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Design, synthesis, and biological evaluation of novel catecholopyrimidine based PDE4 inhibitor for the treatment of atopic dermatitis

European journal of medicinal chemistry, v.145, 2018년, pp.673 - 690  

Purushothaman, Baskaran (Corresponding author.) ,  Arumugam, Parthasarathy ,  Kulsi, Goutam ,  Song, Joon Myong

Abstract AI-Helper 아이콘AI-Helper

Selective inhibition of phosphodiesterase (PDE) 4B favorably suppresses the synthesis of inflammatory cytokines and subsequently arrest the development of atopic dermatitis via modulating the intracellular CAMP levels. Considering the side effects of corticosteroids, selective PDE4 inhibition could ...

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참고문헌 (62)

  1. Lancet Beasley 351 1225 1998 10.1016/S0140-6736(97)07302-9 T.I.S. of Asthma, Worldwide variation in prevalence of symptoms of asthma, allergic rhinoconjunctivitis, and atopic eczema: ISAAC 

  2. J. Allergy Clin. Immunol. Odhiambo 124 2009 10.1016/j.jaci.2009.10.009 Global variations in prevalence of eczema symptoms in children from ISAAC phase three 

  3. J. Am. Acad. Dermatol. Simpson 74 491 2016 10.1016/j.jaad.2015.10.043 Patient burden of moderate to severe atopic dermatitis (AD): insights from a phase 2b clinical trial of dupilumab in adults 

  4. J. Hum. Genet. Wu 60 675 2015 10.1038/jhg.2015.99 The genomic landscape of human immune-mediated diseases 

  5. Immunol. Rev. Boguniewicz 242 233 2011 10.1111/j.1600-065X.2011.01027.x Atopic dermatitis: a disease of altered skin barrier and immune dysregulation 

  6. Cell. Signal. Mosenden 23 1009 2011 10.1016/j.cellsig.2010.11.018 Cyclic AMP-mediated immune regulation-overview of mechanisms of action in T cells 

  7. J. Pharmacol. Exp. Therapeut. Jimenez 299 753 2001 Phosphodiesterase 4 inhibitors prevent cytokine secretion by T lymphocytes by inhibiting nuclear factor-κB and nuclear factor of activated T cells activation 

  8. J. Immunol. Wen 185 6413 2010 10.4049/jimmunol.1001829 The role of the transcription factor CREB in immune function 

  9. J. Am. Acad. Dermatol. Hanifin 75 2 297 2016 10.1016/j.jaad.2016.04.001 OPA-15406, a novel, topical, nonsteroidal, selective phosphodiesterase-4 (PDE4) inhibitor, in the treatment of adult and adolescent patients with mild to moderate atopic dermatitis (AD): a phase-II randomized, double-blind, placebo-controlled study 

  10. Nat. Rev. Drug Discov. Maurice 13 290 2014 10.1038/nrd4228 Advances in targeting cyclic nucleotide phosphodiesterases 

  11. Circ. Res. Omori 100 309 2007 10.1161/01.RES.0000256354.95791.f1 Overview of PDEs and their regulation 

  12. J. Med. Chem. Kodimuthali 51 5471 2008 10.1021/jm800582j Recent advances on phosphodiesterase 4 inhibitors for the treatment of asthma and chronic obstructive pulmonary disease 

  13. Mol. Pharmacol. Wang 56 170 1999 10.1124/mol.56.1.170 Phosphodiesterase 4B2 is the predominant phosphodiesterase species and undergoes differential regulation of gene expression in human monocytes and neutrophils 

  14. J. Clin. Invest. Robichaud 110 1045 2002 10.1172/JCI0215506 Deletion of phosphodiesterase 4D in mice shortens α2-adrenoceptor-mediated anesthesia, a behavioral correlate of emesis 

  15. Org. Biomol. Chem. Gorja 11 2075 2013 10.1039/c3ob27424a Novel N-indolylmethyl substituted olanzapine derivatives: their design, synthesis and evaluation as PDE4B inhibitors 

  16. Bioorg. Med. Chem. Lett Naganuma 19 3174 2009 10.1016/j.bmcl.2009.04.121 Discovery of selective PDE4B inhibitors 

  17. Bioorg. Med. Chem. Lett Goto 24 893 2014 10.1016/j.bmcl.2013.12.076 Identification of the 5, 5-dioxo-7, 8-dihydro-6H-thiopyrano [3, 2-d] pyrimidine derivatives as highly selective PDE4B inhibitors 

