메뉴 건너뛰기




Volumn 60, Issue , 2013, Pages 431-440

Design, synthesis and biological evaluation of sulfur-containing 1,1-bisphosphonic acids as antiparasitic agents

Author keywords

Antiparasitic agents; Chagas disease; Farnesyl diphosphate synthase; Toxoplasma gondii; Toxoplasmosis; Trypanosoma cruzi

Indexed keywords

1 [(ETHYLTHIO)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N BUTYLSULFINYL)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N BUTYLTHIO)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N DECYLTHIO)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N HEPT 2 YLAMINO)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N HEPTYLAMINO)ETHYL] 1 HYDROXY 1,1 BISPHOSPHONIC ACID; 1 [(N HEPTYLSULFINYL)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N HEPTYLTHIO)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N HEXYLSULFINYL)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N HEXYLTHIO)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N NONYLTHIO)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N OCTYLSULFINYL)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N OCTYLTHIO)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N PENTYLSULFINYL)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N PENTYLTHIO)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N PROPYLTHIO)ETHYL] 1,1 BISPHOSPHONIC ACID; ANTIINFECTIVE AGENT; ANTIPARASITIC AGENT; BISPHOSPHONIC ACID DERIVATIVE; GERANYLTRANSFERASE; TETRAETHYL 1 [(ETHYLTHIO)ETHYL] 1,1 BISPHOSPHONATE; TETRAETHYL 1 [(N BUT 1 YLTHIO)ETHYL] 1,1 BISPHOSPHONATE; TETRAETHYL 1 [(N DEC 1 YLTHIO)ETHYL] 1,1 BISPHOSPHONATE; TETRAETHYL 1 [(N HEPT 1 YLTHIO)ETHYL] 1,1 BISPHOSPHONATE; TETRAETHYL 1 [(N HEX 1 YLTHIO)ETHYL] 1,1 BISPHOSPHONATE; TETRAETHYL 1 [(N NON 1 YLTHIO)ETHYL] 1,1 BISPHOSPHONATE; TETRAETHYL 1 [(N OCT 1 YLTHIO)ETHYL] 1,1 BISPHOSPHONATE; TETRAETHYL 1 [(N PENT 1 YLTHIO)ETHYL] 1,1 BISPHOSPHONATE; TETRAETHYL 1 [(N PROP 1 YLTHIO)ETHYL] 1,1 BISPHOSPHONATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 84872132292     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.12.015     Document Type: Article
Times cited : (46)

References (75)
  • 1
    • 78649842994 scopus 로고    scopus 로고
    • Bisphosphonates: Molecular mechanisms of action and effects on bone cells, monocytes and macrophages
    • A.J. Roelofs, K. Thompson, F.H. Ebetino, M.J. Rogers, and F.P. Coxon Bisphosphonates: molecular mechanisms of action and effects on bone cells, monocytes and macrophages Curr. Pharm. Des. 16 2010 2950 2960
    • (2010) Curr. Pharm. Des. , vol.16 , pp. 2950-2960
    • Roelofs, A.J.1    Thompson, K.2    Ebetino, F.H.3    Rogers, M.J.4    Coxon, F.P.5
  • 2
    • 0014029045 scopus 로고
    • Effect of pyrophosphate on hydroxyapatite and its implications in calcium homeostasis
    • H. Fleisch, R.G.G. Russell, and F. Straumann Effect of pyrophosphate on hydroxyapatite and its implications in calcium homeostasis Nature 212 1966 901 903
    • (1966) Nature , vol.212 , pp. 901-903
    • Fleisch, H.1    Russell, R.G.G.2    Straumann, F.3
  • 3
    • 0014684354 scopus 로고
    • Diphosphonates inhibit hydroxyapatite dissolution in vitro and bone resorption in tissue culture and in vivo
    • H. Fleisch, R.G.G. Russell, and M.D. Francis Diphosphonates inhibit hydroxyapatite dissolution in vitro and bone resorption in tissue culture and in vivo Science 165 1969 1262 1264
