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

• tested compounds the most active was diosgenyl 2-deoxy-2-ethylamino-β-D-glucopyranoside (9) with MIC of 0.5, 1, 2, and 8 μg/mL against Staphylococcus epidermidis, Enterococcus faecalis, Staphylococcus aureus, and Rhodococcus equi, respectively. Also the N-propyl derivative 11 was found to be active

• against Enterococcus faecalis, Staphylococcus epidermidis, and Staphylococcus aureus with MIC of 1, 1, and 8 μg/mL, respectively. Importantly, both 9 and 11 exhibit a stronger inhibitory effectivity than diosgenyl 2-deoxy-2-amino-β-D-glucopyranoside hydrochloride (7·HCl), which was found to be very active

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

• ) structures [101], the presence of a 1-phenyl or 12-phenyl substituent on 2,3,8,9-tetramethoxy-5-ethylbenzo[c]phenanthridinium chloride [102] significantly enhances the antibacterial (Staphylococcus aureus and Enterococcus faecalis) activity relative to sanguinarine. Another example, using the strategy of

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

• -hydroxybenzoate, benzyl alcohol, 2-phenoxyethanol) [45]. The authors established a clear relationship between the binding constants and the antimicrobial activity of the preservatives on various strains: Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli and C. albicans. Indeed, highly water-soluble

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

• the synthesis of the interesting compound vibrindole A (Scheme 2), an isolated metabolite of the marine bacteria Vibrio parahaemolyticus, which is active against Bacillus subtilis, Staphylococcus aureus and Staphylococcus albus as has been previously demonstrated [43]. In order to prevent the loss of

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

• tricyclic intermediate 121. Cleavage of the TBS ethers and hydrogenolysis of the benzyl ester in presence of amidine 122 yielded trinem 23a as its amidinium salt 123. Trinem 123 exhibited antibacterial activity against a variety of strains, with MIC’s of 1.0 μg/mL against Staphylococcus aureus 853E and 0.1

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

• . Antimicrobial testing against four Gram-positive bacteria (Bacillus subtilis, Micrococcus luteus, Staphylococcus aureus, and Streptomyces lividans), one Gram-negative bacterium (Escherichia coli), two yeasts (Candida albicans and Saccharomyces cerevisiae), and two fungi (Aspergillus oryzae and Penicillum

• the growth of Gram-positive bacteria (Micrococcus luteus, Streptomyces lividans, Staphylococcus aureus, Bacillus subtilis), a yeast (Saccharomyces cerevisiae) and a fungus (Penicillium chrysogenum) (Table 2). Moreover, 1 was cytotoxic to 3Y1 rat fibroblasts (GI50 4.5 μM). Under microscopic observation

• strains were grown on agar media (Staphylococcus aureus FDA209P JC-1, Micrococcus luteus ATCC9341, Escherichia coli NIHJ JC-2, Saccharomyces cerevisiae S100, and Candida albicans A9540) or in Sabouraud broth (Penicillum chrysogenum NBRC4626, Streptomyces lividans TK23) overnight and then diluted with

Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid

• Patrick Rabe,
• Tim A. Klapschinski,
• Nelson L. Brock,
• Christian A. Citron,
• Paul D’Alvise,
• Lone Gram and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2014, 10, 1796–1801, doi:10.3762/bjoc.10.188

• several structural analogues of TDA and used them in bioactivity tests against Staphylococcus aureus and Vibrio anguillarum for a structure–activity relationship (SAR) study, revealing that the sulfur-free analogue of TDA, tropone-2-carboxylic acid, has an antibiotic activity that is even stronger than

• , the Gram-positive Staphylococcus aureus 8325 and the Gram-negative Vibrio anguillarum 90-11-287 (Table 1). These organisms were selected for our bioactivity tests, because S. aureus is a clinically important human pathogen and strains with resistances against multiple antibiotic drugs cause severe

• . All synthetic compounds were used in bioactivity tests towards two bacterial strains, Staphylococcus aureus 8325 [22] and Vibrio anguillarum 90-11-287 [23] (Table 1). The two strains were grown as precultures overnight with agitation at 25 °C in 20 mL cation-adjusted Mueller Hinton II Broth (Cat. No

Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery

• Jens Schmidt,
• Zeinab Khalil,
• Robert J. Capon and
• Christian B. W. Stark

Beilstein J. Org. Chem. 2014, 10, 1228–1232, doi:10.3762/bjoc.10.121

• near Heron Island, Queensland, Australia (Figure 1) [1]. As first in class examples of natural products featuring a 2-nitropyrrole, further elaborated by a farnesyl side chain, the heronapyrroles exhibited promising antibacterial activity against Staphylococcus aureus (ATCC 2593 and 9144) and Bacillus

• activity against the Gram-positive bacteria Staphylococcus aureus ATCC 25923 (IC50 1.8 μM), Staphylococcus epidermidis ATCC 12228 (IC50 0.9 μM) and Bacillus subtilis ATCC 6633 (IC50 1.8 μM), but was inactive (IC50 > 30 μM) against the Gram-negative bacteria Pseudomonas aeruginosa ATCC 10145 and Escherichia

