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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Design, Synthesis and Antimicrobial Study of Novel 1-(1,3-benzothiazol-2- yl)-3-chloro-4H-spiro[azetidine-2,3'-indole]-2',4(1'H)-diones Through Ketene– imine Cycloaddition Reaction

Author(s): Divyani Gandhi, Ayushi Sethiya, Dinesh Kr. Agarwal, Prakash Prajapat and Shikha Agarwal*

Volume 17, Issue 2, 2020

Page: [141 - 148] Pages: 8

DOI: 10.2174/1570178616666190705153224

Price: $65

Abstract

The present study deals with the synthesis of novel 1-(1,3-benzothiazol-2-yl)-3-chloro-4Hspiro[ azetidine-2,3'-indole]-2',4(1'H)-dione derivatives from the reaction of 3-(1,3-benzothiazol-2- ylimino)-1,3-dihydro-2H-indol-2-one derivatives with chloroacetyl chloride in the presence of triethylamine (TEA). The mechanism involved simple acid or base catalysed reaction through the formation of Schiff base followed by cyclisation via ketene–imine cycloaddition reaction. All synthesized compounds were characterized by FT-IR, 1H-NMR, 13C-NMR, and elemental analysis. The antimicrobial activities of the synthesized derivatives 5a-5g were examined via Micro Broth Dilution method against bacterial strains Bacillius subtilis, Staphylcoccus aureus, E. coli, P. aeruginosa, and fungal strain Candida albicans for determining MIC values. Ampicillin, chloramphenicol, and griseofulvin were used as standard drugs.

The MIC values for antimicrobial activity of synthesized compounds were examined using Micro Broth Dilution method. Compounds 5a, 5b, and 5c were found effective against E. coli (MTCC 442) and P.aeruginosa (MTCC 441) and all compounds showed moderate to excellent activity against Streptococcus aureus (MTCC 96) and Bacillius subtilis (MTCC 441). Regarding the antifungal screening, compounds 5a, 5b, and 5c exhibited excellent activity against Candida albicans MTCC 227. 1-(1,3-benzothiazol-2-yl)-3-chloro-4H-spiro[azetidine-2,3'-indole]-2',4(1'H)-dione derivatives may be used as potential lead molecules as effective antimicrobial agents.

Keywords: Spirooxindole, azetidine, benzothiazole, cycloaddition, antimicrobial activity, Candida albicans.