    • (1969) Science , vol.165 , pp. 1262-1264
    • Fleisch, H.1    Russell, R.G.G.2    Francis, M.D.3
  • 4
    • 0014684364 scopus 로고
    • Diphosphonates inhibit formation of calcium phosphate crystals in vitro and pathological calcification in vivo
    • M.D. Francis, R.G.G. Russell, and H. Fleisch Diphosphonates inhibit formation of calcium phosphate crystals in vitro and pathological calcification in vivo Science 165 1969 1264 1266
    • (1969) Science , vol.165 , pp. 1264-1266
    • Francis, M.D.1    Russell, R.G.G.2    Fleisch, H.3
  • 5
    • 79958695940 scopus 로고    scopus 로고
    • Bisphosphonates: The first 40 years
    • R.G.G. Russell Bisphosphonates: the first 40 years Bone 49 2011 2 19
    • (2011) Bone , vol.49 , pp. 2-19
    • Russell, R.G.G.1
  • 6
    • 4344677917 scopus 로고    scopus 로고
    • Nitrogen-containing bisphosphonate mechanism of action
    • A.A. Reszka, and G.A. Rodan Nitrogen-containing bisphosphonate mechanism of action Mini-rev Med. Chem. 4 2004 711 717
    • (2004) Mini-rev Med. Chem. , vol.4 , pp. 711-717
    • Reszka, A.A.1    Rodan, G.A.2
  • 7
    • 0033065233 scopus 로고    scopus 로고
    • Bisphosphonates: From the laboratory to the clinic and back again
    • M.J. Rogers Bisphosphonates: from the laboratory to the clinic and back again Bone 25 1999 97 106
    • (1999) Bone , vol.25 , pp. 97-106
    • Rogers, M.J.1
  • 8
  • 10
    • 70349784954 scopus 로고    scopus 로고
    • Targeting bone metastases with a bispecific anticancer and antiangiogenic polymer-alendronate-taxane conjugate
    • K. Miller, R. Erez, E. Segal, D. Shabat, and R. Satchi-Fainaro Targeting bone metastases with a bispecific anticancer and antiangiogenic polymer-alendronate-taxane conjugate Angew. Chem. Int. Ed. 48 2009 2949 2954
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 2949-2954
    • Miller, K.1    Erez, R.2    Segal, E.3    Shabat, D.4    Satchi-Fainaro, R.5
  • 11
    • 78649861292 scopus 로고    scopus 로고
    • Nitrogen-containing bisphosphonates and cancer immunotherapy
    • P. Clézardin, and M. Massaia Nitrogen-containing bisphosphonates and cancer immunotherapy Curr. Pharm. Des. 16 2010 3007 3014
    • (2010) Curr. Pharm. Des. , vol.16 , pp. 3007-3014
    • Clézardin, P.1    Massaia, M.2
  • 12
    • 44349185434 scopus 로고    scopus 로고
    • Risks and benefits of bisphosphonates
    • R.E. Coleman Risks and benefits of bisphosphonates Br. J. Cancer 98 2008 1736 1740
    • (2008) Br. J. Cancer , vol.98 , pp. 1736-1740
    • Coleman, R.E.1
  • 20
    • 84858686219 scopus 로고    scopus 로고
    • New antibacterials for the treatment of toxoplasmosis; A patent review
    • J.B. Rodriguez, and S.H. Szajnman New antibacterials for the treatment of toxoplasmosis; a patent review Expert Opin. Ther. Pat. 22 2012 311 334
    • (2012) Expert Opin. Ther. Pat. , vol.22 , pp. 311-334
    • Rodriguez, J.B.1    Szajnman, S.H.2
  • 21
    • 33645883558 scopus 로고    scopus 로고
    • Progresses in the field of drug design to combat tropical protozoan parasitic diseases
    • G. García Liñares, E.L. Ravaschino, and J.B. Rodriguez Progresses in the field of drug design to combat tropical protozoan parasitic diseases Curr. Med. Chem. 13 2006 335 360
    • (2006) Curr. Med. Chem. , vol.13 , pp. 335-360
    • García Liñares, G.1    Ravaschino, E.L.2    Rodriguez, J.B.3
  • 23
    • 44349178631 scopus 로고    scopus 로고
