Efficient, Stereoselective Approach to the Synthesis of 3-(1-Phenyl-2-(Z-styrylsulfonyl)-1H-imidazol-4-yl)-2H-chromen-2-ones

REFERENCES

• Egan , D. A. ; Cox , D. ; O'Kennedy , R. ; Moran , E. ; Prosser , E. ; Thornes , R. D. The pharmacology, metabolism, analysis, and applications of coumarin and coumarin-related compounds . Drugs Metab. Rev. 1990 , 22 , 503 – 529 .
   PubMed Web of Science ®Google Scholar
• Hoult , J. R. R. ; Paya , M. Pharmacological and biochemical actions of simple coumarins: Natural products with therapeutic potential . Gen. Pharmacol. 1996 , 27 , 713 – 722 .
   PubMedGoogle Scholar
• Madhavan , G. R. ; Balraju , V. ; Mallesham , B. ; Chakrabarti , R. ; Lohray , V. B. Novel coumarin derivatives of heterocyclic compounds as lipid-lowering agents . Bioorg. Med. Chem. Lett. 2003 , 13 , 2547 – 2551 .
   PubMed Web of Science ®Google Scholar
• Paya , M. ; Halliwell , B. ; Hoult , J. R. Interactions of a series of coumarins with reactive oxygen species . Biochem. Pharmacol. 1992 , 44 , 205 – 214 .
   PubMed Web of Science ®Google Scholar
• Yu , D. ; Suzuki , M. ; Xie , L. ; Morris-Natschke , S. L. ; Lee , K. H. Recent progress in the development of coumarin derivatives as potent anti-HIV agents . Med. Res. Rev. 2003 , 23 , 322 – 345 .
   PubMed Web of Science ®Google Scholar
• Kempen , I. ; Papapostolou , D. ; Thierry , N. ; Pochet , L. ; Counerotte , S. ; Masereel , B. ; Foidart , J.-M. ; Reboud-Ravaux , M. ; Noel , A. ; Pirotte , B. 3-Bromophenyl 6-acetoxymethyl-2-oxo-2H-1-benzopyran-3-carboxylate inhibits cancer cell invasion in vitro and tumour growth in vivo . Br. J. Cancer. 2003 , 88 , 1111 – 1118 .
   PubMed Web of Science ®Google Scholar
• Finn , G. ; Creaven , B. ; Egan , D. Modulation of mitogen-activated protein kinases by 6-nitro-7-hydroxycoumarin mediates apoptosis in renal carcinoma cells . Eur. J. Pharmacol. 2003 , 481 , 159 – 167 .
   PubMed Web of Science ®Google Scholar
• Finn , G. J. ; Creaven , B. S. ; Egan , D. A. Investigation of intracellular signalling events mediating the mechanism of action of 7-hydroxycoumarin and 6-nitro-7-hdroxycoumarin in human renal cells . Cancer Lett. 2004 , 205 , 69 – 79 .
   PubMedGoogle Scholar
• Morita , H. ; Dota , T.; Kobayashi, J. Antimitotic activity of glaupalol-related coumarins from Glaucidium palmatum . Bioorg. Med. Chem. Lett. 2004 , 14 , 3665 – 3668 .
   PubMedGoogle Scholar
• Reddy , N. S. ; Mallireddigari , M. R. ; Cosenza , S. ; Gumireddy , K. ; Bell , S. C. ; Reddy , E. P. ; Reddy , M. V. R. Synthesis of new coumarin 3-(N-aryl) sulfonamides and their anticancer activity . Bioorg. Med. Chem. Lett. 2004 , 14 , 4093 – 4097 .
   PubMed Web of Science ®Google Scholar
• Ramana Reddy , M. V. ; Muralidhar Reddy , M. ; Cosenza , C. S. ; Venkat , R. P. ; Iqbal , N. ; Kang , M. ; Anthony , D. ; Premkumar Reddy , E. Design, Synthesis, and biological evaluation of (E)-styrylbenzylsulfones as novel anticancer agents . J. Med. Chem. 2008 , 51 , 86 – 100 .
   PubMed Web of Science ®Google Scholar
• Ramana Reddy , M. V. ; Muralidhar Reddy , M.. ; Venkat , R. P. ; Padmavathi , V. , Rengasamy , B. ; Stanley , C. B. ; Premkumar Reddy , E. Design, synthesis, and biological evaluation of (E)- and (Z)-styryl-2-acetoxyphenyl sulfides and sulfones as cyclooxygenase-2 inhibitors . J. Bioorg. Med. Chem. 2005 , 13 , 1715 – 1723 .
   PubMed Web of Science ®Google Scholar
• Manohar Sharma , V. ; Aravind Babu , P. ; Chandrasekhar , V. ; Vamseekrishna , C. ; Sreenu , J. ; Venkata Adiseshu , K. ; Ravikrishna , V. ; Vishnu , B. ; Venkateswarlu , A. ; Rajgopal , S. ; Ajaya kumar , R. ; Sravankumar , T. ; Prem Kumar , M. ; Ramanujam , R. , Gopalakrishnan , B. ; Akash , K. ; Vijay , U. V. ; Srinivas Rao , M. New styryl sulfones as anticancer agents . Eur. J. Med. Chem. 2003 , 38 , 811 – 824 .
   PubMed Web of Science ®Google Scholar
• Rajeswar Rao , V. ; Vijaya Kumar , P. Facile one-pot synthesis of 3-{2-[5-hydroxy- 4-(2-hydroxy-ethyl)-3-methyl-pyrazole-1-yl]-thiazol-4-yl}-chromen-2-ones via a three-component reaction . Synth. Commmun. 2006 , 36 , 2157 – 2161 .
   Web of Science ®Google Scholar
• Rajeswar Rao , V. ; Ravi Kumar , V. Synthesis of 3-(1-aryl-2-mercaptoimidazolyl)-2H-1-benzopyran-2-one. Ind. J. Chem. 2002, 415–418.
   Google Scholar
• Guraviah , N. ; Rajeswar Rao , V. Solvent-free synthesis of new heteryl β-ketosulfones . J. Chem. Res. 2009 , 2 , 87 – 89 .
   Google Scholar
• Rajeswar Rao , V. ; Srimanth , K. A facile one step synthesis of 3-[2-(3,5-dimethyl-1H-pyrazol-1-yl)-4-imidazolyl]-2H-1-benzopyran-2-ones under solvent-free conditions . J. Chem. Res. 2002 , 420 – 421 .
   Google Scholar
• Rajeswar Rao , V. ; Vijaya Kumar , P. ; Reddy , R. V. Studies in Hantzsch thiazole synthesis of 3-(2-allylamino-4-thiazolyl)-2H-1-benzopyran-2-ones and 3-(4-phenylthiazoline-2-anil)-2H-1-benzopyran-2-enes in solid state . Ind. J. Chem. 2003 , 42B , 1338 – 1341 .
   Google Scholar
• Rajeswar Rao , V. ; Mohan Reddy , M. M. A facile one-step synthesis of 3-(2-hydroxy benzalhydrazino-4-thiazolyl)coumarins under solvent-free conditions and their biological activity . Ind. J. Heterocycl. Chem. 2003 , 13 , 69 – 72 .
   Google Scholar