Skeletocutins M–Q: biologically active compounds from the fruiting bodies of the basidiomycete Skeletocutis sp. collected in Africa

• Tian Cheng,
• Clara Chepkirui,
• Cony Decock,
• Josphat C. Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2782–2789, doi:10.3762/bjoc.15.270

• isolated and characterized five previously undescribed secondary metabolites, skeletocutins M–Q (1–5), along with the known metabolite tyromycin A (6) from the fruiting bodies of the polypore Skeletocutis sp. The new compounds did not exhibit any antimicrobial, cytotoxic, or nematicidal activities. However

• antimicrobial, cytotoxic, and nematicidal activities, as described in the Experimental section. However, compounds 1–5 were devoid of activity in these assays, whereas tyromycin A (6) and skeletocutin A–L had been reported before to be active against several Gram-positive bacteria [4], namely Bacillus subtilis

• (B. subtilis), S. aureus, methicillin-resistant S. aureus (MRSA), and Micrococcus luteus (M. luteus). In the antimicrobial assay, compounds 3 and 5 were observed to interfere with the formation of biofilms commonly associated with S. aureus. When compounds 3 and 5 were evaluated for biofilm

Diversity-oriented synthesis of spirothiazolidinediones and their biological evaluation

• Sambasivarao Kotha,
• Gaddamedi Sreevani,
• Lilya U. Dzhemileva,
• Milyausha M. Yunusbaeva,
• Usein M. Dzhemilev and
• Vladimir A. D’yakonov

Beilstein J. Org. Chem. 2019, 15, 2774–2781, doi:10.3762/bjoc.15.269

• promising activity shown by the compounds containing a thiazolidinedione nucleus cover numerous categories such as antihyperglycaemics [5], aldose reductase inhibitors (ARI) [6][7], anti-inflammatory [8][9], anti-arthritics [10], anticancer [11][12][13] and antimicrobial [14][15][16][17][18], etc., has made

Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids

• Gerardo M. Ojeda,
• Prabhat Ranjan,
• Pavel Fedoseev,
• Lisandra Amable,
• Upendra K. Sharma,
• Daniel G. Rivera and
• Erik V. Van der Eycken

Beilstein J. Org. Chem. 2019, 15, 2447–2457, doi:10.3762/bjoc.15.237

• variety of pharmacological and antimicrobial properties [5][6], including analgesic, antihypertensive, anti-inflammatory, anticancer, antifungal and antimalarial activity (Figure 1). A key feature of the tetrazole ring is its bioisosteric character with the carboxylic acid and amide functional groups

Reversible switching of arylazopyrazole within a metal–organic cage

• Anton I. Hanopolskyi,
• Soumen De,
• Michał J. Białek,
• Yael Diskin-Posner,
• Liat Avram,
• Moran Feller and
• Rafal Klajn

Beilstein J. Org. Chem. 2019, 15, 2398–2407, doi:10.3762/bjoc.15.232

• selectivity [35][36][37][38][39][40]. Consequently, arylazopyrazoles have been employed as photoresponsive gelators [41] and adhesives [42] and for controlling antimicrobial response [43][44], cell adhesion to surfaces [45], as well as DNA [46] and microtubule [47] self-assembly using light. Here, we focused

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

• Irina G. Tkachenko,
• Sergey A. Komykhov,
• Vladimir I. Musatov,
• Svitlana V. Shishkina,
• Viktoriya V. Dyakonenko,
• Vladimir N. Shvets,
• Mikhail V. Diachkov,
• Valentyn A. Chebanov and
• Sergey M. Desenko

Beilstein J. Org. Chem. 2019, 15, 2390–2397, doi:10.3762/bjoc.15.231

• biological properties. They have been reported to have anticancer [1], antimicrobial [2][3] and antioxidant [3] activities and to act as inhibitors of hepatitis B virus [4]. The dihydro derivatives of tetrazolo[1,5-a]pyrimidines belong to a bit special kind of dihydropyrimidines due to the strong electron

Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.

