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Novel 8-heterocyclyl xanthine derivatives in drug development – an update

, , PhD, , PhD, , PhD & , PhD
Pages 1161-1183 | Published online: 29 Aug 2007

Bibliography

  • BRUNS RF: Adenosine antagonism by purines, pteridines and benzopteridines in human fibroblasts. Biochem. Pharmacol. (1981) 30(4):325-333.
  • DALY JW: Adenosine receptors: targets for future drugs. J. Med. Chem. (1982) 25(3):197-207.
  • LAINEZ MJ, GALVAN J, HERAS J, VILA C: Crossover, double-blind clinical trial comparing almotriptan and ergotamine plus caffeine for acute migraine therapy. Eur. J. Neurol. (2007) 14(3):269-275.
  • ABO-SALEM OM, HAYALLAH AM, BILKEI-GORZO A, FILIPEK B, ZIMMER A, MULLER CE: Antinociceptive effects of novel A2B adenosine receptor antagonists. J. Pharmacol. Exp. Ther. (2004) 308(1):358-366.
  • BARNES PJ: Drugs for asthma. Br. J. Pharmacol. (2006) 147(1):S297-S303.
  • BOSWELL-SMITH V, CAZZOLA M, PAGE CP: Are phosphodiesterase 4 inhibitors just more theophylline? J. Allergy Clin. Immunol. (2006) 117(6):1237-1243.
  • BOSWELL-SMITH V, SPINA D, PAGE CP: Phosphodiesterase inhibitors. Br. J. Pharmacol. (2006) 147(1):S252-S257.
  • BARNES PJ: Reduced histone deacetylase in COPD: clinical implications. Chest (2006) 129(1):151-155.
  • JACOBSON KA, GAO ZG: Adenosine receptors as therapeutic targets. Nat. Rev. Drug. Discov. (2006) 5(3):247-264.
  • EL-SABBAGH OI, EL-SADEK ME, EL-KALYOUBI S, ISMAIL I: Synthesis, DNA binding and antiviral activity of new uracil, xanthine, and pteridine derivatives. Arch. Pharm. Chem. Life Sci. (2007) 340(1):26-31.
  • VLOK N, MALAN SF, CASTAGNOLI NJR, BERGH JJ, PETZER JP: Inhibition of monoamine oxidase B by analogues of the adenosine A2A receptor antagonist (E)-8-(3-chlorostyryl)caffeine (CSC). Bioorg. Med. Chem. (2006) 14(10):3512-3521.
  • SUZUKI H, SAWANISHI H, YAMAMOTO K, YOKOGAWA K, MIYAMOTO K: Phosphodiesterase 4 isoenzyme inhibitory activity of 3-phenylxanthines and 4-phenyl[i]condensed-purines. Chem. Pharm. Bull. (2001) 49(2):188-191.
  • WANG Y, CHACKALAMANNIL S, HU Z et al.: Design and synthesis of xanthine analogues as potent and selective PDE5 inhibitors. Bioorg. Med. Chem. Lett. (2002) 12(21):3149-3152.
  • COTTAM HB, SHIH H, TEHRANI LR, WASSON DB, CARSON DA: Substituted xanthines, pteridinediones, and related compounds as potential antiinflammatory agents. Synthesis and biological evaluation of inhibitors of TNF. J. Med. Chem. (1996) 39(1):2-9.
  • KLINGER M, FREISSMUTH M, NANOFF C: Adenosine receptors: G protein-mediated signalling and the role of accessory proteins. Cell. Signal. (2002) 14(2):99-108.
  • DALY JW, BUTTS-LAMB P, PADGETT W: Subclasses of adenosine receptors in the central nervous system: interaction with caffeine and related methylxanthines. Cell. Mol. Neurobiol. (1983) 3(1):69-80.
  • STEHLE JH, RIVKEES SA, LEE JJ, WEAVER DR, DEEDS JD, REPPERT SM: Molecular cloning and expression of the cDNA for a novel A2-adenosine receptor subtype. Mol. Endocrinol. (1992) 6(3):384-393.
