Synthesis of acremines A, B and F and studies on the bisacremines

• Nils Winter and
• Dirk Trauner

Beilstein J. Org. Chem. 2019, 15, 2271–2276, doi:10.3762/bjoc.15.219

• biogenetic precursor of acremines A (1) and B (2), we wanted to access these antifungal derivatives through selective oxidations. Indeed, treatment of 5 with IBX preferentially oxidized the C1-allylic alcohol, giving 1 in respectable yield. Prolonged treatment (9 h) of 5 with a large excess of IBX oxidized

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

• . To guarantee that the device was sealed properly, commercial aquarium safe silicone without antifungal additive was applied to the edges. All materials and tools were sterilized by autoclaving or surface disinfection and the procedure was performed under the laminar airflow cabinet. The sample-loaded

• each other with six M3 hex bolt screws, sandwiching the central plate with the attached membranes between them. To ensure the devices seal commercial aquarium safe and antifungal-less silicone (Soudal) was applied to the edges of the device. The silicone was given time to dry and the device was

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

• peptidyl nucleosides with primarily antifungal properties. The stereoselective synthesis of (+)-polyoxamic acid ((2S,3S,4S)-144) was successfully carried out starting with Horner–Wadsworth–Emmons olefination of the aziridine aldehyde (2R,1'R)-6 which provided a 98:2 mixture of trans- and cis-acrylates 69b

• it was transformed into a silylated (4S,5S)-5-benzyl-4-hydroxy-1-methylpyrrolidin-2-one 167, a molecule having a structural core of antifungal (+)-preussin [98]. (3R,5S)-5-(Aminomethyl)-3-(4-methoxyphenyl)dihydrofuran-2(3H)-one ((3R,5S)-168) was discovered as a potential medication in Parkinson’s

Synthesis of ([1,2,4]triazolo[4,3-a]pyridin-3-ylmethyl)phosphonates and their benzo derivatives via 5-exo-dig cyclization

• Aleksandr S. Krylov,
• Artem A. Petrosian,
• Julia L. Piterskaya,
• Nataly I. Svintsitskaya and
• Albina V. Dogadina

Beilstein J. Org. Chem. 2019, 15, 1563–1568, doi:10.3762/bjoc.15.159

• number of drugs and [1,2,4]triazolo[4,3-a]pyridines were shown to have herbicidal [5][6], antifungal [7], neuroprotective [8][9] and antibacterial activity [10]. In addition, [1,2,4]triazolopyridine has been used as electron-acceptor unit in the synthesis of organic light emitting diodes (OLED) [11]. 2

Molecular basis for the plasticity of aromatic prenyltransferases in hapalindole biosynthesis

• Takayoshi Awakawa and
• Ikuro Abe

Beilstein J. Org. Chem. 2019, 15, 1545–1551, doi:10.3762/bjoc.15.157

• beneficial bioactivities, exemplified by 12-epi-hapalindole E isonitrile, which exhibits antibacterial, antifungal, and antimycobacterial activities [16], and ambiguine I, which induces apoptosis and cell-cycle arrest through the inhibition of an NF-κB-related regulation pathway [17]. To investigate their

A heteroditopic macrocycle as organocatalytic nanoreactor for pyrroloacridinone synthesis in water

• Piyali Sarkar,
• Sayan Sarkar and
• Pradyut Ghosh

Beilstein J. Org. Chem. 2019, 15, 1505–1514, doi:10.3762/bjoc.15.152

• antitumor, antifungal, anthelmintic, anticancer activities, etc. [5][6][7]. Although a few syntheses of these molecules have been reported in the literature, these generally consist of multistep protocols and require harsh acidic catalysts [5][8][9][10][11][12]. Moreover, only in a very few cases, the

Synthesis of pyrrolo[1,2-a]quinolines by formal 1,3-dipolar cycloaddition reactions of quinolinium salts

