Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

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

Research Article

Synthesis and Evaluation of Isatin Derivatives as Antifungal Agents

Author(s): Monika Dawar , Divya Utreja*, Ritu Rani and Komalpreet Kaur

Volume 17, Issue 3, 2020

Page: [199 - 205] Pages: 7

DOI: 10.2174/1570178616666190724120308

Price: $65

Abstract

Various types of isatin derivatives were synthesized by reacting isatin with different reagents viz substituted acetophenones, sodium nitrate, hydroxylamine hydrochloride and hydrazine hydrate. Characterization of the synthesized compounds was done by using various spectral techniques such as IR, 1HNMR, 13CNMR, elemental analysis and mass spectrometry. Synthesized compounds were further evaluated for their antifungal activity against Helminthosporium oryzae, Rhizoctonia solani and Fusarium moniliforme using poison food technique. 3-(2-Oxo-2-phenylethylidene) indolin- 2-one showed significant mycelium inhibition against all tested rice fungi.

Keywords: Isatin, antifungal activity, poison food technique, Helminthosporium oryzae, Rhizoctonia solani and Fusarium moniliforme, acetophenones.

Graphical Abstract
[1]
Khan, F.A.; Maalik, A.; Noor, T.; Zaidi, A.; Farooq, U.; Bukhari, S.M. Trop. J. Pharm. Res., 2015, 14, 1937-1942.
[http://dx.doi.org/10.4314/tjpr.v14i10.28]
[2]
Gang, C.; Hui, J.S.; Zhang, M.; Huo, F.; Zhang, J.; Hao, X.J.; Zhao, J. J. Chem. Cent. J., 2012, 6, 90-94.
[3]
Tang, Q.; Lin, L.; Ji, J.; Hu, H.; Liu, X.; Feng, X. Hetero., 2017, 23, 16447-16451.
[4]
Da Silva, J.F.M.; Garden, S.J.; Pinto, A.C. J. Braz. Chem. Soc., 2001, 12, 273-324.
[http://dx.doi.org/10.1590/S0103-50532001000300002]
[5]
Singh, G.S.; Desta, Z.Y. Chem. Rev., 2012, 112(11), 6104-6155.
[http://dx.doi.org/10.1021/cr300135y] [PMID: 22950860]
[6]
Mathur, G.; Nain, S. Med. Chem., 2014, 4, 417-427.
[7]
Sonawane, R.; Tripathi, R. Int. Lett. Chem. Phy. Astron., 2013, 12, 30-36.
[http://dx.doi.org/10.18052/www.scipress.com/ILCPA.12.30]
[8]
Tatsugi, J.; Ikuma, K.; Izawa, Y. Heterocycles, 1996, 43, 7-10.
[http://dx.doi.org/10.3987/COM-95-7272]
[9]
Patel, A.; Bari, S.; Talele, G.; Patel, J.; Sarangapani, M. Iran. J. Pharm. Res., 2006, 4, 249-254.
[10]
Vasanthi, R.; Rajendraprasad, Y.; Ramana, H. Int. J. Pharm. Chem. Biol. Sci., 2014, 4, 1066-1071.
[11]
Selvam, P.; Murgesh, N.; Chandramohan, M.; De Clercq, E.; Keyaerts, E.; Vijgen, L.; Maes, P.; Neyts, J.; Ranst, M.V. Indian J. Pharm. Sci., 2008, 70(1), 91-94.
[http://dx.doi.org/10.4103/0250-474X.40339] [PMID: 20390088]
[12]
Paira, P.; Hazra, A.; Kumar, S.; Paira, R.; Sahu, K.B.; Naskar, S.; Saha, P.; Mondal, S.; Maity, A.; Banerjee, S.; Mondal, N.B. Bioorg. Med. Chem. Lett., 2009, 19(16), 4786-4789.
[http://dx.doi.org/10.1016/j.bmcl.2009.06.049] [PMID: 19564109]
[13]
Chen, G.; Su, H.J.; Song, Y.P.; Gao, Y.; Zhang, J.; Hao, X.J.; Zhao, J.R. Res. Chem. Intermed., 2013, 39, 3669-3678.
[http://dx.doi.org/10.1007/s11164-012-0870-9]
[14]
Andreani, A.; Burnelli, S.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Varoli, L.; Cremonini, M.A.; Placucci, G.; Cervellati, R.; Greco, E. Eur. J. Med. Chem., 2010, 45(4), 1374-1378.
[http://dx.doi.org/10.1016/j.ejmech.2009.12.035] [PMID: 20060202]
[15]
González, A.; Quirante, J.; Nieto, J.; Almeida, M.R.; Saraiva, M.J.; Planas, A.; Arsequell, G.; Valencia, G. Bioorg. Med. Chem. Lett., 2009, 19(17), 5270-5273.
[http://dx.doi.org/10.1016/j.bmcl.2009.03.004] [PMID: 19651509]
[16]
