European Journal of Chemistry 2014, 5(4), 557-562. doi:10.5155/eurjchem.5.4.557-562.1077

Synthesis and evaluation of antibacterial activity for a series of N-phthaloylglycine derivatives


Samreen Begum (1) , Shaikh Sirajuddin Nizami (2) , Sumayya Saied (3) , Syed Muhammad Shahid (4) , Fatima Zehra Basha (5,*)

(1) Department of Chemistry, University of Karachi, Karachi-75270, Pakistan
(2) Department of Chemistry, University of Karachi, Karachi-75270, Pakistan
(3) Department of Chemistry, University of Karachi, Karachi-75270, Pakistan
(4) The Karachi Institute of Biotechnology and Genetic Engineering (KIBGE), University of Karachi, Karachi-75270, Pakistan
(5) Hussain Ebrahim Jamal Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan
(*) Corresponding Author

Received: 19 Apr 2014, Accepted: 16 Jun 2014, Published: 31 Dec 2014

Abstract


Two series of N-phthaloylglycine derivatives were synthesized under Schotten-Baumann conditions. The first series consists of N-phthaloylglycine amides (4a-h), and the second one consists of benzimidazole derivatives of N-phthaloylglycine (6a-d). All the synthesized analogues were evaluated for their in vitro antimicrobial activity by using disc diffusion method. In the first series, compounds 4h (MIC, 0.5 mg/L), 4a (MIC, 0.6 mg/L), and 4e (MIC, 0.7 mg/L) were found to be the most potent against vancomycin-resistant Staphylococcus aureus (VRSA). Furthermore, three compounds i.e. 4g (MIC, 0.8 mg/L), 6b (MIC, 1.5 mg/L), and 4h (MIC, 1.6 mg/L) displayed good activity against methicillin-resistant Staphylococcus aureus (MRSA). All the synthesized compounds exhibited a wide range of antibacterial activity against all of the Staphylococcus aureus resistant strains tested. The structures of the synthesized compounds were characterized by IR, 1H NMR, 13C NMR and MS (EI).


Keywords


Antibacterial; Benzimidazole; Phthaloylglycine derivatives; Schotten-Baumann reaction; Methicillin-resistant Staphylococcus aureus; Vancomycin-resistant Staphylococcus aureus

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DOI: 10.5155/eurjchem.5.4.557-562.1077

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Citations

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[1]. Samreen Begum, Shaikh Sirajuddin Nizami, Uzma Mahmood, Summyia Masood, Sahar Iftikhar, Summayya Saied
In-vitro evaluation and in-silico studies applied on newly synthesized amide derivatives of N-phthaloylglycine as Butyrylcholinesterase (BChE) inhibitors
Computational Biology and Chemistry  74, 212, 2018
DOI: 10.1016/j.compbiolchem.2018.04.003
/


References

[1]. Beceiro, A.; Tomas, M.; Bou, G. Clin. Microbiol. Rev. 2013, 26, 185-230.
http://dx.doi.org/10.1128/CMR.00059-12

[2]. Bishnoi, A.; Singh, S.; Tiwari, A. K.; Sethi, A.; Tripathi, C. M. Med. Chem. 2013, 9, 45-52.
http://dx.doi.org/10.2174/157340613804488422

[3]. Batabyal, B.; Kundu, G. K. R.; Biswas, S. I. Res. J. Biological Sci. 2012, 1, 7, 65-71.

[4]. Kobayashi, S. D.; Musser, J. M.; DeLeo, F. R. mBio. 2012, 3, e00170-12.

[5]. Chambers, H. F.; DeLeo, F. R. Nat. Rev. Microbiol. 2009, 7, 629-641
http://dx.doi.org/10.1038/nrmicro2200

[6]. Grundmann, H.; Aires-de-Sousa, M.; Boyce, J.; Tiemersma, E. Lancet 2006, 368, 874-885.
http://dx.doi.org/10.1016/S0140-6736(06)68853-3

[7]. Klevens, R. M.; Morrison, M. A.; Nadle, J.; Petit, S.; Gershman, K.; Ray, S.; Harrison, L. H.; Lynfield, R.; Dumyati, G.; Townes, J. M.; Craig, A. S.; Zell, E. R.; Fosheim, G. E.; McDougal, L. K.; Carey, R. B.; Fridkin, S. K. JAMA 2007, 298, 1763-1771.
http://dx.doi.org/10.1001/jama.298.15.1763

[8]. Gravatt, G. L.; Baguley, B. C.; Wilson. J. Med. Chem. 1994, 37, 4338-4345.
http://dx.doi.org/10.1021/jm00051a010

[9]. Ahamed, A. J.; Kaliapillai, N. V.; Bathey, R. V.; Govindaraj, V. Orbital Elec. J. Chem. 2009, 1, 306-309.

[10]. Julijay, M. S.; Zduka, C. Acta. Pharm. 2005, 55, 387-399.

[11]. Neto, M. D. C.; Propheric, M. C. F.; Neto, B. B. J. Braz. Chem. Soc. 1993, 4, 139-142.
http://dx.doi.org/10.5935/0103-5053.19930030

[12]. Antunes, R.; Batista, H.; Srivastava, R. M.; Thomas, G.; Araujo, C. C. Bioorg. Med. Chem. Lett. 1998, 8, 3071-3076.
http://dx.doi.org/10.1016/S0960-894X(98)00558-7

[13]. Brana, M. F.; Ramose, A. Curr. Med. Chem. 2001, 1, 237-255.

