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Marine natural products are characterized by high chemical diversity, biochemical specificity, and other molecular properties that make them favorable as lead structures for drug discovery. In this field, one of the main problems is often the reduced natural availability of isolated substances, which can complicate both the structural characterization and possible future developments. For these reasons, the study of bioactive marine metabolites should rely on the development of chemical synthesis and synthetic strategies aimed at the preparation of pure compounds and analogs both for structural confirmation and/or for the large-scale preparation necessary for future applications. Moreover, natural products can be a crucial starting point for the preparation of molecules structurally inspired by the latter, opening the path to new classes of biologically active compounds with pharmacological potential. This book collects original research articles regarding synthetic strategies for secondary marine metabolites and/or analogs that favor applications of these molecules and/or solve structural challenges common in the field of natural substances.

Language --- organic synthesis --- meroterpenoids --- thiazinoquinones --- antiproliferative activity --- G0/G1 cell-cycle arrest --- cytostatic --- solid tumor cell lines --- alkylglycerol (AKG) --- ricinoleic acid (RA) --- antimicrobial activity --- structure-activity relationship (SAR) studies --- antibiotics (gentamicin --- tetracycline --- ciprofloxacin and ampicillin) --- marine-inspired --- breast cancer --- bis-indoles --- synthesis --- apoptosis --- carbohydrates --- polysaccharides --- semi-synthesis --- sulfation --- glycosylation --- fucose --- fucosylated chondroitin sulfate --- marine natural product --- largazole --- HDAC inhibitors --- modification --- fluoro olefin --- total synthesis --- natural product --- 7-deazapurine nucleoside --- disaccharide nucleoside --- tubercidin --- aureol --- tetracyclic meroterpenoids --- natural products synthesis --- labdane scaffold --- bioactive diterpenes --- sclareolide --- structure-activity relationships --- TRPV4 channel --- amides/esters --- COVID-19 --- SARS-CoV-2 --- lipophilic iminosugars --- polymer-supported triphenyl phosphine --- cholesterol --- antibacterial iminosugars --- organic synthesis --- meroterpenoids --- thiazinoquinones --- antiproliferative activity --- G0/G1 cell-cycle arrest --- cytostatic --- solid tumor cell lines --- alkylglycerol (AKG) --- ricinoleic acid (RA) --- antimicrobial activity --- structure-activity relationship (SAR) studies --- antibiotics (gentamicin --- tetracycline --- ciprofloxacin and ampicillin) --- marine-inspired --- breast cancer --- bis-indoles --- synthesis --- apoptosis --- carbohydrates --- polysaccharides --- semi-synthesis --- sulfation --- glycosylation --- fucose --- fucosylated chondroitin sulfate --- marine natural product --- largazole --- HDAC inhibitors --- modification --- fluoro olefin --- total synthesis --- natural product --- 7-deazapurine nucleoside --- disaccharide nucleoside --- tubercidin --- aureol --- tetracyclic meroterpenoids --- natural products synthesis --- labdane scaffold --- bioactive diterpenes --- sclareolide --- structure-activity relationships --- TRPV4 channel --- amides/esters --- COVID-19 --- SARS-CoV-2 --- lipophilic iminosugars --- polymer-supported triphenyl phosphine --- cholesterol --- antibacterial iminosugars

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The Special Issue “Molecules from Side Reactions” is a collection of papers reporting on the synthesis and characterization of the molecules that come from unexpected synthetic routes. This is the first example of a Special Issue based on such a topic, notwithstanding that all synthetic chemists have isolated a side product during a chemical reaction. Instead of continuing to store the side products in the freezer, I have thought to give them the dignity of publication, making them available to the scientific community. The short manuscripts collected here respect the principle of “one compound per paper” and have the purpose of preserving the molecular diversity deriving from a chemical reaction. The molecular scaffolds are unexpected and intriguing, and could be useful starting points or intermediates for exploring novel reactions.

oxazole --- furan --- RORC reaction --- (E,Z)-isomerization --- nitration --- azaheterocycles --- N–C bond cleavage --- pyridine-imidazolium --- ribose --- psicose --- ketose --- rare sugar --- hydroxy methylation --- AICAR --- acadesine --- phosphorylation --- fluorination --- fluorinated nucleosides --- nucleoside analogues --- modified nucleosides --- chlorinated nucleosides --- AMPK --- organic synthesis --- bidentate directing groups --- benzamides --- chelation assistance --- bis-chelates --- C–H bond functionalization --- X-ray structure determination --- N′-acetylhydrazide --- 3-acetyl-2,3-dihydro-1,3,4-oxadiazole --- 1H-pyrazolo[3,4-b]pyridine --- heterocycle --- oxetane --- epoxide --- rearrangement --- carbohydrate --- C-glycosylation --- spiro-oxetane --- ester group migration --- glycosyl sulfoxide --- uronate --- thioglycoside oxidation --- mannose --- 8-Fluoro-2′-deoxyguanosine --- 19F NMR spectroscopy --- solid phase synthesis --- phosphoramidite --- muraymycins --- caprazamycins --- nucleosides --- uridine --- cyclization --- seven-membered rings --- conjugated diyne --- LAH reduction --- diacetal --- pent-1,2,3,4-tetraene intermediate --- ligand --- pyridine derivatives --- allenic compounds --- N-alkylation --- copper --- cyanide --- network --- guanidinium --- unexpected iminium cation --- n/a --- N-C bond cleavage --- C-H bond functionalization --- N'-acetylhydrazide --- 8-Fluoro-2'-deoxyguanosine

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Coumarins are widely distributed in nature and can be found in a large number of naturally occurring and synthetic bioactive molecules. The unique and versatile oxygen-containing heterocyclic structure makes them a privileged scaffold in Medicinal Chemistry. Many coumarin derivatives have been extracted from natural sources, designed, synthetized, and evaluated on different pharmacological targets. In addition, coumarin-based ion receptors, fluorescent probes, and biological stains are growing quickly and have extensive applications to monitor timely enzyme activity, complex biological events, as well as accurate pharmacological and pharmacokinetic properties in living cells. The extraction, synthesis, and biological evaluation of coumarins have become extremely attractive and rapidly developing topics. A large number of research and review papers have compiled information on this important family of compounds in 2020. Research articles, reviews, communications, and concept papers focused on the multidisciplinary profile of coumarins, highlighting natural sources, most recent synthetic pathways, along with the main biological applications and theoretical studies, were the main focus of this book. The huge and growing range of applications of coumarins described in this book is a demonstration of the potential of this family of compounds in Organic Chemistry, Medicinal Chemistry, and different sciences related to the study of natural products. This book includes 23 articles: 17 original papers and six review papers.

Research & information: general --- Biology, life sciences --- coumarin --- hydroxyl-modified coumarin --- photophysical --- thermal and structural characterization --- Glycyrrhiza uralensis --- glycyrol --- liquiritigenin --- cholinesterases --- human monoamine oxidases --- kinetics --- docking simulation --- chalcone --- neurodegenerative diseases --- adenosine receptors --- binding affinity --- docking --- 4-hydroxy-7-methoxycoumarin --- macrophage --- inflammation --- NF-κB --- MAPK --- calanolides --- pseudocalanolides --- calanolide A --- Calophyllum --- Calophyllaceae --- anti-HIV --- reverse transcriptase --- non-nucleoside reverse transcriptase inhibitors (NNRTIs) --- osthole --- umbelliferone --- esculin --- 4-hydroxycoumarin --- sorafenib --- apoptosis --- autophagy --- Yin Chen Hao --- constitutive androstane receptor --- scoparone --- coumarins --- quorum sensing --- QS inhibitors --- plant-derived molecules --- Chromobacterium violaceum --- immunoproteasome --- psoralen core --- non-peptidic --- electrophilic compounds --- warhead scan --- inflammatory bowel disease --- isocoumarin --- Crohn’s disease --- ulcerative colitis --- glutathione --- oxidative stress --- complementary therapies --- intestinal inflammation --- benzopyrones --- five-membered aromatic heterocycles --- furan --- pyrrole --- thiophene --- selenophen --- dihydrocoumarin-fused dihydropyranones --- 3-aroylcoumarines --- benzyl 2,3-butadienoate --- 6’-(4-biphenyl)-β-iso-cinchonine --- biological applications --- drug discovery --- fluorescent probes --- warfarin --- acenocoumarol --- mechanical valve --- time in therapeutic range --- anticoagulation --- Ruta chalepensis --- Rutaceae --- chalepin --- chalepensin --- bioactivity --- biosynthesis --- coumarin3-carboxamides --- pyranocoumarins --- anticancer activity --- antibacterial activity --- free radical polymerization --- LED --- photocomposites --- direct laser write --- analytical methods --- model plant --- natural genetic variation --- natural products --- simple coumarins --- chalcocoumarin --- MAO-B --- molecular dynamics --- in silico studies --- dye-sensitized solar cells --- coumarin dyes --- thieno [3,2-b] thiophene --- charge transfer --- ethynylaryl --- esculetin --- antiplatelet activity --- impedance aggregometry --- COX --- polyphenols --- pyrazole --- imidazole --- thiazole --- oxazole --- triazole --- thiadiazole --- curcumin --- curcumin–coumarin hybrids --- neuroprotection --- monoamine oxidase inhibition --- cholinesterase inhibition --- scavenging activity --- Escherichia coli --- biotransformation --- ferulenol --- structural annotation --- in silico tools --- n/a --- Crohn's disease --- 6'-(4-biphenyl)-β-iso-cinchonine --- curcumin-coumarin hybrids

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Coumarins are widely distributed in nature and can be found in a large number of naturally occurring and synthetic bioactive molecules. The unique and versatile oxygen-containing heterocyclic structure makes them a privileged scaffold in Medicinal Chemistry. Many coumarin derivatives have been extracted from natural sources, designed, synthetized, and evaluated on different pharmacological targets. In addition, coumarin-based ion receptors, fluorescent probes, and biological stains are growing quickly and have extensive applications to monitor timely enzyme activity, complex biological events, as well as accurate pharmacological and pharmacokinetic properties in living cells. The extraction, synthesis, and biological evaluation of coumarins have become extremely attractive and rapidly developing topics. A large number of research and review papers have compiled information on this important family of compounds in 2020. Research articles, reviews, communications, and concept papers focused on the multidisciplinary profile of coumarins, highlighting natural sources, most recent synthetic pathways, along with the main biological applications and theoretical studies, were the main focus of this book. The huge and growing range of applications of coumarins described in this book is a demonstration of the potential of this family of compounds in Organic Chemistry, Medicinal Chemistry, and different sciences related to the study of natural products. This book includes 23 articles: 17 original papers and six review papers.

Research & information: general --- Biology, life sciences --- coumarin --- hydroxyl-modified coumarin --- photophysical --- thermal and structural characterization --- Glycyrrhiza uralensis --- glycyrol --- liquiritigenin --- cholinesterases --- human monoamine oxidases --- kinetics --- docking simulation --- chalcone --- neurodegenerative diseases --- adenosine receptors --- binding affinity --- docking --- 4-hydroxy-7-methoxycoumarin --- macrophage --- inflammation --- NF-κB --- MAPK --- calanolides --- pseudocalanolides --- calanolide A --- Calophyllum --- Calophyllaceae --- anti-HIV --- reverse transcriptase --- non-nucleoside reverse transcriptase inhibitors (NNRTIs) --- osthole --- umbelliferone --- esculin --- 4-hydroxycoumarin --- sorafenib --- apoptosis --- autophagy --- Yin Chen Hao --- constitutive androstane receptor --- scoparone --- coumarins --- quorum sensing --- QS inhibitors --- plant-derived molecules --- Chromobacterium violaceum --- immunoproteasome --- psoralen core --- non-peptidic --- electrophilic compounds --- warhead scan --- inflammatory bowel disease --- isocoumarin --- Crohn's disease --- ulcerative colitis --- glutathione --- oxidative stress --- complementary therapies --- intestinal inflammation --- benzopyrones --- five-membered aromatic heterocycles --- furan --- pyrrole --- thiophene --- selenophen --- dihydrocoumarin-fused dihydropyranones --- 3-aroylcoumarines --- benzyl 2,3-butadienoate --- 6'-(4-biphenyl)-β-iso-cinchonine --- biological applications --- drug discovery --- fluorescent probes --- warfarin --- acenocoumarol --- mechanical valve --- time in therapeutic range --- anticoagulation --- Ruta chalepensis --- Rutaceae --- chalepin --- chalepensin --- bioactivity --- biosynthesis --- coumarin3-carboxamides --- pyranocoumarins --- anticancer activity --- antibacterial activity --- free radical polymerization --- LED --- photocomposites --- direct laser write --- analytical methods --- model plant --- natural genetic variation --- natural products --- simple coumarins --- chalcocoumarin --- MAO-B --- molecular dynamics --- in silico studies --- dye-sensitized solar cells --- coumarin dyes --- thieno [3,2-b] thiophene --- charge transfer --- ethynylaryl --- esculetin --- antiplatelet activity --- impedance aggregometry --- COX --- polyphenols --- pyrazole --- imidazole --- thiazole --- oxazole --- triazole --- thiadiazole --- curcumin --- curcumin-coumarin hybrids --- neuroprotection --- monoamine oxidase inhibition --- cholinesterase inhibition --- scavenging activity --- Escherichia coli --- biotransformation --- ferulenol --- structural annotation --- in silico tools --- coumarin --- hydroxyl-modified coumarin --- photophysical --- thermal and structural characterization --- Glycyrrhiza uralensis --- glycyrol --- liquiritigenin --- cholinesterases --- human monoamine oxidases --- kinetics --- docking simulation --- chalcone --- neurodegenerative diseases --- adenosine receptors --- binding affinity --- docking --- 4-hydroxy-7-methoxycoumarin --- macrophage --- inflammation --- NF-κB --- MAPK --- calanolides --- pseudocalanolides --- calanolide A --- Calophyllum --- Calophyllaceae --- anti-HIV --- reverse transcriptase --- non-nucleoside reverse transcriptase inhibitors (NNRTIs) --- osthole --- umbelliferone --- esculin --- 4-hydroxycoumarin --- sorafenib --- apoptosis --- autophagy --- Yin Chen Hao --- constitutive androstane receptor --- scoparone --- coumarins --- quorum sensing --- QS inhibitors --- plant-derived molecules --- Chromobacterium violaceum --- immunoproteasome --- psoralen core --- non-peptidic --- electrophilic compounds --- warhead scan --- inflammatory bowel disease --- isocoumarin --- Crohn's disease --- ulcerative colitis --- glutathione --- oxidative stress --- complementary therapies --- intestinal inflammation --- benzopyrones --- five-membered aromatic heterocycles --- furan --- pyrrole --- thiophene --- selenophen --- dihydrocoumarin-fused dihydropyranones --- 3-aroylcoumarines --- benzyl 2,3-butadienoate --- 6'-(4-biphenyl)-β-iso-cinchonine --- biological applications --- drug discovery --- fluorescent probes --- warfarin --- acenocoumarol --- mechanical valve --- time in therapeutic range --- anticoagulation --- Ruta chalepensis --- Rutaceae --- chalepin --- chalepensin --- bioactivity --- biosynthesis --- coumarin3-carboxamides --- pyranocoumarins --- anticancer activity --- antibacterial activity --- free radical polymerization --- LED --- photocomposites --- direct laser write --- analytical methods --- model plant --- natural genetic variation --- natural products --- simple coumarins --- chalcocoumarin --- MAO-B --- molecular dynamics --- in silico studies --- dye-sensitized solar cells --- coumarin dyes --- thieno [3,2-b] thiophene --- charge transfer --- ethynylaryl --- esculetin --- antiplatelet activity --- impedance aggregometry --- COX --- polyphenols --- pyrazole --- imidazole --- thiazole --- oxazole --- triazole --- thiadiazole --- curcumin --- curcumin-coumarin hybrids --- neuroprotection --- monoamine oxidase inhibition --- cholinesterase inhibition --- scavenging activity --- Escherichia coli --- biotransformation --- ferulenol --- structural annotation --- in silico tools