    • The acidocalcisome as a target for chemotherapeutic agents in protozoan parasites
    • R. Docampo, and S.N.J. Moreno The acidocalcisome as a target for chemotherapeutic agents in protozoan parasites Curr. Pharm. Des. 14 2008 882 888
    • (2008) Curr. Pharm. Des. , vol.14 , pp. 882-888
    • Docampo, R.1    Moreno, S.N.J.2
  • 24
    • 79953227657 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of new 2-alkylaminoethyl-1,1- bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii targeting farnesyl diphosphate synthase
    • V.S. Rosso, S.H. Szajnman, L. Malayil, M. Galizzi, S.N.J. Moreno, R. Docampo, and J.B. Rodriguez Synthesis and biological evaluation of new 2-alkylaminoethyl-1,1-bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii targeting farnesyl diphosphate synthase Bioorg. Med. Chem. 19 2011 2211 2217
    • (2011) Bioorg. Med. Chem. , vol.19 , pp. 2211-2217
    • Rosso, V.S.1    Szajnman, S.H.2    Malayil, L.3    Galizzi, M.4    Moreno, S.N.J.5    Docampo, R.6    Rodriguez, J.B.7
  • 26
    • 0035953026 scopus 로고    scopus 로고
    • Bisphosphonates derived from fatty acids are potent growth inhibitors of Trypanosoma cruzi
    • S.H. Szajnman, B.N. Bailey, R. Docampo, and J.B. Rodriguez Bisphosphonates derived from fatty acids are potent growth inhibitors of Trypanosoma cruzi Bioorg. Med. Chem. Lett. 11 2001 789 792
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 789-792
    • Szajnman, S.H.1    Bailey, B.N.2    Docampo, R.3    Rodriguez, J.B.4
  • 27
    • 0041330424 scopus 로고    scopus 로고
    • Bisphosphonates derived from fatty acids are potent inhibitors of Trypanosoma cruzi farnesyl pyrophosphate synthase
    • S.H. Szajnman, A. Montalvetti, Y. Wang, R. Docampo, and J.B. Rodriguez Bisphosphonates derived from fatty acids are potent inhibitors of Trypanosoma cruzi farnesyl pyrophosphate synthase Bioorg. Med. Chem. Lett. 13 2003 3231 3235
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 3231-3235
    • Szajnman, S.H.1    Montalvetti, A.2    Wang, Y.3    Docampo, R.4    Rodriguez, J.B.5
  • 28
    • 25444525132 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of 1-amino-1,1-bisphosphonates derived from fatty acids against Trypanosoma cruzi targeting farnesyl pyrophosphate synthase
    • S.H. Szajnman, E.L. Ravaschino, R. Docampo, and J.B. Rodriguez Synthesis and biological evaluation of 1-amino-1,1-bisphosphonates derived from fatty acids against Trypanosoma cruzi targeting farnesyl pyrophosphate synthase Bioorg. Med. Chem. Lett. 15 2005 4685 4690
    • (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 4685-4690
    • Szajnman, S.H.1    Ravaschino, E.L.2    Docampo, R.3    Rodriguez, J.B.4
  • 29
    • 18244410156 scopus 로고    scopus 로고
    • Bisphosphonate inhibitors of Toxoplasma gondii growth: In vitro, QSAR, and in vivo investigations
    • Y. Ling, G. Sahota, S. Odeh, J.M. Chan, F.G. Araujo, S.N. Moreno, and E. Oldfield Bisphosphonate inhibitors of Toxoplasma gondii growth: in vitro, QSAR, and in vivo investigations J. Med. Chem. 48 2005 3130 3140
    • (2005) J. Med. Chem. , vol.48 , pp. 3130-3140
    • Ling, Y.1    Sahota, G.2    Odeh, S.3    Chan, J.M.4    Araujo, F.G.5    Moreno, S.N.6    Oldfield, E.7
  • 30
    • 35648981004 scopus 로고    scopus 로고
    • The farnesyl-diphosphate/geranylgeranyl-diphosphate synthase of Toxoplasma gondii is a bifunctional enzyme and a molecular target of bisphosphonates
