메뉴 건너뛰기




Volumn 52, Issue 4, 2009, Pages 1126-1143

Third-generation immucillins: Syntheses and bioactivities of acyclic immucillin inhibitors of human purine nucleoside phosphorylase

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 7 [[(1,3 DIHYDROXYPROPAN 2 YL)AMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 2 AMINO 7 [[[1,3,4 TRIHYDROXYBUTAN 2 YL]AMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 3 [(4 HYDROXY 5H PYRROLO[3,2 D]PYRIMIDIN 7 YL)METHYLAMINO] PROPANOL; 7 [1 [(1,3 DIHYDROXYPROPAN 2 YL)AMINO] 2 HYDROXYETHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [[(1,3 DIHYDROXYPROPAN 2 YL)(2 HYDROXYETHYL)AMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [[(1,3 DIHYDROXYPROPAN 2 YL)(METHYL)AMINO]METHYL]] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [[(1,3 DIHYDROXYPROPAN 2 YL)AMINO]METHYL]] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [[(2 HYDROXYETHYL)(3 HYDROXYPROPYL)AMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [[(2 HYDROXYETHYL)AMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [[(2,3 DIHYDROXYPROPYL)(2 HYDROXYETHYL)AMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [[(2,3 DIHYDROXYPROPYL)AMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [[(2,3,4 TRIHYDROXYBUTYL)AMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [[(2,3,4,5 TETRAHYDROXYPENTYL)AMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [[(2,4 DIHYDROXYBUTYL)METHYLAMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [[(4 HYDROXYBUTYL)AMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [[[1,3 DIHYDROXY 2 (HYDROXYMETHYL)PROPAN 2 YL]AMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [[[1,3,4 TRIHYDROXYBUTAN 2 YL]AMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [[[3 HYDROXY 2 (HYDROXYMETHYL)PROPYL]AMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [[[3 HYDROXY 2 (HYDROXYMETHYL)PROPYLMETHYL]AMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [[[3,4 DIHYDROXY 2 (HYDROXYMETHYL)BUTYL]AMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [[BIS(2 HYDROXYETHYL)AMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [[METHYL[ 1,3,4 TRIHYDROXYBUTAN 2 YL]AMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; 7 [BENZYL[(2,3 DIHYDROXYPROPYL)AMINO]METHYL] 3,5 DIHYDRO 4H PYRROLO[3,2 D]PYRIMIDIN 4 ONE; ACYCLIC IMMUCILLIN INHIBITOR; FORODESINE; PURINE NUCLEOSIDE PHOSPHORYLASE; UNCLASSIFIED DRUG;

EID: 64349107005     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm801421q     Document Type: Article
Times cited : (67)

References (49)
  • 1
    • 34250205219 scopus 로고    scopus 로고
    • Acyclic ribooxacarbenium ion mimics as transition state analogues of human and malarial purine nucleoside phosphorylases
    • Taylor, E. A.; Clinch, K.; Kelly, P. M.; Li, L.; Evans, G. B.; Tyler, P. C.; Schramm, V. L. Acyclic ribooxacarbenium ion mimics as transition state analogues of human and malarial purine nucleoside phosphorylases. J. Am. Chem. Soc. 2007, 129, 6984-6985.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 6984-6985
    • Taylor, E.A.1    Clinch, K.2    Kelly, P.M.3    Li, L.4    Evans, G.B.5    Tyler, P.C.6    Schramm, V.L.7
  • 3
  • 5
    • 0032537481 scopus 로고    scopus 로고
    • One-third-the-sites transition-state inhibitors for purine nucleoside phosphorylase
    • Miles, R. W.; Tyler, P. C.; Furneaux, R. H.; Bagdassarian, C. K.; Schramm, V. L. One-third-the-sites transition-state inhibitors for purine nucleoside phosphorylase. Biochemistry. 1998, 37, 8615-8621.