• Anthony Choi,
• Rebecca M. Morley and
• Iain Coldham

Beilstein J. Org. Chem. 2019, 15, 1480–1484, doi:10.3762/bjoc.15.149

• with a quinoline. Pyrroloquinolines have been found to show antibacterial and antifungal activity, to be ligands for the NK1 receptor, and to be effective against the Hif hypoxia pathway in cancer cell lines [36][37][38]. Almost all of the examples of dipolar cycloaddition reactions involving

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

• ) skeletons. These azasteroids, in which one or more nitrogen atoms are present in the side chain, were designed as promising compounds since such classes of antifungal steroids were known in the literature. Some of the resulting azasteroids showed inhibitory effects on the growth of fungi such Fusarium

• . This could indicate that the antifungal properties of such azasteroids very much depend on the phenyl moieties attached to the side chain. This type of biological comparison could be established because of the versatility of the synthetic strategy based on the MCR tool. On the other hand, the family of

• library of androstanic derivatives 21 (Figure 2B) and their reduced analogues bearing the 3β-hydroxy group were biologically tested showing antifungal activity against Fusarium virguliforme and Fusarium solani. The generation of this compound library suffered from the formation of the Passerini reaction

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

• derivatives show a large variety of biological activities [21][22][23], such as COX-2 inhibition [24], glucokinase activation [25], sodium channel blocking [26], antimycobacterial [27], antiproliferative [28] or carbonic anhydrase inhibition [29], as well as antifungal and antibacterial properties [30

Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds

• Victoria V. Lipson,
• Tetiana L. Pavlovska,
• Nataliya V. Svetlichnaya,
• Anna A. Poryvai,
• Nikolay Yu. Gorobets,
• Erik V. Van der Eycken,
• Irina S. Konovalova,
• Svetlana V. Shiskina,
• Alexander V. Borisov,
• Vladimir I. Musatov and
• Alexander V. Mazepa

Beilstein J. Org. Chem. 2019, 15, 1032–1045, doi:10.3762/bjoc.15.101

• antagonists [8], cyclin-dependent kinases GSK-3β, CK1 [9] and nitric oxide synthase activity inhibitors [10][11], as well as antibacterial [2], antifungal [12], antihistamine [13] and antitumor activities [14]. Remarkable immunosuppressive properties are inherent to palau’amine (VI) [15]. Ceratamines XIII are

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

An efficient and concise access to 2-amino-4H-benzothiopyran-4-one derivatives

• Peng Li,
• Yongqi Wu,
• Tingting Zhang,
• Chen Ma,
• Ziyun Lin,
• Gang Li and
• Haihong Huang

Beilstein J. Org. Chem. 2019, 15, 703–709, doi:10.3762/bjoc.15.65

• due to their structural relationship with benzopyranones, which are known as one privileged scaffold in medicinal chemistry [1]. The corresponding 2-aminobenzothiopyranones are molecules of high interest as they have remarkable anticancer, antifungal and antitubercular activities [2][3][4][5

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

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

Metal-free C–H mercaptalization of benzothiazoles and benzoxazoles using 1,3-propanedithiol as thiol source

• Yan Xiao,
• Bing Jing,
• Xiaoxia Liu,
• Hongyu Xue and
• Yajun Liu

Beilstein J. Org. Chem. 2019, 15, 279–284, doi:10.3762/bjoc.15.24

• cancer cells [3][4][5]. 2-Mercapto-N-(substituted arylidine)benzoxazole-5-carbohydrazide derivatives have promising anti-inflammatory activities [6]. 2-Mercapto-5-nitro-1,3-benzoxazole and its derivatives shows strong anthelmintic activity [7]. 2-Mercapto-5-chloro-1,3-benzothiazoles possess antifungal

Synthesis of nonracemic hydroxyglutamic acids

• Dorota G. Piotrowska,
• Iwona E. Głowacka,
• Andrzej E. Wróblewski and
• Liwia Lubowiecka

Beilstein J. Org. Chem. 2019, 15, 236–255, doi:10.3762/bjoc.15.22

• and (2R,3R)-2 were found as components of antifungal and antimicrobial hexadepsipeptides called kutznerides isolated from the actinomycete Kutzneria sp. 744 [26][27]. And finally, threo-3-hydroxyglutamic acid was identified in the cell wall of Mycobacterium lacticum [28]. 4-Hydroxy-L-glutamic acid