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[1]
Barry, A.L. The antimicrobial susceptibility test; Principle and Practice; Illus Lea and Febiger: Philadelphia, USA, 1976.
[2]
Nathan, C. Nature, 2004, 431(7011), 899-902.
[http://dx.doi.org/10.1038/431899a] [PMID: 15496893]
[3]
Ishige, T.; Honda, K.; Shimizu, S. Curr. Opin. Chem. Biol., 2005, 9(2), 174-180.
[http://dx.doi.org/10.1016/j.cbpa.2005.02.001] [PMID: 15811802]
[4]
Isenberg, H.D. Clinical microbiology procedure handbook; ASM Press, 2004, Vol. II, .
[5]
Jones, K.E.; Patel, N.G.; Levy, M.A.; Storeygard, A.; Balk, D.; Gittleman, J.L.; Daszak, P. Nature, 2008, 451(7181), 990-993.
[http://dx.doi.org/10.1038/nature06536] [PMID: 18288193]
[6]
Wills, E.A.; Redinbo, M.R.; Perfect, J.R.; Poeta, M.D. Expert Opin. Ther. Targets, 2000, 4, 265-296.
[7]
Desai, N.C.; Shihora, P.N.; Moradia, D.L. Indian J. Chem., 2007, 46B, 550-553.
[http://dx.doi.org/10.1002/chin.200729138]
[8]
Arun, Y.; Saranraj, K.; Balachandran, C.; Perumal, P.T. Eur. J. Med. Chem., 2014, 74, 50-64.
[http://dx.doi.org/10.1016/j.ejmech.2013.12.027] [PMID: 24445312]
[9]
Kumar, A.; Gupta, G.; Srivastava, S.; Bishnoi, A.K.; Saxena, R.; Kant, R.; Khanna, R.S.; Maulik, P.R.; Dwivedi, A. RSC Advances, 2013, 3, 4731-4735.
[http://dx.doi.org/10.1039/c3ra21595d]
[10]
Yu, B.; Shi, X.J.; Qi, P.P.; Yu, D.Q.; Liu, H.M.J. J. Steroid Biochem. Mol. Biol., 2014, 141, 121-134.
[http://dx.doi.org/10.1016/j.jsbmb.2014.01.015] [PMID: 24508598]
[11]
Sapnakumaria, M.; Narayanaa, B.; Shashidharab, K.S.; Sarojinic, B.K. J. Taibah Uni. Sci., 2017, 11, 1008-1018.
[http://dx.doi.org/10.1016/j.jtusci.2017.04.002]
[12]
Kidwai, M.; Jain, A.; Singh, S.; Nemayash, V.; Luthra, P.M. Indian J. Chem., 2014, 53B, 399-411.
[13]
Pelit, E. J. Chem., 2017, 9161505, 1-9.
[http://dx.doi.org/10.1155/2017/9161505]
[14]
Hagiwara, K.; Murakami, T.; Xue, G.; Shimizu, Y.; Takeda, E.; Hashimoto, Y.; Honda, K.; Kondoh, Y.; Osada, H.; Tsunetsugu-Yokota, Y.; Aida, Y. Biochem. Biophys. Res. Commun., 2010, 403(1), 40-45.
[http://dx.doi.org/10.1016/j.bbrc.2010.10.107] [PMID: 21036153]
[15]
Battles, M.B.; Langedijk, J.P.; Furmanova-Hollenstein, P.; Chaiwatpongsakorn, S.; Costello, H.M.; Kwanten, L.; Vranckx, L.; Vink, P.; Jaensch, S.; Jonckers, T.H.; Koul, A.; Arnoult, E.; Peeples, M.E.; Roymans, D.; McLellan, J.S. Nat. Chem. Biol., 2016, 12(2), 87-93.
[http://dx.doi.org/10.1038/nchembio.1982] [PMID: 26641933]
[16]
Wang, Q.Y.; Dong, H.; Zou, B.; Karuna, R.; Wan, K.F.; Zou, J.; Susila, A.; Yip, A.; Shan, C.; Yeo, K.L.; Xu, H.; Ding, M.; Chan, W.L.; Gu, F.; Seah, P.G.; Liu, W.; Lakshminarayana, S.B.; Kang, C.; Lescar, J.; Blasco, F.; Smith, P.W.; Shi, P.Y. J. Virol., 2015, 89(16), 8233-8244.
[http://dx.doi.org/10.1128/JVI.00855-15] [PMID: 26018165]
[17]
Zou, B.; Chan, W.L.; Ding, M.; Leong, S.Y.; Nilar, S.; Seah, P.G.; Liu, W.; Karuna, R.; Blasco, F.; Yip, A.; Chao, A.; Susila, A.; Dong, H.; Wang, Q.Y.; Xu, H.Y.; Chan, K.; Wan, K.F.; Gu, F.; Diagana, T.T.; Wagner, T.; Dix, I.; Shi, P.Y.; Smith, P.W. ACS Med. Chem. Lett., 2015, 6(3), 344-348.
[http://dx.doi.org/10.1021/ml500521r] [PMID: 25878766]
[18]
He, W.Y.; Gao, R.M.; Li, X.Q.; Jiang, J.D.; Li, Y.H. Yao Xue Xue Bao, 2010, 45(3), 395-398.
[PMID: 21351519]
