Literature DB >> 16178559

Synthesis of chiral 2-(4-phenoxyphenylsulfonylmethyl)thiiranes as selective gelatinase inhibitors.

Mijoon Lee1, M Margarida Bernardo, Samy O Meroueh, Stephen Brown, Rafael Fridman, Shahriar Mobashery.   

Abstract

[reactions: see text] Compound 1, 2-(4-phenoxyphenylsulfonylmethyl)thiirane, is a selective inhibitor of gelatinases, which is showing high promise in studies of animal models for cancer metastasis and stroke. The (R)-1 and (S)-1 enantiomers of compound 1 were each synthesized in this study and were shown to be equally active in inhibition of gelatinases.

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Year:  2005        PMID： 16178559     DOI： 10.1021/ol0517269

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  21 in total

Review 1.  Matrix metalloproteinase inhibitors: a critical appraisal of design principles and proposed therapeutic utility.

Authors:  György Dormán; Sándor Cseh; István Hajdú; László Barna; Dénes Kónya; Krisztina Kupai; László Kovács; Péter Ferdinandy
Journal:  Drugs       Date:  2010-05-28       Impact factor: 9.546

2.  QM/MM Studies of the Matrix Metalloproteinase 2 (MMP2) Inhibition Mechanism of (S)-SB-3CT and its Oxirane Analogue.

Authors:  Jia Zhou; Peng Tao; Jed F Fisher; Qicun Shi; Shahriar Mobashery; H Bernhard Schlegel
Journal:  J Chem Theory Comput       Date:  2010-11-09       Impact factor: 6.006

Review 3.  Matrix metalloproteinase inhibitors as investigative tools in the pathogenesis and management of vascular disease.

Authors:  Mina M Benjamin; Raouf A Khalil
Journal:  Exp Suppl       Date:  2012

4.  Conformational analyses of thiirane-based gelatinase inhibitors.

Authors:  Mijoon Lee; Dusan Hesek; Qicun Shi; Bruce C Noll; Jed F Fisher; Mayland Chang; Shahriar Mobashery
Journal:  Bioorg Med Chem Lett       Date:  2007-12-05       Impact factor: 2.823

5.  Structure-Activity Relationship for Thiirane-Based Gelatinase Inhibitors.

Authors:  Mijoon Lee; Masahiro Ikejiri; Dennis Klimpel; Marta Toth; Mana Espahbodi; Dusan Hesek; Christopher Forbes; Malika Kumarasiri; Bruce C Noll; Mayland Chang; Shahriar Mobashery
Journal:  ACS Med Chem Lett       Date:  2012-05-02       Impact factor: 4.345

6.  Selective water-soluble gelatinase inhibitor prodrugs.

Authors:  Major Gooyit; Mijoon Lee; Valerie A Schroeder; Masahiro Ikejiri; Mark A Suckow; Shahriar Mobashery; Mayland Chang
Journal:  J Med Chem       Date:  2011-09-06       Impact factor: 7.446

7.  Sulfonate-containing thiiranes as selective gelatinase inhibitors.

Authors:  Sebastian A Testero; Mijoon Lee; Rachel T Staran; Mana Espahbodi; Leticia I Llarrull; Marta Toth; Shahriar Mobashery; Mayland Chang
Journal:  ACS Med Chem Lett       Date:  2010-12-13       Impact factor: 4.345

8.  Matrix metalloproteinase 2 inhibition: combined quantum mechanics and molecular mechanics studies of the inhibition mechanism of (4-phenoxyphenylsulfonyl)methylthiirane and its oxirane analogue.

Authors:  Peng Tao; Jed F Fisher; Qicun Shi; Thom Vreven; Shahriar Mobashery; H Bernhard Schlegel
Journal:  Biochemistry       Date:  2009-10-20       Impact factor: 3.162

9.  Synthesis, kinetic characterization and metabolism of diastereomeric 2-(1-(4-phenoxyphenylsulfonyl)ethyl)thiiranes as potent gelatinase and MT1-MMP inhibitors.

Authors:  Major Gooyit; Mijoon Lee; Dusan Hesek; Bill Boggess; Allen G Oliver; Rafael Fridman; Shahriar Mobashery; Mayland Chang
Journal:  Chem Biol Drug Des       Date:  2009-10-12       Impact factor: 2.817

10.  A potent gelatinase inhibitor with anti-tumor-invasive activity and its metabolic disposition.

Authors:  Mijoon Lee; Giuseppe Celenza; Bill Boggess; Jennifer Blase; Qicun Shi; Marta Toth; M Margarida Bernardo; William R Wolter; Mark A Suckow; Dusan Hesek; Bruce C Noll; Rafael Fridman; Shahriar Mobashery; Mayland Chang
Journal:  Chem Biol Drug Des       Date:  2009-02       Impact factor: 2.817
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