Literature DB >> 20102178

Convergent synthesis of alpha-ketoamide inhibitors of Pin1.

Guoyan G Xu1, Felicia A Etzkorn.   

Abstract

A convergent synthesis of alpha-ketoamide inhibitors of Pin1 is described. An alpha-hydroxyorthothioester derivative of Ser was reacted directly with an amine synthon. The reaction was catalyzed by HgO and HgCl(2) to form alpha-hydroxyamide. Thus, hydrolysis and coupling were combined in one step with 80% yield. Two diastereomers of a phospho-Ser-Pro alpha-ketoamide analogue were synthesized. The IC(50) values of 100 and 200 microM were surprisingly weak for Pin1 peptidyl prolyl isomerase.

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Year:  2010        PMID： 20102178      PMCID： PMC2844255          DOI： 10.1021/ol9027013

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


  36 in total

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Authors:  Kun Ping Lu
Journal:  Cancer Cell       Date:  2003-09       Impact factor: 31.743

2.  Synthesis and activity studies of conformationally restricted alpha-ketoamide factor Xa inhibitors.

Authors:  J Cacciola; J M Fevig; P F Stouten; R S Alexander; R M Knabb; R R Wexler
Journal:  Bioorg Med Chem Lett       Date:  2000-06-05       Impact factor: 2.823

3.  Synthesis of a substrate of protein kinase C and its corresponding phosphopeptide.

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4.  Exploration of orally available calpain inhibitors. Part 3: Dipeptidyl alpha-ketoamide derivatives containing pyridine moiety.

Authors:  Yoshihisa Shirasaki; Hiroyuki Miyashita; Masazumi Yamaguchi
Journal:  Bioorg Med Chem       Date:  2006-05-02       Impact factor: 3.641

5.  Prolyl isomerase Pin1: a catalyst for oncogenesis and a potential therapeutic target in cancer.

Authors:  Akihide Ryo; Yih-Cherng Liou; Kun Ping Lu; Gerburg Wulf
Journal:  J Cell Sci       Date:  2003-03-01       Impact factor: 5.285

6.  Prevalent overexpression of prolyl isomerase Pin1 in human cancers.

Authors:  Lere Bao; Amy Kimzey; Guido Sauter; Janusz M Sowadski; Kun Ping Lu; Da-Gong Wang
Journal:  Am J Pathol       Date:  2004-05       Impact factor: 4.307

7.  Alpha-keto amide peptides: a synthetic strategy to resin-bound peptide isosteres for protease inhibitor screening on solid support.

Authors:  Alexandra Papanikos; Morten Meldal
Journal:  J Comb Chem       Date:  2004 Mar-Apr

8.  Serine-cis-proline and serine-trans-proline isosteres: stereoselective synthesis of (Z)- and (E)-alkene mimics by Still-Wittig and Ireland-Claisen rearrangements.

Authors:  Xiaodong J Wang; Scott A Hart; Bailing Xu; Matthew D Mason; John R Goodell; Felicia A Etzkorn
Journal:  J Org Chem       Date:  2003-03-21       Impact factor: 4.354

9.  Alpha-keto amides as inhibitors of histone deacetylase.

Authors:  Carol K Wada; Robin R Frey; Zhiqin Ji; Michael L Curtin; Robert B Garland; James H Holms; Junling Li; Lori J Pease; Jun Guo; Keith B Glaser; Patrick A Marcotte; Paul L Richardson; Shannon S Murphy; Jennifer J Bouska; Paul Tapang; Terrance J Magoc; Daniel H Albert; Steven K Davidsen; Michael R Michaelides
Journal:  Bioorg Med Chem Lett       Date:  2003-10-06       Impact factor: 2.823

Review 10.  Histone deacetylase inhibitors: the Abbott experience.

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Journal:  Curr Med Chem       Date:  2003-11       Impact factor: 4.530
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  4 in total

1.  A reduced-amide inhibitor of Pin1 binds in a conformation resembling a twisted-amide transition state.

Authors:  Guoyan G Xu; Yan Zhang; Ana Y Mercedes-Camacho; Felicia A Etzkorn
Journal:  Biochemistry       Date:  2011-10-18       Impact factor: 3.162

2.  Kinetic isotope effects support the twisted amide mechanism of Pin1 peptidyl-prolyl isomerase.

Authors:  Ana Y Mercedes-Camacho; Ashley B Mullins; Matthew D Mason; Guoyan G Xu; Brendan J Mahoney; Xingsheng Wang; Jeffrey W Peng; Felicia A Etzkorn
Journal:  Biochemistry       Date:  2013-10-24       Impact factor: 3.162

3.  Cyclohexyl ketone inhibitors of Pin1 dock in a trans-diaxial cyclohexane conformation.

Authors:  Guoyan G Xu; Carla Slebodnick; Felicia A Etzkorn
Journal:  PLoS One       Date:  2012-09-19       Impact factor: 3.240

4.  Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst.

Authors:  Takatsugu Murata; Tatsuya Kawanishi; Akihiro Sekiguchi; Ryo Ishikawa; Keisuke Ono; Kenya Nakata; Isamu Shiina
Journal:  Molecules       Date:  2018-08-10       Impact factor: 4.411
  4 in total

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