Literature DB >> 25147729

Modern Multicomponent Reactions for better Drug Syntheses**

Tryfon Zarganes-Tzitzikas, Alexander Dömling.   

Abstract

Multicomponent reaction (MCR) technology is now widely recognized for its impact on drug discovery projects and is strongly endorsed by industry as well as academia. However, still relatively few products based on MCRs are marketed or under development. This provides tremendous opportunities for organic chemists to shorten synthetic pathways thus reducing the cost-of-goods considerably. A recent example of the HCV drug Telaprevir is highlighted where introduction of two MCRs could lead to a shortening of the synthesis route by more than 50%.

Entities:  

Year:  2014        PMID: 25147729      PMCID: PMC4136525          DOI: 10.1039/C4QO00088A

Source DB:  PubMed          Journal:  Org Chem Front        ISSN: 2052-4110            Impact factor:   5.281


  12 in total

1.  Alcohols in isonitrile-based multicomponent reaction: Passerini reaction of alcohols in the presence of o-iodoxybenzoic acid.

Authors:  Tifelle Ngouansavanh; Jieping Zhu
Journal:  Angew Chem Int Ed Engl       Date:  2006-05-19       Impact factor: 15.336

Review 2.  Chemistry and biology of multicomponent reactions.

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

3.  Efficient multicomponent reaction synthesis of the schistosomiasis drug praziquantel.

Authors:  Haiping Cao; Haixia Liu; Alexander Dömling
Journal:  Chemistry       Date:  2010-11-02       Impact factor: 5.236

4.  Highly stereoselective synthesis of substituted prolyl peptides using a combination of biocatalytic desymmetrization and multicomponent reactions.

Authors:  Anass Znabet; Eelco Ruijter; Frans J J de Kanter; Valentin Köhler; Madeleine Helliwell; Nicholas J Turner; Romano V A Orru
Journal:  Angew Chem Int Ed Engl       Date:  2010-07-19       Impact factor: 15.336

5.  Enantioselective biocatalytic oxidative desymmetrization of substituted pyrrolidines.

Authors:  Valentin Köhler; Kevin R Bailey; Anass Znabet; James Raftery; Madeleine Helliwell; Nicholas J Turner
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-15       Impact factor: 15.336

6.  2-Azetidinones as inhibitors of cholesterol absorption.

Authors:  D A Burnett; M A Caplen; H R Davis; R E Burrier; J W Clader
Journal:  J Med Chem       Date:  1994-06-10       Impact factor: 7.446

7.  MCR synthesis of praziquantel derivatives.

Authors:  Haixia Liu; Samia William; Eberhardt Herdtweck; Sanaa Botros; Alexander Dömling
Journal:  Chem Biol Drug Des       Date:  2012-01-30       Impact factor: 2.817

8.  Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.

Authors:  Alan D Borthwick; John Liddle; Dave E Davies; Anne M Exall; Christopher Hamlett; Deirdre M Hickey; Andrew M Mason; Ian E D Smith; Fabrizio Nerozzi; Simon Peace; Derek Pollard; Steve L Sollis; Michael J Allen; Patrick M Woollard; Mark A Pullen; Timothy D Westfall; Dinesh J Stanislaus
Journal:  J Med Chem       Date:  2012-01-12       Impact factor: 7.446

9.  2-Azetidinone cholesterol absorption inhibitors: structure-activity relationships on the heterocyclic nucleus.

Authors:  J W Clader; D A Burnett; M A Caplen; M S Domalski; S Dugar; W Vaccaro; R Sher; M E Browne; H Zhao; R E Burrier; B Salisbury; H R Davis
Journal:  J Med Chem       Date:  1996-09-13       Impact factor: 7.446

10.  The homo-PADAM protocol: stereoselective and operationally simple synthesis of α-oxo- or α-hydroxy-γ-acylaminoamides and chromanes.

Authors:  Fabio Morana; Andrea Basso; Renata Riva; Valeria Rocca; Luca Banfi
Journal:  Chemistry       Date:  2013-02-12       Impact factor: 5.236

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  11 in total

1.  One-pot organocatalytic/multicomponent approach for the preparation of novel enantioenriched non-natural selenium-based peptoids and peptide-peptoid conjugates.

Authors:  Alexander F de la Torre; Akbar Ali; Fábio Z Galetto; Antonio L Braga; José A C Delgado; Márcio W Paixão
Journal:  Mol Divers       Date:  2019-02-18       Impact factor: 2.943

Review 2.  Expanding the medicinal chemistry synthetic toolbox.

Authors:  Jonas Boström; Dean G Brown; Robert J Young; György M Keserü
Journal:  Nat Rev Drug Discov       Date:  2018-08-24       Impact factor: 84.694

Review 3.  The status of isocyanide-based multi-component reactions in Iran (2010-2018).

Authors:  Ronak Afshari; Seyyed Emad Hooshmand; Mohammad Taghi Nazeri; Siamak Javanbakht; Ahmad Shaabani; Reza Mohammadian
Journal:  Mol Divers       Date:  2020-02-18       Impact factor: 2.943

Review 4.  Isocyanide-Based Multicomponent Reactions in Water: Advanced Green Tools for the Synthesis of Heterocyclic Compounds.

Authors:  Siamak Javanbakht; Mohammad Taghi Nazeri; Hassan Farhid; Tahereh Nasiriani; Vida Khodkari; Ahmad Shaabani
Journal:  Top Curr Chem (Cham)       Date:  2022-09-22

5.  Multicomponent reaction-based synthesis and biological evaluation of tricyclic heterofused quinolines with multi-trypanosomatid activity.

Authors:  Ornella Di Pietro; Esther Vicente-García; Martin C Taylor; Diana Berenguer; Elisabet Viayna; Anna Lanzoni; Irene Sola; Helena Sayago; Cristina Riera; Roser Fisa; M Victòria Clos; Belén Pérez; John M Kelly; Rodolfo Lavilla; Diego Muñoz-Torrero
Journal:  Eur J Med Chem       Date:  2015-10-19       Impact factor: 6.514

Review 6.  Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)-The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules.

Authors:  Heiner Eckert
Journal:  Molecules       Date:  2017-02-25       Impact factor: 4.411

7.  Stereoselective Four-Component Synthesis of Functionalized 2,3-Dihydro-4-Nitropyrroles.

Authors:  Dong Wang; Xinyue Ma; Linru Dong; Hairong Feng; Peng Yu; Laurent Désaubry
Journal:  Front Chem       Date:  2019-11-26       Impact factor: 5.221

Review 8.  Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects.

Authors:  Shivani Gulati; Stephy Elza John; Nagula Shankaraiah
Journal:  Beilstein J Org Chem       Date:  2021-04-19       Impact factor: 2.883

Review 9.  Copper-Catalyzed Borylative Couplings with C-N Electrophiles.

Authors:  Fabien J T Talbot; Quentin Dherbassy; Srimanta Manna; Chunling Shi; Shibo Zhang; Gareth P Howell; Gregory J P Perry; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-28       Impact factor: 15.336

10.  Greener Synthesis of Antiproliferative Furoxans via Multicomponent Reactions.

Authors:  Mariana Ingold; Victoria de la Sovera; Rosina Dapueto; Paola Hernández; Williams Porcal; Gloria V López
Journal:  Molecules       Date:  2022-03-08       Impact factor: 4.411

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