It is the cache of http://www.eurjchem.com/index.php/eurjchem/article/view/282. It is a snapshot of the page. The current page could have changed in the meantime.
Tip: To quickly find your search term on this page, press Ctrl+F or ⌘-F (Mac) and use the find bar.

Synthesis, antimicrobial and antioxidant activities of 1-(1,4-benzodioxane-2-carbonyl)piperazine derivatives | Mallesha | European Journal of Chemistry

Synthesis, antimicrobial and antioxidant activities of 1-(1,4-benzodioxane-2-carbonyl)piperazine derivatives

Lingappa Mallesha, Kikkeri Narasimhasetty Mohana

Abstract


A series of novel 1-(1,4-benzodioxane-2-carbonyl)piperazine derivatives (6a-h) and (7a-e) were synthesized by nucleophilic substitution reaction of 1-(1,4-benzodioxane-2-carbonyl)piperazine (3) with various sulfonyl and acid chlorides. The newly synthesized compounds were characterized by elemental analyses, UV-visible, FT-IR, 1H NMR and LC-MS spectral studies. All compounds were evaluated for in vitro antibacterial, antifungal and antioxidant activities. Compound, 4-(2-trifluoromethyl)-benzenesulfonyl-1-(1,4-benzodioxane -2-carbonyl)piperazine (6b) exhibited significant antimicrobial activity against tested pathogenic bacterial and fungal strains. Compound, 4-(3-methoxy)-benzoyl-1-(1,4-benzodioxane-2-carbonyl)piperazine (7a) showed moderate antioxidant activity compared to standard drug by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay method.

2_2_193_199_800


Keyword(s)


1-(1,4-Benzodioxane-2-carbonyl)piperazine; Antimicrobial activity; Antioxidant activity; Structure-activity relationship; Sulphonyl chlorides; Acid chlorides

European Journal of Chemistry, 2 (2), (2011), 193-199

Full Text:

PDF    /    /

DOI: http://dx.doi.org/10.5155/eurjchem.2.2.193-199.282

 

Cited-By

[1]. Synthesis, characterization and antimicrobial activity of benzodioxane ring containing 1,3,4-oxadiazole derivatives
Habibullah Khalilullah, Shamshir Khan, Md. Shivli Nomani, Bahar Ahmed
Arabian Journal of Chemistry  Year: 2011  
/

[2]. Studies on synthesis of pyrimidine derivatives and their antimicrobial activity
C. Mallikarjunaswamy, L. Mallesha, D.G. Bhadregowda, Othbert Pinto
Arabian Journal of Chemistry  Year: 2012  
/

 


References

[1]. Bolognesi, M. L.; Budriesi, R.; Cavalli, A.; Chiarini, A.; Gotti, R.; Leonardi, A.; Minarini, A.; Poggesi, E.; Recanatini, M.; Rosini, M.; Tummiatti, V.; Melchiorre, C. J. Med. Chem. 1999, 42, 4214-4224.
doi:10.1021/jm991065j
PMid:10514291

[2]. Cantuti-Castelvetri, I.; Shukitt-Hale, B.; Joseph, J. A. Int. J. Dev. Neurosci. 2000, 18, 367-381.
doi:10.1016/S0736-5748(00)00008-3

[3]. Vaya, J.; Aviram, M. Curr. Med. Chem.-Immunol. Endocr. Metab. Agents 2001, 1, 99-117.
doi:10.2174/1568013013359168

[4]. Blokhina, O.; Virolainen, E.; Fagerstedt, K. V. Ann. Bot. 2003, 91, 179-194.
doi:10.1093/aob/mcf118
PMid:12509339

[5]. Hollman, P. C. H.; Katan, M. B. Food Chem. Toxicol. 1999, 37, 937-942.
doi:10.1016/S0278-6915(99)00079-4

[6]. Berkheij, M. Tetrahedron Lett. 2005, 46, 2369-2371.
doi:10.1016/j.tetlet.2005.02.085

[7]. Upadhayaya, R. S.; Sinha, N.; Jain, S.; Kishore, N.; Chandra, R.; Arora, S. K. Bioorg. Med. Chem. 2004, 12, 2225-2238.
doi:10.1016/j.bmc.2004.02.014