    • (1998) Biochemistry , vol.37 , pp. 8615-8621
    • Miles, R.W.1    Tyler, P.C.2    Furneaux, R.H.3    Bagdassarian, C.K.4    Schramm, V.L.5
  • 6
    • 0035836674 scopus 로고    scopus 로고
    • Immucillin H, a powerful transition-state analog inhibitor of purine nucleoside phos- phorylase, selectively inhibits human T lymphocytes
    • Kicska, G. A.; Long, L.; Horig, H.; Fairchild, C.; Tyler, P. C.; Furneaux, R. H.; Schramm, V. L.; Kaufman, H. L. Immucillin H, a powerful transition-state analog inhibitor of purine nucleoside phos- phorylase, selectively inhibits human T lymphocytes. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 4593-4598.
    • (2001) Proc. Natl. Acad. Sci. U.S.A , vol.98 , pp. 4593-4598
    • Kicska, G.A.1    Long, L.2    Horig, H.3    Fairchild, C.4    Tyler, P.C.5    Furneaux, R.H.6    Schramm, V.L.7    Kaufman, H.L.8
  • 7
    • 0034607824 scopus 로고    scopus 로고
    • Synthesis of Transition State Analogue Inhibitors for Purine Nucleoside Phosphorylase and N-Riboside Hydrolases
    • Evans, G. B.; Furneaux, R. H.; Gainsford, G. J.; Schramm, V. L.; Tyler, P. C. Synthesis of Transition State Analogue Inhibitors for Purine Nucleoside Phosphorylase and N-Riboside Hydrolases. Tetrahedron 2000, 56, 3053-3062.
    • (2000) Tetrahedron , vol.56 , pp. 3053-3062
    • Evans, G.B.1    Furneaux, R.H.2    Gainsford, G.J.3    Schramm, V.L.4    Tyler, P.C.5
  • 8
    • 0037817418 scopus 로고    scopus 로고
    • Exploring structure-activity relationships of transition state analogues of human purine nucleoside phosphorylase
    • Evans, G. B.; Furneaux, R. H.; Lewandowicz, A.; Schramm, V. L.; Tyler, P. C. Exploring structure-activity relationships of transition state analogues of human purine nucleoside phosphorylase. J. Med. Chem. 2003, 46, 3412-3423.
    • (2003) J. Med. Chem , vol.46 , pp. 3412-3423
    • Evans, G.B.1    Furneaux, R.H.2    Lewandowicz, A.3    Schramm, V.L.4    Tyler, P.C.5
  • 9
    • 0042357238 scopus 로고    scopus 로고
    • Achieving the ultimate physiological goal in transition state analogue inhibitors for purine nucleoside phosphorylase
    • Lewandowicz, A.; Tyler, P. C.; Evans, G. B.; Furneaux, R. H.; Schramm, V. L. Achieving the ultimate physiological goal in transition state analogue inhibitors for purine nucleoside phosphorylase. J. Biol. Chem. 2003, 278, 31465-31468.
    • (2003) J. Biol. Chem , vol.278 , pp. 31465-31468
    • Lewandowicz, A.1    Tyler, P.C.2    Evans, G.B.3    Furneaux, R.H.4    Schramm, V.L.5
  • 10
    • 0142106430 scopus 로고    scopus 로고
    • Synthesis of a transition state analogue inhibitor of purine nucleoside phospho- rylase via the Mannich reaction
    • Evans, G. B.; Furneaux, R. H.; Schramm, V. L.; Tyler, P. C. Synthesis of a transition state analogue inhibitor of purine nucleoside phospho- rylase via the Mannich reaction. Org. Lett. 2003, 5, 3639-3640.
    • (2003) Org. Lett , vol.5 , pp. 3639-3640
    • Evans, G.B.1    Furneaux, R.H.2    Schramm, V.L.3    Tyler, P.C.4
  • 11
    • 33750289426 scopus 로고    scopus 로고
    • Drug evaluation: Forodesine-PNP inhibitor for the treatment of leukemia, lymphoma and solid tumor
    • Galmarini, C. M. Drug evaluation: forodesine-PNP inhibitor for the treatment of leukemia, lymphoma and solid tumor. IDrugs 2006, 9,712-722.