[14]. Cyril, O. U.; Didier, M. L.; Johan, W. G.; Sriba, K. E. Arch. Pharm. Chem. 2001, 334, 323-331.
http://dx.doi.org/10.1002/1521-4184(200110)334:10<323::AID-ARDP323>3.0.CO;2-O

[15]. Nilotpal, B.; Rupam, J. S.; Andrei, S. B.; Jubaraj, B. B. Polyhedron 2006, 25, 17-24.
http://dx.doi.org/10.1016/j.poly.2005.06.057

[16]. Nilotpal, B.; Rupam, J. S.; Andrei, S. B.; Jubaraj, B. B. J. Mol. Struct. 2006, 791, 122-130.
http://dx.doi.org/10.1016/j.molstruc.2006.01.025

[17]. Shariat, M.; Abdollahi, S. Molecules 2004, 9, 705-712.
http://dx.doi.org/10.3390/90800705

[18]. Uzma, Y.; Mohammad, K. T.; Mohammad, H. B.; Naveeda, Y.; Madeleine, H. Acta. Cryt. E 2008, 64, o476-o477.

[19]. Wagner, E. C.; Millett, W. H. Org. Synth. Coll. 1943, 2, 65-67.

[20]. Laszlo, K.; Barbra, C. Strategic application of named reactions in organic synthesis Elsevier Academic Press, 2005.

[21]. Wilcox, C. F. Experimental Organic Chemistry, 5th edition Macmillan Publishing Company, New York, 1984.

[22]. Karami, B.; Ghashghaee, V.; Khodobakhshi, S. Chin. J. Chem. 2012, 30, 959-964.
http://dx.doi.org/10.1002/cjoc.201100206

[23]. Navneet, K.; Pratima, S.; Aastha, P.; Prasand, A. Int. J. Chem. Pharm. Sci. 2013, 14, 12-18.

[24]. Anshul, C.; Gurpreet, K.; Anil, K. S. Int. J. Pharm. Phytopharmacol. Res. 2012, 2, 148-159.

[25]. Kalirajan, R.; Leela, R.; Jubie, S.; Gowramma, B.; Gomathy, S.; Sankar, S.; Elango, K. Ind. J. Pharm. Edu. Res. 2010, 44, 358-362.

[26]. Haishan, W.; Ganesan, A. J. Org. Chem. 2000, 65, 1022-1030.
http://dx.doi.org/10.1021/jo9914364

[27]. Jennifer, D. K.; Philip, M.; Edward, G. M. Tetrahedron Lett. 2001, 42, 627-629.
http://dx.doi.org/10.1016/S0040-4039(00)02023-2

[28]. Celia, B. S.; Maria, I. A.; Isabel, A. P. J. Heterocyclic Chem. 1985, 22, 577-581.
http://dx.doi.org/10.1002/jhet.5570220274

[29]. Andreichikov, Yu. S.; Zalesov, V. V.; Podushkina, N. A. Khim. Farm. Zh. 1980, 14, 25-30.

[30]. Ashok, P.; Ganguly, S.; Murugesan, S. Der Pharma Chem. 2013, 5, 10-19.

[31]. Smith, E. C.; Althouse, P. M.; Shigley, J. W. J. Am. Oilchem. Soc. 1960, 37, 288-290.

[32]. Bauer, A. W.; Kirby, E.; Sherris, E. M.; Turk, M. Am. J. Clin. Pathol. 1966, 45, 493-496.

[33]. National Committee for Clinical Laboratory Standards (NCCLS). National committee for clinical laboratory standards for antimicrobial disc susceptibility test: approved standards. 6th edition. NCCLS, Wayen, Pennsylvania, USA, 2005.

[34]. Chandrasekaran, M.; Venkatesalu, V. J. Ethonopharmacol. 2005, 91, 105-108.
http://dx.doi.org/10.1016/j.jep.2003.12.012


How to cite


Begum, S.; Nizami, S.; Saied, S.; Shahid, S.; Basha, F. Eur. J. Chem. 2014, 5(4), 557-562. doi:10.5155/eurjchem.5.4.557-562.1077
Begum, S.; Nizami, S.; Saied, S.; Shahid, S.; Basha, F. Synthesis and evaluation of antibacterial activity for a series of N-phthaloylglycine derivatives. Eur. J. Chem. 2014, 5(4), 557-562. doi:10.5155/eurjchem.5.4.557-562.1077
Begum, S., Nizami, S., Saied, S., Shahid, S., & Basha, F. (2014). Synthesis and evaluation of antibacterial activity for a series of N-phthaloylglycine derivatives. European Journal of Chemistry, 5(4), 557-562. doi:10.5155/eurjchem.5.4.557-562.1077
Begum, Samreen, Shaikh Sirajuddin Nizami, Sumayya Saied, Syed Muhammad Shahid, & Fatima Zehra Basha. "Synthesis and evaluation of antibacterial activity for a series of N-phthaloylglycine derivatives." European Journal of Chemistry [Online], 5.4 (2014): 557-562. Web. 6 Dec. 2019
Begum, Samreen, Nizami, Shaikh, Saied, Sumayya, Shahid, Syed, AND Basha, Fatima. "Synthesis and evaluation of antibacterial activity for a series of N-phthaloylglycine derivatives" European Journal of Chemistry [Online], Volume 5 Number 4 (31 December 2014)

DOI Link: https://doi.org/10.5155/eurjchem.5.4.557-562.1077

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