• Amit Raj Sharma,
• Enjuro Harunari,
• Tao Zhou,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2019, 15, 2327–2332, doi:10.3762/bjoc.15.225

• ) was obtained from 1 L of culture supplemented with ʟ-[methyl-13C]methionine (total 80 mg; 2.0 mg × 10 flasks × 4 days). The 13C NMR spectrum showed an enriched signal at δ 21.3 ppm Antimicrobial assay Antimicrobial activity was evaluated by the liquid microculture method using round-bottomed 96-well

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

• antimicrobial activities against Gram-negative and Gram-positive bacteria, an ascomycete, a basidiomycete and a zygomycete, i.e., Escherichia coli, Bacillus megaterium, Eurotium rubrum, Microbotryum violaceum and Mycotypha microspora. Ethyl acetate extracts of C. rosea, I. europaea grown on BM medium and of the

• , the structure was established as 2-methyl-5-((1S,5S,6S)-2,6-dimethyl-4-oxobicyclo[3.1.1]hept-2-en-6-yl)pentanoic acid, named as heydenoic acid B. Compounds 1 and 2 were also tested in antimicrobial assays and showed no effect. Discussion Our experiments demonstrated the potential of the FIND

• were limited to mycotoxins [34] where in the other cases the isolated structures showed remarkable activities in the field of anticancer and antimicrobial agents [35][36][37][38][39][40]. H. alpina is one of only six species known from the less examined genus Heydenia, and was mistaken for a member of

An overview of the cycloaddition chemistry of fulvenes and emerging applications

• Ellen Swan,
• Kirsten Platts and
• Anton Blencowe

Beilstein J. Org. Chem. 2019, 15, 2113–2132, doi:10.3762/bjoc.15.209

•  21) [105][237]. ROMP of the monomers, followed by deprotection yielded facially amphiphilic polynorbornenes that displayed lipid membrane disruption and antimicrobial activities [237][238]. The facially amphiphilic polynorbornenes with pendent ammonium groups were found to disrupt negatively charged

• phospholipid unilamellar vesicles at low concentrations (5 µg/mL), and in a dose and molecular weight dependent fashion, indicating their potential antimicrobial properties. Further studies revealed that co-polymerisation of norbornene imide monomers with different alkyl groups provided optimal antimicrobial

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

• biological effects. In plants, they are synthesized, among others, for pesticidal and antimicrobial effects. Two such compounds, archangelolide and trilobolide of the guaianolide type, are structurally similar to the well-known and clinically tested lactone thapsigargin. While trilobolide has already been

• fluorescent conjugate; sarco/endoplasmic reticulum calcium ATPase; sesquiterpene lactone; trilobolide analogue; Introduction Sesquiterpene lactones (SLs) have been attracting interest already for some time due to the plethora of biological effects they elicit. Various SLs show anticancer, antimicrobial

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

• (DMS) [52]. By functionalization at C2 and C3: Florfenicol ((1R,2S)-49) is used as antimicrobial in veterinary medicine [54]. Recently another strategy which applied the (1-phenylethyl)aziridine chemistry has been disclosed (Scheme 15) [55]. The aziridine ketone (2R,1'S)-51 (de 98.8%) was obtained when

Synthesis of 9-O-arylated berberines via copper-catalyzed C_Ar–O coupling reactions

• Qiaoqiao Teng,
• Xinhui Zhu,
• Qianqian Guo,
• Weihua Jiang,
• Jiang Liu and
• Qi Meng

Beilstein J. Org. Chem. 2019, 15, 1575–1580, doi:10.3762/bjoc.15.161

• Qiaoqiao Teng Xinhui Zhu Qianqian Guo Weihua Jiang Jiang Liu Qi Meng Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China 10.3762/bjoc.15.161 Abstract Berberine is a widely used antimicrobial

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

• substances inhibited the growth of the test microorganisms demonstrating weak antimicrobial effect (Table 2). The growth of gram-positive bacteria (strains of S. aureus and B. subtilis) was inhibited in a more effective way. Particularly, compound 11b inhibited the growth of B. subtilis at a concentration of

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

• 10 amino acid residues [64]. As shown in Scheme 18, the procedure comprised the growth of the antimicrobial peptide sequence 60 followed by the multicomponent incorporation of cholestanic steroids functionalized as isocyanide component. Two related on-resin Ugi-4CRs were employed, i.e., the Ugi-azide

Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

• Dimitri Fayolle,
• Nathalie Berthet,
• Bastien Doumeche,
• Olivier Renaudet,
• Peter Strazewski and
• Michele Fiore

Beilstein J. Org. Chem. 2019, 15, 937–946, doi:10.3762/bjoc.15.90

• Fisher reaction between pyranoses and fatty alcohols of different lengths [8][9]. Alkyl thioglycosides are known for their properties as co-surfactants [10] and present interesting antimicrobial activities [11], acting as glycosidase inhibitors and being resistant towards glycoside hydrolases [12][13

Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine moiety

• Iteng Ng-Choi,
• Àngel Oliveras,
• Lidia Feliu and
• Marta Planas

Beilstein J. Org. Chem. 2019, 15, 761–768, doi:10.3762/bjoc.15.72

• File 410: Experimental, synthesis, and characterization of all the compounds. Acknowledgements Parts of this manuscript are adapted from the Ph. D. dissertation of Iteng Ng-Choi, Universitat de Girona, 2015: Solid-Phase Synthesis of 5-Arylhistidine-Containing Peptides: from Linear Antimicrobial

Synthesis of 2H-furo[2,3-c]pyrazole ring systems through silver(I) ion-mediated ring-closure reaction

• Vaida Milišiūnaitė,
• Rūta Paulavičiūtė,
• Eglė Arbačiauskienė,
• Vytas Martynaitis,
• Wolfgang Holzer and
• Algirdas Šačkus

Beilstein J. Org. Chem. 2019, 15, 679–684, doi:10.3762/bjoc.15.62

• , the dihydro-1H-furo[2,3-c]pyrazole system, consisting of an aromatic pyrazole ring fused with a five-membered 2,3-dihydrofuran ring, was formed [8]. Derivatives of the latter system are known for their antimicrobial [9] and antiproliferative activities [10]. Nevertheless, methods to access 2H-furo[2,3

Design and synthesis of multivalent α-1,2-trimannose-linked bioerodible microparticles for applications in immune response studies of Leishmania major infection

• Chelsea L. Rintelmann,
• Tara Grinnage-Pulley,
• Kathleen Ross,
• Daniel E. K. Kabotso,
• Angela Toepp,
• Anne Cowell,
• Christine Petersen,
• Balaji Narasimhan and
• Nicola Pohl

Beilstein J. Org. Chem. 2019, 15, 623–632, doi:10.3762/bjoc.15.58

• pathogenesis, the parasite infects and propagates in immune cells, the very cells responsible for host protection. Through a range of mechanisms not entirely understood, Leishmania subverts activation of antimicrobial (nitric oxide) and cytokine inducible functions that initiate effective immunity [5]. There

Synthesis and SAR of the antistaphylococcal natural product nematophin from Xenorhabdus nematophila

• Frank Wesche,
• Hélène Adihou,
• Thomas A. Wichelhaus and
• Helge B. Bode

Beilstein J. Org. Chem. 2019, 15, 535–541, doi:10.3762/bjoc.15.47

• soil-living nematodes of the genera Steinernema [2][3]. During a complex life cycle the nematode–bacteria pair infects and kills insect larvae, whereby Xenorhabdus produce a broad range of natural products with antimicrobial properties [4][5][6][7][8]. As the Steinernema–Xenorhabdus complex is not

• , like xenocoumacins [12][13]. The quite simple amide nematophin (1) is another well-known member of natural products common in all Xenorhabdus nematophila strains and was first described by Li et al. in 1997 for their antimicrobial properties [14]. Simply, 1 is the condensation product of 3-methyl-2

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

Synthesis and biological activity of methylated derivatives of the Pseudomonas metabolites HHQ, HQNO and PQS

• Sven Thierbach,
• Max Wienhold,
• Susanne Fetzner and
• Ulrich Hennecke

Beilstein J. Org. Chem. 2019, 15, 187–193, doi:10.3762/bjoc.15.18

• effect of methylation of AQs on their biological properties more systematically. To this end, we prepared selectively methylated derivatives of the most important heptyl-AQs including HHQ, HQNO and PQS derivatives. These synthetic compounds were tested for their antimicrobial properties against S. aureus

Repurposing the anticancer drug cisplatin with the aim of developing novel Pseudomonas aeruginosa infection control agents

• Mingjun Yuan,
• Song Lin Chua,
• Yang Liu,
• Daniela I. Drautz-Moses,
• Joey Kuok Hoong Yam,
• Thet Tun Aung,
• Roger W. Beuerman,
• May Margarette Santillan Salido,
• Stephan C. Schuster,
• Choon-Hong Tan,
• Michael Givskov,
• Liang Yang and
• Thomas E. Nielsen

Beilstein J. Org. Chem. 2018, 14, 3059–3069, doi:10.3762/bjoc.14.284

• 637371 Costerton Biofilm Center, Department of Immunology and Microbiology, University of Copenhagen, 2200 København N, Denmark 10.3762/bjoc.14.284 Abstract Antibiotic resistance threatens effective treatment of microbial infections globally. This situation has spurred the hunt for new antimicrobial

• compounds in both academia and the pharmaceutical industry. Here, we report how the widely used antitumor drug cisplatin may be repurposed as an effective antimicrobial against the nosocomial pathogen Pseudomonas aeruginosa. Cisplatin was found to effectively kill strains of P. aeruginosa. In such

• biofilms are encased by an extracellular matrix, which protects them from antimicrobial treatment and the host’s immune clearance [5]. Clinical P. aeruginosa isolates are mostly multidrug-resistant (MDR) strains [6], with robust ability to form biofilms [7]. P. aeruginosa also secretes virulence factors

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

N-Acylated amino acid methyl esters from marine Roseobacter group bacteria

• Hilke Bruns,
• Lisa Ziesche,
• Nargis Khakin Taniwal,
• Laura Wolter,
• Thorsten Brinkhoff,
• Jennifer Herrmann,
• Rolf Müller and
• Stefan Schulz

Beilstein J. Org. Chem. 2018, 14, 2964–2973, doi:10.3762/bjoc.14.276

• and ESI mass spectra revealed fragmentation patterns helpful for the detection of similar compounds derived from other amino acids. Some of these compounds showed antimicrobial activity. The structural similarity of N-acylated amino acid methyl esters and similar lipophilicity to AHLs might indicate a

• program for their antimicrobial activity (Table 3). While the valine derivative 9 was virtually inactive, the other compounds showed some activity. Glycine compound 11 showed good activity against the Gram-positive bacteria Bacillus subtilis, Staphylococcus aureus, and Micrococcus luteus, and against the

• on the LuxR type receptors for AHLs in bacteria [23][24]. Other potential functions are antimicrobial or cytotoxic activity of the tested derivatives. Roseovarius sp. D12_1.68 showed antimicrobial activity against a Rhodobacteraceae sp. TL and antialgal activity against Skeletonema costatum while

Protein–protein interactions in bacteria: a promising and challenging avenue towards the discovery of new antibiotics

• Laura Carro

Beilstein J. Org. Chem. 2018, 14, 2881–2896, doi:10.3762/bjoc.14.267

• of the currently available pharmacotherapies. Even though antimicrobial resistance is not a new problem, antibiotic development has failed to match the growth of resistant pathogens and hence, it is highly critical to discover new anti-infective drugs with novel mechanisms of action which will help

• antibiotic-insensitive strains, the steady decline in the number of new antibacterial drugs and the insufficient investment in antimicrobial research and development (R&D) by the major pharmaceutical companies have led to a global health crisis in which the prospect of a future without a safe and effective

• antimicrobial molecules are presented below. β-Sliding clamp Sliding clamps are prokaryotic ring-shaped proteins that secure DNA polymerases to the DNA template and slide along the double helix, enabling enzyme activity at a specific region of the DNA and increasing the rapid and processive DNA synthesis [52

Synthesis of pyrrolidine-based hamamelitannin analogues as quorum sensing inhibitors in Staphylococcus aureus

• Jakob Bouton,
• Kristof Van Hecke,
• Reuven Rasooly and
• Serge Van Calenbergh

Beilstein J. Org. Chem. 2018, 14, 2822–2828, doi:10.3762/bjoc.14.260

• , Foodborne Toxin Detection & Prevention Research Unit, Agricultural Research Service, United States Department of Agriculture, Albany, CA 94710, USA 10.3762/bjoc.14.260 Abstract Interfering with bacterial cell-to-cell communication is a promising strategy to combat antimicrobial resistance. The natural

• ; quorum sensing; Staphylococcus aureus; Introduction Antimicrobial resistance is rapidly becoming a global threat [1][2]. It is estimated that worldwide, at least 700 000 people die every year from drug-resistant strains of common bacterial infections. Strategies to deal with the global antimicrobial