New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized

• Maryna V. Murlykina,
• Maryna N. Kornet,
• Sergey M. Desenko,
• Svetlana V. Shishkina,
• Oleg V. Shishkin,
• Aleksander A. Brazhko,
• Vladimir I. Musatov,
• Erik V. Van der Eycken and
• Valentin A. Chebanov

Beilstein J. Org. Chem. 2017, 13, 1050–1063, doi:10.3762/bjoc.13.104

• obtained were evaluated for their antibacterial activity and several of them demonstrated a weak antimicrobial effect, but for most of the compounds a 30–50% increase in biomass of Gram-positive strains (mainly B. subtilis) compared to control was observed. Keywords: 3-amino-5-methylisoxazole; 5-amino-N

• -aryl-1H-pyrazole-4-carboxamides; antibacterial activity; Groebke–Blackburn–Bienaymé reaction; isocyanide Ugi reaction; Introduction An intensive progress in pharmaceutical and medicinal chemistry, as well as in the generation and improvement of medicinal technologies has led to defeating a wide scope

• compound 9e (Figure 5). Antibacterial activity The antibacterial activity of compounds 4, 6 and 9 (Table 7) was studied (see Experimental part in Supporting Information File 1 for details) against reference bacterial cultures: Bacillus subtilis (strain 1211), Staphylococcus aureus (strain 2231) (Gram

Glyco-gold nanoparticles: synthesis and applications

• Federica Compostella,
• Olimpia Pitirollo,
• Alessandro Silvestri and
• Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

• nanocomposite, carrying either a targeting agent towards E. coli pili and an antibacterial polymer, resulted able to bind E. coli specifically and to kill the attached bacteria, by enhancing the local concentration of biocidal agent on the bacterial surface [90]. GAuNPs find interesting application also in the

A practical and efficient approach to imidazo[1,2-a]pyridine-fused isoquinolines through the post-GBB transformation strategy

• Taofeng Shao,
• Zhiming Gong,
• Tianyi Su,
• Wei Hao and
• Chao Che

Beilstein J. Org. Chem. 2017, 13, 817–824, doi:10.3762/bjoc.13.82

• (Figure 1) [6]. Furthermore, the isoquinoline motif represents a privileged medicinal skeleton widely found in a number of natural alkaloids and pharmaceutically active compounds [7]. Some of them exhibit diversified biological properties, including anti-inflammatory [8], antibacterial [9], antiviral [10

Isoxazole derivatives as new nitric oxide elicitors in plants

• Anca Oancea,
• Emilian Georgescu,
• Florentina Georgescu,
• Alina Nicolescu,
• Elena Iulia Oprita,
• Catalina Tudora,
• Lucian Vladulescu,
• Marius-Constantin Vladulescu,
• Florin Oancea and
• Calin Deleanu

Beilstein J. Org. Chem. 2017, 13, 659–664, doi:10.3762/bjoc.13.65

• ]. The thiophene is a core system of a large number of bioactive molecules such as antineoplastic agents [49], non-steroidal anti-inflammatory drugs [50] or compounds with antibacterial activities against several Gram-positive strains [51]. Thus, 3,5-disubstituted isoxazole derivatives were obtained by

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

• , have been performed. This review also covers the most important studies on the biological activity of 1-indanones and their derivatives which are potent antiviral, anti-inflammatory, analgesic, antimalarial, antibacterial and anticancer compounds. Moreover, they can be used in the treatment of

• as antiviral and antibacterial agents [5] (I and II), anticancer drugs [6] (VI), pharmaceuticals used in the Alzheimer’s disease treatment [7] (III), cardiovascular drugs [7] (IV), insecticides, fungicides, herbicides [8] (V) and non-nucleoside, low molecular drugs for the hepatitis C treatment

• antibacterial activity against Escherichia coli and Bacillus subtilis, and antifungal activity against Aspergillus niger and Penicillium notatum. Among the synthesized series of 1-indanone derivatives 64, the highest antibacterial activity was exhibited by derivatives 64k and 64l, whereas the most potent

Posttranslational isoprenylation of tryptophan in bacteria

• Masahiro Okada,
• Tomotoshi Sugita and
• Ikuro Abe

Beilstein J. Org. Chem. 2017, 13, 338–346, doi:10.3762/bjoc.13.37

• derived from cyanobacteria, including dimethylallylated cyclic peptides, are called cyanobactins [2][37][38]. Although several cyanobactins exhibit significant biological activities, such as antibacterial and enzyme inhibitory properties, the actual biological role of prenylation in cyanobactins is still

