A modular phosphate tether-mediated divergent strategy to complex polyols

• Paul R. Hanson,
• Susanthi Jayasinghe,
• Soma Maitra,
• Cornelius N. Ndi and
• Rambabu Chegondi

Beilstein J. Org. Chem. 2014, 10, 2332–2337, doi:10.3762/bjoc.10.242

• stereochemically divergent olefin partners [33]. Recently, the potential of phosphate tethered facilitated processes were highlighted in the pot-economical and efficient total synthesis of the antifungal agent strictifolione, whereby two consecutive phosphate tether-mediated, one-pot, sequential protocols were

Effect of cyclodextrin complexation on phenylpropanoids’ solubility and antioxidant activity

• Miriana Kfoury,
• David Landy,
• Lizette Auezova,
• Hélène Greige-Gerges and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2014, 10, 2322–2331, doi:10.3762/bjoc.10.241

• antioxidant activity and therefore are considered to have beneficial effects on human health [3][4]. PPs are also known to have antibacterial, antifungal and anti-inflammatory properties [5][6][7]. However, they have restricted applications as pharmaceutical products and food preservatives because they have

De novo macrolide–glycolipid macrolactone hybrids: Synthesis, structure and antibiotic activity of carbohydrate-fused macrocycles

• Richard T. Desmond,
• Anniefer N. Magpusao,
• Chris Lorenc,
• Jeremy B. Alverson,
• Nigel Priestley and
• Mark W. Peczuh

Beilstein J. Org. Chem. 2014, 10, 2215–2221, doi:10.3762/bjoc.10.229

• part of ester linkages; in 4 they are a carbamate and ether, respectively. Modest antifungal activity against C. neoformans and A. fumigatis were also noted for 4 [13]. Here we report on two new natural product-like 12-membered ring macrolides 5 and 6 (Scheme 1) where the pyranose is fused to the

A new approach for the synthesis of bisindoles through AgOTf as catalyst

• Jorge Beltrá,
• M. Concepción Gimeno and
• Raquel P. Herrera

Beilstein J. Org. Chem. 2014, 10, 2206–2214, doi:10.3762/bjoc.10.228

• bisindolylmethane derivatives (BIMs), many of them isolated from marine natural sources [15][16] and are an important class of indole derivatives which exhibit an appealing range of biological properties such as antibacterial, antifungal, antimicrobial or anti-inflammatory, among others (Figure 1) [17

N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines

• Jaipal R. Nagireddy,
• Geoffrey K. Tranmer,
• Emily Carlson and
• William Tam

Beilstein J. Org. Chem. 2014, 10, 2200–2205, doi:10.3762/bjoc.10.227

• isoxazoline-cleavage methodology to the preparation of biologically active natural products, including novel antibacterial, antifungal and anticancer treatments [8][9][10][11]. Some common methods of reductive N–O bond cleavage in isoxazolines include hydrogenolysis using Raney nickel, reduction by LiAlH4

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

• Thilo Focken and
• Stephen Hanessian

Beilstein J. Org. Chem. 2014, 10, 1848–1877, doi:10.3762/bjoc.10.195

• absolute stereochemistry of the molecule [43][126][127][128][129][130][131][132]. Ambruticin S and jerangolid A (2010) The jerangolids [133][134] and the ambruticins [135][136][137] are part of two closely related families of linear polyketides with potent antifungal properties produced by a variety of

Sacrolide A, a new antimicrobial and cytotoxic oxylipin macrolide from the edible cyanobacterium Aphanothece sacrum

• Naoya Oku,
• Miyako Matsumoto,
• Kohsuke Yonejima,
• Keijiroh Tansei and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2014, 10, 1808–1816, doi:10.3762/bjoc.10.190

• chrysogenum) revealed that all these layers varied in the extent of activity against certain test organism(s). Especially intriguing was the antifungal activity exhibited by the n-hexane-soluble fraction, which, in most cases, comprises lipids. To identify the responsible constituent, the fraction was

• successively purified by silica gel chromatography, gel filtration on Sephadex LH-20, and finally by ODS HPLC to yield 1 (1.5 mg, 3.0 × 10−4% w/w). In addition, the antifungal principle in the aqueous MeOH fraction was isolated and identified as the same substance (6.0 mg, 1.2 × 10−3% w/w). The molecular

• cytotoxicity of 1 raised concerns about potential food intoxication. To evaluate the presence of 1 in these products, extracts were prepared and examined by antifungal testing and LC–MS analysis. The products were softened or desalted by soaking in water and then subjected to the same extraction and