  • FEOKTISTOV I, BIAGGIONI I: Adenosine A2B receptors. Pharmacol. Rev. (1997) 49(4):381-402.
  • FREDHOLM BB, IJZERMAN AP, JACOBSON KA, KLOTZ KN, LINDEN J: International union of pharmacology. XXV. Nomenclature and classification of adenosine receptors. Pharmacol. Rev. (2001) 53(4):527-552.
  • Volpini R, COSTANZI S, VITTORI S, CRISTALLI G, KLOTZ KN: Medicinal chemistry and pharmacology of A2B adenosine receptors. Curr. Top. Med. Chem. (2003) 3(4):427-443.
  • Cacciari B, PASTORIN G, BOLCATO C, SPALLUTO G, BACILIERI M, MORO S: A2B adenosine receptor antagonists: recent developments. Mini Rev. Med. Chem. (2005) 5(12):1053-1060.
  • RORKE S, HOLGATE ST: Targeting adenosine receptors: novel therapeutic targets in asthma and chronic obstructive pulmonary disease. Am. J. Respir. Med. (2002) 1(2):99-105.
  • RYZHOV S, GOLDSTEIN AE, MATAFONOV A, ZENG D, BIAGGIONI I, FEOKTISTOV I: Adenosine-activated mast cells induce IgE synthesis by B Lymphocytes: an A2B-mediated process involving Th2 cytokines IL-4 and IL-13 with implications for asthma. J. Immunol. (2004) 172(12):7726-7733.
  • SANDS WA, PALMER TM: Adenosine receptors and the control of endothelial cell function in inflammatory desease. Immunol. Lett. (2005) 101(1):1-11.
  • LIVINGSTON M, HEANEY LG, ENNIS M: Adenosine, inflammation and asthma-a review. Inflamm. Res. (2004) 53(5):171-178.
  • BEUKERS MW, MEURS I, IJZERMAN AP: Structure-affinity relationships of adenosine A2B receptor ligands. Med. Res. Rev. (2006) 26(5):667-698.
  • FEOKTISTOV I, WELLS JN, BIAGGIONI I: Adenosine A2B receptors as therapeutic targets. Drug Dev. Res. (1998) 45(3):198-206.
  • KIM SA, MARSHALL MA, MELMAN N et al.: Structure-activity relationships at human and rat A2B adenosine receptors of xanthine derivatives substituted at the 1-, 3-, 7-, and 8-positions. J. Med. Chem. (2002) 45(11):2131-2138.
  • KIM YC, JI XD, MELMAN N, LINDEN J, JACOBSON KA: Anilide derivatives of an 8-phenylxanthine carboxylic congener are highly potent and selective antagonists at human A2B adenosine receptor. J. Med. Chem. (2000) 43(6):1165-1172.
  • BARALDI PG, TABRIZI MA, PRETI D et al.: Design, synthesis and biological evaluation of new 8-heterocyclic xanthine derivatives as highly potent and selective human A2B adenosine receptor antagonists. J. Med. Chem. (2004) 47(6):1434-1447.
  • ZABLOCKI J, KALLA R, PERRY T et al.: The discovery of a selective, high affinity A2B receptor antagonist for the potential treatment of asthma. Bioorg. Med. Chem. Lett. (2005) 15(3):609-612.
  • ELZEIN E, KALLA RV, LI X et al.: Novel 1,3-dipropyl-8-(1-heteroarylmethyl-1H-pyrazol-4-yl)-xanthine derivatives as high affinity and selective A2B adenosine receptor antagonists. Bioorg. Med. Chem. Lett. (2006) 16(2):302-306.
  • KALLA RV, ELZEIN E, PERRY T et al.: Novel 1,3-Disubstituted 8-(1-benzyl-1H-pyrazol-4-yl) xanthines: high affinity and selective A2B adenosine receptor antagonists. J. Med. Chem. (2006) 49(12):3682-3692.