  18. Bioorg. Med. Chem. Kranz 17 5336 2009 10.1016/j.bmc.2009.03.061 Identification of PDE4B over 4D subtype-selective inhibitors revealing an unprecedented binding mode 

  19. Dermatol. Ther. Wittmann 3 1 2013 10.1007/s13555-013-0023-0 Phosphodiesterase 4 inhibition in the treatment of psoriasis, psoriatic arthritis and other chronic inflammatory diseases 

  20. J. Clin. Gastroenterol. Buchman 33 289 2001 10.1097/00004836-200110000-00006 Side effects of corticosteroid therapy 

  21. Sci. Rep. Bordag 5 2015 10.1038/srep15954 Glucocorticoid (dexamethasone)-induced metabolome changes in healthy males suggest prediction of response and side effects 

  22. Curr. Med. Chem. Parikh 23 129 2016 10.2174/0929867323666151117121334 Phosphodiesterase 4 (PDE4) inhibitors in the treatment of COPD: promising drug candidates and future directions 

  23. Curr. Pharmaceut. Des. Contreras 23 2073 2017 10.2174/1381612823666170214105651 Selective inhibition of phosphodiesterases 4A, B, C and D Isoforms in chronic respiratory diseases: current and future evidences 

  24. Mol. Cell Biol. Arp 23 8042 2003 10.1128/MCB.23.22.8042-8057.2003 Regulation of T-cell activation by phosphodiesterase 4B2 requires its dynamic redistribution during immunological synapse formation 

  25. J. Immunol. Asirvatham 173 4806 2004 10.4049/jimmunol.173.8.4806 A-kinase anchoring proteins interact with phosphodiesterases in T lymphocyte cell lines 

  26. Biochem. J. Small-Howard 388 465 2005 10.1042/BJ20041682 Anti-inflammatory potential of CB1-mediated cAMP elevation in mast cells 

  27. Br. J. Pharmacol. Spina 155 308 2008 10.1038/bjp.2008.307 PDE4 inhibitors: current status 

  28. PLoS One Konrad 10 2015 10.1371/journal.pone.0121725 The unrecognized effects of phosphodiesterase 4 on epithelial cells in pulmonary inflammation 

  29. Am. J. Respir. Crit. Care Med. Calverley 176 154 2007 10.1164/rccm.200610-1563OC Effect of 1-year treatment with roflumilast in severe chronic obstructive pulmonary disease 

  30. Br. J. Pharmacol. Rabe 163 53 2011 10.1111/j.1476-5381.2011.01218.x Update on roflumilast, a phosphodiesterase 4 inhibitor for the treatment of chronic obstructive pulmonary disease 

  31. Curr. Opin. Neurobiol. Gray 8 330 1998 10.1016/S0959-4388(98)80057-3 Regulation of ion channels by cAMP-dependent protein kinase and A-kinase anchoring proteins 

  32. J. Cell. Physiol. Carvajal 184 409 2000 10.1002/1097-4652(200009)184:3<409::AID-JCP16>3.0.CO;2-K Molecular mechanism of cGMP-mediated smooth muscle relaxation 

  33. Expet Rev. Mol. Med. Carroll 15 2013 Differentiation of mesenchymal stem cells to osteoblasts and chondrocytes: a focus on adenosine receptors 

  34. Proc. Natl. Acad. Sci. U.S.A. Khan 113 746 2016 10.1073/pnas.1524272113 Sympathetic innervation controls homeostasis of neuromuscular junctions in health and disease 

  35. Nat. Rev. Mol. Cell Biol. Wang 16 678 2015 10.1038/nrm4074 Transcriptional regulation of hepatic lipogenesis 

  36. Cell Death Dis. Wang 7 2016 10.1038/cddis.2016.106 A cardiac mitochondrial cAMP signaling pathway regulates calcium accumulation, permeability transition and cell death 

  37. J. Am. Acad. Dermatol. Bissonnette 75 99 2016 10.1016/j.jaad.2016.02.1164 

  38. J. Med. Chem. Felding 57 5893 2014 10.1021/jm500378a Discovery and early clinical development of 2-{6-[2-(3, 5-dichloro-4-pyridyl) acetyl]-2, 3-dimethoxyphenoxy}-N-propylacetamide (LEO 29102), a soft-drug inhibitor of phosphodiesterase 4 for topical treatment of atopic dermatitis 

