Facile and rapid route for the synthesis of novel norstatine analogs via PADAM-cyclization methodology

Arthur Y. Shaw; Federico Medda; Christopher Hulme

doi:10.1016/j.tetlet.2011.12.073

Facile and rapid route for the synthesis of novel norstatine analogs via PADAM-cyclization methodology

Arthur Y. Shaw, Federico Medda, Christopher Hulme

Research output: Contribution to journal › Article › peer-review

28 Scopus citations

Abstract

The following report describes novel methodology for the rapid synthesis of unique conformationally constrained norstatine analogs of potential biological relevance. A PADAM (Passerini reaction-Amine Deprotection-Acyl Migration reaction) sequence is followed by a TFA-mediated microwave-assisted cyclization to generate the final benzimidazole isostere of the norstatine scaffold in moderate to good yields. The applicability of this solution phase methodology to the preparation of a small collection of compounds is discussed.

Original language	English (US)
Pages (from-to)	1313-1315
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	11
DOIs	https://doi.org/10.1016/j.tetlet.2011.12.073
State	Published - Mar 14 2012

Keywords

Benzimidazole
Multicomponent reactions
Passerini reaction
Peptidomimetics
Protease inhibitor

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2011.12.073

Cite this

@article{72ccdffd21194fdaa674d1b9dfb3758c,

title = "Facile and rapid route for the synthesis of novel norstatine analogs via PADAM-cyclization methodology",

abstract = "The following report describes novel methodology for the rapid synthesis of unique conformationally constrained norstatine analogs of potential biological relevance. A PADAM (Passerini reaction-Amine Deprotection-Acyl Migration reaction) sequence is followed by a TFA-mediated microwave-assisted cyclization to generate the final benzimidazole isostere of the norstatine scaffold in moderate to good yields. The applicability of this solution phase methodology to the preparation of a small collection of compounds is discussed.",

keywords = "Benzimidazole, Multicomponent reactions, Passerini reaction, Peptidomimetics, Protease inhibitor",

author = "Shaw, \{Arthur Y.\} and Federico Medda and Christopher Hulme",

note = "Funding Information: We would like to thank the Office of the Director, NIH, and the National Institute of Mental Health for funding ( 1RC2MH090878-01 ). Particular thanks to N. Schechter PSM for copy editing. ",

year = "2012",

month = mar,

day = "14",

doi = "10.1016/j.tetlet.2011.12.073",

language = "English (US)",

volume = "53",

pages = "1313--1315",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "11",

}

TY - JOUR

T1 - Facile and rapid route for the synthesis of novel norstatine analogs via PADAM-cyclization methodology

AU - Shaw, Arthur Y.

AU - Medda, Federico

AU - Hulme, Christopher

N1 - Funding Information: We would like to thank the Office of the Director, NIH, and the National Institute of Mental Health for funding ( 1RC2MH090878-01 ). Particular thanks to N. Schechter PSM for copy editing.

PY - 2012/3/14

Y1 - 2012/3/14

N2 - The following report describes novel methodology for the rapid synthesis of unique conformationally constrained norstatine analogs of potential biological relevance. A PADAM (Passerini reaction-Amine Deprotection-Acyl Migration reaction) sequence is followed by a TFA-mediated microwave-assisted cyclization to generate the final benzimidazole isostere of the norstatine scaffold in moderate to good yields. The applicability of this solution phase methodology to the preparation of a small collection of compounds is discussed.

AB - The following report describes novel methodology for the rapid synthesis of unique conformationally constrained norstatine analogs of potential biological relevance. A PADAM (Passerini reaction-Amine Deprotection-Acyl Migration reaction) sequence is followed by a TFA-mediated microwave-assisted cyclization to generate the final benzimidazole isostere of the norstatine scaffold in moderate to good yields. The applicability of this solution phase methodology to the preparation of a small collection of compounds is discussed.

KW - Benzimidazole

KW - Multicomponent reactions

KW - Passerini reaction

KW - Peptidomimetics

KW - Protease inhibitor

UR - https://www.scopus.com/pages/publications/84856760746

UR - https://www.scopus.com/inward/citedby.url?scp=84856760746&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2011.12.073

DO - 10.1016/j.tetlet.2011.12.073

M3 - Article

AN - SCOPUS:84856760746

SN - 0040-4039

VL - 53

SP - 1313

EP - 1315

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

Facile and rapid route for the synthesis of novel norstatine analogs via PADAM-cyclization methodology

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this