Synthesis and biological evaluation of new 2-azetidinones with sulfonamide structures

Molecules

Volumn 18, Issue 4, 2013, Pages 4140-4157

  Dragostin, Oana Maria ^a   Lupascu, Florentina ^a   Vasile, Cornelia ^b   Mares, Mihai ^c   Nastasa, Valentin ^c   Moraru, Ramona Florina ^c   Pieptu, Dragos ^a   Profire, Lenuta ^a  

^a GRIGORE T POPA UNIVERSITY OF MEDICINE AND PHARMACY   (Romania)

^b PETRU PONI INSTITUTE OF MACROMOLECULAR CHEMISTRY   (Romania)

^c UNIVERSITY OF AGRICULTURAL SCIENCES AND VETERINARY MEDICINE   (Romania)

Author keywords

Antimicrobial activity; Antioxidant effect; Azetidinone; Sulfonamide; Synthesis

Indexed keywords

2 AZETIDINONE; 2-AZETIDINONE; ANTIINFECTIVE AGENT; ANTIOXIDANT; AZETIDINE DERIVATIVE; SULFONAMIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; INFRARED SPECTROSCOPY; MICROBIAL SENSITIVITY TEST; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTI-BACTERIAL AGENTS; ANTIOXIDANTS; AZETIDINES; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 84876762795     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18044140     Document Type: Article

References (27)

