European Journal of Chemistry 2017, 8(2), 183-187 | doi: https://doi.org/10.5155/eurjchem.8.2.183-187.1565 | Get rights and content






  OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

Some new [(chromen-4-ylamino)-ethyl]-azetidin-2-ones and their antibacterial activity


Ramiz Hoti (1) , Naser Troni (2,*) , Hamit Ismaili (3) , Gjyle Mulliqi-Osmani (4) , Veprim Thaçi (5)

(1) Department of Chemistry, University of Prishtina, Prishtina, 10000, Kosovo
(2) Department of Chemistry, University of Prishtina, Prishtina, 10000, Kosovo
(3) Department of Chemistry, University of Prishtina, Prishtina, 10000, Kosovo
(4) Institute of Public Health of Kosovo, Prishtina, 10000, Kosovo
(5) Department of Chemistry, University of Prishtina, Prishtina, 10000, Kosovo
(*) Corresponding Author

Received: 13 Mar 2017 | Revised: 18 May 2017 | Accepted: 29 Apr 2017 | Published: 30 Jun 2017 | Issue Date: June 2017

Abstract


A series of new azetidin-2-ones, on the basis of 3-nitrobenzopyran-2-one were synthesized by cyclo-condensation of various Schiff bases of coumarin with acetyl chloride. 4-(2-Amino-ethylamino)-3-nitro-chromen-2-one (3) is synthesized by condensation of 4-chloro-3-nitrobenzopyran-2-one (2) and ethane-1,2-diamine. The catalytic condensation of compound 3 with benzaldehyde, salicylaldehyde or 3-nitrobenzaldehyde yielded corresponding 4-[4-(benzylidene-amino)-phenylamino]-3-nitrobenzopyran-2-ones, 4a-c. The cyclization reac-tion of compounds 4a-c with acetyl chloride yielded corresponding substituted azetidin-2-ones, 5a-c. The structures of the obtained compounds were established by FT-IR and NMR spectrometric data and their elemental analysis. Prepared compounds 4a-c and 5a-c were screened for their antibacterial activity against S. aureus, E. coli and Klebsiella by disc diffusion method. Compounds 4a-c exhibited moderate antibacterial activity, whereas compounds 5a-c displayed significant activity against these microorganisms. The impact of substitutions in antimicrobial activity was also explored.


Keywords


Coumarin; Schiff bases; Azetidin-2-one; Benzopyran-2-one; Antibacterial activity; Catalytic condensation

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.8.2.183-187.1565

Links for Article


| | | | | | |

| | | | | | |

| |

Related Articles




Article Metrics

This Abstract was viewed 735 times | PDF Article downloaded 286 times

Funding information


Division of Organic Chemistry and Biochemistry Institute “Rudjer Boskovic”, Zagreb, Croatia

References

[1]. Christos, A.; Kontogiorgis, D.; Hadjipavlou-Litina, J. Bioorg. Med. Chem. Lett. 2004, 14(3), 611-614.
https://doi.org/10.1016/j.bmcl.2003.11.060

[2]. Stockley, I. Br. Med. J. (Clin. Res. Ed). 1982, 285(6350), 1278-1278.
https://doi.org/10.1136/bmj.285.6350.1278-b

[3]. Mohamed, H. M.; Abd El-Wahab, A. H. F.; Ahmed, K. A.; El-Agrody, A. M.; Bedair, A. H.; Eid, F. A.; Khafagy, M. M. Molecules 2012, 17, 971-988.
https://doi.org/10.3390/molecules17010971

[4]. De Souza, S. M.; Delle Monache, F.; Smania, A. Jr. Z. Naturforsch. C 2005, 60(9-10), 693-700.
https://doi.org/10.1515/znc-2005-9-1006

[5]. Rajasekaran, S.; Rao, G. K.; Pai, S.; Rajan, A. Inter. J. Chem. Tech. Res. 2011, 3(2), 555-559.

[6]. Montagner, C.; De Souza, S. M.; Groposoa, C.; Delle Monache, F.; Smania, E. F.; Smania, A. Jr. Z. Naturforsch. C 2008, 63(1-2), 21-28.
https://doi.org/10.1515/znc-2008-1-205

[7]. Pingaew, R.; Saekee, A.; Mandi, P.; Nantasenamat, C.; Prachayasittikul, S.; Ruchirawat, S.; Prachayasittikul, V. Eur. J. Med. Chem. 2014, 6(85), 65-76.
https://doi.org/10.1016/j.ejmech.2014.07.087

[8]. Bubols, G. B.; Vianna, D. R.; Medina-Remon, A.; von Poser, G.; Lamuela-Raventos, R. M.; Eifler-Lima, V. L.; Garcia, S. C. Mini Rev. Med. Chem. 2013, 13(3), 318-334.