    • Y. Ling, Z.-H. Li, K. Miranda, E. Oldfield, and S.N. Moreno The farnesyl-diphosphate/geranylgeranyl-diphosphate synthase of Toxoplasma gondii is a bifunctional enzyme and a molecular target of bisphosphonates J. Biol. Chem. 282 2007 30804 30816
    • (2007) J. Biol. Chem. , vol.282 , pp. 30804-30816
    • Ling, Y.1    Li, Z.-H.2    Miranda, K.3    Oldfield, E.4    Moreno, S.N.5
  • 31
    • 84863012657 scopus 로고    scopus 로고
    • Design, synthesis and biological evaluation of 1-(fluoroalkylidene)-1,1- bisphosphonic acids against Toxoplasma gondii targeting farnesyl diphosphate synthase
    • S.H. Szajnman, V.S. Rosso, L. Malayil, A. Smith, S.N. Moreno, R. Docampo, and J.B. Rodriguez Design, synthesis and biological evaluation of 1-(fluoroalkylidene)-1,1-bisphosphonic acids against Toxoplasma gondii targeting farnesyl diphosphate synthase Org. Biomol. Chem. 10 2012 1424 1433
    • (2012) Org. Biomol. Chem. , vol.10 , pp. 1424-1433
    • Szajnman, S.H.1    Rosso, V.S.2    Malayil, L.3    Smith, A.4    Moreno, S.N.5    Docampo, R.6    Rodriguez, J.B.7
  • 32
    • 0142227145 scopus 로고    scopus 로고
    • Specific chemotherapy of Chagas' disease: Controversies and advances
    • J.A. Urbina, and R. Docampo Specific chemotherapy of Chagas' disease: controversies and advances Trends Parasitol. 19 2003 495 501
    • (2003) Trends Parasitol. , vol.19 , pp. 495-501
    • Urbina, J.A.1    Docampo, R.2
  • 33
    • 77953082627 scopus 로고    scopus 로고
    • Specific chemotherapy of Chagas disease: Relevance, current limitations and new approaches
    • J.A. Urbina Specific chemotherapy of Chagas disease: relevance, current limitations and new approaches Acta Trop. 115 2010 55 68
    • (2010) Acta Trop. , vol.115 , pp. 55-68
    • Urbina, J.A.1
  • 34
    • 77955436769 scopus 로고    scopus 로고
    • New insights in Chagas' disease treatment
    • J.A. Urbina New insights in Chagas' disease treatment Drugs Future 35 2010 409 420
    • (2010) Drugs Future , vol.35 , pp. 409-420
    • Urbina, J.A.1
  • 35
    • 0015869325 scopus 로고
    • Biology of Trypanosoma cruzi
    • Z. Brener Biology of Trypanosoma cruzi Annu. Rev. Microbiol. 27 1973 347 382
    • (1973) Annu. Rev. Microbiol. , vol.27 , pp. 347-382
    • Brener, Z.1
  • 36
    • 79960992162 scopus 로고    scopus 로고
    • Epidemiology of American trypanosomiasis (Chagas disease)
    • V.L. Kirchhoff Epidemiology of American trypanosomiasis (Chagas disease) Adv. Parasitol. 75 2011 1 18
    • (2011) Adv. Parasitol. , vol.75 , pp. 1-18
    • Kirchhoff, V.L.1
  • 37
    • 74049092077 scopus 로고    scopus 로고
    • A brief history and overview of Toxoplasma gondii
    • E.A. Innes A brief history and overview of Toxoplasma gondii Zoonoses Public Health 57 2010 1 7
    • (2010) Zoonoses Public Health , vol.57 , pp. 1-7
    • Innes, E.A.1
  • 39
    • 0031958697 scopus 로고    scopus 로고
    • Structures of Toxoplasma gondii tachyzoites, bradyzoites, and sporozoites and biology and development of tissue cysts
    • J.P. Dubey, D.S. Linsday, and C.A. Speer Structures of Toxoplasma gondii tachyzoites, bradyzoites, and sporozoites and biology and development of tissue cysts Clin. Microbiol. Rev. 11 1998 267 299
    • (1998) Clin. Microbiol. Rev. , vol.11 , pp. 267-299
    • Dubey, J.P.1    Linsday, D.S.2    Speer, C.A.3
  • 40
    • 77949315593 scopus 로고    scopus 로고