First DMAP-mediated direct conversion of Morita–Baylis–Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates

• Marwa Ayadi,
• Haitham Elleuch,
• Emmanuel Vrancken and
• Farhat Rezgui

Beilstein J. Org. Chem. 2016, 12, 2906–2915, doi:10.3762/bjoc.12.290

• inhibiting them, or to have biological activities as for example antibiotics, antibacterial, anti-cancer or antithrombotic agents [22][23][24][25][26]. In this context, α-aminophosphonates have particularly attracted considerable attention owing to their biological activities [27][28][29][30][31][32][33

• . Indeed, they are known for their important role in medicinal chemistry [34][35][36] as anti-HIV agents, enzyme inhibitors and antibacterial agents. In addition, α- and β-aminophosphonates have been widely described in literature. However, γ-aminophosphonates have received much less attention. These

Selective synthesis of thioethers in the presence of a transition-metal-free solid Lewis acid

• Federica Santoro,
• Matteo Mariani,
• Federica Zaccheria,
• Rinaldo Psaro and
• Nicoletta Ravasio

Beilstein J. Org. Chem. 2016, 12, 2627–2635, doi:10.3762/bjoc.12.259

• are a very important field of research as traditional coupling methods, although they proved effective in industrial applications, generate harmful metal waste and many byproducts [3]. Thioethers are important building blocks for the synthesis of antibacterial and antifungal agents [4][5] and as

Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis

• Darcy J. Atkinson,
• Briar J. Naysmith,
• Daniel P. Furkert and
• Margaret A. Brimble

Beilstein J. Org. Chem. 2016, 12, 2325–2342, doi:10.3762/bjoc.12.226

• 10.3762/bjoc.12.226 Abstract Rising resistance to current clinical antibacterial agents is an imminent threat to global public health and highlights the demand for new lead compounds for drug discovery. One such potential lead compound, the peptide antibiotic teixobactin, was recently isolated from an

• -positive bacteria, including resistant strains [2][9][20] and Mycobacterium species [21]. No activity was observed against Gram-negative bacteria (except for Neisseria gonorrhoeae), fungi or yeast [9]. The antibacterial activity arises through inhibition of cell wall synthesis [22] by prevention of

• bacteria [7] with the primary cellular target deduced to be bacterial cell wall synthesis [34]. Extensive derivatisation of both mannopeptimycin α (12) and β (13) was undertaken to improve the antibacterial activity of the parent natural products (highlighted in blue, Figure 6). An array of ether [35][36

Experimental and theoretical investigations into the stability of cyclic aminals

• Edgar Sawatzky,
• Antonios Drakopoulos,
• Martin Rölz,
• Christoph Sotriffer,
• Bernd Engels and
• Michael Decker

Beilstein J. Org. Chem. 2016, 12, 2280–2292, doi:10.3762/bjoc.12.221

• Tetraponera sp. [1][2]. It is also present in ligands of ruthenium-based catalysts for metathesis [3], in imidazolidines acting as antiprotozoal and antibacterial agents [4][5], in Tröger’s base derivatives with diverse applications [6][7][8][9][10][11][12][13][14] (e.g., asymmetric catalysis, supramolecular

New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

• Ze’en Xiao,
• Senhua Chen,
• Runlin Cai,
• Shao’e Lin,
• Kui Hong and
• Zhigang She

Beilstein J. Org. Chem. 2016, 12, 2077–2085, doi:10.3762/bjoc.12.196

• ) as a positive control. Compounds 2, 5, and 6 showed moderate α-glucosidase inhibitory activity with IC50 of 87.8, 52.3, and 95.6 μM, respectively. The other compounds were inactive (> 300 μM). Compounds 1–9 were also evaluated for antibacterial activities against Staphylococcus aureus, Staphylococcus

• performed with High-Performance Grid Computing Platform of Sun Yat-Sen University. Biological assays. The assays for antibacterial [23] and α-glucosidase inhibitory [23] were carried out as described previously. The assay for DPPH radical scavenging activity was measured by a reported method [24][25], with

Varioloid A, a new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative from the marine alga-derived endophytic fungus Paecilomyces variotii EN-291

• Peng Zhang,
• Xiao-Ming Li,
• Xin-Xin Mao,
• Attila Mándi,
• Tibor Kurtán and
• Bin-Gui Wang

