Skip to content
BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access February 16, 2010

Synthesis and biological screening of octasubstituted-triphenodioxazines and its sulphur analogues with some novel intermediates

  • Lalchand Heda EMAIL logo , Chandresh Pareek , Dushyant Pareek and Sonraj Mosalpuri
From the journal Open Chemistry

Abstract

Attempts have been made to prepare for the first time the octasubstituted-triphenodioxazines and triphenodithiazines heterocycles by cyclisation of 3,6-dichloro-2,5-bis(2′,4′,5′-trichloroanilino)-1,4-benzoquinone and condensation. This wasfollowed by cyclisation of substituted 2-aminobenzenethiol respectively with chloranil and bromanil in ethanolic solution of fused sodium acetate in the presence of benzoyl chloride in nitrobenzene. Their structures were confirmed on the basis of their chemical and spectral analyses. Moreover, the biological activity of these compounds was evaluated against the test organisms viz — E.coli, S. aureus, B. subtilis, M.luteus and C. albicans. These compounds synthesized from 2,4,5-trichloroaniline appeared to possess significant antimicrobial activities and an explicit correlation between structure and biological activity was also observed.

[1] K. Numann, Pest Management Science Journal 56, 3 (2000) http://dx.doi.org/10.1002/(SICI)1526-4998(200001)56:1<3::AID-PS107>3.0.CO;2-P10.1002/(SICI)1526-4998(200001)56:1<3::AID-PS107>3.0.CO;2-PSearch in Google Scholar

[2] K. Venkataraman (Ed.), The Chemistry of Synthetic dyes (Academic Press Inc, New York, 1952) Vol. 2, 761 Search in Google Scholar

[3] T. Hirara, Y. Okada, Z. Morita, Dyes and pigments 45(2), 131 (2000) http://dx.doi.org/10.1016/S0143-7208(00)00013-910.1016/S0143-7208(00)00013-9Search in Google Scholar

[4] J. Kraska, Z. Boruszczak, B. Landwiist, Dyes and pigments 43(1), 1 (1999) http://dx.doi.org/10.1016/S0143-7208(99)00023-610.1016/S0143-7208(99)00023-6Search in Google Scholar

[5] H. Walter, R. Vwe, Fiber reactive triphenodioxazine dyes, US patent, 5539109 (July 23, 1996) Search in Google Scholar

[6] R.R. Gupta, K.G. Ojha, Phenothiazines and 1,4-benzophenothiazines: Chemical and Biomedical Aspects (Elsevier, Amsterdam, 1988) Vol. 4, 163 Search in Google Scholar

[7] C.O. Okafor, Phosphorus, sulfur, and silicon 4, 79 (1978) http://dx.doi.org/10.1080/0308664780807996810.1080/03086647808079968Search in Google Scholar

[8] Y.S. Sadanandam, P. Leelavathi, Indian J. Chem. 30B(10), 85 (1991) Search in Google Scholar

[9] A.S. Hammam, M.S.K. Youssef, F.M. Atta, T.A. Mohamed, Chemical Papers 61(4), 292 (2007) http://dx.doi.org/10.2478/s11696-007-0036-110.2478/s11696-007-0036-1Search in Google Scholar

[10] K.G. Ojha, S.P. Mathur, A.K. Mathur, A.S. Chittoria, H. Tahiliani, R.K. Sharma, Indian J. Chem. 43B(10), 2254 (2004) Search in Google Scholar

[11] V.H.J. Frade, M.J. Sousa, J.C.V.P. Moura, M. Sameiro, T. Gonçalves, Tetrahedron Letters 48, 8347 (2007) http://dx.doi.org/10.1016/j.tetlet.2007.09.10810.1016/j.tetlet.2007.09.108Search in Google Scholar

[12] L.I. Belen’kii, N.D. Kruchkovskaya, Adv. Heterocycl. Chem. 55, 31 (1992) http://dx.doi.org/10.1016/S0065-2725(08)60221-410.1016/S0065-2725(08)60221-4Search in Google Scholar

[13] K.G. Kulkarni, F. Milton, Gen. Pharmacol. 17(6), 671 (1986) Search in Google Scholar