  • CAROTTI A, CADAVID MI, CENTENO NB et al.: Design, synthesis and structure-activity relationships of 1-, 3-, 8- and 9-substituted-9-deazaxanthines at the human A2B adenosine receptor. J. Med. Chem. (2006) 49(1):282-299.
  • ESTEVE C, NUEDA A, DIAZ JL et al.: New pyrrolopyrimidin-6-yl benzenesulfonamides: potent A2B adenosine receptor antagonists. Bioorg. Med. Chem. Lett. (2006) 16(14):3642-3645.
  • YAN L, BERTARELLI DCG, HAYALLAH AM et al.: A new synthesis of sulfonamides by aminolysis of p-nitrophenylsulfonates yielding potent and selective adenosine A2B receptor antagonists. J. Med. Chem. (2006) 49(14):4384-4391.
  • FEOKTISTOV I, GARLAND ME, GOLDSTEIN AE et al.: Inhibition of human mast cell activation with the novel selective adenosine A2B receptor antagonist 3-isobutyl-8-pyrrolidinoxanthine (IPDX). Biochem. Pharmacol. (2001) 62(9):1163-1173.
  • BAZIARD-MOUYSSET G, RACHED A, YOUNES S et al.: Synthesis and in vitro bronchospasmolytic activity of 8-aryl, heteroaryl or arylalkyl theophyllines. Eur. J. Med. Chem. (1995) 30(3):253-260.
  • REGNIER GL, GUILLONNEAU CG, DUHAULT JL, TISSERAND FP, SAINT-ROMAS G, HOLSTORP SM: New xanthine derivatives with potent and long lasting anti-bronchoconstrictive activity. Eur. J. Med. Chem. (1987) 22(3):243-250.
  • PROFIRE L, BUMBU GG, COSTULEANU M, DANILA G, VASILE C: Thermal and pharmacological characterization of some new bis-xanthine derivatives. Termochimica Acta (2002) 381(1):19-29.
  • BERK B, AKGUN H, EROL K, SIRMAGUL B, GAO Z-G, JACOBSON KA: New 8-substituted xanthine derivatives as bronchodilators. Farmaco (2005) 60(11-12):974-980.
  • MÜLLER CE: A1 adenosine receptors and their ligands: overview and recent developments. Farmaco (2001) 56(1):77-80.
  • KIESMAN WF, ZHAO J, CONLON PR: Potent and orally bioavailable 8-bicyclo[2.2.2]octylxanthines as adenosine A1 receptor antagonists. J. Med. Chem. (2006) 49(24):7119-7131.
  • YUZLENKO O, KIEC'-KONONOWICZ K: Potent adenosine A1 and A2A receptors antagonists: recent developments. Curr. Med. Chem. (2006) 13(30):3609-3625.
  • DHALLA A V, SHRYOCK JC, SHREENIWAS R, BELARDINELLI L: Pharmacology and therapeutic applications of A1 adenosine receptor ligands. Curr. Top. Med. Chem. (2003) 3(4):369-385.
  • PFISTER JR, BELARDINELLI L, LEE G et al.: Synthesis and biological evaluation of the enantiomers of the potent and selective A1-adenosine antagonist 1,3-dipropyl-8-[2-(5,6-epoxynorbornyl)]-xanthine. J. Med. Chem. (1997) 40(12):1773-1778.
  • KIESMAN WF, ZHAO J, CONLON PR et al.: Norbornyllactone-substituted xanthines as adenosine A1 receptor antagonists. Bioorg. Med. Chem. (2006) 14(11):3654-3661.
  • STRAPPAGHETTI G, CORSANO S, BARBARO R, GIANNACCINI G, BETTI L: Structure–activity relationships in a series of 8-substituted xanthines as A1-adenosine receptor antagonists. Bioorg. Med. Chem. (2001) 9(3):575-583.
  • ILAS J, PECAR S, HOCKEMEYER J, EULER H, KIRFEL A, MULLER CE: Development of spin-labeled probes for adenosine receptors. J. Med. Chem. (2005) 48(6):2108-2114.
