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Volumn 15, Issue 12, 2010, Pages 8689-8701

Concise syntheses of trifluoromethylated cyclic and acyclic analogues of cADPR

Author keywords

Acyclic cADPR analogue; CADPR analogue; Synthesis; Trifluoromethylation

Indexed keywords

CYCLIC ADENOSINE DIPHOSPHATE RIBOSE; DRUG DERIVATIVE; FLUORINATED HYDROCARBON; HYPOXANTHINE; RYANODINE RECEPTOR;

EID: 78650637694     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15128689     Document Type: Article
Times cited : (15)

References (24)
  • 1
    • 0023219685 scopus 로고
    • Pyridine nucleotide metabolites stimulate calcium release from sea urchin egg microsomes desensitized to inositol trisphosphate
    • Clapper, D.L.; Walseth, T.F.; Dargie P.J.; Lee, H C. Pyridine nucleotide metabolites stimulate calcium release from sea urchin egg microsomes desensitized to inositol trisphosphate. J. Biol Chem. 1987, 262, 9561-9568.
    • (1987) J. Biol Chem. , vol.262 , pp. 9561-9568
    • Clapper, D.L.1    Walseth, T.F.2    Dargie, P.J.3    Lee H, C.4
  • 2
    • 1842587485 scopus 로고    scopus 로고
    • Biochemistry biology, and pharmacology of cyclic adenosine diphosphoribose (cADPR)
    • Guse, A.H. Biochemistry, biology, and pharmacology of cyclic adenosine diphosphoribose (cADPR). Curr. Med. Chem. 2004, 11, 847-855.
    • (2004) Curr. Med. Chem. , vol.11 , pp. 847-855
    • Guse, A.H.1
  • 3
    • 1842483034 scopus 로고    scopus 로고
    • Chemistry of cyclic ADP-ribose and its analogs
    • Shuto S.; Matsuda A. Chemistry of cyclic ADP-ribose and its analogs. Curr. Med. Chem. 2004, 11, 827-845.
    • (2004) Curr. Med. Chem. , vol.11 , pp. 827-845
    • Shuto, S.1    Matsuda, A.2
  • 4
    • 78650640309 scopus 로고    scopus 로고
    • Cyclic ADP-ribose analogues with minimal structure: Synthesis and calcium-release activity
    • Huang, Z.W., Ed.; John Wiley & Sons, Inc.: New York, NY, USA
    • Zhang, L.H.; Guse, A.H. Cyclic ADP-ribose analogues with minimal structure: synthesis and calcium-release activity. In Drug Discovery Research: New Frontiers in the Post-Genomic Era; Huang, Z.W., Ed.; John Wiley & Sons, Inc.: New York, NY, USA, 2007; pp.186-202.
    • (2007) Drug Discovery Research: New Frontiers in the Post-Genomic Era , pp. 186-202
    • Zhang, L.H.1    Guse, A.H.2
  • 5
    • 75849144105 scopus 로고    scopus 로고
    • A solid-phase approach to the synthesis of N-1-alkyl analogues of cyclic inosine-diphosphate-ribose (cIDPR)
    • Oliviero, G.; D'Errico, S.; Borbone, N.; Amato, J.; Piccialli, V.; Varra, M.; Piccialli, G.; Mayol, L. A solid-phase approach to the synthesis of N-1-alkyl analogues of cyclic inosine-diphosphate-ribose (cIDPR). Tetrahedron 2010, 66, 1931-1936.
    • (2010) Tetrahedron , vol.66 , pp. 1931-1936
    • Oliviero, G.1    D'Errico, S.2    Borbone, N.3    Amato, J.4    Piccialli, V.5    Varra, M.6    Piccialli, G.7    Mayol, L.8
  • 6
    • 7444230429 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of novel membrane-permeant cyclic ADP-ribose mimics: N1-[(5''-O-phosphorylethoxy)-methyl]-5'-Ophosphorylinosine 5'5''-cyclic pyrophosphate (cIDPRE) and 8-substituted derivatives
