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Volumn 74, Issue 6, 2009, Pages 535-546

Synthesis, kinetic characterization and metabolism of diastereomeric 2-(1-(4-Phenoxyphenylsulfonyl)ethyl)thiiranes as potent gelatinase and MT1-MMP Inhibitors

Author keywords

Enzyme inhibition; Gelatinase; Metabolism

Indexed keywords

2(4 PHENOXYPHENYLSULFONYLMETHYL)THIIRANE; GELATINASE A; GELATINASE B; MATRIX METALLOPROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 70350544040     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2009.00898.x     Document Type: Article
Times cited : (16)

References (30)
  • 1
    • 0038575443 scopus 로고    scopus 로고
    • Extracellular matrix remodeling: The role of matrix metalloproteinases
    • Stamenkovic I. (2003) Extracellular matrix remodeling: the role of matrix metalloproteinases. J Pathol 200 : 448 464.
    • (2003) J Pathol , vol.200 , pp. 448-464
    • Stamenkovic, I.1
  • 3
    • 0037967272 scopus 로고    scopus 로고
    • Angiogenesis: Tumorigenesis and the angiogenic switch
    • Bergers G., Benjamin L.E. (2003) Angiogenesis: tumorigenesis and the angiogenic switch. Nat Rev Cancer 3 : 401 410.
    • (2003) Nat Rev Cancer , vol.3 , pp. 401-410
    • Bergers, G.1    Benjamin, L.E.2
  • 4
    • 0037703383 scopus 로고    scopus 로고
    • Angiogenesis inhibitors: Motivators of metastasis?
    • Steeg P.S. (2003) Angiogenesis inhibitors: motivators of metastasis? Nat Med 9 : 822 823.
    • (2003) Nat Med , vol.9 , pp. 822-823
    • Steeg, P.S.1
  • 5
    • 0030911308 scopus 로고    scopus 로고
    • The regulation of neovascularization by matrix metalloproteinases and their inhibitors
    • Moses M.A. (1997) The regulation of neovascularization by matrix metalloproteinases and their inhibitors. Stem Cells 15 : 180 189.
    • (1997) Stem Cells , vol.15 , pp. 180-189
    • Moses, M.A.1
  • 7
    • 33646584823 scopus 로고    scopus 로고
    • Recent advances in MMP inhibitor design
    • Fisher J., Mobashery S. (2006) Recent advances in MMP inhibitor design. Cancer Metastasis Rev 25 : 115 136.
    • (2006) Cancer Metastasis Rev , vol.25 , pp. 115-136
    • Fisher, J.1    Mobashery, S.2
  • 8
    • 0037192860 scopus 로고    scopus 로고
    • Design, synthesis, and characterization of potent, slow-binding inhibitors that are selective for gelatinases
    • Bernardo M.M., Brown S., Li Z.H., Fridman R., Mobashery S. (2002) Design, synthesis, and characterization of potent, slow-binding inhibitors that are selective for gelatinases. J Biol Chem 277 : 11201 11207.
    • (2002) J Biol Chem , vol.277 , pp. 11201-11207
    • Bernardo, M.M.1    Brown, S.2    Li, Z.H.3    Fridman, R.4    Mobashery, S.5
  • 12
    • 51049100625 scopus 로고    scopus 로고
    • Effect of ablation or inhibition of stromal matrix metalloproteinase-9 on lung metastasis in a breast cancer model is dependent on genetic background
    • Martin M.D., Carter K.J., Jena-Philippe S.R., Chang M., Mobashery S., Thiolloy S., Lynch C.C., Matrisian L.M., Fingleton B. (2008) Effect of ablation or inhibition of stromal matrix metalloproteinase-9 on lung metastasis in a breast cancer model is dependent on genetic background. Cancer Res 68 : 6251 6259.
    • (2008) Cancer Res , vol.68 , pp. 6251-6259
    • Martin, M.D.1    Carter, K.J.2    Jena-Philippe, S.R.3    Chang, M.4    Mobashery, S.5    Thiolloy, S.6    Lynch, C.C.7    Matrisian, L.M.8    Fingleton, B.9
  • 13
    • 21844450866 scopus 로고    scopus 로고
    • A highly specific inhibitor of matrix metalloproteinase-9 rescues laminin from proteolysis and neurons from apoptosis in transient focal cerebral ischemia
    • Gu Z., Cui J., Brown S., Fridman R., Mobashery S., Strongin A.Y., Lipton S.A. (2005) A highly specific inhibitor of matrix metalloproteinase-9 rescues laminin from proteolysis and neurons from apoptosis in transient focal cerebral ischemia. J Neurosci 25 : 6401 6408.
    • (2005) J Neurosci , vol.25 , pp. 6401-6408
    • Gu, Z.1    Cui, J.2    Brown, S.3    Fridman, R.4    Mobashery, S.5    Strongin, A.Y.6    Lipton, S.A.7