[19]
Saha, S.; Acharya, C.; Pal, U.; Chowdhury, S.R.; Sarkar, K.; Maiti, N.C.; Jaisankar, P.; Majumder, H.K. Antimicrob. Agents Chemother., 2016, 60(10), 6281-6293.
[http://dx.doi.org/10.1128/AAC.00352-16] [PMID: 27503653]
[20]
Prasanna, P.; Balamurugan, K.; Perumal, S.; Yogeeswari, P.; Sriram, D. Eur. J. Med. Chem., 2010, 45(12), 5653-5661.
[http://dx.doi.org/10.1016/j.ejmech.2010.09.019] [PMID: 20932607]
[21]
Ding, K.; Wang, G.; Deschamps, J.R.; Parrish, D.A.; Wang, S. Tetrahedron Lett., 2005, 46, 5949-5951.
[http://dx.doi.org/10.1016/j.tetlet.2005.06.114]
[22]
Suresh Kumar, R.; Ashraf Ali, M.; Osman, H.; Ismail, R.; Choon, T.S.; Yoon, Y.K.; Wei, A.C.; Pandian, S.; Manogaran, E. Bioorg. Med. Chem. Lett., 2011, 21(13), 3997-4000.
[http://dx.doi.org/10.1016/j.bmcl.2011.05.003] [PMID: 21621414]
[23]
Agarwal, S.; Gandhi, D.; Kalal, P. Lett. Org. Chem., 2017, 14, 729-742.
[http://dx.doi.org/10.2174/1570178614666170707160654]
[24]
Xu, Y.S.; Zeng, C.C.; Jiao, Z.G.; Hu, L.M.; Zhong, R.G. Molecules, 2009, 14(2), 868-883.
[http://dx.doi.org/10.3390/molecules14020868] [PMID: 19255545]
[25]
Gull, Y.; Rasool, N.; Noreen, M.; Nasim, F.U.; Yaqoob, A.; Kousar, S.; Rasheed, U.; Bukhari, I.H.; Zubair, M.; Islam, M.S. Molecules, 2013, 18(8), 8845-8857.
[http://dx.doi.org/10.3390/molecules18088845] [PMID: 23892631]
[26]
Arora, P.; Das, S.; Ranawat, M.S.; Arora, N.; Gupta, M.M. J. Chem. Pharm. Res., 2010, 2, 317-323.
[27]
Mahajan, D.P.; Bhosale, J.D.; Bendre, R.S. J. Applicable Chem., 2013, 2, 765-771.
[28]
Yar, M.S.; Ansari, Z.H. Acta Pol. Pharm., 2009, 66(4), 387-392.
[PMID: 19702170]
[29]
Mariappan, G.; Prabhat, P.; Sutharson, L.; Banerjee, J.; Patangia, U.; Nath, S. J. Korean Chem. Soc., 2012, 56, 251-256.
[http://dx.doi.org/10.5012/jkcs.2012.56.2.251]
[30]
Sarkar, S.; Dwivedi, J.; Chauhan, R. J. Pharm. Res., 2013, 7, 439-442.
[http://dx.doi.org/10.1016/j.jopr.2013.05.008]
[31]
Wang, S.; Chen, Y.; Zhao, S.; Xu, X.; Liu, X.; Liu, B.F.; Zhang, G. Bioorg. Med. Chem. Lett., 2014, 24(7), 1766-1770.
[http://dx.doi.org/10.1016/j.bmcl.2014.02.031] [PMID: 24618300]
[32]
Ji, Z.; Zhou, F.; Wei, S. Bioorg. Med. Chem. Lett., 2015, 25(19), 4065-4068.
[http://dx.doi.org/10.1016/j.bmcl.2015.08.051] [PMID: 26318996]
[33]
Bandyopadhyay, P.; Sathe, M.; Tikar, S.N.; Yadav, R.; Sharma, P.; Kumar, A.; Kaushik, M.P. Bioorg. Med. Chem. Lett., 2014, 24(13), 2934-2939.
[http://dx.doi.org/10.1016/j.bmcl.2014.04.082] [PMID: 24857290]
[34]
Alborz, M.; Jarrahpour, A.; Pournejati, R.; Karbalaei-Heidari, H.R.; Sinou, V.; Latour, C.; Brunel, J.M.; Sharghi, H.; Aberi, M.; Turos, E.; Wojtas, L. Eur. J. Med. Chem., 2018, 143, 283-291.
[http://dx.doi.org/10.1016/j.ejmech.2017.11.053] [PMID: 29197733]
[35]
Gandhi, D.; Kalal, P.; Agarwal, D.; Bhargava, A.; Jangid, D.; Agarwal, S. Phosphorous Sulfur Silicon, 2018, 193, 840-847.
[http://dx.doi.org/10.1080/10426507.2018.1514502]
[36]
Farajia, L.; Shahkaramib, S.; Nadric, H.; Moradic, A.; Saeedid, M.; Foroumadia, A.; Ramazanib, A.; Haririane, I.; Ganjalif, M.R.; Shafieea, A.; Khoobia, M. J. Chem. Res., 2017, 41, 30-35.
[http://dx.doi.org/10.3184/174751917X14836231670980]
[37]
Nong, W.; Zhao, A.; Wei, J.; Cheng, H.; Luoa, X.; Lin, C. RSC Advances, 2018, 8, 6231-6241.