    • Gu, X.F.; Yang, Z.J.; Zhang, L R.; Zhang, L.H. Synthesis and biological evaluation of novel membrane-permeant cyclic ADP-ribose mimics: N1-[(5''-O-phosphorylethoxy)-methyl]-5'-Ophosphorylinosine 5',5''-cyclic pyrophosphate (cIDPRE) and 8-substituted derivatives. J. Med. Chem. 2004, 47, 5674-5682.
    • (2004) J. Med. Chem. , vol.47 , pp. 5674-5682
    • Gu, X.F.1    Yang, Z.J.2    Zhang L, R.3    Zhang, L.H.4
  • 7
  • 8
    • 0026760246 scopus 로고
    • Trifluoromethylations and related reactions in organic chemistry
    • McClinton, M.A.; McClinton, D.A. Trifluoromethylations and related reactions in organic chemistry. Tetrahedron 1992, 48, 6555-6666
    • (1992) Tetrahedron , vol.48 , pp. 6555-6666
    • McClinton, M.A.1    McClinton, D.A.2
  • 9
    • 77957654837 scopus 로고    scopus 로고
    • Trifluoromethylated cyclic-ADP- Ribose mimic: Synthesis of 8-trifluoromethyl-N1- [(5''-O-Phosphorylethoxy)methyl]-5'-O-phosphorylinosine- 5',5''-cyclic pyrophosphate (8-CF3- cIDPRE) and its calcium release activity in T cells
    • Dong, M.; Kirchberger, T.; Huang, X.C.; Yang, Z.J.; Zhang, L.R.; Guse, A.H.; Zhang, L.H. Trifluoromethylated Cyclic-ADP- Ribose Mimic: Synthesis of 8-trifluoromethyl-N1- [(5''-O-Phosphorylethoxy)methyl]-5'-O-phosphorylinosine- 5',5''-cyclic pyrophosphate (8-CF3- cIDPRE) and its calcium release activity in T Cells. Org. Biomol. Chem. 2010, 8, 4705-4715.
    • (2010) Org. Biomol. Chem. , vol.8 , pp. 4705-4715
    • Dong, M.1    Kirchberger, T.2    Huang, X.C.3    Yang, Z.J.4    Zhang, L.R.5    Guse, A.H.6    Zhang, L.H.7
  • 11
    • 0028026757 scopus 로고
    • Cyclic-ADP-ribose: Synthesis and structure
    • Gu, Q.M.; Sih, C.J. Cyclic-ADP-ribose: synthesis and structure. J. Am. Chem. Soc. 1994, 116, 7481-7486.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 7481-7486
    • Gu, Q.M.1    Sih, C.J.2
  • 12
  • 13
    • 77952570041 scopus 로고    scopus 로고
    • Concise synthesis of acyclic analogues of cADPR with ether chain as northern moiety
    • Wu, H.M.; Yang, Z.J.; Zhang, L.R.; Zhang, L.H. Concise Synthesis of Acyclic Analogues of cADPR with Ether Chain as Northern Moiety. New J. Chem. 2010, 34, 956-966.
    • (2010) New J. Chem. , vol.34 , pp. 956-966
    • Wu, H.M.1    Yang, Z.J.2    Zhang, L.R.3    Zhang, L.H.4
  • 14
    • 33745736446 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of purine derivatives incorporating metal chelating ligands as HIV integrase inhibitors
    • Li, X.; Vince, R. Synthesis and biological evaluation of purine derivatives incorporating metal chelating ligands as HIV integrase inhibitors. Bioorg. Med. Chem. 2006, 14, 5742-5755.
    • (2006) Bioorg. Med. Chem. , vol.14 , pp. 5742-5755
    • Li, X.1    Vince, R.2
  • 15
    • 0019975382 scopus 로고
    • Convenient and high-yield syntheses of N-[(2-hydroxyethoxy) methyl] heterocycles as "acyclic nucleoside'' analogues
    • Robins, M.J.; Hatfield, P.W. Convenient and high-yield syntheses of N-[(2-hydroxyethoxy) methyl] heterocycles as "acyclic nucleoside'' analogues. Can. J. Chem. 1982, 60, 547-553
    • (1982) Can. J. Chem. , vol.60 , pp. 547-553
    • Robins, M.J.1    Hatfield, P.W.2
  • 16
    • 0025789109 scopus 로고
    • Solid-liquid phase catalysis I: Study of the N-alkylation of purines and pyrimidines