Chemistry of polyhalogenated nitrobutadienes, 14: Efficient synthesis of functionalized (Z)-2-allylidenethiazolidin-4-ones

• Viktor A. Zapol’skii,
• Jan C. Namyslo,
• Mimoza Gjikaj and
• Dieter E. Kaufmann

Beilstein J. Org. Chem. 2014, 10, 1638–1644, doi:10.3762/bjoc.10.170

• describe the formation of uniquely substituted thiazolidin-4-ones, a class of compounds which has proven to exhibit distinctive bioactivity, e.g., antifungal, antibacterial, antitubercular, and anticonvulsant properties [18][19][20][21][22][23][24][25][26][27][28]. Additionally, more recent studies often

Microwave-assisted Cu(I)-catalyzed, three-component synthesis of 2-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-benzo[d]imidazoles

• Yogesh Kumar,
• Vijay Bahadur,
• Anil K. Singh,
• Virinder S. Parmar,
• Erik V. Van der Eycken and
• Brajendra K. Singh

Beilstein J. Org. Chem. 2014, 10, 1413–1420, doi:10.3762/bjoc.10.145

• inhibition activity [5][6]. They have also been used to synthesize dyes [7], chemosensitizers [8] and fluorophores [9]. Triazole derivatives have shown antifungal [10], anticancer [11] antituberculosis [12] and antimicrobial [13] activities. Recently, hybrid molecules, connecting two or more distinct drug

Cuevaenes C–E: Three new triene carboxylic derivatives from Streptomyces sp. LZ35ΔgdmAI

• Jing-Jing Deng,
• Chun-Hua Lu,
• Yao-Yao Li,
• Shan-Ren Li and
• Yue-Mao Shen

Beilstein J. Org. Chem. 2014, 10, 858–862, doi:10.3762/bjoc.10.82

• ; found, 354.4193; IR (KBr) vmax: 3338, 3220, 1660, 1592, and 1461 cm−1. For the NMR data see Table 1. Antibacterial and antifungal bioassays: Antibacterial and antifungal activities of compounds 1–5 were tested by the paper disc diffusion method [11]. The bacterial Bacillus subtilis strain ATCC 11060 was

• for 48 h for antifungal activity and at 37 °C for 24 h for antibacterial activity and examined for the presence of a zone of inhibition. Cuevaenes A–E (1–5) isolated from Streptomyces sp. LZ35. Selected NOESY correlations of compounds 1, 3 and 4, 5. 1H and 13C NMR spectroscopy data for compounds 3, 4

Copper–phenanthroline catalysts for regioselective synthesis of pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and of pyrrolo[1,2-a]phenanthrolines under mild conditions

• Rupankar Paira,
• Tarique Anwar,
• Maitreyee Banerjee,
• Yogesh P. Bharitkar,
• Shyamal Mondal,
• Sandip Kundu,
• Abhijit Hazra,
• Prakas R. Maulik and
• Nirup B. Mondal

Beilstein J. Org. Chem. 2014, 10, 692–700, doi:10.3762/bjoc.10.62

• , antifungal, antitumor and anti-HIV candidates [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15]. We have also been pursuing the cycloaddition methodology for several years and established some synthetic routes towards indolizines, pyrrolo[1,2-a]quinolines/isoquinolines, oxazadicyclopenta[a,h]naphthalenes

• etc., some of which have been evaluated as potential antibacterial and antifungal agents [16][17][18][19]. In order to explore the possibility of using structurally more complex dipoles and dipolarophiles to construct more interesting structural networks, we replaced simple alkenes/alkynes with

• /antifungal/spermicidal/lifespan altering agents, where furo[3,2-h]quinoliniums were employed as dipole precursors and maleimide derivatives as dipolarophiles. We initially employed the protocols from our recently developed green methodologies [21][22][23][24][25], which however failed to give any promising

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

• Gijs Koopmanschap,
• Eelco Ruijter and
• Romano V.A. Orru

Beilstein J. Org. Chem. 2014, 10, 544–598, doi:10.3762/bjoc.10.50

• expected compound 109 (Scheme 34). Thiazoles In several natural products, the thiazole ring can be found as a backbone linker, probably resulting from easy cyclization/oxidation of cysteine residues. These compounds show interesting antifungal and antibiotic [95][96], algicidal [97], and antitumor [98][99

• naturally occurring cyclic peptides containing a six-membered core ringsystem. Such DKPs were shown to possess several interesting medicinally relevant properties such as antifungal [133][134], antibacterial [135], and antitumor activity [136][137] but are also used to introduce for example a bitter taste

A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-(arylamino)allyl]chromen-4-ones