  39. Eur. J. Med. Chem. Cherukupalli 126 298 2017 10.1016/j.ejmech.2016.11.019 An insight on synthetic and medicinal aspects of pyrazolo [1, 5-a] pyrimidine scaffold 

  40. Eur. J. Med. Chem. Taltavull 46 4946 2011 10.1016/j.ejmech.2011.07.054 Synthesis and biological activity of pyrido [3′, 2′: 4, 5] furo [3, 2-d] pyrimidine derivatives as novel and potent phosphodiesterase type 4 inhibitors 

  41. Mol. Inform D'Ursi 35 369 2016 10.1002/minf.201501033 Further insights in the binding mode of selective inhibitors to human PDE4D enzyme combining docking and molecular dynamics 

  42. Bioorg. Med. Chem. Lett Donnell 20 2163 2010 10.1016/j.bmcl.2010.02.044 Identification of pyridazino [4, 5-b] indolizines as selective PDE4B inhibitors 

  43. J. Med. Chem. Gillis 58 8315 2015 10.1021/acs.jmedchem.5b00258 Applications of fluorine in medicinal chemistry 

  44. J. Med. Chem. Hagmann 51 4359 2008 10.1021/jm800219f The many roles for fluorine in medicinal chemistry 

  45. J. Am. Chem. Soc. Littke 122 4020 2000 10.1021/ja0002058 Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions 

  46. B. Gopalan, L.A. Gharat, B. Chandrasekhar, B.G. Pillai, Process for the preparation of n-(3, 5-dichloropyrid-4-yl)-4-difluoromethoxy-8-methanesulfonamido-dibenzo [b, d] furan-1-carboxamide, in, Google Patents, 2009. 

  47. Mol. Pharmacol. Dym 61 20 2002 10.1124/mol.61.1.20 Molecular docking of competitive phosphodiesterase inhibitors 

  48. Science Xu 288 1822 2000 10.1126/science.288.5472.1822 Atomic structure of PDE4: insights into phosphodiesterase mechanism and specificity 

  49. Mol. Divers. Guariento 20 77 2016 10.1007/s11030-015-9631-1 New insights into PDE4B inhibitor selectivity: CoMFA analyses and molecular docking studies 

  50. Structure Card 12 2233 2004 10.1016/j.str.2004.10.004 Structural basis for the activity of drugs that inhibit phosphodiesterases 

  51. Smart 57 1994 Organofluorine Chemistry Characteristics of CF systems 

  52. ChemMedChem Morgenthaler 2 1100 2007 10.1002/cmdc.200700059 Predicting and tuning physicochemical properties in lead optimization: amine basicities 

  53. J. Med. Chem. Bissantz 53 5061 2010 10.1021/jm100112j A medicinal chemist's guide to molecular interactions 

  54. Mini Rev. Med. Chem. Zhou 10 309 2010 10.2174/138955710791331016 Rediscovery of halogen bonds in protein-ligand complexes 

  55. J. Recept. Signal. Transduct Perozzo 24 1 2004 10.1081/RRS-120037896 Thermodynamics of protein-ligand interactions: history, presence, and future aspects 

  56. J. Allergy Clin. Immunol. Stone 125 S73 2010 10.1016/j.jaci.2009.11.017 IgE, mast cells, basophils, and eosinophils 

  57. Crit. Rev. Eukaryot. Gene Expr. Parameswaran 20 2010 10.1615/CritRevEukarGeneExpr.v20.i2.10 Tumor necrosis factor-α signaling in macrophages 

  58. Acta Crystallogr. A. Clark 51 887 1995 10.1107/S0108767395007367 The analytical calculation of absorption in multifaceted crystals 

  59. J. Appl. Crystallogr. Dolomanov 42 339 2009 10.1107/S0021889808042726 OLEX2: a complete structure solution, refinement and analysis program 

  60. Proc. Natl. Acad. Sci. U.S.A. Xia 106 2412 2009 10.1073/pnas.0813020106 Identification of compounds that potentiate CREB signaling as possible enhancers of long-term memory 

  61. Biochem. Pharmacol. Pan 48 827 1994 10.1016/0006-2952(94)90062-0 Synergistic interactions between selective pharmacological inhibitors of phosphodiesterase isozyme families PDE III and PDE IV to attenuate proliferation of rat vascular smooth muscle cells 

  62. Int. Immunol. Matsuda 9 461 1997 10.1093/intimm/9.3.461 Development of atopic dermatitis-like skin lesion with IgE hyperproduction in NC/Nga mice 

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