    • Binding of nitrogen-containing bisphosphonates (N-BPs) to the Trypanosoma cruzi farnesyl diphosphate synthase homodimer
    • C.-H. Huang, S.B. Gabelli, E. Oldfield, and L.M. Amzel Binding of nitrogen-containing bisphosphonates (N-BPs) to the Trypanosoma cruzi farnesyl diphosphate synthase homodimer Proteins 78 2010 888 899
    • (2010) Proteins , vol.78 , pp. 888-899
    • Huang, C.-H.1    Gabelli, S.B.2    Oldfield, E.3    Amzel, L.M.4
  • 41
    • 52249106627 scopus 로고    scopus 로고
    • Structures of a potent phenylalkyl bisphosphonate inhibitor bound to farnesyl and geranylgeranyl diphosphate synthases
    • R. Cao, C.K.-M. Chen, R.-T. Guo, A.H.-J. Wang, and E. Oldfield Structures of a potent phenylalkyl bisphosphonate inhibitor bound to farnesyl and geranylgeranyl diphosphate synthases Proteins 73 2008 431 439
    • (2008) Proteins , vol.73 , pp. 431-439
    • Cao, R.1    Chen, C.K.-M.2    Guo, R.-T.3    Wang, A.H.-J.4    Oldfield, E.5
  • 42
    • 30344437272 scopus 로고    scopus 로고
    • Structure and mechanism of the farnesyl diphosphate synthase from Trypanosoma cruzi: Implications for drug design
    • S.B. Gabelli, J.S. McLellan, A. Montalvetti, E. Oldfield, R. Docampo, and L.M. Amzel Structure and mechanism of the farnesyl diphosphate synthase from Trypanosoma cruzi: implications for drug design Proteins 62 2006 80 88
    • (2006) Proteins , vol.62 , pp. 80-88
    • Gabelli, S.B.1    McLellan, J.S.2    Montalvetti, A.3    Oldfield, E.4    Docampo, R.5    Amzel, L.M.6
  • 43
    • 84864209728 scopus 로고    scopus 로고
    • Design, synthesis, calorimetry and crystallographic analysis of 2-Alkylaminoethyl-1,1-Bisphosphonates as inhibitors of Trypanosoma cruzi farnesyl diphosphate synthase
    • S. Aripirala, S.H. Szajnman, J. Jakoncic, J.B. Rodriguez, R. Docampo, S.B. Gabelli, and L.M. Amzel Design, synthesis, calorimetry and crystallographic analysis of 2-Alkylaminoethyl-1,1-Bisphosphonates as inhibitors of Trypanosoma cruzi farnesyl diphosphate synthase J. Med. Chem. 55 2012 6445 6454
    • (2012) J. Med. Chem. , vol.55 , pp. 6445-6454
    • Aripirala, S.1    Szajnman, S.H.2    Jakoncic, J.3    Rodriguez, J.B.4    Docampo, R.5    Gabelli, S.B.6    Amzel, L.M.7
  • 44
    • 0019471750 scopus 로고
    • Prenyltransferase; Determination of the binding mechanism and individual kinetic constants for farnesylpyrophosphate synthetase by rapid quench and isotope partitioning experiments
    • F.M. Laskovics, and C.D. Poulter Prenyltransferase; determination of the binding mechanism and individual kinetic constants for farnesylpyrophosphate synthetase by rapid quench and isotope partitioning experiments Biochemistry 20 1981 1893 1901
    • (1981) Biochemistry , vol.20 , pp. 1893-1901
    • Laskovics, F.M.1    Poulter, C.D.2
  • 45
    • 0018276851 scopus 로고
    • Farnesyl pyrophosphate synthetase. Mechanistic studies of the 1′-4 coupling reaction with 2-fluorogeranyl pyrophosphate
    • C.D. Poulter, J.C. Argyle, and E.A. Mash Farnesyl pyrophosphate synthetase. Mechanistic studies of the 1′-4 coupling reaction with 2-fluorogeranyl pyrophosphate J. Biol. Chem. 253 1978 7227 7233
    • (1978) J. Biol. Chem. , vol.253 , pp. 7227-7233
    • Poulter, C.D.1    Argyle, J.C.2    Mash, E.A.3
  • 46
    • 33845376289 scopus 로고
    • Synthesis of ethenylidenebis (phosphonic acid) and its tetraalkyl esters
