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Journal ArticleDOI: 10.1080/13543776.2021.1858797

Multicomponent reactions (MCR) in medicinal chemistry: a patent review (2010-2020).

04 Mar 2021-Expert Opinion on Therapeutic Patents (Taylor & Francis)-Vol. 31, Iss: 3, pp 267-289
Abstract: Introduction: Multicomponent reactions (MCR) has been utilized to synthesize a vast range of analogs belonging to diverse classes of heterocyclic compounds offering multidimensional pharmaceutical applications. The unique feature of MCR includes the synthesis of highly functionalized molecules in a single pot to build quick libraries of compounds of biological interest to identify new leads as potential therapeutic agents.Area covered: The current review article covers the patents published in the last decade in order to highlight the importance of multicomponent reactions for synthesizing complex-functionalized molecules of high biological significance.Expert opinion: Easily automated one-pot multicomponent reactions (MCRs) has demonstrated successful impact at different stages of the lead discovery, lead optimization, and pre-clinical process development arenas. Application of MCRs is the recent advancement in the field of drug design and discovery which will expectedly lead to the development of medicinally important heterocyclic compounds with a vast range of biological activities.

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13 results found


Journal ArticleDOI: 10.1039/D0QO01480J
Abstract: Multi-component reactions (MCRs) are considered to be an important methodological arsenal in synthetic and medicinal chemistry. These reactions have been strategically employed in various synthetic transformations where classical methods usually involve many steps with tedious procedures. The MCR approach provides high yields, atom-/step economy, reduced reaction time, is eco-friendly, and acts as an amenable tool for the generation of a library of new chemical entities (NCEs), especially in the drug discovery process. Extensive research has led to copious developments in the field of MCRs. The developments have emerged with different synthetic approaches, including C–H activation, coupling, and cycloaddition, and eventually, such an amalgamation has enabled access to a broad spectrum of organic frameworks. The present review summarizes recent advancements in MCRs and their mechanistic insights from the last triennium (2017–2020).

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4 Citations


Journal ArticleDOI: 10.1021/ACS.JOC.1C01075
Nandita Biswas1, Dipankar Srimani1Institutions (1)
Abstract: A Ru-catalyzed acceptorless dehydrogenative multicomponent reaction has been developed. This reaction offers a cost-effective and simple operational strategy to synthesize biologically active 1,8-dioxodecahydroacridine derivatives. The protocol provides a wide range of substrate scope and various functional groups are also well tolerated under the reaction condition. To shed light on the mechanistic and kinetic study, some controlled experiments and deuterium labeling experiments were executed. A time-dependent product distribution experiment is also presented and the reaction scale-up is performed to highlight the practical utility of this strategy.

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1 Citations


Open access
01 Jan 2017-
Abstract: Aim of this dissertation is to address how innovative MCRs are in medicinal chemistry and how they can be used in different cases. The MCR derived products can be considered as a synthetic hub to a vast diversity of novel cyclic or acyclic scaffolds by employing different secondary transformations. This “union of MCRs“ can serve as a strategy for the rational design of novel MCRs combining two (or more) different types of MCRs in a one-pot process.

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1 Citations


Open accessJournal ArticleDOI: 10.1021/ACS.JOC.1C01846
Abstract: We developed an iodine-mediated cascade strategy to synthesize amino pyrazole thioether derivatives (11) in the absence of metals as well as solvents. The present approach provides amino pyrazole thioethers in a highly selective manner without the formation of diaryl sulfide and sulfenyl-enaminonitrile with broad substrate scope. The reactivity of nine sulfenylation sources and synthetic applications of the synthesized compounds have been demonstrated. Thus, the overall iodine-mediated multicomponent reaction (MCR) is more economically feasible, efficient, and environmentally benign.