New sesquiterpene hydroquinones from the Caribbean sponge Aka coralliphagum

• Qun Göthel and
• Matthias Köck

Beilstein J. Org. Chem. 2014, 10, 613–621, doi:10.3762/bjoc.10.52

• -positive and Gram-negative bacteria, fungi, and for antiproliferative activity. The results given in Table 4 show that siphonodictyal E3 (3) and cyclosiphonodictyol A (5) exhibited mild activity against the Gram-positive bacteria Staphylococcus aureus and Micrococcus luteus, while siphonodictyal E4 (4

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

• natural product and synthetic precursor of 193 shows strong antibiotic activity against methicillin-resistant Staphylococcus aureus (MRSA, MIC = 84 nM) and vancomycin-resistant Enterococcus (VRE, MIC = 178 nM) [148]. The structural similarity between pestalachloride A (193) and pestalone (192), which both

• : Lactonamycin (215) and lactonamycin Z (217) were isolated from Streptomyces rishiriensis and Streptomyces anglieri in 1996 and 2003 [157][158]. Both compounds are potent antibacterial agents against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant

Synthesis and antibacterial activity of monocyclic 3-carboxamide tetramic acids

• Yong-Chul Jeong and
• Mark G. Moloney

Beilstein J. Org. Chem. 2013, 9, 1899–1906, doi:10.3762/bjoc.9.224

• ). Antibacterial activity The antibiotic activities of tetramates 2a–h and 3a–f along with analogues 1c and 1d (reported by Novartis [8]) were determined against 4 species of Gram-positive bacteria, consisting of 4 strains of Staphylococcus aureus, including a methicillin-resistant strain (MRSA, S2), vancomycin

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

• (Candida albicans) nor on molds (Mucor hiemalis, Fusarium oxysporum, Alternaria alternata). The natural compound 4 was one of the most active compounds, but also shorter chain analogues 9 and 10 inhibited, for instance, the growth of Staphylococcus aureus at concentrations in the low µg/mL range, whereas

A reductive coupling strategy towards ripostatin A

• Kristin D. Schleicher and
• Timothy F. Jamison

Beilstein J. Org. Chem. 2013, 9, 1533–1550, doi:10.3762/bjoc.9.175

• ribonucleic acid polymerase. These compounds inhibit chain initiation of RNA synthesis in Staphylococcus aureus, a particularly infectious bacterial strain with reported drug resistance to the antibiotics vancomycin and methicillin [3]. Ripostatin A exists as an equilibrium mixture of ketone and hemiketal

Multivalent display of the antimicrobial peptides BP100 and BP143

• Imma Güell,
• Rafael Ferre,
• Kasper K. Sørensen,
• Esther Badosa,
• Iteng Ng-Choi,
• Emilio Montesinos,
• Eduard Bardají,
• Lidia Feliu,
• Knud J. Jensen and
• Marta Planas

Beilstein J. Org. Chem. 2012, 8, 2106–2117, doi:10.3762/bjoc.8.237

• phytopathogenic bacteria Erwinia amylovora, Xanthomonas axonopodis pv. vesicatoria, and Pseudomonas syringae pv. syringae, and of human pathogenic bacteria Escherichia coli, Staphylococcus aureus, Lysteria monocytogenes, and Salmonella enterica at 0.6, 1.2, 2.5, 5, 7.5, 10 and 20 μM (Table 1). The antibacterial

• , Staphylococcus aureus subsp. aureus ATCC 9144 and Salmonella enterica subsp. enterica LT2 ATCC 15277. All bacteria were stored in Luria Bertani (LB) broth except for L. monocytogenes, which was stored in Brain Heart Infusion (BHI) broth (Oxoid, Hampshire, United Kingdom) supplemented with glycerol (20%) and

Modulating the activity of short arginine-tryptophan containing antibacterial peptides with N-terminal metallocenoyl groups

• H. Bauke Albada,
• Alina-Iulia Chiriac,
• Michaela Wenzel,
• Maya Penkova,
• Julia E. Bandow,
• Hans-Georg Sahl and
• Nils Metzler-Nolte

Beilstein J. Org. Chem. 2012, 8, 1753–1764, doi:10.3762/bjoc.8.200

• running dry [1]. For example, the number of methicillin-resistant Staphylococcus aureus (MRSA) infections in hospitals are still very high and new infectious agents like Acinetobacter baumannii are on the rise, both leading to increased numbers of mortality. In view of this, the discovery of host-defense

• in Table 2) The minimal inhibitory concentrations (MIC) were tested against Escherichia coli DSM 30083, Acinetobacter baumannii DSM 30007, Pseudomonas aeruginosa DSM 50071, Bacillus subtilis DSM 402, Staphylococcus aureus DSM 20231 (type strain), and Staphylococcus aureus ATCC 43300 (MRSA) in a

A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues

• James R. Cochrane,
• Dong Hee Yoon,
• Christopher S. P. McErlean and
• Katrina A. Jolliffe