    • C.R. Degenhardt, and D.C. Burdsall Synthesis of ethenylidenebis (phosphonic acid) and its tetraalkyl esters J. Org. Chem. 51 1986 3488 3490
    • (1986) J. Org. Chem. , vol.51 , pp. 3488-3490
    • Degenhardt, C.R.1    Burdsall, D.C.2
  • 47
  • 48
    • 25144478363 scopus 로고    scopus 로고
    • New insights into the chemistry of gem-bis(phosphonates): Unexpected rearrangement of Michael-type acceptors
    • S.H. Szajnman, G.E. García Liñares, P. Moro, and J.B. Rodríguez New insights into the chemistry of gem-bis(phosphonates): unexpected rearrangement of Michael-type acceptors Eur. J. Org. Chem. 2005 3687 3696
    • (2005) Eur. J. Org. Chem. , pp. 3687-3696
    • Szajnman, S.H.1    García Liñares, G.E.2    Moro, P.3    Rodríguez, J.B.4
  • 50
    • 33751541673 scopus 로고    scopus 로고
    • Microwave-assisted solvent-free intramolecular 1,3-dipolar cycloaddition reactions leading to hexahydrochromeno[4,3-b]pyrroles: Scope and limitations
    • J. Pospíšil, and M. Potáček Microwave-assisted solvent-free intramolecular 1,3-dipolar cycloaddition reactions leading to hexahydrochromeno[4,3-b]pyrroles: scope and limitations Tetrahedron 63 2006 337 346
    • (2006) Tetrahedron , vol.63 , pp. 337-346
    • Pospíšil, J.1    Potáček, M.2
  • 51
    • 0029582663 scopus 로고
    • Preparation of (4-Amino-1-Hydroxybutylidene) bisphosphonic acid sodium salt, MK-217 (Alendronate sodium). An improved procedure for the preparation of 1-hydroxy-1,1-bisphosphonic acids
    • G.R. Kieczykowski, R.B. Jobson, D.G. Melillo, D.F. Reinhold, V.J. Grenda, and I. Shinkai Preparation of (4-Amino-1-Hydroxybutylidene) bisphosphonic acid sodium salt, MK-217 (Alendronate sodium). An improved procedure for the preparation of 1-hydroxy-1,1-bisphosphonic acids J. Org. Chem. 60 1995 8310 8312
    • (1995) J. Org. Chem. , vol.60 , pp. 8310-8312
    • Kieczykowski, G.R.1    Jobson, R.B.2    Melillo, D.G.3    Reinhold, D.F.4    Grenda, V.J.5    Shinkai, I.6
  • 52
    • 34447329859 scopus 로고    scopus 로고
    • A click chemistry approach to glycomimetics: Michael addition of 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose to 4-deoxy-1,2-O- isopropylidene-L-glycero-pent-4-enopyranos-3-ulose-a convenient route to novel 4-deoxy-(1→5)-5-C-thiodisaccharides
    • Z.J. Witczak, D. Lorchak, and N. Nguyen A click chemistry approach to glycomimetics: Michael addition of 2,3,4,6-tetra-O-acetyl-1-thio-β-D- glucopyranose to 4-deoxy-1,2-O-isopropylidene-L-glycero-pent-4-enopyranos-3- ulose-a convenient route to novel 4-deoxy-(1→5)-5-C-thiodisaccharides Carbohydr. Res. 352 2007 1929 1933
    • (2007) Carbohydr. Res. , vol.352 , pp. 1929-1933
    • Witczak, Z.J.1    Lorchak, D.2    Nguyen, N.3
  • 53
    • 0346736511 scopus 로고    scopus 로고
    • Thio-sugars VII. Effect of 3-deoxy-4-S-(β-D-gluco- and β-D-galactopyranosyl)-4-thiodisaccharides and their sulfoxides and sulfones on the viability and growth of selected murine and human tumor cell lines
    • Z.J. Witczak, P. Kaplon, and P.M. Dey Thio-sugars VII. Effect of 3-deoxy-4-S-(β-D-gluco- and β-D-galactopyranosyl)-4-thiodisaccharides and their sulfoxides and sulfones on the viability and growth of selected murine and human tumor cell lines Carbohydr. Res. 338 2003 11 18
    • (2003) Carbohydr. Res. , vol.338 , pp. 11-18
    • Witczak, Z.J.1    Kaplon, P.2    Dey, P.M.3
  • 54
    • 34447561628 scopus 로고    scopus 로고
