European Journal of Chemistry 2011, 2(3), 359-364. doi:10.5155/eurjchem.2.3.359-364.439

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, Accepted: 06 May 2011, Published: 30 Sep 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

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DOI: 10.5155/eurjchem.2.3.359-364.439

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[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
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[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
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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. 17 Sep. 2019
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

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