Synthesis and in-vitro antibacterial activity of some alkoxy based N-substituted-5-(furan-2-yl)-phenyl-bis-pyrazolines

Mamta Rani, Mohamad Yusuf

Abstract


Bis-pyrazoline darivatives (2a-e) built around the alkyl chains of varying length were synthesized in good yield by refluxing bis-chalcones (1a-e) with phenyl hydrazine in CH3COOH and ethanol. The structures of these compounds were elucidated by IR, 1H NMR, 13C NMR, Mass (ESI) spectrometries and their purities were confirmed by elemental analyses. The antibacterial activity of these compounds were evaluated by the disc diffusion assay against two Gram-positive and two Gram-negative bacteria and then the minimum inhibitory concentration of compounds were determined. The compounds 1,4-bis[1-(2-oxyphenyl)-5-(furan-2-yl)-4,5-dihydro-1H-pyrazole] butane (2a) and 1,10-bis[1-(2-oxyphenyl)-5-(furan-2-yl)-4,5-dihydro-1H-pyrazole]decane (2e) are better antibacterial agent as compared to Tetracycline and Gentamicin.

3_1_21_25_800


Keyword(s)


Gentamicin; Tetracycline; Bis-chalcones; Bis-pyrazoline; Phenyl hydrazine; Antibacterial activity

European Journal of Chemistry, 3 (1), (2012), 21-25

Full Text:

PDF    /    /

DOI: http://dx.doi.org/10.5155/eurjchem.3.1.21-25.472

 

Cited-By

[1]. Probing the spectral response of a new class of bioactive pyrazoline derivative in homogeneous solvents and cyclodextrin nanocavities: a spectroscopic exploration appended by quantum chemical calculations and molecular docking analysis
Soumya Sundar Mati, Sunandan Sarkar, Soumyadipta Rakshit, Arindam Sarkar, Subhash Chandra Bhattacharya
RSC Advances  Volume: 3  Issue: 21  First page: 8071  Year: 2013  
/

[2]. Synthesis and in-vitro antibacterial activity of some bis-5-(thiophen-2-yl)-carbothioamide-pyrazoline derivatives
Mamta Rani, Mohamad Yusuf
European Journal of Chemistry  Volume: 3  Issue: 4  First page: 406  Year: 2012  
/

 


References

[1]. Deodhar, L. P.; Saraswathi, K.; Varudkar, V. J. Clin. Microbiol. 1991, 29, 853-856.

[2]. Goni-Urriza, M.; Cabdepuy, M.; Arpin, C.; Raymond, N.; Caumette, P.; Quentin, C. Appl. Environ. Microbiol. 2000, 66, 125-132.
http://dx.doi.org/10.1128/AEM.66.1.125-132.2000
PMid:10618213 PMCid:91795

[3]. Goni-Urriza, M.; Pineau, L.; Capdepuy, M.; Roques, C.; Caumette P.; Quentin, C. J. Antimicrob. Chemother. 2000, 46, 297-301.
http://dx.doi.org/10.1093/jac/46.2.297
PMid:10933657

[4]. Altschul, S. F.; Madden, T. L.; Schaffer, A. A.; Zhang, S.; Zhang, Z.; Miller, W.; Lipman, D. J. Nucleic Acids Res. 1997, 25, 3389-3402.
http://dx.doi.org/10.1093/nar/25.17.3389
PMid:9254694 PMCid:146917

[5]. Calzada, F.; Cervantes-Martinez, J. A.; Yepez-Mulia, L. J. Ethnopharmacol. 2005, 98, 191-193.
http://dx.doi.org/10.1016/j.jep.2005.01.019
PMid:15763382

[6]. Kapoor, K.; Chandra, M.; Nag, D.; Paliwal, J. K.; Gupta, R. C.; Saxena, R. C. Int. J. Clin. Pharmacol. Res. 1999, 19, 83-88.
PMid:10761537

[7]. Adagu, I. S.; Nolder, D.; Warhurst, D. C.; Rossignol, J. F. J. Antimicrob. Chemother. 2002, 49, 103-111.
http://dx.doi.org/10.1093/jac/49.1.103
PMid:11751773

[8]. Tiwari, N.; Dwivedi, B.; Nizamuddin, N. Boll. Chim. Farm.-Anno. 1989, 128, 332-335.

[9]. Sangwan, N. K.; Verma, B. S.; Dhindsa, K. S. Indian J. Chem. 1993, 32B, 508-512.

[10]. Farghaly, A. A.; Bekhit, A. A.; Park, J. Y. Arch. Pharm. Pharm. Med. Chem. 2000, 53, 333-337.

[11]. Kawazura, H.; Takahashi, Y.; Shiga, Y.; Shimada, F.; Ohto, N.; Tamura, A. Jpn. J. Pharmacol. 1997, 73, 317-324.
http://dx.doi.org/10.1254/jjp.73.317

[12]. Udupi, R. H.; Rao, S. N.; Bhat, A. R. Indian J. Heterocycl. Chem. 1998, 7, 217-220.

