메뉴 건너뛰기




Volumn 54, Issue 2, 2011, Pages 655-668

Discovery of 7- N -piperazinylthiazolo[5,4- d ]pyrimidine analogues as a novel class of immunosuppressive agents with in vivo biological activity

Author keywords

[No Author keywords available]

Indexed keywords

7 N PIPERAZINYLTHIAZOLO[5,4 D]PYRIMIDINE; CYCLOSPORIN A; IMMUNOSUPPRESSIVE AGENT; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 78751676018     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101254z     Document Type: Article
Times cited : (39)

References (40)
  • 1
    • 33846948640 scopus 로고    scopus 로고
    • T cell- directed therapies: Lessons learned and future prospects
    • Liu, E. H.; Siegel, R. M.; Harlan, D. M.; OShea, J. J. T cell- directed therapies: lessons learned and future prospects Nat. Immunol. 2007, 8, 25-30
    • (2007) Nat. Immunol. , vol.8 , pp. 25-30
    • Liu, E.H.1    Siegel, R.M.2    Harlan, D.M.3    Oshea, J.J.4
  • 2
    • 0347626159 scopus 로고    scopus 로고
    • Current immunosuppressive agents: Efficacy, side effects, and utilization
    • Smith, J. M.; Nemeth, T. L.; McDonald, R. A. Current immunosuppressive agents: efficacy, side effects, and utilization Pediatr. Clin. North Am. 2003, 50, 1283-1300
    • (2003) Pediatr. Clin. North Am. , vol.50 , pp. 1283-1300
    • Smith, J.M.1    Nemeth, T.L.2    McDonald, R.A.3
  • 5
    • 0034023906 scopus 로고    scopus 로고
    • Immunosuppressive agents in organ transplantation: Past, present, and future
    • Hong, J. C.; Kahan, B. D. Immunosuppressive agents in organ transplantation: past, present, and future Semin. Nephrol. 2000, 20, 108-125
    • (2000) Semin. Nephrol. , vol.20 , pp. 108-125
    • Hong, J.C.1    Kahan, B.D.2
  • 10
    • 0025995750 scopus 로고
    • Isosterism and bioisosterism in drug design
    • Burger, A. Isosterism and bioisosterism in drug design Prog. Drug Res. 1991, 37, 287-371
    • (1991) Prog. Drug Res. , vol.37 , pp. 287-371
    • Burger, A.1
  • 11
    • 0022549277 scopus 로고
    • Inhibitors of human purine nucleoside phosphorylase. Synthesis, purine nucleoside phosphorylase inhibition, and T-cell cytotoxicity of 2,5-diaminothiazolo[5,4 -d ]pyrimidin-7(6 H)-one and 2,5-diaminothiazolo[4,5 -d ]pyrimidin-7(6 H)-one. Two thio isosteres of 8-aminoguanine
    • Sircar, J. C.; Suto, M. J.; Scott, M. E.; Dong, M. K.; Gilbertsen, R. B. Inhibitors of human purine nucleoside phosphorylase. Synthesis, purine nucleoside phosphorylase inhibition, and T-cell cytotoxicity of 2,5-diaminothiazolo[5,4 -d ]pyrimidin-7(6 H)-one and 2,5-diaminothiazolo[4,5 -d ]pyrimidin-7(6 H)-one. Two thio isosteres of 8-aminoguanine J. Med. Chem. 1986, 29, 1804-1806
    • (1986) J. Med. Chem. , vol.29 , pp. 1804-1806
    • Sircar, J.C.1    Suto, M.J.2    Scott, M.E.3    Dong, M.K.4    Gilbertsen, R.B.5
  • 17
    • 84970580974 scopus 로고
    • The chemistry of pyrimidinethiols. III. The synthesis of some substituted pyrimidinethiols and some thiazolo[5,4 -d ]pyrimidines
    • Harnden, M. R.; Hurst, D. T. The chemistry of pyrimidinethiols. III. The synthesis of some substituted pyrimidinethiols and some thiazolo[5,4 -d ]pyrimidines Aust. J. Chem. 1990, 43, 55-62
    • (1990) Aust. J. Chem. , vol.43 , pp. 55-62
    • Harnden, M.R.1    Hurst, D.T.2
  • 18
    • 23444431603 scopus 로고    scopus 로고
    • The synthetic versatility of alkoxycarbonyl- and hydroxymethyl- piperazine-2,5-diones
    • Chai, C. L. L.; Elix, J. A.; Huleatt, P. B. The synthetic versatility of alkoxycarbonyl- and hydroxymethyl-piperazine-2,5-diones Tetrahedron 2005, 61, 8722-8739
    • (2005) Tetrahedron , vol.61 , pp. 8722-8739
    • Chai, C.L.L.1    Elix, J.A.2    Huleatt, P.B.3
  • 19
    • 28244432797 scopus 로고    scopus 로고
    • New facile and mild synthesis of 2-substituted oxazolopyridines
