1,474
Views
17
CrossRef citations to date
0
Altmetric
Research Article

Synthesis of novel carbazole chalcones as radical scavenger, antimicrobial and cancer chemopreventive agents

, , , , , , , , , & show all
Pages 593-600 | Received 08 Dec 2011, Accepted 31 Jan 2012, Published online: 01 Mar 2012

References

  • Aruoma O J, Halliwell B. Free Radicals and Food Additives (Eds) Talylor and Francis, London, 1991.
  • Halliwell B, Murcia MA, Chirico S, Aruoma OI. Free radicals and antioxidants in food and in vivo: what they do and how they work. Crit Rev Food Sci Nutr 1995;35:7–20.
  • Bursal E, Gülçin I. Polyphenol contents and in vitro antioxidant activities of lyophilised aqueous extract of kiwifruit (Actinidia deliciosa). Food Research International. 2011;44: 1482–1489
  • Dröge W. Free radicals in the physiological control of cell function. Physiol Rev 2002;82:47–95.
  • Ratnam DV, Ankola DD, Bhardwaj V, Sahana DK, Kumar MN. Role of antioxidants in prophylaxis and therapy: A pharmaceutical perspective. J Control Release 2006;113:189–207.
  • Suzen S. Bioactive Heterocycles V, Chapter: “Antioxidant Activities of Synthetic Indole Derivatives and Possible Activity Mechanisms. Top Heterocycl Chem 2007;11:145–178.
  • Knölker HJ, Reddy KR. Isolation and synthesis of biologically active carbazole alkaloids. Chem Rev 2002;102:4303–4427.
  • Zhang FF, Gan LL, Zhou CH. Synthesis, antibacterial and antifungal activities of some carbazole derivatives. Bioorg Med Chem Lett 2010;20:1881–1884.
  • Asche C, Frank W, Albert A, Kucklaender U. Synthesis, antitumour activity and structure-activity relationships of 5H-benzo[b]carbazoles. Bioorg Med Chem 2005;13:819–837.
  • Long BH, Rose WC, Vyas DM, Matson JA, Forenza S. Discovery of antitumor indolocarbazoles: rebeccamycin, NSC 655649, and fluoroindolocarbazoles. Curr Med Chem Anticancer Agents 2002;2:255–266.
  • Knolker H-J, Reddy KR. Chemistry and biology of carbazole alkaloids The alkaloids: Chemistry and Biology 2008;65:181–193.
  • Asche C, Demeunynck M.Antitumor carbazoles. Anticancer Agents Med Chem 2007;7:247–267.
  • Arbiser JL, Govindarajan B, Battle TE, Lynch R, Frank DA, Ushio-Fukai M et al. Carbazole is a naturally occurring inhibitor of angiogenesis and inflammation isolated from antipsoriatic coal tar. J Invest Dermatol 2006;126:1396–1402.
  • Fousteris MA, Papakyriakou A, Koutsourea A, Manioudaki M, Lampropoulou E, Papadimitriou E et al. Pyrrolo[2,3-a]carbazoles as potential cyclin dependent kinase 1 (CDK1) Inhibitors. Synthesis, biological evaluation, and binding mode through docking simulations. J Med Chem 2008;51:1048–1052.
  • Hu L, Li ZR, Li Y, Qu J, Ling YH, Jiang JD et al. Synthesis and structure-activity relationships of carbazole sulfonamides as a novel class of antimitotic agents against solid tumors. J Med Chem 2006;49:6273–6282.
  • Conchon E, Anizon F, Aboab B, Prudhomme M. Synthesis and biological activities of new checkpoint kinase 1 inhibitors structurally related to granulatimide. J Med Chem 2007;50:4669–4680.
  • Lampropoulou E, Manioudaki M, Fousteris M, Koutsourea A, Nikolaropoulos S, Papadimitriou E. Pyrrolo[2,3-a]carbazole derivatives as topoisomerase I inhibitors that affect viability of glioma and endothelial cells in vitro and angiogenesis in vivo. Biomed Pharmacother 2011;65:142–150.
  • Joseph B, Facompré M, Da Costa H, Routier S, Mérour JY, Colson P et al. Synthesis, cytotoxicity, DNA interaction and topoisomerase II inhibition properties of tetrahydropyrrolo[3,4-a]carbazole-1,3-dione and tetrahydropyrido-[3,2-b]pyrrolo[3,4-g]indole-1,3-dione derivatives. Bioorg Med Chem 2001;9:1533–1541.
  • Noguchi N, Nishino K, Niki E. Antioxidant action of the antihypertensive drug, carvedilol, against lipid peroxidation. Biochem Pharmacol 2000;59:1069–1076.
  • Zall A, Kieser D, Höttecke N, Naumann EC, Thomaszewski B, Schneider K et al. NSAID-derived ?-secretase modulation requires an acidic moiety on the carbazole scaffold. Bioorg Med Chem 2011;19:4903–4909.