[13]. Holla, B. S.; Akberali, P. M.; Shivananda, M. K. Il Farmaco 2000, 55, 256-263.
http://dx.doi.org/10.1016/S0014-827X(00)00030-6

[14]. Palaska, E.; Aytemir, M.; Uzbay, I. T.; Erol, D. Eur. J. Med. Chem. 2001, 36, 539-543.
http://dx.doi.org/10.1016/S0223-5234(01)01243-0

[15]. Abdullah, M. A.; Khan, S. A. Molecules 2011, 16, 523-531.
http://dx.doi.org/10.3390/molecules16010523
PMid:21228758

[16]. Soliman, R.; Habib, N. S.; Ashour, F. A.; El-Taiebi, M. Boll. Chem. Far. 2001, 140, 140-148.

[17]. Abdullah, M. A.; Khan, S. A. Mater. Lett. 2011, 65, 1749-1752.
http://dx.doi.org/10.1016/j.matlet.2011.03.059

[18]. Prasad, Y. R.; Rao, A. L.; Prasoona, L.; Murali, K.; Kumar, P. R. Bioorg. Med. Chem. Lett. 2005, 15, 5030-5034.
http://dx.doi.org/10.1016/j.bmcl.2005.08.040

[19]. Ozdemir, Z.; Kandil, H. B.; Gumusel, B.; Calis, U.; Bilgin, A. A. Eur. J. Med. Chem. 2007, 42, 373-379.
http://dx.doi.org/10.1016/j.ejmech.2006.09.006
PMid:17069933

[20]. Ozdemir, A.; Turan-Zitouni, G.; Kaplancikli, Z. A.; Revial; G.; Guven, K. Eur. J. Med. Chem. 2007, 42, 403-409.
PMid:17125888

[21]. Gursoy, A.; Demirayak, S.; Capan, G.; Erol, K.; Vural, K. Eur. J. Med. Chem. 2000, 35, 359-364.
http://dx.doi.org/10.1016/S0223-5234(00)00117-3

[22]. Tae-Sook, J.; Kyung, S. K.; So-Jin, A.; Kyung-Hyun, C.; Sangku, L.; Woo, S. L. Bioorg. Med. Chem. Lett. 2004, 14, 2715-2717.
http://dx.doi.org/10.1016/j.bmcl.2004.03.079

[23]. Dannahardt, G.; Kiefer, W.; Kramer, G.; Maehrlein, S.; Nowe, U.; Fiebich, B. Eur. J. Med. Chem. 2000, 35, 499-510.
http://dx.doi.org/10.1016/S0223-5234(00)00150-1

[24]. Slee D. H.;, Romano S. J.; Yu, J.; Nguyen, T. N.; John, J. K.; Raheja, N. K.; Axe, F. U.; Jones, T. K.; Ripka, W. C. J. Med. Chem. 2001, 44, 2094-2107.
http://dx.doi.org/10.1021/jm000508c
PMid:11405647

[25]. Ucucu, U.; Karaburun, N. G.; Isıkdag, I. Il Farmaco 2001, 56, 285-290.
http://dx.doi.org/10.1016/S0014-827X(01)01076-X

[26]. Khabnadideh, S.; Rezaei, Z.; Khalafi-Nezhad, A.; Bahrinajafi, R.; Mahamadi, R.; Farrokhroz, A. A. Bioorg. Med. Chem. Lett. 2003, 13, 2863-2865.
http://dx.doi.org/10.1016/S0960-894X(03)00591-2

[27]. Gunay, N. S.; Capan, G.; Ulusoy, N.; Ergenc, N.; Otuk, G.; Kaya D. Il Farmaco 1999, 54, 826-831.
http://dx.doi.org/10.1016/S0014-827X(99)00109-3

[28]. Gupta, P.; Hameed, S.; Jain, R. Euro. J. Med. Chem. 2004, 39, 805-814.
http://dx.doi.org/10.1016/j.ejmech.2004.05.005
PMid:15337293

[29]. Soyer, Z.; Sultan, F.; Erol, K. K.; Pabuccuoglu, V. II Farmaco 2004, 59, 595-600.
http://dx.doi.org/10.1016/j.farmac.2003.07.011
PMid:15262528

[30]. Laufer, S. A.; Striegel, H. G.; Wagner, G. K. J. Med. Chem. 1993, 45, 4695-4705.
http://dx.doi.org/10.1021/jm020873z
PMid:12361396

[31]. Khan, S. A.; Yusuf, M. Eur. J. Med. Chem. 2009, 44, 2270-2274.
http://dx.doi.org/10.1016/j.ejmech.2008.06.008
PMid:18715679

[32]. Khan, S. A.; Yusuf, M. Eur. J. Med. 2009, 44, 2597-2600.
http://dx.doi.org/10.1016/j.ejmech.2008.09.004
PMid:19211172

[33]. Bauer, A. W.; Kirby, W. M. M.; Sherris, J. C.; Truck, M. Am. J. Clin. Pathol. 1966, 36, 493-496.


Refbacks

  • There are currently no refbacks.