Synthesis of a 2,3‘;6‘,3‘ ‘-Terpyridine Scaffold as an α-Helix Mimetic

A terpyridine scaffold has been designed as an α-helix mimetic. A facile synthesis of the ortho-functionalized 2,3‘-oligopyridine has been accomplished using sequential Bohlmann−Rahtz heteroannulation reactions.

[1]  Shibo Jiang,et al.  Design of a protein surface antagonist based on alpha-helix mimicry: inhibition of gp41 assembly and viral fusion. , 2002, Angewandte Chemie.

[2]  J. Bower,et al.  Synthesis of Pyridines and Pyrido[2,3-d]pyrimidines by the Lewis Acid Catalysed Bohlmann-Rahtz Heteroannulation Reaction , 2001 .

[3]  A. Hamilton,et al.  Toward proteomimetics: terphenyl derivatives as structural and functional mimics of extended regions of an alpha-helix. , 2001, Journal of the American Chemical Society.

[4]  J. Bower,et al.  A New Modification of the Bohlmann-Rahtz Pyridine Synthesis , 2001 .

[5]  David R. Williams,et al.  Total synthesis of (-)-stemospironine. , 2001, Organic letters.

[6]  A. Katz,et al.  Bipyridine: the most widely used ligand. A review of molecules comprising at least two 2,2'-bipyridine units. , 2000, Chemical reviews.

[7]  Andrew D. Hamilton,et al.  Development of a Potent Bcl-xL Antagonist Based on α-Helix Mimicry , 2002 .

[8]  R. Meadows,et al.  Structure of Bcl-xL-Bak Peptide Complex: Recognition Between Regulators of Apoptosis , 1997, Science.

[9]  John Calvin Reed Double identity for proteins of the Bcl-2 family , 1997, Nature.

[10]  F. Bohlmann,et al.  Über eine neue Pyridinsynthese , 1957 .

[11]  A. Hamilton,et al.  Protein recognition using synthetic surface-targeted agents , 2004, Molecular Diversity.

[12]  J. Bower,et al.  A new one-pot three-component condensation reaction for the synthesis of 2,3,4,6-tetrasubstituted pyridines. , 2002, Chemical communications.

[13]  M. Bagley,et al.  A new mild method for the one-pot synthesis of pyridines , 2004 .

[14]  J. Bower,et al.  Synthesis of tetrasubstituted pyridines by the acid-catalysed Bohlmann–Rahtz reaction , 2002 .

[15]  I. Charles,et al.  Synthesis and biological evaluation of novel pyrazoles and indazoles as activators of the nitric oxide receptor, soluble guanylate cyclase. , 2001, Journal of medicinal chemistry.

[16]  S. Cory,et al.  The Bcl-2 protein family: arbiters of cell survival. , 1998, Science.

[17]  M. Bagley,et al.  One-pot synthesis of pyridines or pyrimidines by tandem oxidation-heteroannulation of propargylic alcohols , 2003 .

[18]  J. Bower,et al.  One-pot multistep Bohlmann-Rahtz heteroannulation reactions: synthesis of dimethyl sulfomycinamate. , 2005, The Journal of organic chemistry.