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4 pages, 192 KiB

Open AccessEditorial

Featured Reviews in Organic Chemistry

by Roman Dembinski and Vadim Soloshonok

Molecules 2023, 28(16), 5975; https://doi.org/10.3390/molecules28165975 - 9 Aug 2023

Viewed by 1319

Abstract

The field of Organic Chemistry represents one of the most traditional areas of chemistry that has delivered many benefits to the community of chemists [...] Full article

(This article belongs to the Special Issue Featured Reviews in Organic Chemistry)

Review

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21 pages, 3331 KiB

Open AccessReview

New Approved Drugs Appearing in the Pharmaceutical Market in 2022 Featuring Fragments of Tailor-Made Amino Acids and Fluorine

by Nana Wang, Haibo Mei, Gagan Dhawan, Wei Zhang, Jianlin Han and Vadim A. Soloshonok

Molecules 2023, 28(9), 3651; https://doi.org/10.3390/molecules28093651 - 22 Apr 2023

Cited by 19 | Viewed by 3244

Abstract

The strategic fluorination of oxidatively vulnerable sites in bioactive compounds is a relatively recent, widely used approach allowing us to modulate the stability, bio-absorption, and overall efficiency of pharmaceutical drugs. On the other hand, natural and tailor-made amino acids are traditionally used as [...] Read more.

The strategic fluorination of oxidatively vulnerable sites in bioactive compounds is a relatively recent, widely used approach allowing us to modulate the stability, bio-absorption, and overall efficiency of pharmaceutical drugs. On the other hand, natural and tailor-made amino acids are traditionally used as basic scaffolds for the development of bioactive molecules. The main goal of this review article is to emphasize these general trends featured in recently approved pharmaceutical drugs. Full article

(This article belongs to the Special Issue Featured Reviews in Organic Chemistry)

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48 pages, 9787 KiB

Open AccessReview

Catalytic Asymmetric α-Functionalization of α-Branched Aldehydes

by Silvia Vera, Aitor Landa, Antonia Mielgo, Iñaki Ganboa, Mikel Oiarbide and Vadim Soloshonok

Molecules 2023, 28(6), 2694; https://doi.org/10.3390/molecules28062694 - 16 Mar 2023

Cited by 13 | Viewed by 3414

Abstract

Aldehydes constitute a main class of organic compounds widely applied in synthesis. As such, catalyst-controlled enantioselective α-functionalization of aldehydes has attracted great interest over the years. In this context, α-branched aldehydes are especially challenging substrates because of reactivity and selectivity issues. Firstly, the [...] Read more.

Aldehydes constitute a main class of organic compounds widely applied in synthesis. As such, catalyst-controlled enantioselective α-functionalization of aldehydes has attracted great interest over the years. In this context, α-branched aldehydes are especially challenging substrates because of reactivity and selectivity issues. Firstly, the transient trisubstituted enamines and enolates resulting upon treatment with an aminocatalyst or a base, respectively, would exhibit attenuated reactivity; secondly, mixtures of E- and Z-configured enamines/enolates may be formed; and third, effective face-discrimination on such trisubstituted sp² carbon intermediates by the incoming electrophilic reagent is not trivial. Despite these issues, in the last 15 years, several catalytic approaches for the α-functionalization of prostereogenic α-branched aldehydes that proceed in useful yields and diastereo- and enantioselectivity have been uncovered. Developments include both organocatalytic and metal-catalyzed approaches as well as dual catalysis strategies for forging new carbon–carbon and carbon–heteroatom (C-O, N, S, F, Cl, Br, …) bond formation at Cα of the starting aldehyde. In this review, some key early contributions to the field are presented, but focus is on the most recent methods, mainly covering the literature from year 2014 onward. Full article

(This article belongs to the Special Issue Featured Reviews in Organic Chemistry)

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57 pages, 19277 KiB

Open AccessReview

Difunctionalization of Dienes, Enynes and Related Compounds via Sequential Radical Addition and Cyclization Reactions

by Sanjun Zhi, Hongjun Yao and Wei Zhang

Molecules 2023, 28(3), 1145; https://doi.org/10.3390/molecules28031145 - 23 Jan 2023

Cited by 10 | Viewed by 3027

Abstract

Radical reactions are powerful in creating carbon–carbon and carbon–heteroatom bonds. Designing one-pot radical reactions with cascade transformations to assemble the cyclic skeletons with two new functional groups is both synthetically and operationally efficient. Summarized in this paper is the recent development of reactions [...] Read more.