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Topics: Pyrazole (59%), Thioether (59%), Cascade reaction (57%) ... read more

Journal ArticleDOI: 10.1055/A-1471-9080
Xiaofang Lei1, Xiaofang Lei2, Maria Thomaidi1, Giasemi K. Angeli1  +2 moreInstitutions (2)
31 Mar 2021-Synlett
Abstract: Fluorene and fluorenone are privileged structures with extensive utility in both materials science and drug discovery Here, we describe syntheses of those moieties through isocyanide-based multicomponent reactions (IMCRs) and the incorporation of the products in diverse and complex derivatives that can be further utilized We performed six different IMCRs, based on the dual functionality of 9-isocyano-9H-fluorene, and we describe 23 unprecedented adducts

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Topics: Fluorene (56%), Isocyanide (55%), Ugi reaction (55%) ... read more

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44 results found


Open accessJournal ArticleDOI: 10.1021/CR100233R
Alexander Dömling1, Wei Wang2, Wei Wang1, Kan Wang1Institutions (2)
13 Jun 2012-Chemical Reviews
Abstract: Multicomponent reactions (MCRs) are one-pot reactions employing more than two starting materials, e.g. 3, 4, … 7, where most of the atoms of the starting materials are incorporated in the final product.1 Several descriptive tags are regularly attached to MCRs (Fig. 1): they are atom economic, e.g. the majority if not all of the atoms of the starting materials are incorporated in the product; they are efficient, e.g. they efficiently yield the product since the product is formed in one-step instead of multiple sequential steps; they are convergent, e.g. several starting materials combine in one reaction to form the product; they exhibit a very high bond-forming-index (BFI), e.g. several non-hydrogen atom bonds are formed in one synthetic transformation.2 Therefore MCRs are often a useful alternative to sequential multistep synthesis. Open in a separate window Figure 1 Above: multistep syntheses can be divergent (sequential) or convergent; below: in analogy MCR reactions are convergent and one or two component reactions are divergent or less convergent.

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1,578 Citations


Journal ArticleDOI: 10.1002/ANIE.201006515
04 Jul 2011-Angewandte Chemie
Abstract: Multicomponent reactions have become increasingly popular as tools for the rapid generation of small-molecule libraries. However, to ensure sufficient molecular diversity and complexity, there is a continuous need for novel reactions. Although serendipity has always played an important role in the discovery of novel (multicomponent) reactions, rational design strategies have become much more important over the past decade. In this Review, we present an overview of general strategies that allow the design of novel multicomponent reactions. The challenges and opportunities for the future will be discussed.

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918 Citations


Journal ArticleDOI: 10.1039/C4GC00013G
27 May 2014-Green Chemistry
Abstract: Sustainable or green chemistry has established firm ground providing essential design criteria for the development of efficient chemical syntheses of complex, high added value molecules. On the other hand, multicomponent reactions have only recently been recognized as major expansion of the synthetic chemist's toolbox. There is still little awareness, however, of the practical value of these type of reactions for meeting many of the criteria set by the green chemistry philosophy to guide organic chemists and process chemists in the design, synthesis and further development of truly sustainable manufacturing processes of medicines, food additives, catalysts or advanced materials. In this perspective we highlight the utility of multicomponent reactions as methods for green synthesis.

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675 Citations


Journal ArticleDOI: 10.1002/CBER.19660990116
01 Jan 1966-Chemische Berichte
Abstract: Aliphatische Ketone, Aldehyde sowie β-Dicarbonylverbindungen reagieren mit methylenaktiven Nitrilen und Schwefel in Gegenwart von Aminen bei Raumtemperatur zu 2-Aminothiophenen. — Eine Variante der Synthese, die Einwirkung von Schwefel auf vinyloge methylenaktive Nitrile, gestattet auch die Einbeziehung von Alkylarylketonen in die Reaktion.

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666 Citations


Journal ArticleDOI: 10.1039/B917644F
Abstract: Multicomponent reactions are one of the most interesting concepts in modern synthetic chemistry and, as shown in this critical review, they provide an attractive entry into pyrrole derivatives, which are very important heterocycles from many points of view including medicinal and pharmaceutical chemistry and materials science (97 references).

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580 Citations


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