Microwave assisted solid phase synthesis of highly functionalized N-alkylated oligobenzamide α-helix mimetics

Kérya Long; Thomas A. Edwards; Andrew J. Wilson

doi:10.1016/j.bmc.2012.09.053

Microwave assisted solid phase synthesis of highly functionalized N-alkylated oligobenzamide α-helix mimetics

Kérya Long
, Thomas A. Edwards
, Andrew J. Wilson^*

^*Corresponding author for this work

Chemistry

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

38 Citations (Scopus)

Abstract

Protein-protein interactions (PPIs) mediate cellular pathways and are implicated in numerous aberrant conditions. α-Helix mimetics - small molecules that reproduce the spatial projection of key residues from an α-helix involved in a PPI - are attractive generic templates for development of screening libraries, however library syntheses of α-helix mimetics with diverse functionality are less established. This manuscript describes the automated, microwave assisted solid phase synthesis based on one such scaffold; an N-alkylated oligobenzamide.

Original language	English
Pages (from-to)	4034-4040
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	21
Issue number	14
DOIs	https://doi.org/10.1016/j.bmc.2012.09.053
Publication status	Published - 15 Jul 2013

Bibliographical note

Funding Information:
This work builds on previous studies by Dr. F. Campbell and was supported by Yorkshire Cancer Research (L348) and the European Research Council (240324).

Keywords

Aromatic oligoamide
Automated solid phase synthesis
Helix mimetic
Protein-protein interactions

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmc.2012.09.053

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title = "Microwave assisted solid phase synthesis of highly functionalized N-alkylated oligobenzamide α-helix mimetics",

abstract = "Protein-protein interactions (PPIs) mediate cellular pathways and are implicated in numerous aberrant conditions. α-Helix mimetics - small molecules that reproduce the spatial projection of key residues from an α-helix involved in a PPI - are attractive generic templates for development of screening libraries, however library syntheses of α-helix mimetics with diverse functionality are less established. This manuscript describes the automated, microwave assisted solid phase synthesis based on one such scaffold; an N-alkylated oligobenzamide.",

keywords = "Aromatic oligoamide, Automated solid phase synthesis, Helix mimetic, Protein-protein interactions",

author = "K{\'e}rya Long and Edwards, \{Thomas A.\} and Wilson, \{Andrew J.\}",

note = "Funding Information: This work builds on previous studies by Dr. F. Campbell and was supported by Yorkshire Cancer Research (L348) and the European Research Council (240324). ",

year = "2013",

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doi = "10.1016/j.bmc.2012.09.053",

language = "English",

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pages = "4034--4040",

journal = "Bioorganic and Medicinal Chemistry",

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T1 - Microwave assisted solid phase synthesis of highly functionalized N-alkylated oligobenzamide α-helix mimetics

AU - Long, Kérya

AU - Edwards, Thomas A.

AU - Wilson, Andrew J.

N1 - Funding Information: This work builds on previous studies by Dr. F. Campbell and was supported by Yorkshire Cancer Research (L348) and the European Research Council (240324).

PY - 2013/7/15

Y1 - 2013/7/15

N2 - Protein-protein interactions (PPIs) mediate cellular pathways and are implicated in numerous aberrant conditions. α-Helix mimetics - small molecules that reproduce the spatial projection of key residues from an α-helix involved in a PPI - are attractive generic templates for development of screening libraries, however library syntheses of α-helix mimetics with diverse functionality are less established. This manuscript describes the automated, microwave assisted solid phase synthesis based on one such scaffold; an N-alkylated oligobenzamide.

AB - Protein-protein interactions (PPIs) mediate cellular pathways and are implicated in numerous aberrant conditions. α-Helix mimetics - small molecules that reproduce the spatial projection of key residues from an α-helix involved in a PPI - are attractive generic templates for development of screening libraries, however library syntheses of α-helix mimetics with diverse functionality are less established. This manuscript describes the automated, microwave assisted solid phase synthesis based on one such scaffold; an N-alkylated oligobenzamide.

KW - Aromatic oligoamide

KW - Automated solid phase synthesis

KW - Helix mimetic

KW - Protein-protein interactions

UR - https://www.scopus.com/pages/publications/84879015546

U2 - 10.1016/j.bmc.2012.09.053

DO - 10.1016/j.bmc.2012.09.053

M3 - Article

C2 - 23117175

AN - SCOPUS:84879015546

SN - 0968-0896

VL - 21

SP - 4034

EP - 4040

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 14

ER -

Microwave assisted solid phase synthesis of highly functionalized N-alkylated oligobenzamide α-helix mimetics

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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