    • (2006) IDrugs , vol.9 , pp. 712-722
    • Galmarini, C.M.1
  • 12
    • 34548091879 scopus 로고    scopus 로고
    • Systemic monotherapy vs combination therapy for CTCL: Rationale and future strategies
    • Duvic, M. Systemic monotherapy vs combination therapy for CTCL: rationale and future strategies. Oncology 2007, 21, 33-40.
    • (2007) Oncology , vol.21 , pp. 33-40
    • Duvic, M.1
  • 13
    • 33750601477 scopus 로고    scopus 로고
    • Purine nucleoside analogs as immunosuppressive and antineoplastic agents: Mechanism of action and clinical activity
    • Robak, T.; Lech-Maranda, E.; Koerycka, A.; Robak, E. Purine nucleoside analogs as immunosuppressive and antineoplastic agents: mechanism of action and clinical activity. Curr. Med. Chem. 2006, 13, 3165-3189.
    • (2006) Curr. Med. Chem , vol.13 , pp. 3165-3189
    • Robak, T.1    Lech-Maranda, E.2    Koerycka, A.3    Robak, E.4
  • 14
    • 33845224072 scopus 로고    scopus 로고
    • Novel purine nucleoside analogues for T-cell- lineage acute lymphoblastic leukaemia and lymphoma
    • Ravandi, F.; Gandhi, V. Novel purine nucleoside analogues for T-cell- lineage acute lymphoblastic leukaemia and lymphoma. Expert Opin. Investig. Drugs 2006, 15, 1601-1613.
    • (2006) Expert Opin. Investig. Drugs , vol.15 , pp. 1601-1613
    • Ravandi, F.1    Gandhi, V.2
  • 15
    • 33749365341 scopus 로고    scopus 로고
    • Forodesine, an inhibitor of purine nucleoside phosphory- lase, induces apoptosis in chronic lymphocytic leukemia cells
    • Balakrishnan, K.; Nimmanpalli, R.; Ravandi, F.; Keating, M. J.; Gandhi, V. Forodesine, an inhibitor of purine nucleoside phosphory- lase, induces apoptosis in chronic lymphocytic leukemia cells. Blood 2006, 108, 2392-2398.
    • (2006) Blood , vol.108 , pp. 2392-2398
    • Balakrishnan, K.1    Nimmanpalli, R.2    Ravandi, F.3    Keating, M.J.4    Gandhi, V.5
  • 16
    • 29444445067 scopus 로고    scopus 로고
    • Transition states and inhibitors of the purine nucleoside phosphorylase family
    • Taylor Ringia, E. A.; Schramm, V. L. Transition states and inhibitors of the purine nucleoside phosphorylase family. Curr. Top. Med. Chem. 2005, 5, 1237-1258.
    • (2005) Curr. Top. Med. Chem , vol.5 , pp. 1237-1258
    • Taylor Ringia, E.A.1    Schramm, V.L.2
  • 17
    • 84919573117 scopus 로고
    • Nucleoside-phosphorylase deficiency in a child with severely defective T-cell immunity and normal B-cell immunity
    • Giblett, E. R.; Ammann, A. J.; Wara, D. W.; Sandman, R.; Diamond, L. K. Nucleoside-phosphorylase deficiency in a child with severely defective T-cell immunity and normal B-cell immunity. Lancet 1975, 1, 1010-1013.
    • (1975) Lancet , vol.1 , pp. 1010-1013
    • Giblett, E.R.1    Ammann, A.J.2    Wara, D.W.3    Sandman, R.4    Diamond, L.K.5
  • 20
    • 0242691662 scopus 로고    scopus 로고
    • Synthesis of second-generation transition state analogues of human purine nucleoside phosphorylase
    • Evans, G. B.; Furneaux, R. H.; Lewandowicz, A.; Schramm, V. L.; Tyler, P. C. Synthesis of second-generation transition state analogues of human purine nucleoside phosphorylase. J. Med. Chem. 2003, 46, 5271-5276.
