Structure and conformational analysis of spiroketals from 6-O-methyl-9(E)-hydroxyiminoerythronolide A

• Ana Čikoš,
• Irena Ćaleta,
• Dinko Žiher,
• Mark B. Vine,
• Ivaylo J. Elenkov,
• Marko Dukši,
• Dubravka Gembarovski,
• Marina Ilijaš,
• Snježana Dragojević,
• Ivica Malnar and
• Sulejman Alihodžić

Beilstein J. Org. Chem. 2015, 11, 1447–1457, doi:10.3762/bjoc.11.157

• example, in cases of calyculin and okadaic acid it has been proposed [18][19] that the spiroketal unit acts as a β-turn mimic. Naturally occurring spiroketals exhibit a wide spectrum of biological activity: anticancer [20][21][22], antibiotic [23][24], antifungal [25], anthelmintic [26] and anti-HIV [27

New depsidones and isoindolinones from the mangrove endophytic fungus Meyerozyma guilliermondii (HZ-Y₂) isolated from the South China Sea

• Senhua Chen,
• Zhaoming Liu,
• Yayue Liu,
• Yongjun Lu,
• Lei He and
• Zhigang She

Beilstein J. Org. Chem. 2015, 11, 1187–1193, doi:10.3762/bjoc.11.133

• of bioactivities including antibacterial [10], antifungal [6], antiviral [12], antioxidant [5], and cytotoxic [9]. In the last decade, our research group has been focused on isolating novel compounds from endophytic fungi growing on mangroves in the South China Sea and investigating their bioactivity

Thiazole formation through a modified Gewald reaction

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

Beilstein J. Org. Chem. 2015, 11, 875–883, doi:10.3762/bjoc.11.98

• number of therapeutic areas including anticancer, antifungal, antibacterial, anti-inflammatory and as antidepressants (Figure 1) [1]. Several protocols have already been described for the synthesis of substituted thiazoles and benzothiazoles [2][3][4][5][6][7][8][9][10][11]. The current first choice

N-Alkyl derivatives of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside; synthesis and antimicrobial activity

• Agata Walczewska,
• Daria Grzywacz,
• Dorota Bednarczyk,
• Małgorzata Dawgul,
• Andrzej Nowacki,
• Wojciech Kamysz,
• Beata Liberek and
• Henryk Myszka

Beilstein J. Org. Chem. 2015, 11, 869–874, doi:10.3762/bjoc.11.97

• glucopyranoside is presented. Evaluation of antibacterial and antifungal activities of these derivatives indicates that they have no inhibitory activity against Gram-negative bacteria, whereas many of the tested N-alkyl saponins were found to inhibit the growth of Gram-positive bacteria and human pathogenic fungi

• used as detergents, surfactants and emulsifiers. Moreover, they display a wide range of pharmacological activities, including antifungal, antiparasitic, antiinflammatory, antibacterial, and antitumor activities [2][3][4][5]. No wonder, saponins have been evaluated as vaccine adjuvants [6]. Despite the

• their cardiovascular, antifungal, anticancer [33][34][35][36] and antithrombotic activities [37] have been investigated. Gelation ability of the pentose derivatized diosgenyl saponins have also been reported [38]. In the family of diosgenyl β-glycosides D-glucopyranose is the first sugar attached to the

Novel biphenyl-substituted 1,2,4-oxadiazole ferroelectric liquid crystals: synthesis and characterization

• Mahabaleshwara Subrao,
• Dakshina Murthy Potukuchi,
• Girish Sharada Ramachandra,
• Poornima Bhagavath,
• Sangeetha G. Bhat and
• Srinivasulu Maddasani

Beilstein J. Org. Chem. 2015, 11, 233–241, doi:10.3762/bjoc.11.26

• ; SmC* phase; spontaneous polarization; Suzuki coupling; Introduction The 1,2,4-oxadiazole derivatives are prevalently reported compounds with promising biological [1][2][3][4][5] and physiological [6][7][8] activity such as antiinflammatory, antibacterial, antimicrobial, antifungal, anticancer

Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes

• Philipp Röse,
• Steffen Emge,
• Jun-ichi Yoshida and
• Gerhard Hilt

Beilstein J. Org. Chem. 2015, 11, 174–183, doi:10.3762/bjoc.11.18

• are in turn potential substrates for the synthesis of functionalised heterocycles. Particularly, we were interested in the synthesis of tetrahydrofuran and pyran derivatives. Those heterocycles are prevalent substructures in many natural compounds, pesticides and drugs with antifungal and

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

• Lidija-Marija Tumir,
• Marijana Radić Stojković and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2930–2954, doi:10.3762/bjoc.10.312