[14] J. Krapcho, C.F. Turk, J. Med. Chem. 16(7), 776 (1973) http://dx.doi.org/10.1021/jm00265a00710.1021/jm00265a007Search in Google Scholar

[15] M. Batra, P. Kriplani, C. Batra, K.G. Ojha, Bioorg. Med. Chem. 14(24), 8519 (2006) http://dx.doi.org/10.1016/j.bmc.2006.08.03610.1016/j.bmc.2006.08.036Search in Google Scholar

[16] A.J. Ling, K. Sudhaka, J. Heterocycl. Chem. 18, 759 (1981) http://dx.doi.org/10.1002/jhet.557018042510.1002/jhet.5570180425Search in Google Scholar

[17] M. Gordan (Ed.), Psychopharmacological Agents, Medicinal Chemistry (Academic Press, New York, 1967) Vol. III, 119 Search in Google Scholar

[18] J. Krapcho, A. Szabo, J. Williams, J. Med. Chem. 6, 214 (1963) http://dx.doi.org/10.1021/jm00338a03610.1021/jm00338a036Search in Google Scholar

[19] T. Okamoto, M. Kozaki, M. Doe, M. Uchida, G. Wang, K. Okada, Chemistry of Materials 17, 5504 (2005) http://dx.doi.org/10.1021/cm050723n10.1021/cm050723nSearch in Google Scholar

[20] L.S. Sapochak, F. Strohkendl, M.R. Mclean, L.R. Dalton, C.W. Spangler, E.G. Nickel, Mat. Res. Soc. Symp. Proc., Los Angeles CA (MRS, USA, 1992) Search in Google Scholar

[21] L. Yu et al., Polymer 33, 3239 (1992) http://dx.doi.org/10.1016/0032-3861(92)90240-W10.1016/0032-3861(92)90240-WSearch in Google Scholar

[22] S. Yoshida, K. Kozawa, T. Uchida, Bulletin of Chemical Society of Japan 68(3), 738 (1995) http://dx.doi.org/10.1246/bcsj.68.73810.1246/bcsj.68.738Search in Google Scholar

[23] Meister, Lucius and Bruning, British Patent, 8886, I. G. B. P., 313, 094 (1912) Search in Google Scholar

[24] S.K. Jain, K.G. Ojha, R.R. Gupta, Ind. J. Chem. 17B, 278 (1973) Search in Google Scholar

[25] H.P. Kaufmann, K. Kuchler, Chem. Ber. 67B, 944 (1934) 10.1002/cber.19340670607Search in Google Scholar

[26] John L. Wood, In: R. Adams (Ed.), Organic reactions (Willey, New York, 1967) 3 Search in Google Scholar

[27] E.A. Nodiff, M. Hausman, J. Org. Chem. 31, 240 (1966) 625 http://dx.doi.org/10.1021/jo01340a52610.1021/jo01340a526Search in Google Scholar PubMed

[28] N.K. Goswami, R.R. Gupta, S.K. Jain, Chemistry and Industry 349 (1979) Search in Google Scholar

[29] L. Horner, K. Sturm, Chem. Ber. 88, 329 (1955) http://dx.doi.org/10.1002/cber.1955088030410.1002/cber.19550880304Search in Google Scholar

[30] National committee for clinical laboratory standards performance standards for antimicrobial disk susceptibility tests, 6th edition; approved standards M2-A6. NCCLS; Wayne, PA, 1997 Search in Google Scholar

[31] National committee for clinical laboratory standards methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, 3d edition; approved standard, NCCLS publication M7-A3; Villanova, PA, 1993 Search in Google Scholar

[32] National committee for clinical laboratory standards, reference method for broth dilution antifungal susceptibility testing of yeasts, proposed standard, NCCLS Document M27-P; Villanova, PA, 1992 Search in Google Scholar

Published Online: 2010-2-16
Published in Print: 2010-2-1

© 2010 Versita Warsaw

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Downloaded on 23.4.2024 from https://www.degruyter.com/document/doi/10.2478/s11532-009-0100-5/html
Scroll to top button