Reactions of 3-(p-substituted-phenyl)-5-chloromethyl-1,2,4-oxadiazoles with KCN leading to acetonitriles and alkanes via a non-reductive decyanation pathway

• Akın Sağırlı and
• Yaşar Dürüst

Beilstein J. Org. Chem. 2018, 14, 3011–3017, doi:10.3762/bjoc.14.280

• bioactivities, such as anticancer [1], antimicrobial [2], antifungal [3], anti-inflammatory [4], tyrosine kinase inhibition [5] and histamine H3 antagonism properties [6]. In addition, these five-membered heterocycles were widely used as components of organic light emitting diodes (OLEDs), polymers, liquid

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

Design and synthesis of C₃-symmetric molecules bearing propellane moieties via cyclotrimerization and a ring-closing metathesis sequence

• Sambasivarao Kotha,
• Saidulu Todeti and
• Vikas R. Aswar

Beilstein J. Org. Chem. 2018, 14, 2537–2544, doi:10.3762/bjoc.14.230

• units in bioactive natural products and pharmaceuticals. Some of these propellanes exhibit intresting properties like antibiotic, antifungal, anticancer, platelet-activating factor antagonistic and antibacterial activities. The propellane skeleton is present in many alkaloids such as aknadinine (1

Synthesis of dihydroquinazolines from 2-aminobenzylamine: N³-aryl derivatives with electron-withdrawing groups

• Nadia Gruber,
• Jimena E. Díaz and
• Liliana R. Orelli

Beilstein J. Org. Chem. 2018, 14, 2510–2519, doi:10.3762/bjoc.14.227

• antimicrobial [3] and antifungal properties [4]. In addition, antiparasitic activity has been studied for some members of this family as inhibitors of trypanothione reductase [5], an essential enzyme of the kinetoplastid Trypanosoma brucei. Their activity as selective T-type calcium channel blockers [6][7][8][9

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

Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetal

• Antonio Arcadi,
• Sandro Cacchi,
• Giancarlo Fabrizi,
• Francesca Ghirga,
• Antonella Goggiamani,
• Antonia Iazzetti and
• Fabio Marinelli

Beilstein J. Org. Chem. 2018, 14, 2411–2417, doi:10.3762/bjoc.14.218

• ]quinazolines were synthesized and exhibited good antimicrobial as well as notable antifungal activities [9][10][11]. Since the isolation of hinckdentine A, an unusual marine alkaloid from the bryozoan Hincksinoflustra denticulata collected off the eastern coast of Tasmania [12][13], indolo[1,2-c]quinazolines

Semi-synthesis and insecticidal activity of spinetoram J and its D-forosamine replacement analogues

• Kai Zhang,
• Jiarong Li,
• Honglin Liu,
• Haiyou Wang and
• Lamusi A

Beilstein J. Org. Chem. 2018, 14, 2321–2330, doi:10.3762/bjoc.14.207

• , these analogues may also have antibiotic, antifungal, anticancer, antiparasitic, and immunosuppressive properties. Conclusion This study demonstrated a viable approach to synthesize spinetoram J and its analogues. Compared with the previous semi-synthesis of spinetoram J, the improved semi-synthesis

Studies towards the synthesis of hyperireflexolide A

• G. Hari Mangeswara Rao

Beilstein J. Org. Chem. 2018, 14, 2106–2111, doi:10.3762/bjoc.14.185

• antifungal [2] and cytotoxic activities [3]. γ-Lactone-fused cyclopentanes are of vital importance in organic synthesis and are the most abundant substructures found in various naturally occurring molecules [4][5]. A cis-cyclopentane ring-fused γ-lactone is the key structural unit of many complex and

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

• griseofulvum in 1939 [12]. In 1959, it was launched in the market as antifungal agent for the treatment of ringworm in human beings and animals [4][13]. Stepharine (3) is a member of the proaporphine alkaloid family and isolated from an angiosperm Stephania glabra [14]. Tofogliflozin (4) is a synthetic