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

• Autorzy: Lalchand Heda , Chandresh Pareek , Dushyant Pareek , Sonraj Mosalpuri
• Języki publikacji: EN

Abstrakty

EN

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. [...]

Słowa kluczowe

EN

Triphenodioxazines; Triphenodithiazine; Benzoquinones; Antimicrobial activity

• Czasopismo: Open Chemistry
• Rocznik: 2010
• Tom: 8
• Numer: 1
• Strony: 51-57

Daty

wydano

2010-02-01

online

2010-02-16

Twórcy

autor

Lalchand Heda

• P. G. Research Laboratories, Department of Chemistry, S. D. Govt. College, 305901, Beawar, India

autor

Chandresh Pareek

• P. G. Research Laboratories, Department of Chemistry, S. D. Govt. College, 305901, Beawar, India,

autor

Dushyant Pareek

• P. G. Research Laboratories, Department of Chemistry, S. D. Govt. College, 305901, Beawar, India

autor

Sonraj Mosalpuri

• P. G. Research Laboratories, Department of Chemistry, S. D. Govt. College, 305901, Beawar, India

Bibliografia

• [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-P[Crossref]
• [2] K. Venkataraman (Ed.), The Chemistry of Synthetic dyes (Academic Press Inc, New York, 1952) Vol. 2, 761
• [3] T. Hirara, Y. Okada, Z. Morita, Dyes and pigments 45(2), 131 (2000) http://dx.doi.org/10.1016/S0143-7208(00)00013-9[Crossref]
• [4] J. Kraska, Z. Boruszczak, B. Landwiist, Dyes and pigments 43(1), 1 (1999) http://dx.doi.org/10.1016/S0143-7208(99)00023-6[Crossref]
• [5] H. Walter, R. Vwe, Fiber reactive triphenodioxazine dyes, US patent, 5539109 (July 23, 1996)
• [6] R.R. Gupta, K.G. Ojha, Phenothiazines and 1,4-benzophenothiazines: Chemical and Biomedical Aspects (Elsevier, Amsterdam, 1988) Vol. 4, 163
• [7] C.O. Okafor, Phosphorus, sulfur, and silicon 4, 79 (1978) http://dx.doi.org/10.1080/03086647808079968[Crossref]
• [8] Y.S. Sadanandam, P. Leelavathi, Indian J. Chem. 30B(10), 85 (1991)
• [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/s11696-007-0036-1[Crossref]
• [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)
• [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.2007.09.108[Crossref]
• [12] L.I. Belen’kii, N.D. Kruchkovskaya, Adv. Heterocycl. Chem. 55, 31 (1992) http://dx.doi.org/10.1016/S0065-2725(08)60221-4[Crossref]
• [13] K.G. Kulkarni, F. Milton, Gen. Pharmacol. 17(6), 671 (1986)
• [14] J. Krapcho, C.F. Turk, J. Med. Chem. 16(7), 776 (1973) http://dx.doi.org/10.1021/jm00265a007[Crossref]
• [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.2006.08.036[Crossref]
• [16] A.J. Ling, K. Sudhaka, J. Heterocycl. Chem. 18, 759 (1981) http://dx.doi.org/10.1002/jhet.5570180425[Crossref]
• [17] M. Gordan (Ed.), Psychopharmacological Agents, Medicinal Chemistry (Academic Press, New York, 1967) Vol. III, 119
• [18] J. Krapcho, A. Szabo, J. Williams, J. Med. Chem. 6, 214 (1963) http://dx.doi.org/10.1021/jm00338a036[Crossref]
• [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/cm050723n[Crossref]
• [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)
• [21] L. Yu et al., Polymer 33, 3239 (1992) http://dx.doi.org/10.1016/0032-3861(92)90240-W[Crossref]
• [22] S. Yoshida, K. Kozawa, T. Uchida, Bulletin of Chemical Society of Japan 68(3), 738 (1995) http://dx.doi.org/10.1246/bcsj.68.738[Crossref]
• [23] Meister, Lucius and Bruning, British Patent, 8886, I. G. B. P., 313, 094 (1912)
• [24] S.K. Jain, K.G. Ojha, R.R. Gupta, Ind. J. Chem. 17B, 278 (1973)
• [25] H.P. Kaufmann, K. Kuchler, Chem. Ber. 67B, 944 (1934) [Crossref]
• [26] John L. Wood, In: R. Adams (Ed.), Organic reactions (Willey, New York, 1967) 3
• [27] E.A. Nodiff, M. Hausman, J. Org. Chem. 31, 240 (1966) 625 http://dx.doi.org/10.1021/jo01340a526[Crossref]
• [28] N.K. Goswami, R.R. Gupta, S.K. Jain, Chemistry and Industry 349 (1979)
• [29] L. Horner, K. Sturm, Chem. Ber. 88, 329 (1955) http://dx.doi.org/10.1002/cber.19550880304[Crossref]
• [30] National committee for clinical laboratory standards performance standards for antimicrobial disk susceptibility tests, 6th edition; approved standards M2-A6. NCCLS; Wayne, PA, 1997
• [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
• [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

Identyfikatory

DOI

10.2478/s11532-009-0100-5