Beilstein J. Org. Chem. 2016, 12, 2012–2018, doi:10.3762/bjoc.12.188

• prolific source of bioactive secondary metabolites of diverse structures, including, for example, semiviriditoxin derivatives with antibacterial activity [3], cornexistin and hydroxycornexistin with herbicidal activity [4], and paecilocins with antibacterial activity [5]. During our ongoing effort to

Synthesis of the C8’-epimeric thymine pyranosyl amino acid core of amipurimycin

• Pramod R. Markad,
• Navanath Kumbhar and
• Dilip D. Dhavale

Beilstein J. Org. Chem. 2016, 12, 1765–1771, doi:10.3762/bjoc.12.165

• , antiviral, antibacterial and antifungal [2]. Peptidyl nucleosides in which the sugar part is in the furanose form are common, however, the sugar framework in the pyranose form, with a nucleobase and a peptide linker at either ends, are rare in nature. A few examples of this category are amipurimycin and

Rearrangements of organic peroxides and related processes

• Ivan A. Yaremenko,
• Vera A. Vil’,
• Dmitry V. Demchuk and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

• activities, including antibacterial, antiviral, antifungal, anti-allergic, anti-oxidant, and anti-inflammatory [348][349]. The treatment of endoperoxide 238 with Et3N gave 1,4-diketone 240 in quantitative yield instead of expected hydroxy ketone 239 (Scheme 73) [350][351][352]. The endoperoxide 238 is

• rearrangement is one of the steps in the synthesis of the natural compound angelone from Nauclea, a plant species widely acclaimed for its anti-inflammatory and antibacterial utilities in traditional Chinese herbal medical formulations [370]. A Kornblum–DeLaMare enantiomeric resolution was also used to obtain

Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity

• Atul A. Dhavan,
• Rahul D. Kaduskar,
• Loana Musso,
• Leonardo Scaglioni,
• Piera Anna Martino and
• Sabrina Dallavalle

Beilstein J. Org. Chem. 2016, 12, 1624–1628, doi:10.3762/bjoc.12.159

• carried out. Crucial steps for the strategy include a Dieckmann cyclization to obtain the 2,3-pyrrolidinedione ring and a Wittig olefination to install the polymethylene chain. An oxazolidinone-containing leopolic acid A analogue was also synthesized. The antibacterial activity showed by both compounds

• residue, which in turn, is connected to the ureido dipeptide L-Phe-L-Val. The compound showed antifungal and antibacterial activity against Mucor hiemalis and Staphylococcus aureus with a MIC of 32 and 16 μg/mL, respectively [2]. Compounds containing the isomeric 2,4-pyrrolidinedione ring system (tetramic

• acids) are widespread among the fungal metabolites and show a number of biological activities, i.e., antibacterial, antiviral, antifungal and anticancer. More than one hundred of them have been isolated from a variety of natural sources [3]. Conversely, natural compounds with a simple 2,3

Enantioselective addition of diphenyl phosphonate to ketimines derived from isatins catalyzed by binaphthyl-modified organocatalysts

• Hee Seung Jang,
• Yubin Kim and
• Dae Young Kim

Beilstein J. Org. Chem. 2016, 12, 1551–1556, doi:10.3762/bjoc.12.149

• organocatalyst; ketimines; organocatalysis; squaramide; Introduction α-Aminophosphonate derivatives are important compounds as structural mimics of natural α-amino acids [1][2][3]. Chiral α-aminophosphonates have been shown a wide range of biological activities including antibacterial [4] and anticancer

Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides

• Franziska Hemmerling and
• Frank Hahn

Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148

• groups. Besides a common antibacterial activity, many tetronates also have further attractive bioactivities that triggered interest in their research [139][140]. Tetronates and their biosynthesis have recently been extensively reviewed and a classification based on structural characteristics was devised

Flow carbonylation of sterically hindered ortho-substituted iodoarenes

• Carl J. Mallia,
• Gary C. Walter and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2016, 12, 1503–1511, doi:10.3762/bjoc.12.147

• agrochemical active ingredients, for example tecloftalam, flutolanil, fluopyram and diflufenican. Likewise, in pharmaceutical compounds such as 2,4,5-trifluorobenzoic acid, which serve as a starting material for several antibacterial drugs such as ciprofloxacin (Cipro™), norfloxacin (Noroxin™) and pefloxacin

Microwave-assisted synthesis of (aminomethylene)bisphosphine oxides and (aminomethylene)bisphosphonates by a three-component condensation

• Erika Bálint,
• Ádám Tajti,
• Anna Dzielak,
• Gerhard Hägele and
• György Keglevich