    • (2003) J. Med. Chem , vol.46 , pp. 5271-5276
    • Evans, G.B.1    Furneaux, R.H.2    Lewandowicz, A.3    Schramm, V.L.4    Tyler, P.C.5
  • 21
    • 39749114381 scopus 로고    scopus 로고
    • Azetidine Based Transition State Analogue Inhibitors of N-Ribosyl Hydrolases and Phosphorylases
    • Evans, G. B.; Furneaux, R. H.; Greatrex, B.; Murkin, A. S.; Schramm, V. L.; Tyler, P. C. Azetidine Based Transition State Analogue Inhibitors of N-Ribosyl Hydrolases and Phosphorylases. J. Med. Chem. 2008, 51, 948-956.
    • (2008) J. Med. Chem , vol.51 , pp. 948-956
    • Evans, G.B.1    Furneaux, R.H.2    Greatrex, B.3    Murkin, A.S.4    Schramm, V.L.5    Tyler, P.C.6
  • 22
    • 0035854320 scopus 로고    scopus 로고
    • Stereocontrolled syntheses of carbocyclic C-nucleosides and related compounds
    • Chun, B. K.; Song, G. Y.; Chu, C. K. Stereocontrolled syntheses of carbocyclic C-nucleosides and related compounds. J. Org. Chem. 2001, 66, 4852-4858.
    • (2001) J. Org. Chem , vol.66 , pp. 4852-4858
    • Chun, B.K.1    Song, G.Y.2    Chu, C.K.3
  • 25
    • 0027754719 scopus 로고
    • Acyclovir: Discovery, Mechanism of Action and Selectivity
    • Elion, G. B. Acyclovir: Discovery, Mechanism of Action and Selectivity. J. Virol. Med. Supp. 1993, 1, 2-6.
    • (1993) J. Virol. Med. Supp , vol.1 , pp. 2-6
    • Elion, G.B.1
  • 26
    • 34247275133 scopus 로고    scopus 로고
    • The acyclic nucleoside phosphonates from inception to clinical use: Historical perspective
    • De Clercq, E. The acyclic nucleoside phosphonates from inception to clinical use: historical perspective. Antiviral Res. 2007, 75, 1-13.
    • (2007) Antiviral Res , vol.75 , pp. 1-13
    • De Clercq, E.1
  • 27
    • 33749447149 scopus 로고    scopus 로고
    • The synthesis and antiviral properties of acyclic nucleoside analogues with a phospho- nomethoxy fragment in the side chain
    • Khandazhinskaya, A.; Yasko, M.; Shirokova, E. The synthesis and antiviral properties of acyclic nucleoside analogues with a phospho- nomethoxy fragment in the side chain. Curr. Med. Chem. 2006, 13, 2953-2980.
    • (2006) Curr. Med. Chem , vol.13 , pp. 2953-2980
    • Khandazhinskaya, A.1    Yasko, M.2    Shirokova, E.3
  • 28
    • 33746198772 scopus 로고    scopus 로고
    • A synthetic route to 9-(polyhy- droxyalkyl)purines
    • Horton, D.; Thomas, S.; Gallucci, J. A synthetic route to 9-(polyhy- droxyalkyl)purines. Carbohydr. Res. 2006, 341, 2211-2218.
    • (2006) Carbohydr. Res , vol.341 , pp. 2211-2218
    • Horton, D.1    Thomas, S.2    Gallucci, J.3
  • 31
    • 35348956350 scopus 로고    scopus 로고
    • Enzymatic transition state theory and transition state analogue design
    • Schramm, V. L. Enzymatic transition state theory and transition state analogue design. J. Biol. Chem. 2007, 282, 28297-28300.
    • (2007) J. Biol. Chem , vol.282 , pp. 28297-28300
    • Schramm, V.L.1
  • 32
    • 1042299983 scopus 로고    scopus 로고
    • Transition state analysis for human and Plasmodium falciparum purine nucleoside phosphorylases
    • Lewandowicz, A.; Schramm, V. L. Transition state analysis for human and Plasmodium falciparum purine nucleoside phosphorylases. Biochemistry 2004, 43, 1458-1468.