[http://dx.doi.org/10.1039/C7RA13397A]
[38]
Sannigrahi, M. Tetrahedron, 1999, 55, 9007-9071.
[http://dx.doi.org/10.1016/S0040-4020(99)00482-2]
[39]
Kang, T.H.; Matsumoto, K.; Tohda, M.; Murakami, Y.; Takayama, H.; Kitajima, M.; Aimi, N.; Watanabe, H. Eur. J. Pharmacol., 2002, 444(1-2), 39-45.
[http://dx.doi.org/10.1016/S0014-2999(02)01608-4] [PMID: 12191580]
[40]
Garnick, R.L.; LeQuesne, P.W. J. Am. Chem. Soc., 1978, 100, 4213-4219.
[http://dx.doi.org/10.1021/ja00481a034]
[41]
James, M.N.G.; Williams, G.J.B. Can. J. Chem., 1972, 50, 2407-2412.
[http://dx.doi.org/10.1139/v72-386]
[42]
Jossang, A.; Jossang, P.; Hadi, H.A.; Sevenet, T.; Bodo, B. J. Org. Chem., 1991, 56, 6527-6530.
[http://dx.doi.org/10.1021/jo00023a016]
[43]
Singh, G.S.; Desta, Z.Y. Chem. Rev., 2012, 112(11), 6104-6155.
[http://dx.doi.org/10.1021/cr300135y] [PMID: 22950860]
[44]
Afsah, E.M.; Elmorsy, S.S.; Abdelmageed, S.M.; Zaki, E.Z. Heterocycl. Commun, 2016.
[http://dx.doi.org/10.1515/zmb-2016-0130]
[45]
Senwar, K.R.; Sharma, P.; Reddy, T.S.; Jeengar, M.K.; Nayak, V.L.; Naidu, V.G.M.; Kamal, A.; Shankaraiah, N. Eur. J. Med. Chem., 2015, 102, 413-424.
[http://dx.doi.org/10.1016/j.ejmech.2015.08.017] [PMID: 26301558]
[46]
Liu, T.L.; Xue, Z.Y.; Tao, H.Y.; Wang, C.J. Org. Biomol. Chem., 2011, 9(6), 1980-1986.
[http://dx.doi.org/10.1039/c0ob00943a] [PMID: 21270976]
[47]
Wang, L.; Shi, X.M.; Dong, W.P.; Zhu, L.P.; Wang, R. Chem. Commun. (Camb.), 2013, 49(33), 3458-3460.
[http://dx.doi.org/10.1039/c3cc40669e] [PMID: 23507800]
[48]
Wang, Y.M.; Zhang, H.H.; Li, C.; Fan, T.; Shi, F. Chem. Commun. (Camb.), 2016, 52(9), 1804-1807.
[http://dx.doi.org/10.1039/C5CC07924A] [PMID: 26530257]
[49]
Hasaninejada, A.; Golzar, N.; Beyrati, M.; Zare, A.; Doroodmand, M.M. J. Mol. Catal. Chem., 2013, 372, 137-150.
[http://dx.doi.org/10.1016/j.molcata.2013.02.022]
[50]
Du, D.; Hu, Z.; Jin, J.; Lu, Y.; Tang, W.; Wang, B.; Lu, T. Org. Lett., 2012, 14(5), 1274-1277.
[http://dx.doi.org/10.1021/ol300148f] [PMID: 22352352]
[51]
Alizadeh, A.; Mokhtari, J. Tetrahedron, 2011, 67, 3519-3523.
[http://dx.doi.org/10.1016/j.tet.2011.03.032]
[52]
Ghahremanzadeh, R.; Ahadi, S.; Shakibaei, G.I.; Bazgir, A. Tetrahedron Lett., 2010, 51, 499-502.
[http://dx.doi.org/10.1016/j.tetlet.2009.11.041]
[53]
Singh, G.S.; Mmolotsi, B.J. J. Heterocycl. Chem., 2006, 43, 1665.
[http://dx.doi.org/10.1002/jhet.5570430636]
[54]
Singh, G.S.; Luntha, P. Eur. J. Med. Chem., 2009, 44(5), 2265-2269.
[http://dx.doi.org/10.1016/j.ejmech.2008.06.007] [PMID: 18672319]
[55]
Shah, R.J.; Modi, N.R.; Patel, M.J.; Patel, L.J.; Chauhan, B.F.; Patel, M.M. Med. Chem. Res., 2011, 20, 587-594.
[http://dx.doi.org/10.1007/s00044-010-9354-x]
[56]
Suryavanshi, J.P.; Pai, N.R. Ind. J. Chem. B, 2006, 45B, 1227-1230.
[57]
Hassan, K.M.; El-Shafei, A.K.; El-Kashef, H.S. II Zeitschr. fuer Naturfoschg B, 1978, 33B, 1515-1519.
[http://dx.doi.org/10.1515/znb-1978-1230]
[58]
Rathore, B.S.; Kumar, M.; Gupta, R.R. Bioorg. Med. Chem., 2006, 14(16), 5678-5682.
[http://dx.doi.org/10.1016/j.bmc.2006.04.009] [PMID: 16650998]
[59]
Rathore, B.S.; Gupta, V.; Gupta, R.R.; Kumar, M. Heteroatom Chem., 2007, 18, 81-86.
[http://dx.doi.org/10.1002/hc.20235]

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