European Journal of Chemistry 2011, 2(3), 359-364 | doi: https://doi.org/10.5155/eurjchem.2.3.359-364.439 | Get rights and content






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

Facile synthesis of 3-(1-(4'-(3-chloro-2-(substituted phenyl)-4-oxoazetidin-1-yl)biphenyl-4-yl)-5-oxo-2-phenyl-1H-imidazol-4(5H)-ylidene)indolin-2-ones: β-Lactam derivatives as antimicrobes


Abha Bishnoi (1,*) , Krishna Srivastava (2) , Suruchi Singh (3) , Chandrakant Mani Tripathi (4)

(1) Department of Chemistry, Lucknow University, University Road, Lucknow-226007, India
(2) Department of Chemistry, Shri Ramswaroop Memorial College of Engineering and Management, Faizabad Road, Lucknow-227105, India.
(3) Department of Chemistry, Lucknow University, University Road, Lucknow-226007, India
(4) Division of Fermentation Technology, Central Drug Research Institute, Chattar Manzil Palace, Lucknow-226001, India
(*) Corresponding Author

Received: 06 Apr 2011 | Revised: 05 May 2011 | Accepted: 06 May 2011 | Published: 30 Sep 2011 | Issue Date: September 2011

Abstract


A facile synthesis of b-lactam derivatives; 3-(1-(4'-(3-chloro-2-(substituted phenyl)-4-oxoazetidin-1-yl)biphenyl-4-yl)-5-oxo-2-phenyl-1H-imidazol-4(5H)-ylidene)indolin-2-ones (6a-e) and 3-(1-(3-chloro-2-(substituted phenyl)-4-oxoazetidin-1-yl)-5-oxo-2-phenyl-1H-imidazol-4(5H)-ylidene)indolin-2-ones (7a-e) is described herein. The title compounds 6a-e and 7a-e were evaluated for their in vitro antimicrobial activity against Candida albicans and Bacillus subtilis respectively using a two fold serial dilution technique. Investigation revealed that 2-hydroxy phenyl function at b-lactam ring in compounds 6d and 7d is a key factor for both antifungal and antibacterial activity, as newly designed compounds 6d and 7d exhibited good biological activity with minimum inhibitory concentration (MIC)12.5 mg/mL against Candida albicans and Bacillus subtilis respectively.

2_3_359_364_800


Keywords


Imidazole; Azetidinones; β-lactam ring; Bacillus subtilis; Candida albicans; Antimicrobial activity

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.2.3.359-364.439

Links for Article


| | | | |

| | | | | | |

Related Articles




Article Metrics

This Abstract was viewed 1039 times | PDF Article downloaded 319 times

Funding information


University Grants Commission, Central Drug Research Institute, India

Citations

/


[1]. Nikhilesh Arya, Archana Y. Jagdale, Tushar A. Patil, Shradha S. Yeramwar, Sidharam S. Holikatti, Jaya Dwivedi, Chamanlal J. Shishoo, Kishor S. Jain
The chemistry and biological potential of azetidin-2-ones
European Journal of Medicinal Chemistry  74, 619, 2014
DOI: 10.1016/j.ejmech.2014.01.002
/


[2]. Abha Bishnoi, Anil Kumar Tiwari, Suruchi Singh, Arun Sethi, Chandrakant Mani Tripathi, Bikram Banerjee
Synthesis, characterization, and biological evaluation of novel thiazole and pyrazole derivatives of quinoline-4-carboxylic acid as potential antimicrobial agents
Medicinal Chemistry Research  22(7), 3527, 2013
DOI: 10.1007/s00044-012-0333-2
/


References

[1]. Rang, H. P.; Dale, M. M.; Ritter, J. M.; Flower, R. J. Rang and Daleâs Pharmacology, Churchill Livingstone, International Edition, USA, 2003.

