Citation:
Santhisudha Sarva, Jayaprakash Soora Harinath, Siva Prasad Sthanikam, Selvarajan Ethiraj, Mohanasrinivasan Vaithiyalingam, Suresh Reddy Cirandur. Synthesis, antibacterial and anti-inflammatory activity of bis(indolyl)methanes[J]. Chinese Chemical Letters,
;2016, 27(01): 16-20.
doi:
10.1016/j.cclet.2015.08.012
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A series of bioactive bis(indolyl)methanes are synthesized by one-pot green reaction of indole with various substituted aldehydes by microwave irradiation under solvent free conditions. The antibacterial activity against Staphylococcus aureus and anti-inflammatory activity of the synthesized bis(indolyl)-methanes are evaluated in vitro and compared to standard drugs tetracycline and diclofenac, respectively. The majority of the compounds showed good antibacterial and anti-inflammatory activity. Interestingly, compounds 3j, 3i, 3k and 3g exhibited much higher anti-inflammatory activity than the standard diclofenac drug and thus qualify for clinical trials to be used as an anti-inflammatory compound.
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[1]
[1] J. Kluytmans, A. Van Belkum, H. Verbrugh, Nasal carriage of Staphylococcus aureus:epidemiology, underlying mechanisms, and associated risks, Clin. Microbiol. Rev. 10(1997) 505-520.
-
[2]
[2] B. John, Experimental Staph Vaccine Broadly Protective in Animal Studies, National Institute of Health News, 1999.
-
[3]
[3] C. Walsh, Antibiotics:Actions, Origins, Resistance, ASM Press, Washington, DC, 2003.
-
[4]
[4] L. Ferrero-Miliani, O.H. Nielsen, P.S. Andersen, S.E. Girardin, Chronic inflammation:importance of NOD2 and NALP3 in interleukin-1β generation, Clin. Exp. Immunol. 147(2007) 227-235.
-
[5]
[5] A. Kar, Medicinal Chemistry, 2nd ed., New Age International Publishers, New Delhi, 2003, p. 329.
-
[6]
[6] G. Kant, A. Parate, S.C. Chaturvedi, Qsar study of substituted 3,5-di-tert-butyl-4-hydroxy styrene:a series with antiinflammatory activity, Indian J. Pharm. Sci. 67(2005) 116-119.
-
[7]
[7] G.M. Cragg, P.G. Grothaus, D.J. Newman, Impact of natural products on developing new anti-cancer agents, Chem. Rev. 109(2009) 3012-3043.
-
[8]
[8] G.A. Von Cordell, Introduction to Alkaloids:A Biogenetic Approach, Wiley, New York, 1981.
-
[9]
[9] P. Bey, F.N. Bolkenius, N. Seiler, P. Casara, N-(2,3-Butadienyl)-1, 4-butanediamine derivatives:potent irreversible inactivators of mammalian polyamine oxidase, J. Med. Chem. 28(1985) 1-2.
-
[10]
[10] R. Bell, S. Carmeli, N. Sar, Vibrindole A, a metabolite of the marine bacterium, vibrio parahaemolyticus, isolated from the toxic mucus of the boxfish Ostracion cubicus, J. Nat. Prod. 57(1994) 1587-1590.
-
[11]
[11] K. Reddi Mohan Naidu, S.I. Khalivulla, S. Rasheed, et al., Synthesis of bisindolylmethanes and their cytotoxicity properties, Int. J. Mol. Sci. 14(2013) 1843-1853.
-
[12]
[12] M. Lounasmaa, A. Tolvanen, Simple indole alkaloids and those with a nonrearrangedmonoterpenoid unit, Nat. Prod. Rep. 17(2000) 175-191.
-
[13]
[13] K. Sujatha, P.T. Perumal, D. Muralidharan, M. Rajendran, Synthesis, analgesic and anti-inflammatory activities of bis(indolyl)methanes, Indian J. Chem. 48(2009) 267-272.
-
[14]
[14] R.E. Moore, C. Cheuk, X.Q.G. Yang, et al., Hapalindoles, antibacterial and antimycotic alkaloids from the cyanophyte hapalosiphon fontinalis, J. Org. Chem. 52(1987) 1036-1043.
-
[15]
[15] J.S. Yadav, B.V.S. Reddy, C.V.S.R. Murthy, G.M. Kumar, C. Madan, Lithium perchlorate catalyzed reactions of indoles:an expeditious synthesis of bis(indolyl)-methanes, Synthesis(2001) 783-787.
-
[16]
[16] W.L. Deb, P.J. Bhuyan, An efficient and clean synthesis of bis(indolyl)methanes in a protic solvent at room temperature, Tetrahedron Lett. 47(2006) 1441-1443.
-
[17]
[17] R.R. Rahul, D.B. Shinde, Zirconyl(IV) chloride-catalysed reaction of indoles:an expeditious synthesis of bis(indolyl)methanes, Acta Chim. Slov. 53(2006) 210-213.
-
[18]
[18] G. Babu, N. Sridhar, P.T. Perumal, A convenient method of synthesis of bisindolylmethanes:indium trichloride catalyzed reactions of indole with aldehydes and schiff's bases, Synth. Commun. 30(2000) 1609-1614.
-
[19]
[19] H. Firouzabadi, N. Iranpoor, A.A. Jafari, Aluminumdodecatungstophosphate(AlPW12O40), a versatile and a highly water tolerant green Lewis acid catalyzes efficient preparation of indolederivatives, J. Mol. Catal. A Chem. 244(2006) 168-172.