    • Heuser, S.; Keenan, M.; Weichert, A. G. New facile and mild synthesis of 2-substituted oxazolopyridines Tetrahedron Lett. 2005, 46, 9001-9004
    • (2005) Tetrahedron Lett. , vol.46 , pp. 9001-9004
    • Heuser, S.1    Keenan, M.2    Weichert, A.G.3
  • 21
    • 0023198419 scopus 로고
    • Substituted 1,2,3,4-tetrahydroaminonaphthols: Antihypertensive agents, calcium channel blockers, and adrenergic receptor blockers with catecholamine-depleting effects
    • Atwal, K. S.; OReilly, B. C.; Ruby, E. P.; Turk, C. F.; Aberg, G.; Asaad, M. M.; Bergey, J. L.; Moreland, S.; Powell, J. R. Substituted 1,2,3,4-tetrahydroaminonaphthols: antihypertensive agents, calcium channel blockers, and adrenergic receptor blockers with catecholamine-depleting effects J. Med. Chem. 1987, 30, 627-635
    • (1987) J. Med. Chem. , vol.30 , pp. 627-635
    • Atwal, K.S.1    Oreilly, B.C.2    Ruby, E.P.3    Turk, C.F.4    Aberg, G.5    Asaad, M.M.6    Bergey, J.L.7    Moreland, S.8    Powell, J.R.9
  • 22
    • 0000825229 scopus 로고
    • 1-Methyl-2-pyrrolidinone: A well-adapted solvent in benzothiazole synthesis
    • Brembilla, A.; Roizard, D.; Lochon, P. 1-Methyl-2-pyrrolidinone: a well-adapted solvent in benzothiazole synthesis Synth. Commun. 1990, 20, 3379-3384
    • (1990) Synth. Commun. , vol.20 , pp. 3379-3384
    • Brembilla, A.1    Roizard, D.2    Lochon, P.3
  • 24
    • 2542422221 scopus 로고    scopus 로고
    • New fluorescent 1,3-benzothiazoles by the reaction of heterocyclic aldehydes with o -aminobenzenethiol
    • Costa, S. P. G.; Ferreira, J. A.; Kirsch, G.; Oliveira-Campos, A. M. F. New fluorescent 1,3-benzothiazoles by the reaction of heterocyclic aldehydes with o -aminobenzenethiol J. Chem. Res., Synop. 1997, 9, 314-315
    • (1997) J. Chem. Res., Synop. , vol.9 , pp. 314-315
    • Costa, S.P.G.1    Ferreira, J.A.2    Kirsch, G.3    Oliveira-Campos, A.M.F.4
  • 25
    • 64349098241 scopus 로고    scopus 로고
    • Modulating the near-infrared luminescence of neodymium and ytterbium complexes with tridentate ligands based on benzoxazole-substituted 8-hydroxyquinolines
    • Shavaleev, N. M.; Scopelliti, R.; Gumy, F.; Bunzli, J.-C. G. Modulating the near-infrared luminescence of neodymium and ytterbium complexes with tridentate ligands based on benzoxazole-substituted 8-hydroxyquinolines Inorg. Chem. 2009, 48, 2908-2918
    • (2009) Inorg. Chem. , vol.48 , pp. 2908-2918
    • Shavaleev, N.M.1    Scopelliti, R.2    Gumy, F.3    Bunzli, J.-C.G.4
  • 26
    • 33244498053 scopus 로고    scopus 로고
    • Synthesis and evaluation of 7-amino-2-(2(3)-furyl)-5-phenylethylamino- oxazolo[5,4 -d ]pyrimidines as potential A2A adenosine receptor antagonists for positron emission tomography (PET)
    • Holschbach, M. H.; Bier, D.; Stüsgen, S.; Wutz, W.; Sihver, W.; Coenen, H. H.; Olsson, R. A. Synthesis and evaluation of 7-amino-2-(2(3)-furyl)- 5-phenylethylamino-oxazolo[5,4 -d ]pyrimidines as potential A2A adenosine receptor antagonists for positron emission tomography (PET) Eur. J. Med. Chem. 2006, 41, 7-15
    • (2006) Eur. J. Med. Chem. , vol.41 , pp. 7-15
    • Holschbach, M.H.1    Bier, D.2    Stüsgen, S.3    Wutz, W.4    Sihver, W.5    Coenen, H.H.6    Olsson, R.A.7
  • 27
    • 0014906974 scopus 로고
    • Synthesis of derivatives of thiazolo[4,5 -d ]pyrimidine. Part II
    • Baker, J. A.; Chatfield, P. V. Synthesis of derivatives of thiazolo[4,5 -d ]pyrimidine. Part II J. Chem. Soc. C 1970, 2478-2484
    • (1970) J. Chem. Soc. C , pp. 2478-2484
    • Baker, J.A.1    Chatfield, P.V.2
  • 28
    • 30344436368 scopus 로고    scopus 로고
    • Hit-to-lead studies: The discovery of potent, orally bioavailable thiazolopyrimidine CXCR2 receptor antagonists
    • Baxter, A.; Cooper, A.; Kinchin, E.; Moakes, K.; Unitt, J.; Wallace, A. Hit-to-lead studies: the discovery of potent, orally bioavailable thiazolopyrimidine CXCR2 receptor antagonists Bioorg. Med. Chem. Lett. 2006, 16, 960-963