1. Chavan, A.A.; Pai, N.R. Synthesis and biological activity of N-substituted-3-chloro-2- azetidinones. Molecules 2007, 12, 2467-2477.
2. Ishwar, B.K.; Mishra, S.K.; Jainey, P.J.; Shastry, C.S. Antimicrobial studies of synthesized azetidinone derivatives from sulfamethoxazole moiety. J. Chem. Pharm. Res. 2011, 3, 114-118.
3. Jarrahpour, A.; Zarei, M. Synthesis of novel N-sulfonyl monocyclic β-lactams as potential antibacterial agents. Molecules 2006, 11, 49-58.
4. Cerić, H.; Šindler-Kulyk, M.; Kovačević, M.; Perić, M.; Živković, A. Azetidinone-isothiazolidinones: Stereoselective synthesis and antibacterial evaluation of new monocyclic beta-lactams. Bioorg. Med. Chem. 2010, 18, 3053-3058.
5. Sharma, R.; Samadhiya, P.; Srivastava, S.D.; Srivastava, S.K. Synthesis and pharmaceutical importance of 2-azetidinone derivatives of phenothiazine. J. Chem. Sci. 2012, 124, 633-637.
6. Samadhiya, P.; Sharma, R.; Srivastava, S.K.; Srivastava, S.D. Synthesis of 2-azetidinone derivatives of 6-nitro-1H-indazole and their biological importance. Quím. Nova 2012, 35, 914-919.
7. Kumar, A.; Rajput, C.S.; Bhati, S.K. Synthesis of 3-[4'-(p-chlorophenyl)- thiazol-2'-yl]-2- [(substituted azetidinone/thiazolidinone)-aminomethyl]-6- bromoquinazolin-4-ones as anti-inflammatory agent. Bioorg. Med. Chem. 2007, 15, 3089-3096.
8. Smith, E.M.; Sorota, S.; Kim, H.M.; McKittrick, B.A.; Nechuta, T.L.; Bennett, C.; Knutson, C.; Burnett, D.A.; Kieselgof, J.; Tan, Z.; et al. T-type calcium channel blockers: Spiro-piperidine azetidines and azetidinones- optimization, Design and synthesis. Bioorg. Med. Chem. Lett. 2010, 20, 4602-4606.
9. Aoyama, Y.; Uenaka, M.; Kii, M.; Tanaka, M.; Konoike, T.; Hayasaki-Kajiwara, Y.; Naya, N.; Nakajima, M. Design, Synthesis and pharmacological evaluation of 3-benzylazetidine-2-onebased human chymase inhibitors. Bioorg. Med. Chem. 2001, 9, 3065-3075.
10. O'Boyle, N.M.; Greene, L.M.; Bergin, O.; Fichet, J.-B.; McCabe, T.; Lloyd, D.G.; Zisterer, D.M.; Meegan, M.J. Synthesis, Evaluation and structural studies of antiproliferative tubulin-targeting azetidin-2-ones. Bioorg. Med. Chem. 2011, 19, 2306-2325.
11. Galletti, P.; Quintavalla, A.; Ventrici, C.; Giannini, G.; Cabri, W.; Penco, S.; Gallo, G.; Vincenti, S.; Giacomini, D. Azetidinones as zinc-binding groups to design selective HDAC8 inhibitors. Chem. Med. Chem. 2009, 4, 1991-2001.
12. Tripodi, F.; Pagliarin, R.; Fumagalli, G.; Bigi, A.; Fusi, P.; Orsini, F.; Frattini, M.; Coccetti, P. Synthesis and biological evaluation of 1,4-diaryl-2-azetidinones as specific anticancer agents: activation of adenosine monophosphate activated protein kinase and induction of apoptosis. J. Med. Chem. 2012, 55, 2112-2124.
13. Mehta, P.D.; Sengar, N.P.; Pathak, A.K. 2-Azetidinone-a new profile of various pharmacological activities. Eur. J. Med. Chem. 2010, 45, 5541-5560.
14. Gavernet, L.; Barrios, I.A.; Cravero, M.S.; Bruno-Blanch, L.E. Design, Synthesis, and anticonvulsant activity of some sulfamides. Bioorg. Med. Chem. 2007, 15, 5604-5614.
15. Chohan, Z.H. Metal-based antibacterial and antifungal sulfonamides: Synthesis, Characterization, and biological properties. Transit. Metal Chem. 2009, 34, 153-161.
16. Sasidharan, S.; Logeswaran S.; Latha, L.Y. Wound healing activity of Elaeis Guineensis leaf extract ointment. Int. J. Mol. Sci. 2012, 13, 336-347.
17. Schönfelder, U.; Abel, M.; Wiegand, C.; Klemm, D.; Elsner, P.; Hipler, U.-C. Influence of selected wound dressings on PMN elastase in chronic wound fluid and their antioxidative potential in vitro. Biomaterials 2005, 26, 6664-6673.
18. Melo-Silveira, R.F.; Fidelis, G.P.; Costa, M.S.; Telles, C.B.; Dantas-Santos, N.; de Oliveira Elias, S.; Ribeiro, V.B.; Barth, A.L.; Macedo, A.J.; Leite, E.L.; et al. In vitro antioxidant, Anticoagulant and antimicrobial activity and in inhibition of cancer cell proliferation by xylan extracted from Corn Cobs. Int. J. Mol. Sci. 2012, 13, 409-426.
19. Roy, P.; Amdekar, S.; Kumar, A.; Singh, R.; Sharma, P.; Singh, V. In vivo antioxidative property, antimicrobial and wound healing activity of flower extracts of Pyrostegia venusta (Ker Gawl) Miers. J. Ethnopharmacol. 2012, 140, 186-192.
20. Ghaisas, M.M.; Kshirsagar, S.B.; Sahane, R.S. Evaluation of wound healing activity of ferulic acid in diabetic rats. Int. Wound. J. 2012, doi:10.1111/j.1742-481X.2012.01119.x.
21. Chigurupati, S.; Mughal, M.R.; Chan, S.L.; Arumugam, T.V.; Baharani, A.; Tang, S.C.; Yu, Q.S.; Holloway, H.W.; Wheeler, R.; Poosala, S.; et al. A synthetic uric acid analog accelerates cutaneous wound healing in mice. PLoS One 2010, 5, e10044.
22. Naik, H.R.; Naik, H.S.; Naik, T.R.; Naika, H.R.; Gouthamchandra, K.; Mahmood, R.; Ahamed, B.M. Synthesis of novel benzo[h]quinolines: Wound healing, Antibacterial, DNA binding and in vitro antioxidant activity. Eur. J. Med. Chem. 2009, 44, 981-989.
23. Parasca, O.M.; Lupascu, F.; Vasile, C.; Mares, M.; Nastasa, V.; Profire, L. New hydrazynes with sulfonamidic structure: Synthesis, Characterization and biological activity. Rev. Med. Chir. 2013, in press.
24. European Committee for Antimicrobial Susceptibility Testing (EUCAST) of the European Society for Clinical Microbiology and Infectious Diseases (ESCMID). EUCAST Definitive Document E. Def 3.1.: Determination of minimum inhibitory concentrations (MICs) of antibacterial agents by agar dilution. Clin. Microbiol. Infect. 2000, 6, 509-515.
25. Cacic, M.; Molnar, M.; Sarkanj, B.; Has-Schon, E.; Rajkovic, V. Synthessis and antioxidant activity of some new coumarinyl-1,3-Thiazolidine-4- ones. Molecules 2010, 15, 6795-6809.
26. Cervellati, R.; Galletti, P.; Greco, E.; Cocuzza, C.E.; Musumeci, R.; Bardini, L.; Paolucci, F.; Pori, M.; Soldati, R.; Giacomini, D. Monocyclic β-lactams as antibacterial agents: Facing antioxidant activity of N-methylthio-azetidinones. Eur. J. Med. Chem. 2012, 60, 340-349.
27. Osorio, M.; Aravena, J.; Vergara A.; Taborga, L.; Baeza, E.; Catalán, K.; González, C.; Carvajal, M.; Carrasco. H.; Espinoza, L. Synthesis and DPPH radical scavenging activity of prenylated phenol derivatives. Molecules 2012, 17, 556-570.