Synthesis, in vitro antibacterial and carbonic anhydrase II inhibitory activities of N-acylsulfonamides using silica sulfuric acid as an efficient catalyst under both solvent-free and heterogeneous conditions

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 10, 2008, Pages 5465-5472

  Massah, Ahmad Reza ^a   Adibi, Hadi ^b   Khodarahmi, Reza ^c   Abiri, Ramin ^d   Majnooni, Mohammad Bagher ^b   Shahidi, Sherita ^a   Asadi, Beheshteh ^a   Mehrabi, Masomeh ^b   Zolfigol, Mohammad Ali ^e  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b KERMANSHAH UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c KERMANSHAH UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^d KERMANSHAH UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^e BU ALI SINA UNIVERSITY   (Iran)

Author keywords

Antibacterial activity; Carbonic anhydrase II inhibitor; N Acylsulfonamides; Silica sulfuric acid; Solvent free

Indexed keywords

ACID ANHYDRIDE; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBOXYLIC ACID DERIVATIVE; DORZOLAMIDE; N PENTANOYLBENZENESULFONAMIDE; SILICON DIOXIDE; SOLVENT; SULFONAMIDE; SULFURIC ACID;

ANTIBACTERIAL ACTIVITY; ARTICLE; CATALYSIS; CATALYST; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; ENTEROCOCCUS FAECIUM; ENZYME INHIBITION; ESCHERICHIA COLI; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE COCCI; IN VITRO STUDY; KLEBSIELLA PNEUMONIAE; NONHUMAN; PSEUDOMONAS AERUGINOSA; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; ROOM TEMPERATURE; STAPHYLOCOCCUS AUREUS; STEREOCHEMISTRY;

ANTI-BACTERIAL AGENTS; CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; CATALYSIS; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE COCCI; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; SILICON DIOXIDE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; SULFURIC ACIDS;

BACILLI (CLASS); NEGIBACTERIA; POSIBACTERIA;

EID: 43749106022     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.04.011     Document Type: Article

References (35)

1. Hasegawa T., and Yamamoto H. Bull. Chem. Soc. Jpn. 73 (2000) 423
2. Banwell M.G., Crasto C.F., Easton C.J., Forrest A.K., Karoli T., March D.R., Mensah L., Nairn M.R., O'Hanlon P.J., Oldham M.D., and Yue W. Bioorg. Med. Chem. Lett. 10 (2000) 2263
3. Chang L.L., Ashton W.T., Flanagan K.L., Chen T.B., O'Malley S.S., Zingaro G.J., Siegl P.K.S., Kivlighn S.D., Lotti V.J., Chang R.S.L., and Greenless W.J. J. Med. Chem. 37 (1994) 4464
4. Musser J.H., Kreft A.F., Bender R.H.W., Kubrak D.M., Grimes D., Carlson R.P., Hand J.M., and Chang J. J. Med. Chem. 33 (1990) 240
5. Kondo K., Sekimoto E., Nakao J., and Murakami Y. Tetrahedron 56 (2000) 5843
6. Kondo K., Sekimoto E., Miki K., and Murakami Y. J. Chem. Soc. Perkin Trans. 1 (1998) 2973
7. Ishizuka N., Matsumura K.I., Hayashi K., Sakai K., and Yamamori T. Synthesis (2000) 784
8. Ishizuka, N.; Matsumura, K. I. Japanese Patent JP-10045705, 1998.
9. Inoe, T.; Myahara, O.; Takahashi, A.; Nakamura, Y. Japanese Patent JP-08198840, 1996.
10. Wang Y., Soper D.L., Dirr M.J., Delong M.A., De B., and Wos J.A. Chem. Pharm. Bull. 48 (2000) 1332
11. Katritzky A.R., Hoffmann S., and Suzuki K. Arkivoc 12 (2004) 14
12. Morisawa Y., Kataoka M., Negahori H., Sakamoto T., Kitano N., and Kusano K. J. Med. Chem. 23 (1980) 1376
13. Martin M.T., Roschangar F., and Eaddy J.F. Tetrahedron Lett. 44 (2003) 5461
14. Singh D.U., Singh P.R., and Samant S.D. Tetrahedron Lett. 45 (2004) 4805
15. Supuran C.T., and Scozzafava A. Exp. Opin. Ther. Patents 10 (2000) 575
16. Knudsen J.F., Carlsson U., Hammarstrom P., Sokol G.H., and Cantilena L.R. Inflammation 28 (2004) 285
17. Zolfigol M.A. Tetrahedron 57 (2001) 9509
18. See an excellent review about SSA. Salehi P., Zolfigol M.A., Shirini F., and Baghbanzadeh M. Curr. Org. Chem. 10 (2006) 2171
19. Mirjalili B.F., Zolfigol M.A., Bamoniri A., and Hazar A. Bull. Korean Chem. Soc. 25 (2004) 865
20. Shimizu K., Hayashi E., Hatamachi T., Kodama T., and Kitayama Y. Tetrahedron Lett. 45 (2004) 51351
21. Shabani A., and Rahmati A. J. Mol. Catal. A: Chem. 249 (2006) 246
22. Zolfigol M.A., Mohammadpoor-Baltork I., Mirjalili B.F., and Bamoniri A. Synlett (2003) 1877
23. Salehi P., Dabiri M., Zolfigol M.A., and Badaghifard M.A. Phosphorus, Sulfur, Silicon Relat. Elem. 179 (2004) 1113
24. Zolfigol M.A., and Bamoniri A. Synlett (2002) 1621
25. Zolfigol M.A., Mirjalili B.F., Bamoniri A., Karimi M.A., Zarei A., Khazdooz L., and Noei J. Bull. Korean Chem. Soc. 25 (2004) 1
26. Desai U.V., Thopate T.S., Pore D.M., and Wadgaonkar P.P. Cat. Commun. 7 (2006) 508
27. Mukhopadhyay B. Tetrahedron Lett. 47 (2006) 4337
28. Wu H., Shen Y., Fan L.-Y., Wan Y., and Shi D.-Q. Tetrahedron 62 (2006) 7995
29. Massah A.R., Kazemi F., Azadi D., Farzaneh S., Aliyan H., Javaherian Nagash H., and Momeni A.R. Lett. Org. Chem. 3 (2006) 235
30. Baron E.J., and Finegold S.M. Bailey and Scott's Diagnostic Microbiology. 8th ed. (1990), C.V. Mosby, St. Louis 184-188
31. Andrews J.M. J. Antimicrob. Chemother. 48 (2001) 5
32. Nyman P.O. Biochim. Biophys. Acta 52 (1961) 1
33. Yazdanparast R., Khodarahmi R., and Soori E. Arch. Biochem. Biophys. 437 (2005) 178
34. Pocker Y., and Stone G. Biochemistry 6 (1967) 668
35. Laemmli U.K. Nature 227 (1970) 680