Radical reactions are powerful in creating carbon–carbon and carbon–heteroatom bonds. Designing one-pot radical reactions with cascade transformations to assemble the cyclic skeletons with two new functional groups is both synthetically and operationally efficient. Summarized in this paper is the recent development of reactions involving radical addition and cyclization of dienes, diynes, enynes, as well as arene-bridged and arene-terminated compounds for the preparation of difunctionalization cyclic compounds. Reactions carried out with radical initiators, transition metal-catalysis, photoredox, and electrochemical conditions are included. Full article

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39 pages, 10204 KiB

Open AccessReview

Structural Features of Small Molecule Antioxidants and Strategic Modifications to Improve Potential Bioactivity

by Nathan C. Charlton, Maxim Mastyugin, Béla Török and Marianna Török

Molecules 2023, 28(3), 1057; https://doi.org/10.3390/molecules28031057 - 20 Jan 2023

Cited by 46 | Viewed by 4500

Abstract

This review surveys the major structural features in various groups of small molecules that are considered to be antioxidants, including natural and synthetic compounds alike. Recent advances in the strategic modification of known small molecule antioxidants are also described. The highlight is placed [...] Read more.

This review surveys the major structural features in various groups of small molecules that are considered to be antioxidants, including natural and synthetic compounds alike. Recent advances in the strategic modification of known small molecule antioxidants are also described. The highlight is placed on changing major physicochemical parameters, including log p, bond dissociation energy, ionization potential, and others which result in improved antioxidant activity. Full article

(This article belongs to the Special Issue Featured Reviews in Organic Chemistry)

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18 pages, 6647 KiB

Open AccessFeature PaperReview

Metal-Free One-Pot Multi-Functionalization of Unsaturated Compounds with Interelement Compounds by Radical Process

by Yuki Yamamoto and Akiya Ogawa

Molecules 2023, 28(2), 787; https://doi.org/10.3390/molecules28020787 - 12 Jan 2023

Cited by 11 | Viewed by 2074

Abstract

In recent years, the importance of “environmentally friendly manufacturing” has been increasing toward the establishment of a resource-recycling society. In organic synthesis, as well, it is becoming increasingly important to develop new synthetic strategies with resource conservation and the recycling of elemental resources [...] Read more.

In recent years, the importance of “environmentally friendly manufacturing” has been increasing toward the establishment of a resource-recycling society. In organic synthesis, as well, it is becoming increasingly important to develop new synthetic strategies with resource conservation and the recycling of elemental resources in mind, rather than just only synthesis. Many studies on the construction of frameworks of functional molecules using ionic reactions and transition-metal-catalyzed reactions have been reported, but most of them have focused on the formation of carbon–carbon bonds. However, it is essential to introduce appropriate functional groups at appropriate positions in molecules in order for the molecules to express their functions, and furthermore, the highly selective preparation of multiple functional groups is considered important for the creation of new functional molecules. In this review, we focus on radical reactions with high functional group selectivity and overview the recent progress in practical methods for the simultaneous introduction of multiple functional groups and propose future synthetic strategies that emphasize the recycling of elemental resources and environmental friendliness. Full article

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31 pages, 8163 KiB

Open AccessReview

Progress in C-C and C-Heteroatom Bonds Construction Using Alcohols as Acyl Precursors

by Feng Zhao, Bin Tan, Qing Li, Qi Tan and Huawen Huang

Molecules 2022, 27(24), 8977; https://doi.org/10.3390/molecules27248977 - 16 Dec 2022

Cited by 4 | Viewed by 2351

Abstract

Acyl moiety is a common structural unit in organic molecules, thus acylation methods have been widely explored to construct various functional compounds. While the traditional Friedel–Crafts acylation processes work to allow viable construction of arylketones under harsh acid conditions, recent progress on developing [...] Read more.

Acyl moiety is a common structural unit in organic molecules, thus acylation methods have been widely explored to construct various functional compounds. While the traditional Friedel–Crafts acylation processes work to allow viable construction of arylketones under harsh acid conditions, recent progress on developing acylation methods focused on the new reactivity discovery by exploiting versatile and easily accessible acylating reagents. Of them, alcohols are cheap, have low toxicity, and are naturally abundant feedstocks; thus, they were recently used as ideal acyl precursors in molecule synthesis for ketones, esters, amides, etc. In this review, we display and discuss recent advances in employing alcohols as unusual acyl sources to form C-C and C-heteroatom bonds, with emphasis on the substrate scope, limitations, and mechanism. Full article

(This article belongs to the Special Issue Featured Reviews in Organic Chemistry)

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145 pages, 36328 KiB

Open AccessReview

Indane-1,3-Dione: From Synthetic Strategies to Applications

by Corentin Pigot, Damien Brunel and Frédéric Dumur

Molecules 2022, 27(18), 5976; https://doi.org/10.3390/molecules27185976 - 14 Sep 2022

Cited by 15 | Viewed by 7259

Abstract

Indane-1,3-dione is a versatile building block used in numerous applications ranging from biosensing, bioactivity, bioimaging to electronics or photopolymerization. In this review, an overview of the different chemical reactions enabling access to this scaffold but also to the most common derivatives of indane-1,3-dione [...] Read more.