• bioactivity-guided fractionation, the bioactive compound chelerythrine (21, a quaternary benzo[c]phenanthridine alkaloid) was isolated from Chelidonium majus L. [103]. In addition to strong antihelmintic activity (against D. intermedius), chelerythrine also showed antimicrobial, antifungal and anti

Cyclodextrin–polysaccharide-based, in situ-gelled system for ocular antifungal delivery

• Anxo Fernández-Ferreiro,
• Noelia Fernández Bargiela,
• María Santiago Varela,
• Maria Gil Martínez,
• Maria Pardo,
• Antonio Piñeiro Ces,
• José Blanco Méndez,
• Miguel González Barcia,
• Maria Jesus Lamas and
• Francisco.J. Otero-Espinar

Beilstein J. Org. Chem. 2014, 10, 2903–2911, doi:10.3762/bjoc.10.308

• lead to loss of vision. Candida albicans is one of the most widespread fungal pathogens involved in fungal keratitis [1][2]. The most common antifungal treatments include the use of polyenes and azoles; however, a significant treatment failure rate exists with these pharmacological agents [3

• most eye fungal infections; however, there are resistant species that require higher concentrations than usual [5]. Unfortunately, antifungal eye drops have low ocular bioavailability due to their poor water solubility and known effective eye clearance mechanisms [6]. Thus, after administration of

• the drug release for approximately 4 hours. Additionally, a higher dose of fluconazole incorporated in the hydrogels containing cyclodextrins allowed the release of a higher quantity of the antifungal (α < 0.05). Insignificant differences in the drug release properties were observed as a function of

Recent advances in the electrochemical construction of heterocycles

• Robert Francke

Beilstein J. Org. Chem. 2014, 10, 2858–2873, doi:10.3762/bjoc.10.303

• -step of the synthesis of glycozoline 37, an antifungal and antibacterial agent. Analogously, 38 was converted to 39 as a part of the multistep synthesis of two different tetrahydropyrroloiminoquinone alkaloids 40 and 41 (Scheme 15) [58][60]. Tanaka et al. could achieve the electrochemical construction

Thermal and oxidative stability of the Ocimum basilicum L. essential oil/β-cyclodextrin supramolecular system

• Daniel I. Hădărugă,
• Nicoleta G. Hădărugă,
• Corina I. Costescu,
• Ioan David and
• Alexandra T. Gruia

Beilstein J. Org. Chem. 2014, 10, 2809–2820, doi:10.3762/bjoc.10.298

• concentrations of volatile compounds (essential oils or volatile oils), among other compounds (e.g., flavonoids) [10], which furnish different flavoring and medicinal properties, such as antimicrobial, anti-inflammatory, analgesic, or antiseptic properties [11][12][13][14], in addition to antifungal and insect

Aspergiloid I, an unprecedented spirolactone norditerpenoid from the plant-derived endophytic fungus Aspergillus sp. YXf3

• Zhi Kai Guo,
• Rong Wang,
• Wei Huang,
• Xiao Nian Li,
• Rong Jiang,
• Ren Xiang Tan and
• Hui Ming Ge

Beilstein J. Org. Chem. 2014, 10, 2677–2682, doi:10.3762/bjoc.10.282

• , Alternaria solani Jones et Grout, Sclerotinia sclerotiorum de Bary, Fusarium graminearum Schw., Fusarium coeruleum Sacc., and Botrytis cinerea Pers.) were tested. Aspergiloid I (1) showed no antibacterial or antifungal activity at a concentration of 20 μg/mL. It also had no antifungal activity against

Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens

• Véronique Nardello-Rataj and
• Loïc Leclercq

Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273

• antifungal effect of p-hydroxybenzoic acid esters against C. albicans is directly linked to their hydrophobicity: the minimal inhibition concentrations were directly correlated to the nature of the residue. Table 3 also highlights that the antimicrobial activity of the preservatives is reduced in the

• absorption is significantly increased. In other words, the rate of absorption is accelerated because of bioavailability improvement. In 2002, Schirra et al. reported on the inclusion of 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole (named enilconazole, see Figure 2) in the β-CD and the antifungal

• typical examples of CDs/biocide inclusion on textile are reported. In 2008, Wang et al. incorporated the miconazole nitrate (Figure 6) into the cavity of MCT-β-CD covalently bound onto cloth fibers. The miconazole salts are antifungal agents with additional antibacterial and antiparasitic actions [63

A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline

• Chunpu Li,
• Lei Zhang,
• Shuangjie Shu and
• Hong Liu

Beilstein J. Org. Chem. 2014, 10, 2441–2447, doi:10.3762/bjoc.10.254

• pharmaceutical compounds [1][2][3][4][5]. In particular, tetracyclic compounds containing the indole substructure represent an important structural motif in a variety of bioactive compounds, such as antitumor agents A [6] and antifungal agents B [7] (Figure 1). Therefore, it is necessary to develop efficient and

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