  • 18
    • 2442491935 scopus 로고    scopus 로고
    • A convenient synthesis of a selective gelatinase inhibitor as an antimetastatic agent
    • Lim I.T., Brown S., Mobashery S. (2004) A convenient synthesis of a selective gelatinase inhibitor as an antimetastatic agent. J Org Chem 69 : 3572 3573.
    • (2004) J Org Chem , vol.69 , pp. 3572-3573
    • Lim, I.T.1    Brown, S.2    Mobashery, S.3
  • 19
    • 0032492980 scopus 로고    scopus 로고
    • Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine
    • Evans D.A., Katz J.L., West T.H. (1998) Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine. Tetrahedron Lett 39 : 2937 2940.
    • (1998) Tetrahedron Lett , vol.39 , pp. 2937-2940
    • Evans, D.A.1    Katz, J.L.2    West, T.H.3
  • 20
    • 26444612068 scopus 로고    scopus 로고
    • Synthesis of chiral 2-(4-phenoxyphenylsulfonylmethyl)thiiranes as selective gelatinase inhibitors
    • Lee M., Bernardo M.M., Meroueh S.O., Brown S., Fridman R., Mobashery M. (2005) Synthesis of chiral 2-(4-phenoxyphenylsulfonylmethyl)thiiranes as selective gelatinase inhibitors. Org Lett 7 : 4463 4465.
    • (2005) Org Lett , vol.7 , pp. 4463-4465
    • Lee, M.1    Bernardo, M.M.2    Meroueh, S.O.3    Brown, S.4    Fridman, R.5    Mobashery, M.6
  • 21
    • 0000711829 scopus 로고
    • The application of a mechanistic model leads to the extension of the Sharpless asymmetric dihydroxylation to allylic 4-methoxybenzoates and conformationally related amine and homoallylic alcohol derivatives
    • Guzman-Perez A., Noe M.C., Corey E.J. (1995) The application of a mechanistic model leads to the extension of the Sharpless asymmetric dihydroxylation to allylic 4-methoxybenzoates and conformationally related amine and homoallylic alcohol derivatives. J Am Chem Soc 117 : 10805 10816.
    • (1995) J Am Chem Soc , vol.117 , pp. 10805-10816
    • Guzman-Perez, A.1    Noe, M.C.2    Corey, E.J.3
  • 22
    • 33847779053 scopus 로고    scopus 로고
    • Phosphine-dependent stereoselectivity in the Mitsunobu cyclodehydration of 1,2-diols: Stereodivergent approach to triaryl-substituted epoxides
    • Garcia-Delgado N., Riera A., Verdaguer X. (2007) Phosphine-dependent stereoselectivity in the Mitsunobu cyclodehydration of 1,2-diols: stereodivergent approach to triaryl-substituted epoxides. Org Lett 9 : 635 638.
    • (2007) Org Lett , vol.9 , pp. 635-638
    • Garcia-Delgado, N.1    Riera, A.2    Verdaguer, X.3
  • 24
    • 33947333675 scopus 로고
    • Thiiranes
    • Sander M. (1966) Thiiranes Chem Rev 66 : 297 339.
    • (1966) Chem Rev , vol.66 , pp. 297-339
    • Sander, M.1
  • 25
    • 0000840517 scopus 로고    scopus 로고
    • Synthesis of novel (P,S) ligands based on chiral nonracemic episulfides. Use in asymmetric hydrogenation
    • Hauptman E., Fagan P.J., Marshall W. (1999) Synthesis of novel (P,S) ligands based on chiral nonracemic episulfides. Use in asymmetric hydrogenation. Organometallics 18 : 2061 2073.
    • (1999) Organometallics , vol.18 , pp. 2061-2073
    • Hauptman, E.1    Fagan, P.J.2    Marshall, W.3
  • 27
    • 0038784546 scopus 로고    scopus 로고
    • Membrane type matrix metalloproteinase i usurps tumor growth control imposed by the three-dimensional extracellular matrix
    • Hotary K.B., Allen E.D., Brooks P.C., Datta N.S., Long M.W., Weiss S.J. (2003) Membrane type matrix metalloproteinase I usurps tumor growth control imposed by the three-dimensional extracellular matrix. Cell 114 : 33 45.
    • (2003) Cell , vol.114 , pp. 33-45
    • Hotary, K.B.1    Allen, E.D.2    Brooks, P.C.3    Datta, N.S.4    Long, M.W.5    Weiss, S.J.6
  • 30
    • 0007618085 scopus 로고
    • Stereochemistry of the decomposition of 2-butene episulfoxides
    • Hartzell G.E., Paige J.N. (1966) Stereochemistry of the decomposition of 2-butene episulfoxides. J Org Chem 32 : 459 460.
    • (1966) J Org Chem , vol.32 , pp. 459-460
    • Hartzell, G.E.1    Paige, J.N.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.