[9]. Rodriguez, S. V.; Guinez, R. F.; Matos, M. J.; Santana, L.; Uriarte, E.; Lapier, M.; Maya, J. D.; Azar, C. O. Med. Chem. Commun. 2013, 4, 993-1000.
https://doi.org/10.1039/c3md00025g

[10]. Keri, R. S.; Sasidhar, B. S.; Nagaraja, B. M.; Santos, M. A. Eur. J. Med. Chem. 2015, 100, 257-269.
https://doi.org/10.1016/j.ejmech.2015.06.017

[11]. Kamelia, M.; Amin, D. E.; Abdel, R.; Yasmin, A. Bioorg. Med. Chem. 2008, 16(10), 5377-5388.
https://doi.org/10.1016/j.bmc.2008.04.021

[12]. Naveed, M.; Mohammad, S.; Haroon, K.; Achyut, A.; Khalid, M. K. J. Chem. 2013, Article ID 326263, 6 pages.

[13]. Ghate, M.; Kusanur, R. A.; Kulkarni, M. V. Eur. J. Med. Chem. 2005, 40(9), 882-887.
https://doi.org/10.1016/j.ejmech.2005.03.025

[14]. Kostova, I. Curr. HIV. Res. 2006, 4(3), 347-363.
https://doi.org/10.2174/157016206777709393

[15]. Atmaca, M.; Bilgin, H. M.; Obay, B. D.; Diken, H.; Kelle, M.; Kale, E. J. Physiol. Biochem. 2011, 67(4), 569-576.
https://doi.org/10.1007/s13105-011-0103-5

[16]. Kuppers, J.; Schulz-Fincke, A. C.; Palus, J.; Giurg, M.; Skarżewski, J.; Gütschow, M. Pharmaceuticals 2016, 9(3), 43, 1-11.

[17]. Rajasekaran, A.; Periasamy, M.; Venkatesan, S. J. Develop. Bio. Tiss. Eng. 2010, 2(1), 5-6.

[18]. Desai, S. R.; Laddi, U. V.; Bennur, R. S; Bennur, S. C. Indian J. Pharm. Sci. 2011, 73(4), 478-482.

[19]. Gupta, A.; Halve, A. K. Open Chem. J. 2015, 2, 1-6.
https://doi.org/10.2174/1874842201502010001

[20]. Gilani, S. J.; Alam, O.; Khan, S. A.; Siddiqui, N.; Kumar, H. Der Pharm. Lett. 2009, 1(2), 1-8.

[21]. Rao, A.; Carbone, A.; Chimirri, A.; De Clercq, E.; Monforte, A. M.; Monforte, P.; Pannecouque, C.; Zappala, M. Farmaco 2002, 57(9), 747-751.
https://doi.org/10.1016/S0014-827X(02)01268-5

[22]. Hoti, R.; Nura-Lama, A.; Mulliqi-Osmani, Gj.; Troni, N.; Gashi, F.; Ismaili, H.; Thaçi, V. Orbital: The Elect. J. Chem. 2014, 6(3), 184-190.

[23]. Hoti, R.; Kalaj, V.; Vehapi, I.; Ismaili, H.; Thaçi, V.; Bicaj, M. The FASEB J. Exp. Bio. 2010, lb487, Anaheim Ca. Apr. 2010,

[24]. Bauer, A. W. Am. J. Clin. Pathol. 1966, 44, 493-496.

How to cite


Hoti, R.; Troni, N.; Ismaili, H.; Mulliqi-Osmani, G.; Thaçi, V. Eur. J. Chem. 2017, 8(2), 183-187. doi:10.5155/eurjchem.8.2.183-187.1565
Hoti, R.; Troni, N.; Ismaili, H.; Mulliqi-Osmani, G.; Thaçi, V. Some new [(chromen-4-ylamino)-ethyl]-azetidin-2-ones and their antibacterial activity. Eur. J. Chem. 2017, 8(2), 183-187. doi:10.5155/eurjchem.8.2.183-187.1565
Hoti, R., Troni, N., Ismaili, H., Mulliqi-Osmani, G., & Thaçi, V. (2017). Some new [(chromen-4-ylamino)-ethyl]-azetidin-2-ones and their antibacterial activity. European Journal of Chemistry, 8(2), 183-187. doi:10.5155/eurjchem.8.2.183-187.1565
Hoti, Ramiz, Naser Troni, Hamit Ismaili, Gjyle Mulliqi-Osmani, & Veprim Thaçi. "Some new [(chromen-4-ylamino)-ethyl]-azetidin-2-ones and their antibacterial activity." European Journal of Chemistry [Online], 8.2 (2017): 183-187. Web. 3 Dec. 2020
Hoti, Ramiz, Troni, Naser, Ismaili, Hamit, Mulliqi-Osmani, Gjyle, AND Thaçi, Veprim. "Some new [(chromen-4-ylamino)-ethyl]-azetidin-2-ones and their antibacterial activity" European Journal of Chemistry [Online], Volume 8 Number 2 (30 June 2017)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item


DOI Link: https://doi.org/10.5155/eurjchem.8.2.183-187.1565

| | | | | | | |

| | | | | |

Save to Zotero Save to Mendeley



European Journal of Chemistry 2017, 8(2), 183-187 | doi: https://doi.org/10.5155/eurjchem.8.2.183-187.1565 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2010 - 2020  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2020 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.