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      Innovations and Inventions: Why Was the Ugi Reaction Discovered Only 37 Years after the Passerini Reaction?

      review-article
      The Journal of Organic Chemistry
      American Chemical Society

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          Abstract

          This year represents the 100th anniversary of the discovery of the Passerini three-component reaction. The related Ugi four-compound reaction was discovered 37 years after the Passerini reaction. Undoubtedly, both reactions are very important multicomponent reactions but the Ugi reactions outperform the Passerini reactions in terms of combinatorial space according to the equation x y [ x is the number of building blocks per component, and y is the order of the multicomponent reaction (for Passerini, y = 3; for Ugi, y = 4)]. In this work, a historical but contemporary perspective of the discoveries and innovations of the two reactions is given. From a bird’s eye view and in a more general sense, the discovery of novel reactions is discussed and how it relates to inventions and innovations.

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          Most cited references46

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          Multicomponent Reactions with Isocyanides

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            Mittheilungen aus dem Universitätslaboratorium in Pisa: Eine neue Reihe organischer Basen

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              Discovery of AG-120 (Ivosidenib): A First-in-Class Mutant IDH1 Inhibitor for the Treatment of IDH1 Mutant Cancers

              Somatic point mutations at a key arginine residue (R132) within the active site of the metabolic enzyme isocitrate dehydrogenase 1 (IDH1) confer a novel gain of function in cancer cells, resulting in the production of d-2-hydroxyglutarate (2-HG), an oncometabolite. Elevated 2-HG levels are implicated in epigenetic alterations and impaired cellular differentiation. IDH1 mutations have been described in an array of hematologic malignancies and solid tumors. Here, we report the discovery of AG-120 (ivosidenib), an inhibitor of the IDH1 mutant enzyme that exhibits profound 2-HG lowering in tumor models and the ability to effect differentiation of primary patient AML samples ex vivo. Preliminary data from phase 1 clinical trials enrolling patients with cancers harboring an IDH1 mutation indicate that AG-120 has an acceptable safety profile and clinical activity.
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                Author and article information

                Journal
                J Org Chem
                J Org Chem
                jo
                joceah
                The Journal of Organic Chemistry
                American Chemical Society
                0022-3263
                1520-6904
                26 July 2022
                05 May 2023
                : 88
                : 9
                : 5242-5247
                Affiliations
                Department of Drug Design, University of Groningen , Groningen 9700 AD, The Netherlands
                Author notes
                Author information
                https://orcid.org/0000-0002-9923-8873
                Article
                10.1021/acs.joc.2c00792
                10167652
                35881912
                29a5b035-637a-4da2-9efd-ec2c75ec966a
                © 2022 The Author. Published by American Chemical Society

                Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained ( https://creativecommons.org/licenses/by/4.0/).

                History
                : 05 April 2022
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                Perspective
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                jo2c00792
                jo2c00792

                Organic & Biomolecular chemistry
                Organic & Biomolecular chemistry

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