    • (2004) Biochemistry , vol.43 , pp. 1458-1468
    • Lewandowicz, A.1    Schramm, V.L.2
  • 33
    • 9744244983 scopus 로고    scopus 로고
    • Enzymatic transition states: Thermodynamics, dynamics and analogue design
    • Schramm, V. L. Enzymatic transition states: thermodynamics, dynamics and analogue design. Arch. Biochem. Biophys. 2005, 433, 13-26.
    • (2005) Arch. Biochem. Biophys , vol.433 , pp. 13-26
    • Schramm, V.L.1
  • 34
    • 34447622684 scopus 로고    scopus 로고
    • Synthesis of new tridentate chiral aminoalcohols by a multicomponent reaction and their evaluation as ligands for catalytic asymmetric Strecker reaction
    • Banphavichit, V.; Bhanthumnavin, W.; Vilaivan, T. Synthesis of new tridentate chiral aminoalcohols by a multicomponent reaction and their evaluation as ligands for catalytic asymmetric Strecker reaction. Tetrahedron 2007, 63, 8727-8734.
    • (2007) Tetrahedron , vol.63 , pp. 8727-8734
    • Banphavichit, V.1    Bhanthumnavin, W.2    Vilaivan, T.3
  • 35
    • 13844275008 scopus 로고    scopus 로고
    • An improved preparation of the activity-based probe JPM-OET and in situ applications
    • Chehade, K. A. H.; Baruch, A.; Verhelst, S. H. L.; Bogyo, M. An improved preparation of the activity-based probe JPM-OET and in situ applications. Synthesis 2005, 240-244.
    • (2005) Synthesis , pp. 240-244
    • Chehade, K.A.H.1    Baruch, A.2    Verhelst, S.H.L.3    Bogyo, M.4
  • 36
    • 21244479264 scopus 로고    scopus 로고
    • A highly efficient organocatalyst for direct aldol reactions of ketones with aldehydes
    • Tang, Z.; Yang, Z.-H.; Chen, X.-H.; Cun, L.-F.; Mi, A.-Q.; Jiang, Y.-Z.; Gong, L.-Z. A highly efficient organocatalyst for direct aldol reactions of ketones with aldehydes. J. Am. Chem. Soc. 2005, 127, 9285-9289.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 9285-9289
    • Tang, Z.1    Yang, Z.-H.2    Chen, X.-H.3    Cun, L.-F.4    Mi, A.-Q.5    Jiang, Y.-Z.6    Gong, L.-Z.7
  • 37
    • 0142196047 scopus 로고    scopus 로고
    • An improved synthesis of aziridine-2,3-dicarboxylates via azido alcohols-epimerisation studies
    • Breuning, A.; Vicik, R.; Schirmeister, T. An improved synthesis of aziridine-2,3-dicarboxylates via azido alcohols-epimerisation studies. Tetrahedron: Asymmetry 2003, 14, 3301-3312.
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 3301-3312
    • Breuning, A.1    Vicik, R.2    Schirmeister, T.3
  • 38
    • 33845374692 scopus 로고
    • Mixed Solvents Containing Methanol as Useful Reaction Media for Unique Chemoselective Reductions with Lithium Borohydride
    • Soai, K.; Ookawa, A. Mixed Solvents Containing Methanol as Useful Reaction Media for Unique Chemoselective Reductions with Lithium Borohydride. J. Org. Chem. 1986, 51, 4000-4005.
    • (1986) J. Org. Chem , vol.51 , pp. 4000-4005
    • Soai, K.1    Ookawa, A.2
  • 39
    • 0032582733 scopus 로고    scopus 로고
    • Inaba, T.; Birchler, A. G.; Yamada, Y.; Sagawa, S.; Yokata, K.; Ando, K.; Uchida, I. A Practical Synthesis of Nelfinavir, an HIV-Protease Inhibitor, Using a Novel Chiral C4 Building Block: (5R,6S)-2,2-Dimethyl-5- hydroxy-1,3-dioxepan-6-ylammonium Acetate. J. Org. Chem. 1998, 63, 7582-7583.