    • Synthesis of non-glycosidic 4,6′-thioether-linked disaccharides as hydrolytically stable glycomimetics
    • M.L. Uhrig, L. Szilágyi, K.E. Kövér, and O. Varela Synthesis of non-glycosidic 4,6′-thioether-linked disaccharides as hydrolytically stable glycomimetics Carbohydr. Res. 352 2007 1841 1849
    • (2007) Carbohydr. Res. , vol.352 , pp. 1841-1849
    • Uhrig, M.L.1    Szilágyi, L.2    Kövér, K.E.3    Varela, O.4
  • 55
    • 33749262201 scopus 로고    scopus 로고
    • Stereoselective synthesis of 3-deoxy-4-S-(1→4)-thiodisaccharides and their inhibitory activities towards β-glycoside hydrolases
    • M.L. Uhrig, V.E. Manzano, and O. Varela Stereoselective synthesis of 3-deoxy-4-S-(1→4)-thiodisaccharides and their inhibitory activities towards β-glycoside hydrolases Eur. J. Org. Chem. 2006 162 168
    • (2006) Eur. J. Org. Chem. , pp. 162-168
    • Uhrig, M.L.1    Manzano, V.E.2    Varela, O.3
  • 56
    • 0010995106 scopus 로고
    • Synthesis of sulfoxides by oxidation of thioethers
    • M. Madesclaire Synthesis of sulfoxides by oxidation of thioethers Tetrahedron 42 1986 5459 5495
    • (1986) Tetrahedron , vol.42 , pp. 5459-5495
    • Madesclaire, M.1
  • 59
    • 0040365693 scopus 로고
    • Periodate oxidation of sulfides to sulfoxides. Scope of the reaction
    • N.J. Leonard, and C.R. Johnson Periodate oxidation of sulfides to sulfoxides. Scope of the reaction J. Org. Chem. 27 1962 282 284
    • (1962) J. Org. Chem. , vol.27 , pp. 282-284
    • Leonard, N.J.1    Johnson, C.R.2
  • 60
    • 0000631562 scopus 로고
    • α-Phosphorylsulfoxides sulfoxides II. Synthesis of α,β-unsaturated sulfoxides and configurational assignments to geometrical isomers
    • M. Mikołajczyk, S. Grzejszczak, and A. Zatorski α-Phosphorylsulfoxides sulfoxides II. Synthesis of α,β- unsaturated sulfoxides and configurational assignments to geometrical isomers J. Org. Chem. 40 1975 1979 1984
    • (1975) J. Org. Chem. , vol.40 , pp. 1979-1984
    • Mikołajczyk, M.1    Grzejszczak, S.2    Zatorski, A.3
  • 61
    • 84987546312 scopus 로고
    • A facile and selective oxidation of organic sulphides to sulphoxides with hydrogen peroxide/selenium dioxide system
    • J. Drabowicz, and M. Mikołajczyk A facile and selective oxidation of organic sulphides to sulphoxides with hydrogen peroxide/selenium dioxide system Synthesis 1978 758 759
    • (1978) Synthesis , pp. 758-759
    • Drabowicz, J.1    Mikołajczyk, M.2
  • 62
    • 0032537534 scopus 로고    scopus 로고
    • A new class sulfoxide surfactant derived from tris. Synthesis and preliminary assessments of their properties
    • P. Barthélémy, J.C. Maurizis, J.M. Lacombe, and B. Pucci A new class sulfoxide surfactant derived from tris. Synthesis and preliminary assessments of their properties Bioorg. Med. Chem. Lett. 8 1998 1559 1562
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 1559-1562
    • Barthélémy, P.1    Maurizis, J.C.2    Lacombe, J.M.3    Pucci, B.4
  • 63
    • 15444379672 scopus 로고    scopus 로고
    • L-cysteine, a versatile source of sulfenic acids. Synthesis of enantiopure alliin analogues
    • M.C. Aversa, A. Barattucci, P. Bonaccorsi, and P. Giannetto L-cysteine, a versatile source of sulfenic acids. Synthesis of enantiopure alliin analogues J. Org. Chem. 70 2005 1986 1992
    • (2005) J. Org. Chem. , vol.70 , pp. 1986-1992
    • Aversa, M.C.1    Barattucci, A.2    Bonaccorsi, P.3    Giannetto, P.4
  • 65
