Synthesis, inhibition of NO production and antiproliferative activities of some indole derivatives

References

• Hinze C, Sundermann B, Schick H, Henkel B. Preparation of spirocyclic pyrano[4,3-b] indoles and related compounds as μ-opiate receptor ligands WO 2005063769 A1 20050714, CA 143:133272 AN 2005:612304.
   Google Scholar
• Macor JE, Ryan K, Newman ME. The synthesis of pyrano[3,2-e]indoles and pryano[2,3-f] indoles as rotationally restricted phenolic analogs of the neurotransmitter serotonin. Tetrahedron 1992;48(6):1039–1052.
   Google Scholar
• Gopalsamy A, Collette MS, Ellingboe JW, Laporte MG, Mansour TS, Burns CJ, Park K, Condon SM. Preparation of pyranoindole derivatives to treat infection with hepatitis C virus. WO 2003099275 A1 20031204 CA 140:16714 AN 2003:950835.
   Google Scholar
• Kreft AF, Caufield CE, Failli AA, Caggiano TJ, Greenfield AA, Kubrak DM. Preparation of pyranoindole inhibitors of COX-2. US 5776967 A 19980707 CA 129:122569 AN 1998:457268.
   Google Scholar
• Musser JH, Kreft AF, Failli AA, Demerson CA, Shah US, Nelson JA. Substi-tuted indole-, indene-, pyranoindole- and tetrahydrocarbazolealkanoic acid derivatives as inhibitors of PLA2 and lipoxygenase. US 5420289 A1 9950530 CA 124:8801 AN 1995:661173.
   Google Scholar
• Nakkady SS, Fathy MM, Hishmat OH, Mahmond SS, Ebeid MY., New indole, aminoindole and pyranoindole derivatives with anti-inflammatory activity, Boll Chim Farmaceu 2000;39(2):59–66.
   Google Scholar
• Gadaginamath GS, Kavali RR. Synthesis and antimicrobial activity of novel 4H-pyrano[2,3-f]indole derivatives, Ind J Chem Section B 1999;38B(2):178–182.
   Google Scholar
• Fu JM. Preparation of substituted 2,3,7,8,9,10,11,12-octahydro azepino[4,5-b] pyrano[3,2-e]indoles as CNS agents. WO 2002004456 A1 20020117, CA 136:118395 AN 2002:51468.
   Google Scholar
• Zaalishvili T, Kharadze D, Khostaria T, Arabuli N, Kolkhidashvili K, Kutalia K, Omiadze T, Kirmelashvili L, Edilashvili L, Zaalishvili G, Tsetskhladze Z. Design of indole derivatives and studying their inhibitory ability of poly-ADP-ribosylation reaction. Bull Georg Acad Sci 2005;172(2): 314–316.
   Google Scholar
• Macor JE, Blank DH, Post RJ. The synthesis of conformationally/rotationally restricted analogs of the neurotransmitter serotonin. Tetrahedron Lett 1994;35(1):45–48.
   Google Scholar
• Perry EK, Pickering AT, Wang WW, Houghton PJ, Perry NS. Medicinal plants and Alzheimer’s disease: from ethnobotany to phytotherapy. J Pharm Pharmacol 1999;51:527–534.
   PubMed Web of Science ®Google Scholar
• Lin CC, Huang PC. Antioxidant and hepatoprotective effects of Acathopanax senticosus. Phytother Res 2002;14:489–494.
   Google Scholar
• Repetto MG, Llesuy SF. Antioxidant properties of natural compounds used in popular medicine for gastric ulcers. Braz J Med Biol Res 2002;35:523–534.
   PubMed Web of Science ®Google Scholar
• Gutteridge JM. Lipid peroxidation and antioxidants as biomarkers of tissue damage. Clin Chem 1995;41:1819–1828.
   PubMed Web of Science ®Google Scholar
• Winrow VR, Winyard PG, Morris CJ, Blake DR. Free radicals in inflammation: second messengers and mediators of tissue destruction. Br Med Bull 1993;49:506–522.
   PubMed Web of Science ®Google Scholar
• Delaporte RH, Sánchez GM, Cuellar AC, Giuliani A, Palazzo de Mello JC. Anti-inflammatory activity and lipid peroxidation inhibition of iridoid lamiide isolated from Bouchea fluminensis (Vell.) Mold. (Verbenaceae). J Ethnopharmacol 2002;82:127–130.
   PubMed Web of Science ®Google Scholar
• Geronikaki AA, Gavalas AM. Antioxidants and anti-inflammatory diseases: synthetic and natural antioxidants with anti-inflammatory activity. Comb Chem High Throughput Screen 2006;9:425–442.
   PubMed Web of Science ®Google Scholar
• Jackson Roberts L, Morrow JD In Hardman JG, Limbird LE, Goodman Gilman A, Editors Goodman and Gilman’s. The Pharmacological Basis of Therapeutics 10th ed. McGraw-Hill; USA. 2001. pp 687–731.
