Synthesis of Novel Steroid-Peptoid Hybrid Macrocycles by Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs)

Two new groups of cholane-peptoid hybrid macrocycles were produced by implementing novel combinations of the MiB methodology. Steroid-based hybrid macrolactams including heterocycle and aryl moieties were obtained by utilizing cholanic dicarboxylic acids and diamines in a bidirectional double Ugi-Fo...

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Main Authors:	Ludger A. Wessjohann, Daniel G. Rivera
Format:	Article
Language:	English
Published:	MDPI AG 2007-08-01
Series:	Molecules
Subjects:	Bile acids macrocycles steroids peptoids Ugi reaction multicomponent reaction
Online Access:	http://www.mdpi.com/1420-3049/12/8/1890/

id	doaj-41bba2d6709a454c9bd6a2e9fa16e7c3
record_format	Article
spelling	doaj-41bba2d6709a454c9bd6a2e9fa16e7c32020-11-24T22:48:10ZengMDPI AGMolecules1420-30492007-08-011281890189910.3390/12081890Synthesis of Novel Steroid-Peptoid Hybrid Macrocycles by Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs)Ludger A. WessjohannDaniel G. RiveraTwo new groups of cholane-peptoid hybrid macrocycles were produced by implementing novel combinations of the MiB methodology. Steroid-based hybrid macrolactams including heterocycle and aryl moieties were obtained by utilizing cholanic dicarboxylic acids and diamines in a bidirectional double Ugi-Four-Component (Ugi-4CR) based macrocyclization protocol. Alternatively, N-substituted cyclocholamides were produced from a cholanic pseudo-amino acid by an Ugi-4CR-based cyclooligomerization approach. Both types of macrocycles are steroid-peptoid hybrid macrocycles containing exocyclic peptidic chains. These novel frameworks are a result of the use of bile acids bifunctionalized with carboxylic and amino functionalities as bifunctional building blocks of the Ugi-MiB approach.http://www.mdpi.com/1420-3049/12/8/1890/Bile acidsmacrocyclessteroidspeptoidsUgi reactionmulticomponent reaction
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Ludger A. Wessjohann Daniel G. Rivera
spellingShingle	Ludger A. Wessjohann Daniel G. Rivera Synthesis of Novel Steroid-Peptoid Hybrid Macrocycles by Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs) Molecules Bile acids macrocycles steroids peptoids Ugi reaction multicomponent reaction
author_facet	Ludger A. Wessjohann Daniel G. Rivera
author_sort	Ludger A. Wessjohann
title	Synthesis of Novel Steroid-Peptoid Hybrid Macrocycles by Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs)
title_short	Synthesis of Novel Steroid-Peptoid Hybrid Macrocycles by Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs)
title_full	Synthesis of Novel Steroid-Peptoid Hybrid Macrocycles by Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs)
title_fullStr	Synthesis of Novel Steroid-Peptoid Hybrid Macrocycles by Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs)
title_full_unstemmed	Synthesis of Novel Steroid-Peptoid Hybrid Macrocycles by Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs)
title_sort	synthesis of novel steroid-peptoid hybrid macrocycles by multiple multicomponent macrocyclizations including bifunctional building blocks (mibs)
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2007-08-01
description	Two new groups of cholane-peptoid hybrid macrocycles were produced by implementing novel combinations of the MiB methodology. Steroid-based hybrid macrolactams including heterocycle and aryl moieties were obtained by utilizing cholanic dicarboxylic acids and diamines in a bidirectional double Ugi-Four-Component (Ugi-4CR) based macrocyclization protocol. Alternatively, N-substituted cyclocholamides were produced from a cholanic pseudo-amino acid by an Ugi-4CR-based cyclooligomerization approach. Both types of macrocycles are steroid-peptoid hybrid macrocycles containing exocyclic peptidic chains. These novel frameworks are a result of the use of bile acids bifunctionalized with carboxylic and amino functionalities as bifunctional building blocks of the Ugi-MiB approach.
topic	Bile acids macrocycles steroids peptoids Ugi reaction multicomponent reaction
url	http://www.mdpi.com/1420-3049/12/8/1890/
work_keys_str_mv	AT ludgerawessjohann synthesisofnovelsteroidpeptoidhybridmacrocyclesbymultiplemulticomponentmacrocyclizationsincludingbifunctionalbuildingblocksmibs AT danielgrivera synthesisofnovelsteroidpeptoidhybridmacrocyclesbymultiplemulticomponentmacrocyclizationsincludingbifunctionalbuildingblocksmibs
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Synthesis of Novel Steroid-Peptoid Hybrid Macrocycles by Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs)

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