    • (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 960-963
    • Baxter, A.1    Cooper, A.2    Kinchin, E.3    Moakes, K.4    Unitt, J.5    Wallace, A.6
  • 29
    • 0000978075 scopus 로고
    • Purine nucleosides. VII. Direct bromination of adenosine, deoxyadenosine, guanosine, and related purine nucleosides
    • Holmes, R. E.; Robins, R. K. Purine nucleosides. VII. Direct bromination of adenosine, deoxyadenosine, guanosine, and related purine nucleosides J. Am. Chem. Soc. 1964, 86, 1242-1245
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 1242-1245
    • Holmes, R.E.1    Robins, R.K.2
  • 30
    • 74049088722 scopus 로고    scopus 로고
    • Synthesis, immunosuppressive activity and structure-activity relationship study of a new series of 4- N -piperazinyl-thieno[2,3- d ]pyrimidine analogues
    • Jang, M. Y.; De Jonghe, S.; Van Belle, K.; Louat, T.; Waer, M.; Herdewijn, P. Synthesis, immunosuppressive activity and structure-activity relationship study of a new series of 4- N -piperazinyl-thieno[2,3- d ]pyrimidine analogues Bioorg. Med. Chem. Lett. 2010, 20, 844-847
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 844-847
    • Jang, M.Y.1    De Jonghe, S.2    Van Belle, K.3    Louat, T.4    Waer, M.5    Herdewijn, P.6
  • 31
    • 0038121754 scopus 로고    scopus 로고
    • Synthesis and DHFR inhibitory activity of a series of 6-substituted-2,4-diaminothieno[2,3 -d ]pyrimidines
    • Donkor, I. O.; Li, H.; Queener, S. F. Synthesis and DHFR inhibitory activity of a series of 6-substituted-2,4-diaminothieno[2,3 -d ]pyrimidines Eur. J. Med. Chem. 2003, 38, 605-611
    • (2003) Eur. J. Med. Chem. , vol.38 , pp. 605-611
    • Donkor, I.O.1    Li, H.2    Queener, S.F.3
  • 32
    • 37549031766 scopus 로고    scopus 로고
    • The scope and mechanism of phosphonium-mediated S(N)Ar reactions in heterocyclic amides and ureas
    • Wan, Z. K.; Wacharasindhu, S.; Levins, C. G.; Lin, M.; Tabei, K.; Mansour, T. S. The scope and mechanism of phosphonium-mediated S(N)Ar reactions in heterocyclic amides and ureas J. Org. Chem. 2007, 72, 10194-10210
    • (2007) J. Org. Chem. , vol.72 , pp. 10194-10210
    • Wan, Z.K.1    Wacharasindhu, S.2    Levins, C.G.3    Lin, M.4    Tabei, K.5    Mansour, T.S.6
  • 33
    • 33745725794 scopus 로고    scopus 로고
    • An efficient direct amination of cyclic amides and cyclic ureas
    • Wan, Z. K.; Wacharasindhu, S.; Binnun, E.; Mansour, T. An efficient direct amination of cyclic amides and cyclic ureas Org. Lett. 2006, 8, 2425-2428
    • (2006) Org. Lett. , vol.8 , pp. 2425-2428
    • Wan, Z.K.1    Wacharasindhu, S.2    Binnun, E.3    Mansour, T.4
  • 35
    • 78751660871 scopus 로고    scopus 로고
    • OpenEye Scientific Software Inc., Santa Fe, NM; available from
    • OpenEye Scientific Software Inc., Santa Fe, NM; available from http://www.eyesopen.com.
  • 36
    • 33745078578 scopus 로고    scopus 로고
    • The use of three-dimensional shape and electrostatic similarity searching in the identification of a melanin-concentrating hormone receptor 1 antagonist
    • Muchmore, S.; Souers, A. J.; Akritopoulou-Zanze, I. The use of three-dimensional shape and electrostatic similarity searching in the identification of a melanin-concentrating hormone receptor 1 antagonist Chem. Biol. Drug Des. 2006, 67, 174-176
    • (2006) Chem. Biol. Drug Des. , vol.67 , pp. 174-176
    • Muchmore, S.1    Souers, A.J.2    Akritopoulou-Zanze, I.3
  • 38
    • 0030040323 scopus 로고    scopus 로고
    • Reduced surface: An efficient way to compute molecular surfaces
    • Sanner, M. F.; Olson, A. J.; Spehner, J. C. Reduced surface: an efficient way to compute molecular surfaces Biopolymers 1996, 38, 305-320
    • (1996) Biopolymers , vol.38 , pp. 305-320
    • Sanner, M.F.1    Olson, A.J.2    Spehner, J.C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.