   Google Scholar
• Larson RA. The antioxidants of higher plants. Phytochemistry 1988;27:969–978.
   Web of Science ®Google Scholar
• Mora A, Paya M, Rios JL, Alcaraz M. Structure-activity relationships of polymethoxyflavones and other flavonoids as inhibitors of non-enzymic lipid peroxidation. J Biochem Pharmacol 1990;40:793–797.
   PubMed Web of Science ®Google Scholar
• Hoult JRS, Paya M. Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential. Gen Pharmac 1996;27:713–722.
   PubMedGoogle Scholar
• Terasaka T, Kinoshita T, Kuno M, Seki N, Tanaka K, Nakanishi I. Structure-Based Design, Synthesis, and Structure-Activity Relationship Studies of Novel Non-nucleoside Adenosine Deaminase Inhibitors. J Med Chem 2004;47:3730–3743.
   PubMedGoogle Scholar
• Menciu C, Duflos M, Fouchard F, Le Baut G, Emig P, Achterrath U, Szelenyl I, Nickel B, Schimdt J, Kutscher B, Gunther E. New N-(Pyridin-4-yl)-(indol-3-yl)acetamides and Propanamides as Antiallergic Agents. J Med Chem 1999;42:638–648.
   PubMedGoogle Scholar
• Potdar MK, Mohile SS, Salunkhe MM. Coumarin syntheses via Pechmann condensation in Lewis acidic chloroaluminate ionic liquid. Tetrahedron Lett 2001;42:9285–9287.
   Web of Science ®Google Scholar
• Hoefnagel AJ, Gunnewegh EA, Downing RS, van Bekkum H. Synthesis of 7- Hydroxycoumarins catalysed by Solid Acid Catalysts. J Chem Soc Chem Commun 1995; 225-226.
   Google Scholar
• Subhas Bose D, Rudradas AP, Hari Babu M. The indium(III) chloride-catalyzed von Pechmann reaction: a simple and effective procedure for the synthesis of 4-substituted coumarins. Tetrahedron Lett 2002; 43:9195–9197.
   Google Scholar
• Chen G, Yee D, Gubernator N, Sames D. Development of fluorogenic substrates for monoamine oxidases (MAO-A and MAO-B). WO 2006026368.
   Google Scholar
• Wang M, Li J, Rangarajan M, Shao Y, La Voie EJ, Huang CT. Antioxidative Phenolic Compounds from Sage (Salvia officinalis). J Agric Food Chem 1998;46:4869–4873.
   Web of Science ®Google Scholar
• Conforti F, Statti GA, Menichini F. Chemical and biological variability of hot pepper fruits (Capsicum annuum var. acuminatum L.) in relation to maturity stage. Food Chem 2007;102:1096–1104.
   Web of Science ®Google Scholar
• Green LC, Wagner DA, Glogowski J, Skipper PL, Wishnok JS, Tannenbaum SR. Analysis of nitrate, nitrite, and [15N]nitrate in biological fluids. Anal Biochem. 1982;126:131–138.
   PubMed Web of Science ®Google Scholar
• Tubaro A, Florio C, Luxich E, Vertua R, Della Loggia R, Yasumoto T. Suitability of the MTT-based cytotoxicity assay to detect okadaic acid contamination of mussels. Toxicon 1996;34: 965–974.
   PubMed Web of Science ®Google Scholar
• Kim YH, Kim J, Park H, Kim HP. Anti-inflammatory activity of the synthetic chalcone derivatives: inhibition of inducible nitric oxide synthase-catalyzed nitric oxide production from lipopolysaccharide-treated RAW 264.7 cells. Biol Pharm Bull 2007;30:1450–1455.
   PubMed Web of Science ®Google Scholar
• Ahmad S, Israf DA, Lajis NH, Shaari K, Mohamed H, Wahab AA, Ariffin KT, Hoo WY, Aziz NA, Kadir AA, Sulaiman MR, Somchit MN. Cardamonin, inhibits pro-inflammatory mediators in activated RAW 264.7 cells and whole blood. Eur J Pharmacol 2006;538:188–194.
   PubMed Web of Science ®Google Scholar
• Costa D, Gomes A, Reis S, Lima JL, Fernandes E. Hydrogen peroxide scavenging activity by non-steroidal anti-inflammatory drugs. Life Sci 2005;76:2841–2848.
   PubMed Web of Science ®Google Scholar
• Pekoe G, Van Dyke K, Peden D, Mengoli H, English D. Antioxidation theory of non-steroidal anti-inflammatory drugs based upon the inhibition of luminol-enhanced chemiluminescence from the myeloperoxidase reaction. Agents Actions 1982;12:371–376.
   PubMedGoogle Scholar