    • Lazrek, H.B.; Taourirte, M.; Barascut, J.L.; Imbach, J.L. Solid-liquid phase catalysis I: study of the N-alkylation of purines and pyrimidines. Nucleos. Nucleot. 1991, 10, 1285-1293.
    • (1991) Nucleos. Nucleot. , vol.10 , pp. 1285-1293
    • Lazrek, H.B.1    Taourirte, M.2    Barascut, J.L.3    Imbach, J.L.4
  • 17
    • 37049090899 scopus 로고
    • Methyl fluorosulphonyldifluoroacetate, a new trifluoromethylating agent
    • Chen, Q.Y.; Wu, S.W. Methyl fluorosulphonyldifluoroacetate, a new trifluoromethylating agent. J. Chem. Soc., Chem. Commun. 1989, 705-706.
    • (1989) J. Chem. Soc., Chem. Commun. , pp. 705-706
    • Chen, Q.Y.1    Wu, S.W.2
  • 18
    • 84989409179 scopus 로고
    • Use of organosilicon reagents as protective groups in organic synthesis
    • Lalonde, M.; Chan, T.H. Use of organosilicon reagents as protective groups in organic synthesis. Synthesis 1985, 817-845.
    • (1985) Synthesis , pp. 817-845
    • Lalonde, M.1    Chan, T.H.2
  • 19
    • 84988110543 scopus 로고
    • Stereocontrolled total synthesis of lipoxins B
    • Nicolaou, K.C.; Webber, S.E. Stereocontrolled total synthesis of lipoxins B. Synthesis 1986, 453-461.
    • (1986) Synthesis , pp. 453-461
    • Nicolaou, K.C.1    Webber, S.E.2
  • 20
    • 2442720415 scopus 로고
    • A convenient method for the preparation of S,S-diaryl phosphorodithioates
    • Yamaguchi, K.; Honda, S.; Hata, T. A convenient method for the preparation of S,S-diaryl phosphorodithioates. Chem. Lett. 1979, 507-508.
    • (1979) Chem. Lett. , pp. 507-508
    • Yamaguchi, K.1    Honda, S.2    Hata, T.3
  • 22
    • 21544460203 scopus 로고    scopus 로고
    • Mild and chemoselective deacetylation method using a catalytic amount of acetyl chloride in methanol
    • Yeom, C.E.; Lee, S.Y.; Kim, Y.J.; Kim, B.M. Mild and chemoselective deacetylation method using a catalytic amount of acetyl chloride in methanol. Syn. Lett. 2005, 10, 1527-1530.
    • (2005) Syn. Lett. , vol.10 , pp. 1527-1530
    • Yeom, C.E.1    Lee, S.Y.2    Kim, Y.J.3    Kim, B.M.4
  • 23
    • 44749089222 scopus 로고    scopus 로고
    • A concise route for the preparation of nucleobase-simplified cADPR mimics by click chemistry
    • Li, L.J.; Lin, B.C.; Yang, Z.J.; Zhang, L.R.; Zhang, L.H. A concise route for the preparation of nucleobase-simplified cADPR mimics by click chemistry. Tetrahedron Lett. 2008, 49, 4491-4493.
    • (2008) Tetrahedron Lett. , vol.49 , pp. 4491-4493
    • Li, L.J.1    Lin, B.C.2    Yang, Z.J.3    Zhang, L.R.4    Zhang, L.H.5
  • 24
    • 0034714481 scopus 로고    scopus 로고
    • An efficient synthesis of cyclic IDP- and cyclic condensation method to form an intramolecular pyrophosphate linkage as a key step. An entry to a general method for the chemical synthesis of synthesis of cyclic ADP-ribose analogues
    • Fukuoka, M.; Shuto, S.; Shirato, M.; Sumita, Y.; Veno, Y.; Matsuda, A. An efficient synthesis of cyclic IDP- and cyclic condensation method to form an intramolecular pyrophosphate linkage as a key step. An entry to a general method for the chemical synthesis of synthesis of cyclic ADP-ribose analogues. J. Org. Chem. 2000, 65, 5238-5248.
    • (2000) J. Org. Chem. , vol.65 , pp. 5238-5248
    • Fukuoka, M.1    Shuto, S.2    Shirato, M.3    Sumita, Y.4    Veno, Y.5    Matsuda, A.6


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