Abstract
MORE (Microwave oriented reaction enhancement) green methodology was utilized to synthesize benzothiazol/thiazol-2-ylthiazolidin-4-ones and relatively assayed for their antifungal activity w.r.t precursors against three agriculturally important phytopathogenic fungi viz. Colletotrichum falcatum, Pyricularia grisea and Ustilago hordei. Thiazol-2-ylthiazolidin-4-ones displayed better inhibition of growth of fungi than their precursor’s thiazol-2-amines, with some compounds showing results comparable to their standard fungicides endorsing the effectiveness of chemical hybridization of thiazoles/benzothiazoles with thiazolidin-4-ones in a single molecule. In silico toxicity of all the compounds was found to be equivalent to the standard fungicides. Lipinski parameters were used to rationalize structure activity relation using statistical analysis software.
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Jyothsna, M., Kumar, P.M., Rani, D., and Vishwamitra, V., Int. J. Rec. Sci. Res., 2013, vol. 4, pp. 1504–1506.
FRAC CODE LIST 1: Fungicides sorted by FRAC Code, wwwfracinfo/impifasufledu
Pattan, S.R., Dighe, N.S., Nirmal, S.A., Merekar, A.N., Laware, R.B., Shinde, H.V., and Musmade, D.S., Asian J. Res. Chem., 2009, vol. 2, no. 2, pp. 196–201.
Ottana, R., Carotti Maccari, S., Landini, R.I., Chiricosta, G., Caciagli, B., Vigoritaa, M.G., and Mini, E., Bioorg.& Med. Chem., 2005, vol. 15, pp. 3930–3933.
Ottana, R,, Maccari, R., Barreca, M.L., Bruno, G., Rotondo, A., Rossi, A., Giuseppa, C., Paola, R.D., Sautebin, L., Cuzzocrea, S., and Vigorita, M.G., Bioorg.& Med. Chem., 2005, vol. 13, pp. 4243–4252.
Harish, K., Sadique, A.J., Suroor, A.K., and Mohammad, A., Eur. J. Med. Chem., 2008, vol. 43, pp. 2688–2698.
Balzarini, J., Orzeszko, B., Maurin, J.K., and Orzeszko, A., Eur. J. Med. Chem., 2007, vol. 42, pp. 993–1003.
Ghodgaonkar, S., Kulkarni, V.V., Wghulde, S.O., Laddha, S.S., and Shah, J., Int. E-conference on Syn. Org. Chem., 14, p. 1.
Suresh, S.H., Venkateshwara, R.J., and Jayaveera, K.N., Res. J. Pharm., Bio. Chem. Sci., 2010, vol. 1, no. 4, pp. 635–640.
Rahman, V.P. M., Mukhtar, S., Ansari, W.H., and Lemiere, G., Eur. J. Med. Chem., 2005, vol. 40, pp. 173–184.
Warhurst, D.C., Agadu, I.S., Nolder, D., and Rossignol, J., J. Antimicrob.Chemoth., 2002, vol. 49, no. 1, pp. 103–111.
Maru, M. and Shah, M.K., Int. J. Pharm. Sci., 2012, vol. 4, no. 3, pp. 388–391.
Yadav, P.S., Devprakash A, and Senthilkumar G.P., IJPSDR, 2011, vol. 3, no. 1, pp. 1–7.
Kucukguzel, S.G., Oruc, E.E., Rollas, S., Sahin, F., and Ozbek, A., Eur. J. Med. Chem., 2002., vol. 37, pp. 197–206.
Rawal, R.K., Prabhakar, Y.S., Katti, S.B., and De Clercq, E., Bioorg. Med. Chem., 2005, vol. 13, pp. 6771–6776.
Vigorita, M.G., Ottana, R., Monforte, F., Maccari, R., Trovato, A., Monforte, M.T., and Taviano, M.F., Bioorg. Med. Chem. Lett., 2001, vol. 11, pp. 2791–2794.
Sidhu, A. and Kukreja, S., Arabian J. Chem. (in press), 2015.
Luanicer, D. and Mitscher, L.A., The Organic Chemistry of Drug Synthesis, New York: John Wiley and Sons, 1980.
Bansal, R.K., Heterocyclic Chemistry, New Delhi: New Age International Publisher, 2003.
Kaki, S.S., Grey, C., and Adlercreutz, P., J. Biotech., vol. 157, pp. 344–349.
Sreenivasa, M., Jaychand, E., Shivkumar, B., Jayrajkumar, K., and Vijaykumar, J., Arch. Pharm. Sci.& Res., 2009, vol. 1, no. 2, pp. 150–157.
Shukla, J., Hazara, K., Rashmi, P., and Nargund, L.V.G., Der Chemica Sinica, vol. 2, no. 3, pp. 4–10.
Shashank, D., Vishawanth, T., ArifPasha, Md., Balasubramaniam, V., Nagendra, A., Perumal, P. and Suthakaran, R., Int. J. Chem. Tech. Res., 2009, vol. 1, no. 4, pp. 1224–1231.
Zagade, A.A. and Senthilkumar, G.P., Der Pharma Chemica, 2011, vol. 3, no. 1, pp. 523–537.
Devi, O.J. and Chhetry, G.K.N., Int. J. Sci. Res. Pub., 2013, vol. 3, pp. 1–3.
Kumar, V. and Tyagi, D., Int. J. Curr. Microbiol. App. Sci., 2013, vol. 2, pp. 69–78.
Devi, T.R. and Chhetry, G.K.N., Int. J. Sci. Res. Pub. 2012, vol. 2, pp. 1–4.
Grover, R.K. and Moore. J.D., Sclerotoniafructicola and S. laxa. Phytopathology, 1962, vol. 52, pp. 876–880.
Nene, Y.L. and Thapliyal, P.N., Fungicides in Plant Disease Control, New Delhi: Oxford and IBH Publishing Co., 1993. p. 525.
Ahsan, M.J., Samy, J.G., Khalilullah, H., Nomani, M.S., Saraswat, P., Gaur, R., and Singh, A., 2011. Bioorg. Med. Chem. Lett., vol. 21, pp. 7246–7250.
Veber, D.F., Johnson, S.R., Cheng, H.Y., Smith, B.R., Ward, K.W., and Kopple, K.D., J. Med. Chem., 2002, vol. 45, pp. 2615–2623.
Puratchikody, A., Doble, M., and Ramalakshmi, N., J. Pharm. Res., 2012, vol. 5, pp. 340–342.
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Gumber, K., Sidhu, A. & Kumar, V. Green synthesis of thiazol-2-ylthiazolidin-4-ones as potential antifungals. Russ J Appl Chem 88, 2065–2073 (2015). https://doi.org/10.1134/S10704272150120253
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DOI: https://doi.org/10.1134/S10704272150120253