Beilstein J. Org. Chem. 2016, 12, 1493–1502, doi:10.3762/bjoc.12.146

• antibacterial, antiparasitic, anticancer and herbicidal activities [5]. (Aminomethylene)bisphosphonates may be prepared in different ways [5]. One of the most convenient and widespread methods is the three-component condensation involving an amine, an orthoformate and a dialkyl phosphite. Usually, primary or

One-pot synthesis of tetracyclic fused imidazo[1,2-a]pyridines via a three-component reaction

• Bo Yang,
• Chuanye Tao,
• Taofeng Shao,
• Jianxian Gong and
• Chao Che

Beilstein J. Org. Chem. 2016, 12, 1487–1492, doi:10.3762/bjoc.12.145

• broad range of biological activities such as antibacterial [11][12][13], antiviral [14][15], anti-inflammatory [16][17], antitumor [18][19][20], and anti-HIV [21]. It is found as the core structure in several drugs such as Zolpidem, Alpidem and Zolimidine (approved for treatments of insomnia, anxiety

Mutagenic activity of quaternary ammonium salt derivatives of carbohydrates

• Barbara Dmochowska,
• Karol Sikora,
• Anna Woziwodzka,
• Jacek Piosik and
• Beata Podgórska

Beilstein J. Org. Chem. 2016, 12, 1434–1439, doi:10.3762/bjoc.12.138

• their usage reaches hundreds of thousands of tons every year – in 2004 that number reached 0.5 million tons [6]. Antibacterial and antifungal action is the significant property of QAS. Therefore, they are being used as disinfectants, starting from hospital services to wood protection and house

• [22][23][24]. To overcome many problems associated with QASs, they were combined with sugars. We intended to obtain biologically active compounds – especially antibacterial and antifungal – with high biocompatibility and good biodegradation properties. Some examples of fused molecules containing QASs

Discovery of an inhibitor of the production of the Pseudomonas aeruginosa virulence factor pyocyanin in wild-type cells

• Bernardas Morkunas,
• Balint Gal,
• Warren R. J. D. Galloway,
• James T. Hodgkinson,
• Brett M. Ibbeson,
• Yaw Sing Tan,
• Martin Welch and
• David R. Spring

Beilstein J. Org. Chem. 2016, 12, 1428–1433, doi:10.3762/bjoc.12.137

• pathogenicity of P. aeruginosa and there is a wide range of other potential applications where the inhibition of quorum sensing is desirable. Keywords: antibacterial; antivirulence; Pseudomonas aeruginosa; pyocyanin; quorum sensing; Findings The Gram-negative bacterium Pseudomonas aeruginosa is a clinically

Selective bromochlorination of a homoallylic alcohol for the total synthesis of (−)-anverene

• Frederick J. Seidl and
• Noah Z. Burns

Beilstein J. Org. Chem. 2016, 12, 1361–1365, doi:10.3762/bjoc.12.129

• homoallylic alcohol. Critical factors for optimization of this reaction are highlighted. The utility of the product bromochloride is demonstrated by the first total synthesis of an antibacterial polyhalogenated monoterpene, (−)-anverene. Keywords: enantioselective catalysis; halogenation; natural products

Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides

• Andrew W. Truman

Beilstein J. Org. Chem. 2016, 12, 1250–1268, doi:10.3762/bjoc.12.120

• (alternatively named lantipeptides [44]) are large bacterial RiPPs, and the first member to be reported was nisin (Figure 4A) from Lactococcus lactis in 1928 [45]. Many members of this family have antibacterial activity and these are termed lantibiotics [46]; nisin itself is used as a food preservative as it

• are antibacterial towards Gram-positive species by inhibiting protein biosynthesis [75], but some members also exhibit biological activity towards a number of eukaryotic targets, which makes them promising anticancer [76][77] and antimalarial [78] compounds. Intriguingly, a recent study identified

Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates

• Jarosław Lewkowski,
• Maria Rodriguez Moya,
• Anna Wrona-Piotrowicz,
• Janusz Zakrzewski,
• Renata Kontek and
• Gabriela Gajek

Beilstein J. Org. Chem. 2016, 12, 1229–1235, doi:10.3762/bjoc.12.117

• normal lymphocytes (IC50 = 230.8 µM). Keywords: aminophosphonic derivatives; cytotoxicity; fluorescence properties; MTT test; pyrene-1-carboxaldehyde; Introduction The biological activity of aminophosphonic systems is very well known and described, in aspect of their crop protective [1], antibacterial