole, thiazole and peptide alkaloids, and other miscellaneous alkaloids . Nat. Prod. Rep. 1996 , 13 , 435 – 467 .
   Web of Science ®Google Scholar
• Kearney , P. C. ; Fernandez , M. ; Flygare , J. A. Solid-phase synthesis of 2-aminothiazoles . J. Org. Chem. 1998 , 63 , 196 – 200 .
   PubMed Web of Science ®Google Scholar
• Geronikaki , A. A. ; Dearden , J. C. ; Filimonov , D. ; Galaeva , I. ; Garibova , T. L. ; Gloriozova , T. ; Krajneva , V. ; Lagunin , A. ; Macaev , F. Z. ; Molodavkin , G. ; Poroikov , V. V. ; Pogrebnoi , S. I. ; Shepeli , F. ; Voronina , T. A. ; Tsitlakidou , M. ; Vlad , L. Design of new cognition enhancers: From computer prediction to synthesis and biological evaluation . J. Med. Chem. 2004 , 47 , 2870 – 2876 .
   PubMed Web of Science ®Google Scholar
• Li , G. ; Warner , P. M. ; Jebaratnam , D. J. Synthesis of a directly connected thiazole-oxazole ring system present in Microcin B17 . J. Org. Chem. 1996 , 61 , 778 – 780 .
   PubMed Web of Science ®Google Scholar
• Das , J. ; Chen , P. ; Norris , D. ; Padmanabha , R. ; Lin , J. ; Moquin , R. V. ; Shen , Z. ; Cook , L. S. ; Doweyko , A. M. ; Pitt , S. ; Pang , S. ; Shen , D. R. ; Fang , Q. ; de Fex , H. F. ; McIntyre , K. W. ; Shuster , D. J. ; Gillooly , K. M. ; Behnia , K. ; Schieven , G. L. ; Wityak , J. ; Barrish , J. C. 2-Aminothiazole as a novel kinase inhibitor template: Structure–activity relationship studies toward the discovery of N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl)]-2-methyl-4-pyrimidinyl]amino)]-1,3-thiazole-5-carboxamide (Dasatinib, BMS-354825) as a potent pan-Src kinase inhibitor. J. Med. Chem. 2006, 49, 6819–6832.
   PubMed Web of Science ®Google Scholar
• Lombardo , L. J. ; Lee , F. Y. ; Chen , P. ; Norris , D. ; Barrish , J. C. ; Behnia , K. ; Castaneda , S. ; Cornelius , L. A. M. ; Das , J. ; Doweyko , A. M. ; Fairchild , C. ; Hunt , J. T. ; Inigo , I. ; Johnston , K. ; Kamath , A. ; Kan , D. ; Klei , H. ; Marathe , P. ; Pang , S. ; Peterson , R. L. ; Pitt , S. ; Schieven , G. L. ; Schmidt , R. J. ; Tokarski , J. ; Wen , M.-L. ; Wityak , J. ; Borzilleri , R. M. Discovery of N-(2-chloro-6-methyl-phenyl)-2-(6-(4-(2-hydroxyethyl)-piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-carboxamide (BMS-354825), a Dual Src/Abl kinase inhibitor with potent antitumor activity in preclinical assays . J. Med. Chem. 2004 , 47 , 6658 – 6661 .
   PubMed Web of Science ®Google Scholar
• Argyropoulou , I. ; Geronikaki , A. ; Vicini , P. ; Zanib , F. Synthesis and biological evaluation of sulfonamide thiazole and benzothiazole derivatives as antimicrobial agents . Arkivoc 2009 , 6 , 89 – 102 .
   Google Scholar
• Kiryanov , A. A. ; Sampson , P. ; Seed , A. J. Synthesis of 2-alkoxy-substituted thiophenes, 1,3-thiazoles, and related S-heterocycles via Lawesson's reagent-mediated cyclization under microwave irradiation: Applications for liquid crystal synthesis . J. Org. Chem. 2001 , 66 , 7925 – 7929 .
   PubMed Web of Science ®Google Scholar
• Bach , T. ; Heuser , S. Synthesis of 2-(o-hydroxyaryl)-4-arylthiazoles by regioselective Pd(0)-catalyzed cross-coupling . Tetrahedron Lett. 2000 , 41 , 1707 – 1710 .
   Web of Science ®Google Scholar
• Regan , J. ; Capolino , A. ; Cirillo , P. F. ; Gilmore , T. ; Graham , A. G. ; Hicky , E. ; Kroe , R. R. ; Madwed , J. ; Torcellini , C. ; Tsang , M. ; Moss , N. Structure-activity relationships of the p38α MAP kinase inhibitor 1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[4-(2-morpholin-4-yl-ethoxy)naph-thalen-1-yl]urea (BIRB 796) . J. Med. Chem. 2003 , 46 , 4676 – 4686 .
   PubMed Web of Science ®Google Scholar
• Stauffer , S. R. ; Coletta , C. J. ; Tedesco , R. ; Nishiguchi , G. ; Carlson , K. ; Sun , J. ; Katzenellenbogen , B. S. ; Katzenellenbogen , J. A. Pyrazole ligands: Structure-affinity/activity relationships and estrogen receptor-α-selective agonists . J. Med. Chem. 2000 , 43 , 4934 – 4947 .
   PubMed Web of Science ®Google Scholar
• Huang , Y. R. ; Katzenellenbogen , J. A. Regioselective synthesis of 1,3,5-triaryl-4-alkylpyrazoles: Novel ligands for the estrogen receptor . Org. Lett. 2000 , 2 , 2833 – 2836 .
   PubMed Web of Science ®Google Scholar
• Propsavin , M. ; Torovic , L. ; Spaic , S. ; Stankov , S. ; Kapor , A. ; Tomic , Z. ; Popsavin , V. Synthesis and biological evaluation of new pyrazole- and tetrazole-related C-nucleosides with modified sugar moieties . Tetrahedron 2002 , 58 , 569 – 580 .
   Web of Science ®Google Scholar
• Sauzem , P. D. ; Machado , P. ; Rubin , M. A. ; Da , S. ; Sant'Anna , G. ; Faber , H. B. ; De Souza , A. H. ; Mello , C. F. ; Beck , P. ; Burrow , R. A. ; Bonacorso , H. G. ; Zanatta , N. ; Martins , M. A. P. ; Patricia , D. Design and microwave-assisted synthesis of 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles: Novel agents with analgesic and anti-inflammatory properties . Eur. J. Med. Chem. 2008 , 43 , 1237 – 1247 .
   PubMed Web of Science ®Google Scholar
• O'Kennedy , R. ; Thornes , R. D. Coumarins-Biology, Applications and Mode of Action ; John Wiley and Sons : Chichester , UK , 1997 .
   Google Scholar
• Melliou , E. ; Magiatis , P. ; Mitaku , S. ; Skaltsounis , A. L. ; Chinou , E. ; Chinou , I. Natural and synthetic 2,2-dimethylpyranocoumarins with antibacterial activity . J. Nat. Prod. 2005 , 68 , 78 – 82 .
   PubMed Web of Science ®Google Scholar
• Valenti , P. ; Rampa , A. ; Recanatini , M. ; Bisi , A. ; Belluti , F. ; Da Re , P. ; Carrara , M. ; Cima , L. Synthesis, cytotoxicity, and SAR of simple geiparvarin analogues . Anticancer Drug Des. 1997 , 12 , 443 – 451 .
   PubMedGoogle Scholar
• Spino , C. ; Dodier , M. ; Sotheeswaran , S. Anti-HIV coumarins from calophyllum seed oil . Bioorg. Med. Chem. Lett. 1998 , 8 , 3475 – 3478 .
   PubMed Web of Science ®Google Scholar
• Thaisrivongs , S. ; Watenpaugh , K. D. ; Howe , W. J. ; Tomich , P. K. ; Dolak , L. A. ; Chong , K.-T. ; Tomich , C.-S. C. ; Tomasselli , A. G. ; Turner , S. R. ; Strohbach , J. W. ; Mulichak , A. M. ; Janakiraman , M. N. ; Moon , J. B. ; Lynn , J. C. ; Horng , M.-M. ; Hinshaw , R. R. ; Curry , K. A. ; Rothrock , D. J. Structure-based design of novel HIV protease inhibitors: Carboxamide-containing 4-hydroxycoumarins and 4-hydroxy-2-pyrones as potent nonpeptidic inhibitors. J. Med. Chem. 1995, 38, 3624–3637.
   PubMed Web of Science ®Google Scholar
• Kalluraya , B. K. ; Isloor , A. M. ; Frank , P. V. ; Jagadeesha , R. L. Synthesis and pharmacological activity of some 4-(substituted)-2-[4-aryhydrazono-3-methyl-5-oxo-2-pyrazolin-1-yl] thiazoles . Indian J. Het. Chem. 2004 , 13 , 245 .
   Web of Science ®Google Scholar
• Rajeswar Rao , V. ; Vijaya Kumar , P. A facile one-step synthesis of 3-{2-[5-hydroxy-4-(2-hydroxy-ethyl)-3-methyl-pyrazol-1-yl]-thiazol-4-yl}-chromen-2-ones via a three-component reaction . Synth. Commun. 2006 , 36 , 2157 – 2161 .
   Web of Science ®Google Scholar
• Chunduru , V. S. R. ; Rajeswar Rao , V. One-pot synthesis of 3-[2-(arylamino)thiazol-4-yl]coumarins in a three-component synthesis and a catalyst and solvent-free synthesis on grinding . J. Chem. Res. 2010 , 50 – 53 .
   Web of Science ®Google Scholar
• Srimanth , K. ; Rajeswar Rao , V. A facile one-step synthesis of 3-(2-(3,5-dimethyl-1H-pyrazol-1-yl)-4-thiazolyl)-2H-benzopyran-2-ones under solvent-free condition . J. Chem. Res. 2002 , 420 – 421 .
   Web of Science ®Google Scholar
• Rajeswar Rao , V. ; Padmanabha Rao , T. V. Studies of thiazolyl, imidazolyl-2H-1- benzopyran-2-ones . Indian J. Chem. 1986 , 25B , 413 .
   Google Scholar
• Rajput , A. P. ; Rajput , S. S. Synthesis and microbial screening of seven membered heterocyclic ring compounds from 1,2-diaminobenzene . Int. J. Pharm. Tech. Res. 2009 , 1 , 900 – 904 .
   Google Scholar