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2004 | 2 | 1 | 1-15
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Antiinflammatory, analgesic and kinase inhibition activities of some acridine derivatives

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9-Chloro-2,4-(un)substituted acridines (1) on condensation with sulpha- diazine, sulphathiazole, and sulphaacetamide gave condensation products 3a-h. 3-Aryl-4-phenyl-2-imino-4-thiazolines (4) on condensation with 9-chloro-2,4-(un)substituted acridines (1) gave condensation products 5a–5o. Both 3a–3h and 5a–5o were purified by crystallization or by chromatography. Structures assigned to 3a–3h and 5a–5o are supported by correct spectral data. Antiinflammatory and analgesic activity screening of 3a, 3e, 3f and 5a–5c, 5e, 5g, 5i, 5m, 5n were carried out using carrageenin induced paw oedema and phenyl quinone writhing assay. Some of the compounds exhibited interesting antiinflammatory or analgesic activities.
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  • Department of Chemistry, Indian Institute of Technology, 247667, Roorkee, U.A., India,
  • Department of Chemistry, Indian Institute of Technology, 247667, Roorkee, U.A., India
  • Department of Chemistry, Indian Institute of Technology, 247667, Roorkee, U.A., India
  • Division of Pharmacology, Central Drug Research Insitute, Lucknow-226001, U.P., India
  • Division of Pharmacology, Central Drug Research Insitute, Lucknow-226001, U.P., India
  • Centre National De La Recherche Scientifique, Station Biologique, 29680-Roscoff, Bretagne, France
  • Centre National De La Recherche Scientifique, Station Biologique, 29680-Roscoff, Bretagne, France
  • [1] V.K. Misra and S.C. Bahel: “Synthesis of thaiazolyl compounds as potential fungicides”, Journal of Indian Chemical Society, Vol. 61, (1984), pp. 916–918.
  • [2] A. Srivastava, R.B. Pathak, S.C. Bahel: “Synthesis of antifungal N-acridin-5-yl, N′-α-aryloxy-butanoylhydrazines”, Journal of Indian Chemical Society, Vol. 62, (1985), pp. 486–487.
  • [3] L. Ngadi, N.G. Bisri, A. Mahamoud, A.M. Galy, J.P. Galy, J.C. Soyfer, J. Barbe, M. Placidi: “Synthesis and antiparasitic activity of new 1-nitro, 1-amino and 1-acetamido-9 acridonones”, Arzeimittel Forsch, Vol. 43, (1993), pp. 480–483.
  • [4] I.S. Shul’ga, A.K. Sukhomlinov, I.A. Goncharov, and E.M. Dikaya: “Synthesis and antimicrobial activity of some 4-nitro-aminoacridine derivatives”, Farm. Zh. (Kiev), Vol. 29, (1974), pp. 27–29.
  • [5] N.A. Gaiukevich, G.S. Bashura, I.M. Pestsev, O.A. Pimenov and A.I. Pyatkop: “Antimicrobial activity of some acridine derivatives”, Farm. Zh. (Kiev), Vol. 28, (1973), pp. 50–54.
  • [6] G.W. Gribble, G.D. Jaycox and M. Mosher: “Preparation of bis (9-aminoacridine) DNA intercalating agents having antitumor activity”, PCT Int. Appl. W.O. 9857956; Chem. Abstr., Vol. 130, (1999), 66397u.
  • [7] T. Sugaya, Y. Mimura, Y. Shida, Y. Osawa, I. Matsukuma: “6H-Pyrazolo [4,5,1-de]acridin-6-ones as a novel class of antitumor agents. Synthesis and biological activity”, Journal of Medicinal Chemistry, Vol. 37, (1994), pp. 1028–1032.[Crossref]
  • [8] M. Kimura, I. Okabayashi and A. Kato: “Acridine derivatives V [1]. Synthesis and P388 antitumor activity of novel 9-anilino-2,3-ethylenedioxyacridines”, J. Het. Chem., Vol. 30, (1993), pp. 1101–1104.
  • [9] S.G. Isaev, I.S. Shul’ga, A.V. Kaliman, N.E. Sheveleva and L.F. Silaeva: “Synthesis and biological activity of 9-arylamino acridine nitro derivatives”, Farm. Zh. (Kiev), Vol. 2, (1988), pp. 68–69.
  • [10] I.B. Taraporewala and J.M. Kauffman: “Synthesis and structure activity relationships of anti-inflammatory 9,10-dihydro-9-oxo-2-acridinealkanoic acids and 4-(2-carboxyphenyl) aminobenzene alkanoic acids”, J. Pharm. Sci., Vol. 79, (1990), pp. 173–178.
  • [11] A.N. Gaidukevich, G.P. Kazakov, A.A. Kravchenko, L.A. Porokhnyak, V.V. Dinchuk: “Synthesis and biological activity of acridinyl-9-thioacetic acid and their derivatives”, Khim. Farm. Zh., Vol. 21, (1987), pp. 1067–1070; Chem. Abstr., Vol. 108, (1988), 68486s.
  • [12] W.E. Bondinell, V.A. Reader and T.W.F. Ku: “Subistituted bisacridines and related compounds as CCR5 receptor ligands, antinflammatory agents and antiviral agents”, PCT Int. Appl. W.O. 9830218; Chem. Abstr., Vol. 129, (1998), 122582 u.
  • [13] W.A. Denny, B.C. Baguley, B.F. Cain and M.J. Waring: “Antitumor acridines in molecular aspects of anticancer drug action”, E. Neidle and M.J. Waring (Ed.), Macmillan, London, (1983), pp. 1–34.
  • [14] W.A. Denny, B.F. Cain, E.J. Atwell, C. Hansch, A. Pathananickal and A. Leo: “Potential antitumor agents. 36 Quantitative relationships between experimental antitumor activity, toxicity and structure for the general class of 9-anilinoacridine antitumor agents”, J. Med, Chem., Vol. 25, (1982), pp. 276–315.
  • [15] B.C. Baguley, W.A. Denny, G.J. Atwell, G.J. Finlay, G.W. Rewcastle, S.J. Twigden and W.R. Wilson: “Synthesis, antitumor activity, and DNA binding properties of new derivatives of amsacrine, N-5-dimethyl-9-[(2-methoxy-4-methylsulfonylamino)phenylamino]-4-acridinecarboxamide”, Cancer Res., Vol. 44, (1984), pp. 3245–3251.
  • [16] S.M. Sondhi, M. Johar, S. Rajvanshi, S.G. Dastidar, R. Shukla, R. Raghubir and J.W. Lown: “Anticancer, anti-inflammatory, and analgesic activity evaluation of heterocyclic compouds synthesized by the reaction of 4-isothiocyanato-4-metylpentan-2-one with substituted o-phenylenediamines, o-diaminopyridine and (un) substituted o-diaminopyridines”, Australian Journal of Chemistry, Vol. 54, (2001), pp. 69–74.[Crossref]
  • [17] S.M. Sondhi, M. Johar, R. Shukla, R. Raghubir, N. Bharti and A. Azam: “Synthesis, antiinfalmmatory, analgesic and antiamoebic activity evaluation of some Pyrimidobenizimidazole and pyrimidopyridoimidazole derivatives”, Australian Journal of Chemistry, Vol. 54, (2001), pp. 461–467.[Crossref]
  • [18] S.M. Sondhi, N. Singhal, M. Johar, B.S. Narayan Reddy and J.W. Lown: “Heterocyclic compounds as inflammation inhibitors”, a review., Curr. Med. Chem., Vol. 9, (2002), pp. 1045–1074.[Crossref]
  • [19] S.M. Sondhi, S. Rajvanshi, M. Johar, N. Bharti, A. Azam and A.K. Singh: “Antiinflammatory, analgesic and antiamoebic activityevaluation of pyrimido[1,6-a]benzimidazole derivatives synthesized by the reaction of ketoisothiocyanates with mono and diamines”, Eur. J. Med. Chem., Vol. 37, (2002), pp. 835–843.[Crossref]
  • [20] S.M. Sondhi, N. Singhal, R.P. Verma, S.K. Arora and S.G. Dastidar: “Synthesis of hemin and porphyrin derivatives and their evaluation for anticancer activities”, Indian Journal of Chemistry, Sec. B, Vol. 40, (2001), pp. 113–119.
  • [21] S.M. Sondhi, S. Rajvanshi, M. Johar, S.G. Dastidar: “Synthesis and anticancer activity evaluation of some hemin and hematoporphyrin derivatives”, Indian Journal of Chemistry, Sec. B, Vol. 41, (2002), pp. 388–393.
  • [22] S.M. Sondhi, M. Johar, N. Singh and S.G. Dastidar: “Synthesis of bis coupled hemin-thiazoline derivatives and their anticancertivity evaluation”, Indian Journal of Chemistry Sec. B, (In Press).
  • [23] C.F.H. Allen and G.H.W. Mcbee: “Acridone”, Org. Synthesis Coll., Vol. 2, (1959), pp. 15–17.
  • [24] A. Albert and B. Ritiche: “9-Aminoacridine”, Org. Synthesis Coll., Vol. 3, (1960), pp. 53–56.
  • [25] M.P. Mahajan, S.K. Vasudeva and N.K. Ralhan: “Synthesis of 2-Iminothiazolines”, Indian Journal of Chemistry, Vol. 10, (1972), pp. 318–319.
  • [26] C.A. Winter, E.A. Risley and G.W. Nuss: “Carrageenin induced edema in hind paw of the rat as an assay for anti-inflammatory drugs”, Proc. Soc. Exp. Biol. Med., Vol. 111, (1962), pp. 544–547. [Crossref]
  • [27] P.P. Singh, A.Y. Junnarkar, C.S. Rao, R.K. Verma and D.R. Shridhar: “Acetic acid phenylquinone writhing test: A critical study in mice”, Meth. Find. Exptl. Clinc. Pharmacol., Vol. 5, (1983), pp. 601–606.
  • [28] A. Primot, B. Baratte, M. Gompel, A. Borgan, et. al: “Purification of GSK-3 by affinity chromatography on immobilized axin”, Protein Expression Purification, Vol. 20, (2000), pp. 394–404.[Crossref]
  • [29] S. Lecler, M. Garnier, R. Hoessel, D. Marko, J.A. Bibb, et. al: “Indirubins inhibit glycogen synthase Kinase-3β and CDK-5/p 25, two kinases involved in abnormal tau phosphorylation in Alzheimer’s disease-A property common to most CDK inhibitors?”, J. Biol. Chem., Vol. 276, (2001), pp. 251–260.
  • [30] M. Leost, C. Schultz, A. Link, Y.Z. Wu, J. Biernat, E.M. Mandelkow: “Paullones are potent inhibitors of glycogen synthase kinase-3β and cyclin-dependent 5/p25”, European Journal of Biochemistry, Vol. 267, (2000), pp. 5983–5994.[Crossref]
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