  • Bandgar BP, Sarangdhar RJ, Viswakarma S, Ahamed FA. Synthesis and biological evaluation of orally active prodrugs of indomethacin. J Med Chem 2011;54:1191–1201.
  • Dimmock JR, Elias DW, Beazely MA, Kandepu NM. Bioactivities of chalcones. Curr Med Chem 1999;6:1125–1149.
  • Go ML, Wu X, Liu XL. Chalcones: an update on cytotoxic and chemoprotective properties. Curr Med Chem 2005;12:481–499.
  • Gülçin I, Topal F, Cakmakci R, Bilsel M, Goren A C, Erdogan U. Pomological Features, Nutritional Quality, Polyphenol Content Analysis, and Antioxidant Properties of Domesticated and 3 Wild Ecotype Forms of Raspberries (Rubus idaeusL.). J Food Sci 2011;76:585–593.
  • Gülçin I. Antioxidant Activity of Eugenol: A Structure–Activity Relationship Study. J Medicinal Food 2011;14:975–985.
  • Halliwell B, Gutteridge J.M.C. Free radicals in biology and medicine, 3rd ed. Oxford university press. oxford, UK. 1999.
  • Kancheva VD, Saso L, Boranova PV, Khan A, Saroj MK, Pandey MK et al. Structure-activity relationship of dihydroxy-4-methylcoumarins as powerful antioxidants: correlation between experimental & theoretical data and synergistic effect. Biochimie 2010;92:1089–1100.
  • Kumar R, Ramachandran U, Srinivasan K, Ramarao P, Raichur S, Chakrabarti R. Design, synthesis and evaluation of carbazole derivatives as PPAR alpha/gamma dual agonists and antioxidants. Bioorg Med Chem 2005;13:4279–4290.
  • Shi HP, Xu L, Cheng Y, He JY, Dai JX, Xing LW et al. Experimental and theoretical study of three new benzothiazole-fused carbazole derivatives. Spectrochim Acta A Mol Biomol Spectrosc 2011;81:730–738.
  • Marnett LJ. Oxyradicals and DNA damage. Carcinogenesis 2000;21:361–370.
  • Cooke MS, Evans MD, Dizdaroglu M, Lunec J. Oxidative DNA damage: mechanisms, mutation, and disease. FASEB J 2003;17:1195–1214.
  • Burrows CJ, Muller JG. Oxidative Nucleobase Modifications Leading to Strand Scission. Chem Rev 1998;98:1109–1152.
  • Rahman A, Fazal F, Greensill J, Ainley K, Parish JH, Hadi SM. Strand scission in DNA induced by dietary flavonoids: role of Cu(I) and oxygen free radicals and biological consequences of scission. Mol Cell Biochem 1992;111:3–9.
  • Trush MA, Kensler TW. An overview of the relationship between oxidative stress and chemical carcinogenesis. Free Radic Biol Med 1991;10:201–209.
  • Anto RJ, Sukumaran K, Kuttan G, Rao MN, Subbaraju V, Kuttan R. Anticancer and antioxidant activity of synthetic chalcones and related compounds. Cancer Lett 1995;97:33–37.
  • van de Waterbeemd H, Gifford E. ADMET in silico modelling: towards prediction paradise? Nat Rev Drug Discov 2003;2:192–204.
  • Lipinski C A, Lombardo F, Dominy B W, Feeney P J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Delivery Rev. 1997;23:3–25.
  • Hou T, Wang J, Zhang W, Xu X. ADME evaluation in drug discovery. 6. Can oral bioavailability in humans be effectively predicted by simple molecular property-based rules? J Chem Inf Model 2007;47:460–463.
  • Veber DF, Johnson SR, Cheng HY, Smith BR, Ward KW, Kopple KD. Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem 2002;45:2615–2623.
  • Navia M A, Chaturvedi P R. Design Principles for Orally. Bioavailable Drugs. Drug Discovery Today 1996;1:179–189.
  • Blois M S. Antioxidant Determinations by the Use of a Stable Free Radical. Nature. 1958;181:1199–1200.
  • Yu W, Zhao Y, Shu B. The radical scavenging activites of radix puerariae isoflavanoids: A chemiluminescence study. Food Chem 2004;86:525–529.
  • Wahab S I A, Abdul A B, Mohan S M, Al-Zubairi A S, Elhassan M M, Ibrahim M Y. Biological activities of Pereskia bleo extracts. Int J Pharmacol 2009;5:71–75.
  • Vadlapudi V, Bobbarala V, Penumajji S, Naidu K C. Excoecaria agallocha L. Antimicrobial Properties against Important Pathogenic Microorganisms. Int J Pharm Tech Res. 2009;4:865–867.
  • Miteva MA, Violas S, Montes M, Gomez D, Tuffery P, Villoutreix BO. FAF-Drugs: free ADME/tox filtering of compound collections. Nucleic Acids Res 2006;34:W738–W744.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.