[8]. Choudhary, P.; Kumar, R.; Verma, A. K.; Singh, D. Bioorg. Med. Chem. 2006, 14, 1819-1826.
doi:10.1016/j.bmc.2005.10.032

[9]. Rossen, K.; Weissman, S. A.; Sager, J.; Reamer, R. A.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1995, 36, 6419-6422.
doi:10.1016/0040-4039(95)01345-I

[10]. Amin, E. A.; Welsh, W. J. J. Med. Chem. 2003, 44, 3849-3855.
doi:10.1021/jm010236t

[11]. Torisu, K.; Kobayashi, K.; Iwahashi, M.; Nakai, Y.; Onoda, T.; Nagase, T.; Sugimoto, I.; Okada, Y.; Matsumoto, R.; Nanbu, F.; Ohuchida, S.; Nakai, H.; Toda, M. Bioorg. Med. Chem. 2004, 12, 5361-5378.
doi:10.1016/j.bmc.2004.07.048

[12]. Bolchi, C.; Pallavicini, M.; Fumagalli, L.; Marchini, N.; Moroni, B.; Rusconi, C.; Valoti, E. Tetrahedron: Asymmetry 2005, 16, 1639-1643.
doi:10.1016/j.tetasy.2005.01.052

[13]. Marchini, N.; Bombieri, G.; Artali, R.; Bolchi, C.; Pallavicini, M.; Valoti, E. Tetrahedron: Asymmetry 2005, 16, 2099-2106.
doi:10.1016/j.tetasy.2005.05.010

[14]. Fang, Q. K.; Grover, P.; Han, Z.; McConville, F. X.; Rossi, R. F.; Olsson, D. J.; Kessler, D. W.; Wald, S. A.; Senanayake, C. H. Tetrahedron: Asymmetry 2001, 12, 2169-2174.
doi:10.1016/S0957-4166(01)00368-8

[15]. Yasuda, G.; Hasegawa, K.; Kuji, T.; Ogawa, N.; Shimura, G.; Umemura, S.; Tochikubo, O. Diabet. Med. 2005, 22, 1394-1400.
doi:10.1111/j.1464-5491.2005.01636.x
PMid:16176202

[16]. Grcman, M.; Vrecer, F.; Meden, A. J. Therm. Anal. Cal. 2002, 68, 373-387.
doi:10.1023/A:1016019214704

[17]. Sohn, Y. T.; Lee, Y. H. Arch. Pharm. Res. 2005, 28, 730-735.
doi:10.1007/BF02969365
PMid:16042084

[18]. Bolchi, C.; Fumagalli, L.; Moroni, B.; Pallavicini, M.; Valoti, E. Tetrahedron: Asymmetry 2003, 14, 2247-2251.
doi:10.1016/j.tetasy.2003.09.012

[19]. Bauer, A. W.; Kirby, W. M.; Sherris, J. C.; Turck, M. Am. J. Clin. Pathol. 1966, 45, 493-496.
PMid:5325707

[20]. Satish, S.; Mohana, D. C.; Raghavendra, M. P.; Raveesha, K. A. J. Agric. Technol. 2007, 3, 109-119.

[21]. Shih, M. H.; Ke, F. Y. Bioorg. Med. Chem. 2004, 12, 4633-4643.
doi:10.1016/j.bmc.2004.06.033

[22]. Gulcin, I.; Beydemir, S; Alici, H. A.; Elmastas, M.; Buyukokuroglu, M. E. Pharmacol. Res. 2004, 49, 59-66.
doi:10.1016/j.phrs.2003.07.012

[23]. Elmastas, M.; Gulcin, I.; Beydemir, S.; Kufrevioglu, O. I.; Aboul-Enein, H. Y. Anal. Lett. 2006, 39, 47-65.
doi:10.1080/00032710500423385

[24]. Hadi, J. S.; Alsalami, B. K.; Essa, A. H. J. Sci. Res. 2009, 1, 563-568.

[25]. Shafiee, A.; Emami, S.; Ghodsi, S.; Najjari, S.; Sorkhi, M.; Samadi, N.; Faramarzi, M. A.; Foroumadi, A. J. Iran. Chem. Soc. 2009, 6, 325-333.

[26]. Roopan, S. M.; Khan, F. N. Arkivoc 2009, 13, 161-169.


Refbacks

  • There are currently no refbacks.