Zhen, X.; Peng, Z.; Zhao, S.; Han, Y.; Jin, Q.; Guan, L. Acta Pharm. Sin. B, 2015, 5(4), 343-349.
[http://dx.doi.org/10.1016/j.apsb.2015.01.008] [PMID: 26579465]
[17]
Pandeya, S.N.; Sriram, D.; Nath, G.; DeClercq, E. Eur. J. Pharm. Sci., 1999, 9(1), 25-31.
[http://dx.doi.org/10.1016/S0928-0987(99)00038-X] [PMID: 10493993]
[18]
Vine, K.L.; Matesic, L.; Locke, J.M.; Ranson, M.; Skropeta, D. Anticancer. Agents Med. Chem., 2009, 9(4), 397-414.
[http://dx.doi.org/10.2174/1871520610909040397] [PMID: 19442041]
[19]
London, C.A.; Malpas, P.B.; Wood-Follis, S.L.; Boucher, J.F.; Rusk, A.W.; Rosenberg, M.P.; Henry, C.J.; Mitchener, K.L.; Klein, M.K.; Hintermeister, J.G.; Bergman, P.J.; Couto, G.C.; Mauldin, G.N.; Michels, G.M. Clin. Cancer Res., 2009, 15(11), 3856-3865.
[http://dx.doi.org/10.1158/1078-0432.CCR-08-1860] [PMID: 19470739]
[20]
Mahlein, A.K. Plant Dis., 2016, 100(2), 241-251.
[http://dx.doi.org/10.1094/PDIS-03-15-0340-FE] [PMID: 30694129]
[21]
Liu, J.; Wang, X.; Mitchell, T.; Hu, Y.; Liu, X.; Dai, L.; Wang, G.L. Mol. Plant Pathol., 2010, 11(3), 419-427.
[http://dx.doi.org/10.1111/j.1364-3703.2009.00607.x] [PMID: 20447289]
[22]
Shaikh, M.H.; Subdedar, D.D.; Khan, F.A.K.; Khan, K.; Sangshetti, N.J.; Nawale, L. J. Heterocycl. Chem., 2016, 6, 1104-1116.
[23]
Yu, F.; Yan, S.; Hu, L.; Wang, Y. J. Org. Lett., 2011, 13, 4782-4785.
[http://dx.doi.org/10.1021/ol201783d]
[24]
Sharma, R.K.; Singh, S.; Utreja, D. Curr. Org. Synth., 2016, 13, 484-593.
[http://dx.doi.org/10.2174/1570179412666150905002356]
[25]
Vibha; Utreja, D.; Kaur, J.; Kaur, M. Agric. Res. J., 2018, 55, 313-317.
[http://dx.doi.org/10.5958/2395-146X.2018.00056.X]
[26]
Verma, V.; Utreja, D.; Kaur, J. Indian J. Heterocycl. Chem., 2019, 29, 11-20.
[27]
Kaur, J.; Utreja, D. Ekta; Jain, N.; Sharma, S. Curr. Org. Synth., 2019, 16, 17-37.
[http://dx.doi.org/10.2174/1570179415666181113144939]
[28]
Goyal, A.; Utreja, D.; Garg, A.; Sharma, V.K. Agric. Res. J., 2018, 55, 377-379.
[http://dx.doi.org/10.5958/2395-146X.2018.00070.4]
[29]
Kaur, K.; Utreja, D.; Grag, A.; Sharma, V.K. Plant Dis. Res., 2016, 31, 171-173.
[30]
Kaur, G.; Utreja, D. Ekta; Kaur, J. J. Pl. Dis. Res.,, 2016, 32, 288-231.
[31]
Anamika; Utreja, D.; Kaur, J.; Sharma, S. Indian J. Heterocycl. Chem., 2018, 28, 433-439.
[32]
Anamika; Utreja, D.; Ekta; Jain, N.; Sharma, S. Curr. Org. Chem., 2018, 22, 2507-2534.
[33]
Pakravan, P.; Kashanian, S.; Khodaei, M.M.; Harding, F.J. Pharmacol. Rep., 2013, 65(2), 313-335.
[http://dx.doi.org/10.1016/S1734-1140(13)71007-7] [PMID: 23744416]
[34]
Bedi, P.M.S.; Kaur, C.; Nepali, K.; Sharma, S. Indian Pat. Applic. 2012DE02318.12; , 2014.
[35]
Orsu, R.; Narsimha, S.; Reddy, V. Adv. Appl. Sci. Res., 2015, 6, 62-66.
[36]
Magiatis, P.; Polychronopoulos, P.; Skaltsounis, A.L.; Lozach, O.; Meijer, L.; Miller, D.B. J. Neurotoxicol. Teratol., 2010, 32, 212-219.
[http://dx.doi.org/10.1016/j.ntt.2009.12.005]
[37]
Siddiqui, N.; Singh, P.K.; Kumar, N.; Pathak, D. Pharm. Sin., 2015, 6, 30-40.
[38]
Mo, X.; Chen, C.H.; Liang, C.; Mo, D.L. Eur. J. Org. Chem., 2018, 2, 150-159.
[http://dx.doi.org/10.1002/ejoc.201701324]
[39]
Coffey, K.E.; Moreira, R.; Abbas, F.Z.; Murphy, G.K. Org. Biorg. Chem., 2014.
[http://dx.doi.org/10.1039/c4ob02213k]
[40]
Grover, R.K.; Moore, J.D. Phytopathology, 1962, 52, 876-879.
[41]
Singh, J.; Tripathi, N.N. Flavour Fragrance J., 1999, 14, 1-4.
[http://dx.doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<1:AID-FFJ735>3.0.CO;2-R]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy