Isolation of fungi using the diffusion chamber device FIND technology

• Benjamin Libor,
• Henrik Harms,
• Stefan Kehraus,
• Ekaterina Egereva,
• Max Crüsemann and
• Gabriele M. König

Beilstein J. Org. Chem. 2019, 15, 2191–2203, doi:10.3762/bjoc.15.216

• antibiotics (e.g., cephalosporins), immunosuppressants (e.g., mycophenolic acid) and immunomodulators (e.g., fingolimod), as well as cholesterol lowering agents (statins). Generally, fungal metabolites were shown to have antiviral, cytotoxic, antineoplastic, cardiovascular, anti-inflammatory, immune

Harnessing enzyme plasticity for the synthesis of oxygenated sesquiterpenoids

• Melodi Demiray,
• David J. Miller and
• Rudolf K. Allemann

Beilstein J. Org. Chem. 2019, 15, 2184–2190, doi:10.3762/bjoc.15.215

• -derived sesquiterpenes β-sesquiphellandrene [38][39][40] and zingiberene [40], a hydrocarbon with antifertility, antiviral and anticancer activity [41], suggested that the major compound was 12-methoxy-β-sesquiphellandrene (26), while the minor product was identified as 12-methoxyzingiberene (27). The two

Cyclopropanation–ring expansion of 3-chloroindoles with α-halodiazoacetates: novel synthesis of 4-quinolone-3-carboxylic acid and norfloxacin

• Sara Peeters,
• Linn Neerbye Berntsen,
• Pål Rongved and
• Tore Bonge-Hansen

Beilstein J. Org. Chem. 2019, 15, 2156–2160, doi:10.3762/bjoc.15.212

• compounds with biological activities ranging from antitumor, antiviral, antibiotic and antiparasitic to cannabinoid receptor modulating [22][23][24][25][26][27][28]. Despite the attractive features of the quinolone-3-carboxylate scaffold, there are only four reported routes towards this valuable structural

Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica

• Silvie Rimpelová,
• Michal Jurášek,
• Lucie Peterková,
• Jiří Bejček,
• Vojtěch Spiwok,
• Miloš Majdl,
• Michal Jirásko,
• Miloš Buděšínský,
• Juraj Harmatha,
• Eva Kmoníčková,
• Pavel Drašar and
• Tomáš Ruml

Beilstein J. Org. Chem. 2019, 15, 1933–1944, doi:10.3762/bjoc.15.189

• , antioxidant, antiprotozoal, antiviral and immunobiological activities (reviewed in [1][2]). Two SLs remarkable for their immunobiological potential are archangelolide (1) and trilobolide (2), depicted in Figure 1. Compound 2 exhibits strong induction of nitric oxide (NO) in eukaryotic cells, which in turn

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

• Iwona E. Głowacka,
• Aleksandra Trocha,
• Andrzej E. Wróblewski and
• Dorota G. Piotrowska

Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168

Synthesis of non-racemic 4-nitro-2-sulfonylbutan-1-ones via Ni(II)-catalyzed asymmetric Michael reaction of β-ketosulfones

• Alexander N. Reznikov,
• Anastasiya E. Sibiryakova,
• Marat R. Baimuratov,
• Eugene V. Golovin,
• Victor B. Rybakov and
• Yuri N. Klimochkin

Beilstein J. Org. Chem. 2019, 15, 1289–1297, doi:10.3762/bjoc.15.127

• 5-HT1 receptor agonist for the treatment of migraine) [7], and apremilast (3, Otezla®, inhibitor of the PDE4 for the treatment of certain types of psoriasis and psoriatic arthritis) [8] (Figure 1). Recently we have shown that racemic sulfone 4 exhibits high antiviral activity against BVDV with low

Doebner-type pyrazolopyridine carboxylic acids in an Ugi four-component reaction

• Maryna V. Murlykina,
• Oleksandr V. Kolomiets,
• Maryna M. Kornet,
• Yana I. Sakhno,
• Sergey M. Desenko,
• Victoriya V. Dyakonenko,
• Svetlana V. Shishkina,
• Oleksandr A. Brazhko,
• Vladimir I. Musatov,
• Alexander V. Tsygankov,
• Erik V. Van der Eycken and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2019, 15, 1281–1288, doi:10.3762/bjoc.15.126

• biological actions: antiproliferative [6][7][8][9], antimicrobial [10][11], anxiolytic [12], analgesic [13], hypnotic [13], antiviral [13], anti-HIV [13] activities, etc. Soural et al. [14] explored different data and showed the relevance of compounds composed of two or more heterocyclic rings for drug

Steroid diversification by multicomponent reactions

• Leslie Reguera,
• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

• displaying biological activities such as antimicrobial, antiviral and anti-inflammatory, among others. Scheme 3 exemplifies the reaction of cholestan-6-one 7 with 2-aminopyridine and phenyl isocyanide to afford the heterocycle–steroid hybrid 8 in good yield and diastereoselectivity, whereas different

• compound class 18 was evaluated for the inhibition of the viral multiplication and for their implication in intracellular localization of viral glycoproteins [23]. Two compounds showed antiviral effects against herpes simplex virus 1 (HSV-1, KOS strain) and vesicular stomatitis virus (VSV). The key

• substitution pattern at the phenyl moiety (Figure 2A). The small library of compounds enabled a better understanding of the structural factors determining the antiviral activity versus the cytotoxic one, with the major effect found for substituents at the para-position [23]. Eventually, this work allowed the

Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams

• Edorta Martínez de Marigorta,
• Jesús M. de Los Santos,
• Ana M. Ochoa de Retana,
• Javier Vicario and
• Francisco Palacios

Beilstein J. Org. Chem. 2019, 15, 1065–1085, doi:10.3762/bjoc.15.104

• , that shows antimalarial activity [40] and satavaptan, a selective V2-receptor antagonist that is useful for the treatment of cirrhosis (Figure 5) [41][42]. Additionally, methisazone is a 2-oxindole derivative that has been used as antiviral drug, especially for the prophylactic treatment of small-pox

An improved synthesis of adefovir and related analogues

• David J. Jones,
• Eileen M. O’Leary and
• Timothy P. O’Sullivan

Beilstein J. Org. Chem. 2019, 15, 801–810, doi:10.3762/bjoc.15.77

• Sciences, Cork Institute of Technology, Cork, Ireland 10.3762/bjoc.15.77 Abstract An improved synthesis of the antiviral drug adefovir is presented. Problems associated with current routes to adefovir include capricious yields and a reliance on problematic reagents and solvents, such as magnesium tert

• the versatility of our approach. Keywords: acyclic nucleoside phosphonate; adefovir; alkylation; antiviral; N-alkylation; purine; Introduction The acyclic nucleoside phosphonate adefovir (1) [1], administered as its dipivoxil prodrug form (2) [2], is used clinically for the treatment of infections

• was also isolated in 16% yield, which was readily separable from 6 by column chromatography. The synthesis of 20 has been reported only once before and the resulting phosphonic acid also possesses antiviral activity [54]. The authors report that 20 was prepared in four steps while our three step route

Diastereo- and enantioselective preparation of cyclopropanol derivatives

• Marwan Simaan and
• Ilan Marek

Beilstein J. Org. Chem. 2019, 15, 752–760, doi:10.3762/bjoc.15.71

• transformations [1]. The cyclopropane subunit is also present in many biologically important compounds such as pheromones, fatty acid metabolites, unusual amino acids and possess interesting herbicidal, insecticidal, antibiotic, antibacterial, antifungal, antiviral and antitumor activities [2]. For these reasons

• are also important precursors in the synthesis of various biologically active molecules and pharmaceuticals such as antidepressants, antiviral and antibacterial drugs [4]. Cyclopropanols and their derivatives are considered to be carbocyclic homologues of enols presenting similar chemical properties

Synthesis and biological investigation of (+)-3-hydroxymethylartemisinin

• Toni Smeilus,
• Farnoush Mousavizadeh,
• Johannes Krieger,
• Xingzhao Tu,
• Marcel Kaiser and
• Athanassios Giannis

Beilstein J. Org. Chem. 2019, 15, 567–570, doi:10.3762/bjoc.15.51

• sesquiterpene lactone is still unknown [5]. Whereas artemisinins are almost non-toxic to normal cells, several studies have confirmed their potent antitumor activity [6][7]. In addition, they have been reported to possess immunosuppressive, anti-inflammatory, antiviral, antifungal and antiparasitic activities

Study on the regioselectivity of the N-ethylation reaction of N-benzyl-4-oxo-1,4-dihydroquinoline-3-carboxamide

• Pedro N. Batalha,
• Luana da S. M. Forezi,
• Maria Clara R. Freitas,
• Nathalia M. de C. Tolentino,
• Ednilsom Orestes,
• José Walkimar de M. Carneiro,
• Fernanda da C. S. Boechat and
• Maria Cecília B. V. de Souza

Beilstein J. Org. Chem. 2019, 15, 388–400, doi:10.3762/bjoc.15.35

• antibacterial and antiviral. The presence of a carboxamide unit connected to carbon C-3 of the 4-oxoquinoline core has been associated with various biological activities. Experimentally, the N-ethylation reaction of N-benzyl-4-oxo-1,4-dihydroquinoline-3-carboxamide occurs at the nitrogen of the oxoquinoline

• been explored and were successfully described by researchers around the world [3][4], such as antiviral [5][6], antiplasmoidal [7][8], anticancer [9][10], and trypanocide [11] activities. 4-Oxoquinoline-3-carboxamide derivatives, more specifically, have shown to be a promising structural scaffold for

• work we described the synthesis and antiviral activity of some 4-oxoquinoline acyclonucleosides 3a and 3b [15] and studies on their anticancer activity are also underway. It is also worth mentioning that derivative 4 presented an excellent inhibitory profile for the enzyme hystone deacetylase (HDAC

Reusable and highly enantioselective water-soluble Ru(II)-Amm-Pheox catalyst for intramolecular cyclopropanation of diazo compounds

• Hamada S. A. Mandour,
• Yoko Nakagawa,
• Masaya Tone,
• Hayato Inoue,
• Nansalmaa Otog,
• Ikuhide Fujisawa,
• Soda Chanthamath and
• Seiji Iwasa

Beilstein J. Org. Chem. 2019, 15, 357–363, doi:10.3762/bjoc.15.31

• nature and have excellent biological activity, including strong antibiotic, antihelmetic, antifungal, antitumor, antiviral and anti-inflammatory, which make them interesting lead structures for new drugs [34]. That is why a great deal of attention has been paid to the synthesis of the lactone ring [35

Regioselective addition of Grignard reagents to N-acylpyrazinium salts: synthesis of substituted 1,2-dihydropyrazines and Δ⁵-2-oxopiperazines

• Valentine R. St. Hilaire,
• William E. Hopkins,
• Yenteeo S. Miller,
• Srinivasa R. Dandepally and
• Alfred L. Williams

Beilstein J. Org. Chem. 2019, 15, 72–78, doi:10.3762/bjoc.15.8

• ; Introduction Pyrazine and piperazine ring systems are key structural elements in a large number of biologically active molecules [1][2][3][4][5][6]. Compounds containing these scaffolds were shown to behave as anticancer agents [2][3][4][5], sodium channel blockers [5], and also display antiviral activity [7

Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4-(arylselanyl)-1H-pyrazoles

• Camila S. Pires,
• Daniela H. de Oliveira,
• Maria R. B. Pontel,
• Jean C. Kazmierczak,
• Roberta Cargnelutti,
• Diego Alves,
• Raquel G. Jacob and
• Ricardo F. Schumacher

Beilstein J. Org. Chem. 2018, 14, 2789–2798, doi:10.3762/bjoc.14.256

• commercially available drugs such as celecoxib, lonazolac, rimonabant and sildenafil [12][13]. In special, 5-amino-1H-pyrazoles are valuable compounds that present several biological and pharmaceutical activities including antiviral, anticancer, antituberculosis, anti-inflammatory, antifungal and

Targeting the Pseudomonas quinolone signal quorum sensing system for the discovery of novel anti-infective pathoblockers

• Christian Schütz and
• Martin Empting

Beilstein J. Org. Chem. 2018, 14, 2627–2645, doi:10.3762/bjoc.14.241

• appears quite attractive. In analogy to current antiviral and anticancer strategies, more personalized pathogen-specific drug combinations should be pursued also in the bacterial infections field. As a consequence, more advanced diagnostic tools have to be devised to enable fast and reliable analysis of

Gold-catalyzed post-Ugi alkyne hydroarylation for the synthesis of 2-quinolones

• Xiaochen Du,
• Jianjun Huang,
• Anton A. Nechaev,
• Ruwei Yao,
• Jing Gong,
• Erik V. Van der Eycken,
• Olga P. Pereshivko and
• Vsevolod A. Peshkov

Beilstein J. Org. Chem. 2018, 14, 2572–2579, doi:10.3762/bjoc.14.234

• derivatives, 2-quinolone and 4-quinolone, are the core structural elements of many natural products and pharmaceutical agents [1][2][3]. In particular, 2-quinolone derivatives show a broad range of biological activities including antiviral [4][5][6][7], antimicrobial [8][9], antiparasitic [10][11], anti

Synthesis of a leopolic acid-inspired tetramic acid with antimicrobial activity against multidrug-resistant bacteria

• Luce Mattio,
• Loana Musso,
• Leonardo Scaglioni,
• Andrea Pinto,
• Piera Anna Martino and
• Sabrina Dallavalle

Beilstein J. Org. Chem. 2018, 14, 2482–2487, doi:10.3762/bjoc.14.224

• antibacterial, antiviral, antifungal and anticancer activities [13]. More than one hundred of them have been isolated from a variety of natural sources and numerous analogues have been synthesized and studied for their multiple biological activities [13]. For this reason, we planned the synthesis of a leopolic

Stereoselective total synthesis and structural revision of the diacetylenic diol natural products strongylodiols H and I