• Pitchaimani Prasanna,
• Pethaiah Gunasekaran,
• Subbu Perumal and
• J. Carlos Menéndez

Beilstein J. Org. Chem. 2014, 10, 459–465, doi:10.3762/bjoc.10.43

• ; Introduction Chromones are widely present in nature, especially in the plant kingdom, and a wide variety of useful biological properties are associated with them [1][2]. Chromone derivatives act as effective tyrosine and protein kinase C inhibitors [3] and display antifungal [4][5], antimycobacterial [6

Total synthesis of (+)-grandiamide D, dasyclamide and gigantamide A from a Baylis–Hillman adduct: A unified biomimetic approach

• Andivelu Ilangovan and
• Shanmugasundar Saravanakumar

Beilstein J. Org. Chem. 2014, 10, 127–133, doi:10.3762/bjoc.10.9

• aglaforbesin A (1) and pyramidatin (4) for pyramidaglain (3) as shown in Figure 1 [3]. The benzopyran and benzoxepine containing flavaglins showed insecticidal, antifungal and antiproliferative activity against various cancer cell lines [4]. Apart from acting as precursors for flavaglins, some of the cyclic

SF002-96-1, a new drimane sesquiterpene lactone from an Aspergillus species, inhibits survivin expression

• Silke Felix,
• Louis P. Sandjo,
• Till Opatz and
• Gerhard Erkel

Beilstein J. Org. Chem. 2013, 9, 2866–2876, doi:10.3762/bjoc.9.323

• promoter and subsequently triggering apoptosis in Colo 320 cells. Drimane sesquiterpenes are widespread in plants, fungi and marine organisms such as algae, sponges and corals and have attracted some attention for their potent antibacterial, antifungal, cytotoxic, antifeedant, phytotoxic, piscicidal and

The myxocoumarins A and B from Stigmatella aurantiaca strain MYX-030

• Tobias A. M. Gulder,
• Snežana Neff,
• Traugott Schüz,
• Tammo Winkler,
• René Gees and
• Bettina Böhlendorf

Beilstein J. Org. Chem. 2013, 9, 2579–2585, doi:10.3762/bjoc.9.293

• described in this work. These compounds comprise an unusual structural framework and exhibit remarkable antifungal properties. Keywords: antifungal activity; myxobacteria; natural products; Stigmatella aurantiaca; structure elucidation; Introduction Despite declining interest of most big R&D-driven

• the context of antifungal compounds with around 50% of myxobacteria-derived natural products exhibiting such properties [10]. This activity of myxobacterial metabolites results from diverse modes of action, such as inhibition of DNA replication, transcription and translation, as well as interference

• with cell membrane stability [21]. Inhibition of acetyl-CoA carboxylase is exerted by soraphen A1α (2), which has been shown to be a potent and broad spectrum fungicide [22][23]. The most dominant target of myxobacterial antifungal agents, however, is the mitochondrial respiratory chain [21]. The

The regulation and biosynthesis of antimycins

• Ryan F. Seipke and
• Matthew I. Hutchings

Beilstein J. Org. Chem. 2013, 9, 2556–2563, doi:10.3762/bjoc.9.290

• significant interest in bioengineering new antimycin analogues with improved pharmacological properties for use as antifungal therapeutics and to be used to treat cancers, alongside traditional chemotherapy agents. Substantial progress has been made in a relatively short time and has mostly been driven by

• bioactivity of 5-fluoroantimycins and reported they retained potent antifungal activity against Candida albicans, but were significantly reduced in cytotoxity in a leukemia P388 mouse cell line compared to the parent compounds [25]. Sandy et al. recently showed AntB can accept both acyl-CoAs and acyl-SNACs to

Microwave-assisted synthesis of 5,6-dihydroindolo[1,2-a]quinoxaline derivatives through copper-catalyzed intramolecular N-arylation

• Fei Zhao,
• Lei Zhang,
• Hailong Liu,
• Shengbin Zhou and
• Hong Liu

Beilstein J. Org. Chem. 2013, 9, 2463–2469, doi:10.3762/bjoc.9.285

• , compound A shows pronounced antihistaminic activity [12]. Compound B is identified as a promising antifungal reagent against phytopathogenic fungi in vitro [13], and both compounds C and D exhibit a good inhibitory activity against VEGFR-3 kinase cells [14]. Therefore, an efficient access to this fused

Silica sulfuric acid: a reusable solid catalyst for one pot synthesis of densely substituted pyrrole-fused isocoumarins under solvent-free conditions