[2]. Yu, L. T.; Ho, M. T.; Chang, C. Y.; Yang, T. K. Tetrahedron: Asym. 2007, 18(8), 949-962.
http://dx.doi.org/10.1016/j.tetasy.2007.03.015

[3]. Gupta, A.; Unadkat, J. D.; Mao, Q. J. Pharma. Sci. 2007, 96(12), 3226-3235.
http://dx.doi.org/10.1002/jps.20963
PMid:17518356

[4]. Schiller, S. D.; Fung, H. B. Clin. Ther. 2007, 29(9), 1862-1886.
http://dx.doi.org/10.1016/j.clinthera.2007.09.015
PMid:18035188

[5]. Ashok, M.; Holla, B. S.; Poojary, B. Eur. J. Med. Chem. 2007, 42(8), 1095-1101.
http://dx.doi.org/10.1016/j.ejmech.2007.01.015
PMid:17346860

[6]. Van Cutsem, J. M.; Thienpont, D. Chemotherapy 1972, 17(6), 392-404.
http://dx.doi.org/10.1159/000220875
PMid:4563141

[7]. Kokjohn, K.; Bradly, M.; Griffiiths, B.; Ghannoum, M. Int. J. Dermatol. 2003, 42(S1), 11-17.
http://dx.doi.org/10.1046/j.1365-4362.42.s1.4.x

[8]. McLean, K. J.; Marshall, K. R.; Richmond, A.; Hunter, I. S.; Fowler, K.; Kieser, T. Microbiology 2002, 148, 2937-2949.
PMid:12368427

[9]. Ucucu, U.; Karaburun, N. G.; Isikdag, I. Farmaco. 2001, 56(4), 285-290.
http://dx.doi.org/10.1016/S0014-827X(01)01076-X

[10]. Yesilada, A.; Koyunoglu, S.; Saygilia, N.; Kupeli, E.; Yesilada, E.; Bedir, E. Khanc, I. Arch. Pharm. Pharm. Med. Chem. 2004, 337, 96-104.

[11]. Quattara, L.; Debaert, M.; Cavier, R. Farmaco. (Sci) 1987, 42(6), 449-456.
PMid:2888689

[12]. Dutta, S.; Mariappan, G.; Roy, S.; Verma, M. Indian Drugs 2009, 46(7), 50-53.

[13]. Sengupta, A. K.; Bhattacharya, T. J. Indian Chem. Soc. 1983, 60, 373-376.

[14]. Navidpour, L.; Shadnia, H.; Shafaroodi, H.; Amini, M.; Dehpour, A. R.; Shafiee, A. Bioorg. Med. Chem. 2007, 15(5), 1976-1982.
http://dx.doi.org/10.1016/j.bmc.2006.12.041

[15]. Driscoll, M. O.; Greenhalgh, K.; Young, A.; Turos, E.; Dickey, S.; Lim, D. V. Bioorg. Med Chem. 2008, 16(16), 7832-7837.
http://dx.doi.org/10.1016/j.bmc.2008.06.035

[16]. Banik, B. K.; Becker, F. F.; Banik, I. Bioorg. Med Chem. 2004, 12(10), 2523-2528.
http://dx.doi.org/10.1016/j.bmc.2004.03.033

[17]. Banik, B. K.; Banik, I.; Becker, F. F. Bioorg. Med Chem. 2005, 13(11), 3611-3622.
http://dx.doi.org/10.1016/j.bmc.2005.03.044

[18]. Banik, B. K.; Banik, I.; Becker, F. F. Eur. J. Med Chem. 2010, 45(2), 846-848.
http://dx.doi.org/10.1016/j.ejmech.2009.11.024
PMid:19962794

[19]. Zhang, W.; Richardson, R. D.; Chamni, S.; Smith, J. W.; Romo, D. Bioorg. Med Chem. Lett. 2008, 18(7), 2491-2494.
http://dx.doi.org/10.1016/j.bmcl.2008.02.043

[20]. National Committee for Clinical Laboratory Standards. Performance standards for antimicrobial disk susceptibility tests. Approved standard. NCCLS document M2-A5. Wayne, Pa: National Committee for Clinical Laboratory Standards; 1997.

[21]. Sahm, D. F.; Washington, J. A. Manual of Clinical Microbiology, 5th Ed., ASM, Washington DC, 1991.