Indane-1,3-dione is a versatile building block used in numerous applications ranging from biosensing, bioactivity, bioimaging to electronics or photopolymerization. In this review, an overview of the different chemical reactions enabling access to this scaffold but also to the most common derivatives of indane-1,3-dione are presented. Parallel to this, the different applications in which indane-1,3-dione-based structures have been used are also presented, evidencing the versatility of this structure. Full article

(This article belongs to the Special Issue Featured Reviews in Organic Chemistry)

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39 pages, 17847 KiB

Open AccessReview

Asymmetric Michael Addition in Synthesis of β-Substituted GABA Derivatives

by Jianlin Han, Jorge Escorihuela, Santos Fustero, Aitor Landa, Vadim A. Soloshonok and Alexander Sorochinsky

Molecules 2022, 27(12), 3797; https://doi.org/10.3390/molecules27123797 - 13 Jun 2022

Cited by 20 | Viewed by 4898

Abstract

γ-Aminobutyric acid (GABA) represents one of the most prolific structural units widely used in the design of modern pharmaceuticals. For example, β-substituted GABA derivatives are found in numerous neurological drugs, such as baclofen, phenibut, tolibut, pregabalin, phenylpiracetam, brivaracetam, and rolipram, to mention just [...] Read more.

γ-Aminobutyric acid (GABA) represents one of the most prolific structural units widely used in the design of modern pharmaceuticals. For example, β-substituted GABA derivatives are found in numerous neurological drugs, such as baclofen, phenibut, tolibut, pregabalin, phenylpiracetam, brivaracetam, and rolipram, to mention just a few. In this review, we critically discuss the literature data reported on the preparation of substituted GABA derivatives using the Michael addition reaction as a key synthetic transformation. Special attention is paid to asymmetric methods featuring synthetically useful stereochemical outcomes and operational simplicity. Full article

(This article belongs to the Special Issue Featured Reviews in Organic Chemistry)

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23 pages, 6333 KiB

Open AccessReview

Synthesis of Functionalized Six-Membered-Ring Azahelicenes

by Francesca Fontana and Benedetta Bertolotti

Molecules 2022, 27(8), 2522; https://doi.org/10.3390/molecules27082522 - 14 Apr 2022

Cited by 5 | Viewed by 2993

Abstract

Functionalization, namely the introduction of side groups onto the molecular scaffold of a helicene, may have either the purpose of modifying the electronic properties of the parent helicene, e.g., by adding electron-withdrawing or electron-donating groups, or the scope of providing the helicene with [...] Read more.

Functionalization, namely the introduction of side groups onto the molecular scaffold of a helicene, may have either the purpose of modifying the electronic properties of the parent helicene, e.g., by adding electron-withdrawing or electron-donating groups, or the scope of providing the helicene with a “handle”, which can be reacted to bind the molecule to another molecule or to a solid structure, such as a carbon or metal surface, or again to allow for complexation of the helicene with metal ions. The possible approaches are two-fold: the synthesis of the helicene can be performed using starting materials that already contain a side group, or the side group can be introduced after the synthesis of the parent helicene. As azahelicenes are helicenes bearing one or more nitrogen atom(s) in the molecular framework, parent azahelicenes can be functionalized on carbon atoms by exploiting the presence of the electron-withdrawing nitrogen atom. Moreover, they can be transformed into quaternary salts, whose properties are quite different from those of the parent azahelicenes in terms of the solubility and electronic properties. This review aims to provide a survey of the different synthetic methods available to attain this fascinating class of compounds. Full article

(This article belongs to the Special Issue Featured Reviews in Organic Chemistry)

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17 pages, 4050 KiB

Open AccessReview

Recent Advances in the Synthesis of Isoquinoline-Fused Benzimidazoles

by Dylan J. Twardy, Kraig A. Wheeler, Béla Török and Roman Dembinski

Molecules 2022, 27(7), 2062; https://doi.org/10.3390/molecules27072062 - 23 Mar 2022

Cited by 12 | Viewed by 3794

Abstract

This review includes recent developments in the synthesis of benzo[4,5]imidazo[2,1-a]isoquinolines with particular attention given to categorizing protocols based on the structural features of the ring architecture and crystallographically characterized reaction products. Full article

(This article belongs to the Special Issue Featured Reviews in Organic Chemistry)

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55 pages, 83405 KiB

Open AccessEditor’s ChoiceReview

Sulforaphane and Its Bifunctional Analogs: Synthesis and Biological Activity

by Łukasz Janczewski

Molecules 2022, 27(5), 1750; https://doi.org/10.3390/molecules27051750 - 7 Mar 2022

Cited by 35 | Viewed by 6226

Abstract

For decades, various plants have been studied as sources of biologically active compounds. Compounds with anticancer and antimicrobial properties are the most frequently desired. Cruciferous plants, including Brussels sprouts, broccoli, and wasabi, have a special role in the research studies. Studies have shown [...] Read more.