  • ENGEL M, HOFFMANN T, MANHART S et al.: Rigidity and flexibility of dipeptidyl peptidase IV: crystal structures of and docking experiments with DPIV. J. Mol. Biol. (2006) 355(4):768-783.
  • WEBER AE: Dipeptidyl peptidase IV inhibitors for the treatment of diabetes. J. Med. Chem. (2004) 47(17):4135-4141.
  • KOLTERMAN OG, BUSE JB, FINEMAN MS et al.: Synthetic exendin-4 (Exenatide) significantly reduces postprandial and fasting plasma glucose in subjects with Type 2 diabetes. Clin. Endocrinol. Metab. (2003) 88(7):3082-3089.
  • AUGUSTYNS K, VAN DER VEKEN P, HAEMERS A: Inhibitors of proline-specific dipeptidyl peptidases: DPP IV inhibitors as a novel approach for the treatment of Type 2 diabetes. Expert Opin. Ther. Patents (2005) 15(10):1387-1407.
  • AUGUSTYNS K, VAN DER VEKEN P, SENTEN K, HAEMERS A: The therapeutic potential of inhibitors of dipeptidyl peptidase IV (DPP IV) and related proline-specific dipeptidyl aminopeptidases. Curr. Med. Chem. (2005) 12(8):971-998.
  • KURUKULASURIYA R, ROHDE JJ, SZCZEPANKIEWICZ BG et al.: Xanthine mimetics as potent dipeptidyl peptidase IV inhibitors. Bioorg. Med. Chem. Lett. (2006) 16(24):6226-6230.
  • LONGENECKER KL, STEWART KD, MADAR DJ et al.: Crystal structures of DPP-IV (CD26) from rat kidney exhibit flexible accommodation of peptidase-selective inhibitors. Biochemistry (2006) 45(24):7474-7482.
  • SZCZEPANKIEWICZ BG, KURUKULASURIYA R: Aromatic heterocycle-based DPP-IV inhibitors: xanthines and related structural types. Curr. Top. Med. Chem. (2007) 7(6):569-578.
  • BRADLEY MN, TONTONOZ P: LXR: a nuclear receptor target for cardiovascular disease? Drug Discov. Today Ther. Strat. (2005) 2(2):97-103.
  • JAYE M: LXR agonists for the treatment of atherosclerosis. Curr. Opin. Investig. Drugs (2003) 4(9):1053-1058.
  • BENNETT DJ, BROWN LD, COOKE AJ, EDWARDS AS: An update on non-steroidal liver X receptor agonists and their potential use in the treatment of atherosclerosis. Expert Opin. Ther. Patents (2006) 16(12):1673-1699.
  • CAO G, BALES KR, DEMATTOS RB, PAUL SM: Liver X receptor-mediated gene regulation and cholesterol homeostasis in brain: relevance to Alzheimer's disease therapeutics. Curr. Alzheimer Res. (2007) 4(2):179-184.
  • DELVECCHIO CJ, BILAN P, RADFORD K et al.: Liver X receptor stimulates cholesterol efflux and inhibits expression of pro-inflammatory mediators in human airway smooth muscle cells. Mol. Endocrinol. (2007) (In Press).
  • CHUU CP, KOKONTIS JM, HIIPAKKA RA, LIAO S: Modulation of liver X receptor signaling as novel therapy for prostate cancer. J. Biomed. Sci. (2007) (In Press).
  • CHUU CP, HIIPAKKA RA, KOKONTIS JM, FUKUCHI J, CHEN RY, LIAO S: Inhibition of tumor growth and progression of LNCaP prostate cancer cells in athymic mice by androgen and liver X receptor agonist. Cancer Res. (2006) 66(13):6482-6486.
  • BARALDI PG, ROMAGNOLI R, PRETI D, FRUTTAROLO F, CARRION MD, TABRIZI MA: Ligands for A2B adenosine receptor subtype. Curr. Med. Chem. (2006) 13(28):3467-3482.

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