[22]. Lopez, R.; Sordo, T. L.; Sordo, J. A.; Gonzalez, J. J. Org. Chem. 1993, 58, 7036-7037.
http://dx.doi.org/10.1021/jo00077a022

[23]. VanBrabandt, W.; Vanwalleghem, M.; Dâhooghe, M.; De Kimpe, N. J. Org. Chem. 2006, 71, 7083-7086.
PMid:16930070

How to cite


Bishnoi, A.; Srivastava, K.; Singh, S.; Tripathi, C. Eur. J. Chem. 2011, 2(3), 359-364. doi:10.5155/eurjchem.2.3.359-364.439
Bishnoi, A.; Srivastava, K.; Singh, S.; Tripathi, C. Facile synthesis of 3-(1-(4'-(3-chloro-2-(substituted phenyl)-4-oxoazetidin-1-yl)biphenyl-4-yl)-5-oxo-2-phenyl-1H-imidazol-4(5H)-ylidene)indolin-2-ones: β-Lactam derivatives as antimicrobes. Eur. J. Chem. 2011, 2(3), 359-364. doi:10.5155/eurjchem.2.3.359-364.439
Bishnoi, A., Srivastava, K., Singh, S., & Tripathi, C. (2011). Facile synthesis of 3-(1-(4'-(3-chloro-2-(substituted phenyl)-4-oxoazetidin-1-yl)biphenyl-4-yl)-5-oxo-2-phenyl-1H-imidazol-4(5H)-ylidene)indolin-2-ones: β-Lactam derivatives as antimicrobes. European Journal of Chemistry, 2(3), 359-364. doi:10.5155/eurjchem.2.3.359-364.439
Bishnoi, Abha, Krishna Srivastava, Suruchi Singh, & Chandrakant Mani Tripathi. "Facile synthesis of 3-(1-(4'-(3-chloro-2-(substituted phenyl)-4-oxoazetidin-1-yl)biphenyl-4-yl)-5-oxo-2-phenyl-1H-imidazol-4(5H)-ylidene)indolin-2-ones: β-Lactam derivatives as antimicrobes." European Journal of Chemistry [Online], 2.3 (2011): 359-364. Web. 22 Jan. 2020
Bishnoi, Abha, Srivastava, Krishna, Singh, Suruchi, AND Tripathi, Chandrakant. "Facile synthesis of 3-(1-(4'-(3-chloro-2-(substituted phenyl)-4-oxoazetidin-1-yl)biphenyl-4-yl)-5-oxo-2-phenyl-1H-imidazol-4(5H)-ylidene)indolin-2-ones: β-Lactam derivatives as antimicrobes" European Journal of Chemistry [Online], Volume 2 Number 3 (30 September 2011)

DOI Link: https://doi.org/10.5155/eurjchem.2.3.359-364.439

| | | | |

| | | | | |

Save to Zotero Save to Mendeley

European Journal of Chemistry 2011, 2(3), 359-364 | doi: https://doi.org/10.5155/eurjchem.2.3.359-364.439 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2019  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 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.

hatay escort hatay escort corlu escort corum escort burgaz escort giresun escort aydin escort ordu escort erzincan escort hatay escort sivas escort rize escort edirne escort aksaray escort kibris escort isparta escort erzurum escort tekirdag escort usak escort urfa escort kastamonu escort kibris escort manisa escort giresun escort urfa escort nevsehir escort sivas escort yalova escort ordu escort hatay escort yalova escort amasya escort kayseri escort ordu escort maras escort canakkale escort yalova escort balikesir escort manisa escort urfa escort mugla escort trabzon escort bolu escort corlu escort diyarbakir escort isparta escort kutahya escort elazig escort erzurum escort sakarya escort afyon escort kutahya escort konya escort agri escort cesme escort sinop escort sivas escort konya escort kibris escort adapazari escort luleburgaz escort adana escort kibris escort rize escort sakarya escort alanya escort isparta escort burdur escort konya escort bitlis escort canakkale escort sivas escort amasya escort mus escort aydin escort van escort yalova escort kastamonu escort mardin escort bolu escort afyon escort sakarya escort isparta escort tokat escort trakya escort bayburt escort urfa escort mardin escort