    • Inaba, T.; Birchler, A. G.; Yamada, Y.; Sagawa, S.; Yokata, K.; Ando, K.; Uchida, I. A Practical Synthesis of Nelfinavir, an HIV-Protease Inhibitor, Using a Novel Chiral C4 Building Block: (5R,6S)-2,2-Dimethyl-5- hydroxy-1,3-dioxepan-6-ylammonium Acetate. J. Org. Chem. 1998, 63, 7582-7583.
  • 40
    • 0027262421 scopus 로고    scopus 로고
    • Harnden, M. R.; Parkin, A.; Parratt, M. J.; Perkins, R. M. Novel Acyclonucleotides: Synthesis and Antiviral Activity of Alkenylphos- phonic Acid Derivatives of Purines and a Pyrimidine. J. Med. Chem. 1993, 36, 1343-1355.
    • Harnden, M. R.; Parkin, A.; Parratt, M. J.; Perkins, R. M. Novel Acyclonucleotides: Synthesis and Antiviral Activity of Alkenylphos- phonic Acid Derivatives of Purines and a Pyrimidine. J. Med. Chem. 1993, 36, 1343-1355.
  • 41
    • 0029033924 scopus 로고
    • Formal Synthesis of a 2- and 8-Functionalized 1,4,7-Trioxa-10-azaspiro[5.5]undecane
    • Lemaire, M.; Posada, F.; Gourcy, J.-G.; Jeminet, G. Formal Synthesis of a 2- and 8-Functionalized 1,4,7-Trioxa-10-azaspiro[5.5]undecane. Synthesis 1995, 627-629.
    • (1995) Synthesis , pp. 627-629
    • Lemaire, M.1    Posada, F.2    Gourcy, J.-G.3    Jeminet, G.4
  • 43
    • 26844471110 scopus 로고
    • Degradation of D-ribono-1→4-lactone to D-erythro- 1→4-lactone
    • Mitchell, D. L. Degradation of D-ribono-1→4-lactone to D-erythro- 1→4-lactone. Can. J. Chem. 1963, 41, 214-221.
    • (1963) Can. J. Chem , vol.41 , pp. 214-221
    • Mitchell, D.L.1
  • 46
    • 0030575792 scopus 로고    scopus 로고
    • Stereoselective syntheses and reactions of chiral oxygenated α,β-unsaturated-γ- and (δ-lactones
    • Sanchez-Sancho, F.; Valverde, S.; Herradon, B. Stereoselective syntheses and reactions of chiral oxygenated α,β-unsaturated-γ- and (δ-lactones. Tetrahedron: Asymmetry 1996, 7, 3209-3246.
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 3209-3246
    • Sanchez-Sancho, F.1    Valverde, S.2    Herradon, B.3
  • 48
    • 0020610472 scopus 로고
    • Synthesis of "9- deazaguanosine" and other new pyrrolo[3,2-d]pyrimidine C-nucleo- sides
    • Lim, M.-I.; Ren, Y.-Y.; Otter, B. A.; Klein, R. S. Synthesis of "9- deazaguanosine" and other new pyrrolo[3,2-d]pyrimidine C-nucleo- sides. J. Org. Chem. 1983, 48, 780-788.
    • (1983) J. Org. Chem , vol.48 , pp. 780-788
    • Lim, M.-I.1    Ren, Y.-Y.2    Otter, B.A.3    Klein, R.S.4
  • 49
    • 84869272043 scopus 로고    scopus 로고
    • -1) due to a recent modification in the calculation algorithm; see also http://www.expasy.org/ tools/protparam.html
    • -1) due to a recent modification in the calculation algorithm; see also http://www.expasy.org/ tools/protparam.html


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.