Literature DB >> 19205916

Emerging molecular diversity from the intra-molecular Ugi reaction: iterative efficiency in medicinal chemistry.

Christopher Hulme1, Justin Dietrich.   

Abstract

This review details a now established area within the isonitrile multi-component reaction (IMCR) field of study, namely employing bi-functional reagents in the Ugi reaction for the construction of screening sets with the additional element or even possibly 'metric' of enhanced 'iterative efficiency potential'. The concept of 'iterative efficiency' will be briefly introduced, coupled with discussion on new synthetic routes to select bi-functional IMCR precursors and their use in the generation of pharmacologically relevant 'molecular diversity'.

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Year:  2009        PMID: 19205916     DOI: 10.1007/s11030-009-9111-6

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   3.364


  31 in total

1.  Unique Structures Generated by Ugi 3CC Reactions Using Bifunctional Starting Materials Containing Aldehyde and Carboxylic Acid.

Authors:  Jundong Zhang; Alan Jacobson; James R. Rusche; Walter Herlihy
Journal:  J Org Chem       Date:  1999-02-05       Impact factor: 4.354

2.  Generating diverse skeletons of small molecules combinatorially.

Authors:  Martin D Burke; Eric M Berger; Stuart L Schreiber
Journal:  Science       Date:  2003-10-24       Impact factor: 47.728

3.  Library generation via postcondensation modifications of isocyanide-based multicomponent reactions.

Authors:  Christopher Hulme; Hugues Bienaymé; Thomas Nixey; Balan Chenera; Wyeth Jones; Paul Tempest; Adrian L Smith
Journal:  Methods Enzymol       Date:  2003       Impact factor: 1.600

4.  Ugi reaction in aqueous solutions: a simple protocol for libraries production.

Authors:  Maxim A Mironov; Maria N Ivantsova; Vladimir S Mokrushin
Journal:  Mol Divers       Date:  2003       Impact factor: 2.943

5.  One-step construction of peptidomimetic 5-carbamoyl-4-sulfonyl-2-piperazinones.

Authors:  Alexei P Ilyin; Andrey S Trifilenkov; Irina D Kurashvili; Mikhail Krasavin; Alexandre V Ivachtchenko
Journal:  J Comb Chem       Date:  2005 May-Jun

6.  Overcoming roadblocks in lead optimization: a thermodynamic perspective.

Authors:  Adam J Ruben; Yoshiaki Kiso; Ernesto Freire
Journal:  Chem Biol Drug Des       Date:  2006-01       Impact factor: 2.817

Review 7.  The art and practice of structure-based drug design: a molecular modeling perspective.

Authors:  R S Bohacek; C McMartin; W C Guida
Journal:  Med Res Rev       Date:  1996-01       Impact factor: 12.944

8.  Liquid-phase parallel synthesis of combinatorial libraries of substituted 6-carbamoyl-3,4-dihydro-2H-benzo[1,4]thiazines.

Authors:  Andrey S Trifilenkov; Vladimir V Kobak; Marina A Salina; Julya A Kusovkova; Alexey P Ilyin; Alexander V Khvat; Sergey E Tkachenko; Alexandre V Ivachtchenko
Journal:  J Comb Chem       Date:  2006 Jul-Aug

9.  Synthesis of cis,cis,cis-tetrasubstituted cyclobutanes. Trapping of tetrahedral intermediates in intramolecular nucleophilic addition

Authors: 
Journal:  J Org Chem       Date:  2000-10-06       Impact factor: 4.354

10.  Versatile, fragrant, convertible isonitriles.

Authors:  Michael C Pirrung; Subir Ghorai
Journal:  J Am Chem Soc       Date:  2006-09-13       Impact factor: 15.419

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  31 in total

Review 1.  Chemistry and biology of multicomponent reactions.

Authors:  Alexander Dömling; Wei Wang; Kan Wang
Journal:  Chem Rev       Date:  2012-03-22       Impact factor: 60.622

2.  Synthesis of some new triamide derivatives via Ugi five-component reaction in aqueous solution.

Authors:  Ali Asghar Mohammadi; Salman Taheri; Arman Amini; Reza Ahdenov
Journal:  Mol Divers       Date:  2018-06-27       Impact factor: 2.943

3.  Multicomponent synthesis of dihydrobenzoxazepinones, bearing four diversity points, as potential α-helix mimics.

Authors:  Luca Banfi; Andrea Basso; Valentina Cerulli; Giuseppe Guanti; Paulina Lecinska; Ilaria Monfardini; Renata Riva
Journal:  Mol Divers       Date:  2009-11-28       Impact factor: 2.943

Review 4.  On the industrial applications of MCRs: molecular diversity in drug discovery and generic drug synthesis.

Authors:  Cédric Kalinski; Michael Umkehrer; Lutz Weber; Jürgen Kolb; Christoph Burdack; Günther Ross
Journal:  Mol Divers       Date:  2010-03-16       Impact factor: 2.943

5.  Special issue on Mini-MCR issue and SCS-09--Second International Symposium on Combinatorial Sciences in Biology, Chemistry, Catalysts and Materials. Editorial.

Authors:  Alexander Dömling; Christopher Hulme
Journal:  Mol Divers       Date:  2011-02       Impact factor: 2.943

6.  Concise Two-Step Solution Phase Syntheses of four novel Dihydroquinazoline scaffolds.

Authors:  Justin Dietrich; Christine Kaiser; Nathalie Meurice; Christopher Hulme
Journal:  Tetrahedron Lett       Date:  2010-07-28       Impact factor: 2.415

7.  Novel succinct routes to Quinoxalines and 2-Benzimidazolylquinoxalines via the Ugi reaction.

Authors:  Muhammad Ayaz; Zhigang Xu; Christopher Hulme
Journal:  Tetrahedron Lett       Date:  2014-06-04       Impact factor: 2.415

Review 8.  Tetrazoles via Multicomponent Reactions.

Authors:  Constantinos G Neochoritis; Ting Zhao; Alexander Dömling
Journal:  Chem Rev       Date:  2019-02-01       Impact factor: 60.622

9.  Aldol reactions in multicomponent reaction based domino pathways: a multipurpose enabling tool in heterocyclic chemistry.

Authors:  Zhigang Xu; Fabio De Moliner; Alexandra P Cappelli; Christopher Hulme
Journal:  Org Lett       Date:  2013-05-29       Impact factor: 6.005

10.  Multicomponent synthesis of diverse 1,4-benzodiazepine scaffolds.

Authors:  Yijun Huang; Kareem Khoury; Tyler Chanas; Alexander Dömling
Journal:  Org Lett       Date:  2012-11-16       Impact factor: 6.005

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