-
[20]
[20] S.J. Ji, J.F. Zhou, D.G. Gu, S.Y. Wang, S.Y. Loh, Efficient synthesis of bis(indolyl)-methanes catalyzed by lewis acids in ionic liquids, Synlett 35(2003) 2077-2079.
-
[21]
[21] G.V.M. Sharma, J.J. Reddy, P.S. Lakshmi, P.R. Krishna, A versatile and practical synthesis of bis(indolyl)methanes/bis(indolyl)glycoconjugates catalyzed by trichloro-1,3, 5-triazine, Tetrahedron Lett. 45(2004) 7729-7732.
-
[22]
[22] S. Khaksar, S.M.J. Ostad, Pentafluorophenylammonium triflate as an efficient, environmentally friendly and novel organocatalyst for synthesis of bis-indolyl methane derivatives, J. Fluorine Chem. 132(2011) 937-939.
-
[23]
[23] A. Kamal, A.A. Qureshi, Syntheses of some substituted di-indolylmethanes in aqueous medium at room temperature, Tetrahedron 19(1963) 513-520.
-
[24]
[24] R. Nagarajan, P.T. Perumal, Potassium hydrogen sulfate-catalyzed reactions of indoles:a mild, expedient synthesis of bis-indolylmethanes, Chem. Lett. 33(2004) 288-289.
-
[25]
[25] S.J. Ji, S.Y. Wang, Y. Zhang, T.P. Loh, Facile synthesis of bis(indolyl)methanes using catalytic amount of iodine at room temperature under solvent-free conditions, Tetrahedron 60(2004) 2051-2055.
-
[26]
[26] A. Loupy, Microwaves in Organic Synthesis, Wiley-VCH, Weinheim, 2006.
-
[27]
[27] M. Chakrabarti, S. Sarkar, Novel clay-mediated, tandem addition-elimination-(Michael) addition reactions of indoles with 3-formylindole:an eco-friendly route to symmetrical and unsymmetrical triindolylmethanes, Tetrahedron Lett. 43(2002) 1351-1353.
-
[28]
[28] G.S. Rashinkar, S.B. Pore, K.B. Mote, R.S. Salunkhe, An efficient synthesis of novel 2-amino-4-aryl-6-ferrocenyl pyrimidine, Indian J. Chem. 48B(2009) 606-610.
-
[29]
[29] B.C. Das, G. Marippan, S. Saha, D. Bhowmik, J. Chiranjib, Anthelmintic and antimicrobial activity of some novel chalcone derivatives, J. Chem. Pharm. Res. 2(2010) 113-120.
-
[30]
[30] S.Y. Wang, S.J. Ji, T.P. Loh, The Michael addition of indole to aα,β-unsaturated ketones catalyzed by iodine at room temperature, Synlett(2003) 2377-2379.
-
[31]
[31] A. Ravaei, Z.H. poor, T.Z. Salehi, et al., Evaluation of antimicrobial activity of three Lactobacillus spp. against antibiotic resistance Salmonella typhimurium, Adv. Stud. Biol. 5(2013) 61-70.
-
[32]
[32] R. Vadivu, K.S. Lakshmi, In vitro and in vivo anti-inflammatory activity of leaves of Symplocos cochinchinensis(Lour) Moore ssp laurina, Bangladesh J. Pharmacol. 3(2008) 121-124.
-
[33]
[33] J.S. Yadav, B.V.S. Reddy, C.V.S.R. Murthy, G.M. Kumar, C. Madan, Lithium perchlorate catalyzed reactions of indoles:an expeditious synthesis of bis(indolyl)-methanes, Synthesis 5(2001) 783-787.
-
[34]
[34] K. Reddi Mohan Naidu, P.S.I. Khalivulla, P. Chenna Rohini Kumar, O. Lasekan, KHSO4-SiO2 catalyzed facile synthesis of bis(indolyl)methanes, Org. Commun. 5(2012) 150-159.
-
[35]
[35] M.A. Zolfigol, P. Salehi, M. Shiri, Z. Tanbakouchian, A new catalytic method for the preparation of bis-indolyl and tris-indolyl methanes in aqueous media, Catal. Commun. 8(2007) 173-178.
-
[36]
[36] S. Handy, N.M. Westbrook, A mild synthesis of bis(indolyl)methanes using a deep eutectic solvent, Tetrahedron Lett. 55(2014) 4969-4971.
-
[37]
[37] S.P.A. Boehringer Mannheim Italia, Bis-Indole derivatives having antimetastatic activity, a process for their preparation and pharmaceutical compositions containing them, Eur. Pat. Appl.(1998) 13, CODEN:EPXXDW; EP887348.
-
[38]
[38] A.K. Mallik, R. Pal, T.K. Mandal, Facile formation of bis(3-indolyl)methylarenes by Iodine-catalyzed reaction of indole with α,α'-bis(arylmethylene)ketones and α-substituted arylmethyleneketones in dry ethanol, Indian J. Chem. 46B(2007) 2056-2059.
-
[39]
[39] R. Martínez, A. Espinosa, A. Tárraga, P. Molina, Bis(indolyl)methane derivatives as highly selective colourimetric and ratiometric fluorescent molecular chemosensors for Cu2+ cations, Tetrahedron 64(2008) 2184-2191.
-
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