Literature DB >> 18335950

Synthesis and structure of 1,4-dipiperazino benzenes: chiral terphenyl-type peptide helix mimetics.

Prantik Maity1, Burkhard König.   

Abstract

The terphenyl structure has been proven to be an ideal scaffold mimicking side-chain functionalities of peptidic alpha-helices. The synthesis of 1,4-dipiperazino benzenes, using stepwise transition metal-catalyzed N-arylation of chiral piperazines to a central benzene core is reported. The structure determination by X-ray crystallography reveals a geometrical arrangement of the hydrophobic side chains resembling the orientation of key i, i + 3, and i + 7 positions in a peptidic alpha-helix or in terphenyl helix mimetics.

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Year:  2008        PMID： 18335950     DOI： 10.1021/ol8002749

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


  15 in total

1.  Evaluating minimalist mimics by exploring key orientations on secondary structures (EKOS).

Authors:  Dongyue Xin; Eunhwa Ko; Lisa M Perez; Thomas R Ioerger; Kevin Burgess
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2.  Potential pharmacological chaperones targeting cancer-associated MCL-1 and Parkinson disease-associated α-synuclein.

Authors:  Misook Oh; Ji Hoon Lee; Wei Wang; Hui Sun Lee; Woo Sirl Lee; Christopher Burlak; Wonpil Im; Quyen Q Hoang; Hyun-Suk Lim
Journal:  Proc Natl Acad Sci U S A       Date:  2014-07-14       Impact factor: 11.205

3.  Expanding the scope of oligo-pyrrolinone-pyrrolidines as protein-protein interface mimics.

Authors:  Arjun Raghuraman; Dongyue Xin; Lisa M Perez; Kevin Burgess
Journal:  J Org Chem       Date:  2013-05-08       Impact factor: 4.354

4.  Synthesis of a tetrasubstituted tetrahydronaphthalene scaffold for α-helix mimicry via a MgBr2-catalyzed Friedel-Crafts epoxide cycloalkylation.

Authors:  Devan Naduthambi; Santosh Bhor; Michael B Elbaum; Neal J Zondlo
Journal:  Org Lett       Date:  2013-09-09       Impact factor: 6.005

5.  Novel pyrrolopyrimidine-based α-helix mimetics: cell-permeable inhibitors of protein−protein interactions.

Authors:  Ji Hoon Lee; Qi Zhang; Sunhwan Jo; Sergio C Chai; Misook Oh; Wonpil Im; Hua Lu; Hyun-Suk Lim
Journal:  J Am Chem Soc       Date:  2011-02-02       Impact factor: 15.419

6.  Oligobenzamide proteomimetic inhibitors of the p53-hDM2 protein-protein interaction.

Authors:  Jeffrey P Plante; Thomas Burnley; Barbora Malkova; Michael E Webb; Stuart L Warriner; Thomas A Edwards; Andrew J Wilson
Journal:  Chem Commun (Camb)       Date:  2009-06-24       Impact factor: 6.222

7.  Synthesis and biological evaluation of a 5-6-5 imidazole-phenyl-thiazole based alpha-helix mimetic.

Authors:  Christopher G Cummings; Nathan T Ross; William P Katt; Andrew D Hamilton
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

8.  Design, synthesis, and evaluation of an alpha-helix mimetic library targeting protein-protein interactions.

Authors:  Alex Shaginian; Landon R Whitby; Sukwon Hong; Inkyu Hwang; Bilal Farooqi; Mark Searcey; Jiandong Chen; Peter K Vogt; Dale L Boger
Journal:  J Am Chem Soc       Date:  2009-04-22       Impact factor: 15.419

9.  Computational analysis of protein-protein interfaces involving an alpha helix: insights for terphenyl-like molecules binding.

Authors:  Adriana Isvoran; Dana Craciun; Virginie Martiny; Olivier Sperandio; Maria A Miteva
Journal:  BMC Pharmacol Toxicol       Date:  2013-06-14       Impact factor: 2.483

10.  The diketopiperazine-fused tetrahydro-β-carboline scaffold as a model peptidomimetic with an unusual α-turn secondary structure.

Authors:  Francesco Airaghi; Andrea Fiorati; Giordano Lesma; Manuele Musolino; Alessandro Sacchetti; Alessandra Silvani
Journal:  Beilstein J Org Chem       Date:  2013-01-22       Impact factor: 2.883
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