    • 24144449924 scopus 로고    scopus 로고
    • Sulfenic acids in the carbohydrate field. An example of straightforward access to novel multivalent thiosaccharides
    • M.C. Aversa, A. Barattucci, M.C. Bilardo, P. Bonaccorsi, P. Giannetto, P. Rollin, and A. Tatibouët Sulfenic acids in the carbohydrate field. An example of straightforward access to novel multivalent thiosaccharides J. Org. Chem. 70 2005 7389 7396
    • (2005) J. Org. Chem. , vol.70 , pp. 7389-7396
    • Aversa, M.C.1    Barattucci, A.2    Bilardo, M.C.3    Bonaccorsi, P.4    Giannetto, P.5    Rollin, P.6    Tatibouët, A.7
  • 66
    • 34447643379 scopus 로고    scopus 로고
    • Separation of a mixture of paraconic acids from Cetraria islandica (L.) Ach. employing a fluorous tag - Catch and release strategy
    • D. Horhant, A.-C. Le Lamer, J. Boustie, P. Uriac, and N. Gouault Separation of a mixture of paraconic acids from Cetraria islandica (L.) Ach. employing a fluorous tag - catch and release strategy Tetrahedron Lett. 48 2007 6031 6033
    • (2007) Tetrahedron Lett. , vol.48 , pp. 6031-6033
    • Horhant, D.1    Le Lamer, A.-C.2    Boustie, J.3    Uriac, P.4    Gouault, N.5
  • 70
    • 0037228729 scopus 로고    scopus 로고
    • High-throughput growth assay for Toxoplasma gondii using yellow fluorescent protein
    • M.J. Gubbels, C. Li, and B. Striepen High-throughput growth assay for Toxoplasma gondii using yellow fluorescent protein Antimicrob. Agents Chemother. 43 2003 309 316
    • (2003) Antimicrob. Agents Chemother. , vol.43 , pp. 309-316
    • Gubbels, M.J.1    Li, C.2    Striepen, B.3
  • 71
    • 70450251981 scopus 로고    scopus 로고
    • Genetic evidence that an endosymbiont-derived endoplasmic reticulum-associated protein degradation (ERAD) system functions in import of apicoplast proteins
    • S. Agrawal, G.G. van Dooren, W.L. Beatty, and B. Striepen Genetic evidence that an endosymbiont-derived endoplasmic reticulum-associated protein degradation (ERAD) system functions in import of apicoplast proteins J. Biol. Chem. 284 2009 33683 33691
    • (2009) J. Biol. Chem. , vol.284 , pp. 33683-33691
    • Agrawal, S.1    Van Dooren, G.G.2    Beatty, W.L.3    Striepen, B.4
  • 72
    • 30444438035 scopus 로고    scopus 로고
    • Design, synthesis and biological evaluation of phosphinopeptides against Trypanosoma cruzi targeting trypanothione biosynthesis
    • E.L. Ravaschino, R. Docampo, and J.B. Rodriguez Design, synthesis and biological evaluation of phosphinopeptides against Trypanosoma cruzi targeting trypanothione biosynthesis J. Med. Chem. 49 2006 426 435
    • (2006) J. Med. Chem. , vol.49 , pp. 426-435
    • Ravaschino, E.L.1    Docampo, R.2    Rodriguez, J.B.3
  • 73
  • 74
    • 0038268177 scopus 로고    scopus 로고
    • Farnesyl pyrophosphate synthase is an essential enzyme in Trypanosoma brucei. in vitro RNA interference and in vivo inhibition studies
    • A. Montalvetti, A. Fernandez, J.M. Sanders, S. Ghosh, E. Van Brussel, E. Oldfield, and R. Docampo Farnesyl pyrophosphate synthase is an essential enzyme in Trypanosoma brucei. In vitro RNA interference and in vivo inhibition studies J. Biol. Chem. 278 2003 17075 17083
    • (2003) J. Biol. Chem. , vol.278 , pp. 17075-17083
    • Montalvetti, A.1    Fernandez, A.2    Sanders, J.M.3    Ghosh, S.4    Van Brussel, E.5    Oldfield, E.6    Docampo, R.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.