• Sudipta Pathak,
• Kamalesh Debnath and
• Animesh Pramanik

Beilstein J. Org. Chem. 2013, 9, 2344–2353, doi:10.3762/bjoc.9.269

• attention of chemists because of their various biological activities such as antioxidative [4], anticancer [5] and antifungal activities [6]. The development of a new and efficient methodology for the synthesis of biologically potent isocoumarins and their carbo/hetero annulated analogues has drawn great

Synthesis and characterization of novel bioactive 1,2,4-oxadiazole natural product analogs bearing the N-phenylmaleimide and N-phenylsuccinimide moieties

• Catalin V. Maftei,
• Elena Fodor,
• Peter G. Jones,
• M. Heiko Franz,
• Gerhard Kelter,
• Heiner Fiebig and
• Ion Neda

Beilstein J. Org. Chem. 2013, 9, 2202–2215, doi:10.3762/bjoc.9.259

• tissue [20][21]. Therefore, designed prodrugs have a higher antitumor efficacy in vivo than drugs. Furthermore, maleimides possess strong antifungal activities against important human opportunistic pathogenic fungi. These antifungal drugs appear to be excellent candidates for further development [22][23

Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives

• Pablo Morán-Poladura,
• Eduardo Rubio and
• José M. González

Beilstein J. Org. Chem. 2013, 9, 2120–2128, doi:10.3762/bjoc.9.249

• for functional applications. Thus, for instance, this molecular frame has been associated with photochromic crystals [7], photochromic organogelators [8], selective cyclooxygenase-2 inhibitors [9][10], antifungal [11] and antitrypanocidal activity [12], transforming growth factor-β receptors [13] and

The chemistry of isoindole natural products

• Klaus Speck and
• Thomas Magauer

Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243

• interesting biological properties, such as high antiviral activity (156) [141], inhibition of the HIV-1 protease (157) [132], antibacterial and antifungal activities (159–160) [133] or neuritogenic properties (161) [134]. So far, only a few total syntheses were accomplished and the exact biosynthetic pathways

• completed the synthesis of stachybotrylactam I (157). Chlorinated isoindolinone alkaloids: Pestalachloride A (193) was isolated from the plant endophytic fungus Pestalotiopsis adusta as a racemate and displays potent antifungal activities against Fusarium culmorum (IC50 = 0.89 µM) [147]. Pestalone (192), a

• trichlorocarbinol ester. A first biological evaluation showed that 204 displays antifungal activity. However, only 90 µg could be isolated and further biological screening was not possible [151]. Several sponge-derived macrolides have proven to be effective cytotoxic agents [152][153] and one could speculate that

AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldoximes with α,β-unsaturated carbonyl compounds

• Qiuping Ding,
• Dan Wang,
• Puying Luo,
• Meiling Liu,
• Shouzhi Pu and
• Liyun Zhou

Beilstein J. Org. Chem. 2013, 9, 1949–1956, doi:10.3762/bjoc.9.231

• processes. Isoquinoline derivatives, an important class of nitrogen-containing polycyclic heteroarenes, have attracted considerable attention because of their pharmacological activities, including antitumor, antifungal, antimalarial, antihypertensive and antihistaminic activity, and their photo- and

Synthesis and biological activities of the respiratory chain inhibitor aurachin D and new ring versus chain analogues

• Xu-Wen Li,
• Jennifer Herrmann,
• Yi Zang,
• Philippe Grellier,
• Soizic Prado,
• Rolf Müller and
• Bastien Nay

Beilstein J. Org. Chem. 2013, 9, 1551–1558, doi:10.3762/bjoc.9.176

• some ring as opposed to chain analogues, allowing for the description of structure–activity relationships. Biological screening of the analogues showed antiparasitic, cytotoxic, antibacterial and antifungal activities, and depletion of the mitochondrial membrane potential. The strongest activity was

• , Lionel Dubost and Caroline Bance for performing NMR, MS and antifungal tests, respectively. The CNRS and the MNHN are acknowledged for daily financial support.

Coupling of C-nitro-NH-azoles with arylboronic acids. A route to N-aryl-C-nitroazoles

• Marta K. Kurpet,
• Aleksandra Dąbrowska,
• Małgorzata M. Jarosz,
• Katarzyna Kajewska-Kania,
• Nikodem Kuźnik and
• Jerzy W. Suwiński

Beilstein J. Org. Chem. 2013, 9, 1517–1525, doi:10.3762/bjoc.9.173

• veterinary science [3], and as propellants and precursors of energetic materials [4]. Special attention has been paid to the development of their application in medicine where so far they are used as antiprotozoal, antifungal, and antibacterial drugs [5][6], as hypoxic cell sensitizers in radiation therapy