• Pamarthi Gangadhar,
• Sayini Ramakrishna,
• Ponneri Venkateswarlu and
• Pabbaraja Srihari

Beilstein J. Org. Chem. 2018, 14, 2313–2320, doi:10.3762/bjoc.14.206

• continue to attract significant interest owing to their structural architectures and impressive biological properties that include antibacterial [3], anticancer [4][5][6], antiviral [7] and neuritogenic activities [8]. Watanabe et al. [9][10] have isolated strongylodiols A–J (1–10, Figure 1) [11] from the

Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions

• Siva Sankar Murthy Bandaru,
• Darinka Dzubiel,
• Heiko Ihmels,
• Mohebodin Karbasiyoun,
• Mohamed M. A. Mahmoud and
• Carola Schulzke

Beilstein J. Org. Chem. 2018, 14, 1871–1884, doi:10.3762/bjoc.14.161

• ligand may interfere with DNA–enzyme recognition events, which are essential for DNA-based cellular processes, e.g., gene replication or transcription [1]. To this end, it was shown that DNA-binding ligands may operate as chemotherapeutic anticancer, antiviral or antibacterial drugs, for example as

Synthesis of spirocyclic scaffolds using hypervalent iodine reagents

• Fateh V. Singh,
• Priyanka B. Kole,
• Saeesh R. Mangaonkar and
• Samata E. Shetgaonkar

Beilstein J. Org. Chem. 2018, 14, 1778–1805, doi:10.3762/bjoc.14.152

• starting from catechol derivative 142. Marine sesquiterpenoids are mainly known for their biological importance such as antitumor, antiviral and antibiotic properties [132]. In this report, the catechol-derived starting substrate 142 was cyclized to spirocyclic product 143 in 67% yield using PIFA (31) as

Synthesis and photophysical studies of a multivalent photoreactive Ru^II-calix[4]arene complex bearing RGD-containing cyclopentapeptides

• Sofia Kajouj,
• Lionel Marcelis,
• Alice Mattiuzzi,
• Adrien Grassin,
• Damien Dufour,
• Pierre Van Antwerpen,
• Didier Boturyn,
• Eric Defrancq,
• Mathieu Surin,
• Julien De Winter,
• Pascal Gerbaux,
• Ivan Jabin and
• Cécile Moucheron

Beilstein J. Org. Chem. 2018, 14, 1758–1768, doi:10.3762/bjoc.14.150

• that calixarenes themselves display antibacterial, antiviral, and anticancer properties [64]. Herein, we describe the synthesis of a multivalent phototherapeutic agent designed in order to specifically target membrane receptors involved in the angiogenesis process. The multivalent system is composed of

Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates

• Yuichi Yoshimura,
• Hideaki Wakamatsu,
• Yoshihiro Natori,
• Yukako Saito and
• Noriaki Minakawa

Beilstein J. Org. Chem. 2018, 14, 1595–1618, doi:10.3762/bjoc.14.137

• , we have steadily pursued the identification of novel antitumor and antiviral nucleoside derivatives [17][20][21][22]. Matsuda and co-workers reported a 2’-substituted cytidine derivative, DMDC (1), with potent antitumor activity [23][24]. In other reports, Walker [25] and Secrist [26] independently

• class of nucleosides with antiviral activity [74]. First, they tried to synthesize acyclic nucleosides in a stepwise manner. The substrates 128 and 129 for the fragmentation reaction were synthesized from ribose in a few steps by the conventional method. The oxidative scission of 128 and 129 was carried

Lanyamycin, a macrolide antibiotic from Sorangium cellulosum, strain Soce 481 (Myxobacteria)

• Lucky S. Mulwa,
• Rolf Jansen,
• Dimas F. Praditya,
• Kathrin I. Mohr,
• Patrick W. Okanya,
• Joachim Wink,
• Eike Steinmann and
• Marc Stadler

Beilstein J. Org. Chem. 2018, 14, 1554–1562, doi:10.3762/bjoc.14.132

• million people are infected with Hepatitis C virus. Hepatitis C virus (HCV) is a major cause of liver cirrhosis and hepatocellular carcinoma. Although a variety of potent direct-acting antiviral drugs have been licensed recently, their high costs exclude the majority of infected individuals from treatment

• of actions [2]. Myxobacteria have emerged as a productive source of antiviral and antimicrobial molecules with unique structures and novel modes of action [3]. The potential of myxobacteria as source of anti-invectives may be illustrated by phenoxan, phenalamide A1, thiangazole and aetheramide A, all

• , nematodes, insects, immunosuppressant or with antitumor activities [12][13][14][15]. Therefore, lanyamycin (1/2) was tested in our screening panel against bacteria, fungi, mammalian cell cultures and for antiviral activity against HCV in human liver cells. Lanyamycin (1/2) was analyzed for antimicrobial