For decades, various plants have been studied as sources of biologically active compounds. Compounds with anticancer and antimicrobial properties are the most frequently desired. Cruciferous plants, including Brussels sprouts, broccoli, and wasabi, have a special role in the research studies. Studies have shown that consumption of these plants reduce the risk of lung, breast, and prostate cancers. The high chemopreventive and anticancer potential of cruciferous plants results from the presence of a large amount of glucosinolates, which, under the influence of myrosinase, undergo an enzymatic transformation to biologically active isothiocyanates (ITCs). Natural isothiocyanates, such as benzyl isothiocyanate, phenethyl isothiocyanate, or the best-tested sulforaphane, possess anticancer activity at all stages of the carcinogenesis process, show antibacterial activity, and are used in organic synthesis. Methods of synthesis of sulforaphane, as well as its natural or synthetic bifunctional analogues with sulfinyl, sulfanyl, sulfonyl, phosphonate, phosphinate, phosphine oxide, carbonyl, ester, carboxamide, ether, or additional isothiocyanate functional groups, and with the unbranched alkyl chain containing 2–6 carbon atoms, are discussed in this review. The biological activity of these compounds are also reported. In the first section, glucosinolates, isothiocyanates, and mercapturic acids (their metabolites) are briefly characterized. Additionally, the most studied anticancer and antibacterial mechanisms of ITC actions are discussed. Full article

(This article belongs to the Special Issue Featured Reviews in Organic Chemistry)

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23 pages, 3936 KiB

Open AccessEditor’s ChoiceReview

New Halogen-Containing Drugs Approved by FDA in 2021: An Overview on Their Syntheses and Pharmaceutical Use

by Davide Benedetto Tiz, Luana Bagnoli, Ornelio Rosati, Francesca Marini, Luca Sancineto and Claudio Santi

Molecules 2022, 27(5), 1643; https://doi.org/10.3390/molecules27051643 - 2 Mar 2022

Cited by 76 | Viewed by 12892

Abstract

This review describes the recent Food and Drug Administration (FDA)-approved drugs (in the year 2021) containing at least one halogen atom (covalently bound). The structures proposed throughout this work are grouped according to their therapeutical use. Their synthesis is presented as well. The [...] Read more.

This review describes the recent Food and Drug Administration (FDA)-approved drugs (in the year 2021) containing at least one halogen atom (covalently bound). The structures proposed throughout this work are grouped according to their therapeutical use. Their synthesis is presented as well. The number of halogenated molecules that are reaching the market is regularly preserved, and 14 of the 50 molecules approved by the FDA in the last year contain halogens. This underlines the emergent role of halogens and, in particular, of fluorine and chlorine in the preparation of drugs for the treatment of several diseases such as viral infections, several types of cancer, cardiovascular disease, multiple sclerosis, migraine and inflammatory diseases such as vasculitis. Full article

(This article belongs to the Special Issue Featured Reviews in Organic Chemistry)

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54 pages, 24757 KiB

Open AccessReview

Recent Advances on the Halo- and Cyano-Trifluoromethylation of Alkenes and Alkynes

by Bo Fu, Jorge Escorihuela, Jianlin Han, Santos Fustero, Pablo Barrio, Mikiko Sodeoka, Shintaro Kawamura, Alexander Sorochinsky and Vadim A. Soloshonok

Molecules 2021, 26(23), 7221; https://doi.org/10.3390/molecules26237221 - 28 Nov 2021

Cited by 19 | Viewed by 3831

Abstract

Incorporation of fluorine into organic molecules is a well-established strategy in the design of advanced materials, agrochemicals, and pharmaceuticals. Among numerous modern synthetic approaches, functionalization of unsaturated bonds with simultaneous addition of trifluoromethyl group along with other substituents is currently one of the [...] Read more.

Incorporation of fluorine into organic molecules is a well-established strategy in the design of advanced materials, agrochemicals, and pharmaceuticals. Among numerous modern synthetic approaches, functionalization of unsaturated bonds with simultaneous addition of trifluoromethyl group along with other substituents is currently one of the most attractive methods undergoing wide-ranging development. In this review article, we discuss the most significant contributions made in this area during the last decade (2012−2021). The reactions reviewed in this work include chloro-, bromo-, iodo-, fluoro- and cyano-trifluoromethylation of alkenes and alkynes. Full article

(This article belongs to the Special Issue Featured Reviews in Organic Chemistry)

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