Beilstein J. Org. Chem. 2012, 8, 1344–1351, doi:10.3762/bjoc.8.154

• strains of Bacillus (Paenebacillus) and exhibit antifungal and antibacterial activity against a range of clinically relevant species, including Candida albicans, Cryptococcus neoformans, Staphylococcus aureus and Micrococcus luteus [1][2][3][4][5][6][7]. These compounds have a cyclic hexadepsipeptide core

Binaphthyl-anchored antibacterial tripeptide derivatives with hydrophobic C-terminal amino acid variations

• John B. Bremner,
• Paul A. Keller,
• Stephen G. Pyne,
• Mark J. Robertson,
• K. Sakthivel,
• Kittiya Somphol,
• Dean Baylis,
• Jonathan A. Coates,
• John Deadman,
• Dharshini Jeevarajah and
• David I. Rhodes

Beilstein J. Org. Chem. 2012, 8, 1265–1270, doi:10.3762/bjoc.8.142

• -terminal amino acid component, is described. Moderate to good activity was seen against Gram-positive bacteria in vitro. One cyclohexyl-substituted compound 2c was tested more widely and showed good potency (MIC values ranging from 2–4 μg/mL) against antibiotic-resistant strains of Staphylococcus aureus

• salts 2a–g were tested against the Gram-positive bacteria Staphylococcus aureus (ATCC 6538) and four clinical isolates of vancomycin-resistant (and sensitive) enterococci (VRE; Enterococcus faecium), and the results are shown in Table 1; some compounds were also tested against Staphylococcus epidermidis

• % pure. Determination of minimum inhibitory concentration (MIC) MIC studies (Table 1) were performed on Staphylococcus aureus wild type (ATCC 6538P), and Staphylococcus epidermidis (ATCC 12228) in Mueller–Hinton broth (Oxoid Ltd, England) supplemented with 50 mg/L CaCl2. As in [6], MIC determinations for

Partial thioamide scan on the lipopeptaibiotic trichogin GA IV. Effects on folding and bioactivity

• Marta De Zotti,
• Barbara Biondi,
• Cristina Peggion,
• Matteo De Poli,
• Haleh Fathi,
• Simona Oancea,
• Claudio Toniolo and
• Fernando Formaggio

Beilstein J. Org. Chem. 2012, 8, 1161–1171, doi:10.3762/bjoc.8.129

• bacterial strains. We found that [Leu11-OMe] trichogin GA IV is active on the Gram-positive bacteria Staphylococcus aureus and Streptococcus pyrogenes, whereas the spectrum of action of its three analogues is more restricted, as they are not active on the latter strain. The activities of the analogues on S

• activity assay was performed in a similar way to that described in reference [77]. The activity of peptides was tested against clinical isolates of bacteria and reference bacterial strains: Staphylococcus aureus American Type Culture Collection strains (ATCC) 25923, Streptococcus pyogenes ATCC 19615

Similarity analysis, synthesis, and bioassay of antibacterial cyclic peptidomimetics

• Workalemahu M. Berhanu,
• Mohamed A. Ibrahim,
• Girinath G. Pillai,
• Alexander A. Oliferenko,
• Levan Khelashvili,
• Farukh Jabeen,
• Bushra Mirza,
• Farzana Latif Ansari,
• Ihsan ul-Haq,
• Said A. El-Feky and
• Alan R. Katritzky

Beilstein J. Org. Chem. 2012, 8, 1146–1160, doi:10.3762/bjoc.8.128

• -, O-, C- and S-acylations. Results and Discussion Similarity analysis Our literature search identified the thirty three cyclic peptides and peptidomimetic structures given in Table 1. All the minimum inhibition constants (MIC) are pertinent to Staphylococcus aureus. These include (i) one 12-membered

• dataset of existing analogues. As abundant data can be found in the literature for Staphylococcus aureus, this was chosen as a reference for antibacterial activity. SciFinder Scholar was used to retrieve the structures of 33 cyclic peptides with reported antibacterial activity (Table 1). The minimum

Synthesis of szentiamide, a depsipeptide from entomopathogenic Xenorhabdus szentirmaii with activity against Plasmodium falciparum

• Friederike I. Nollmann,
• Andrea Dowling,
• Marcel Kaiser,
• Klaus Deckmann,
• Sabine Grösch,
• Richard ffrench-Constant and
• Helge B. Bode

Beilstein J. Org. Chem. 2012, 8, 528–533, doi:10.3762/bjoc.8.60

• different Gram-positive (Micrococcus luteus, Bacillus subtilis, Staphylococcus aureus) and Gram-negative (Escherichia coli, Pseudomonas aeroginosa) bacteria, as well as yeast (Candida albicans, Saccharomyces cerivisiae). However, consistent with the published data [12], no antibacterial or antifungal

Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities

• Hany M. Mohamed,
• Ashraf H. F. Abd EL-Wahab,
• Ahmed M. EL-Agrody,
• Ahmed H. Bedair,
• Fathy A. Eid,
• Mostafa M. Khafagy and
• Kamal A. Abd-EL-Rehem

Beilstein J. Org. Chem. 2011, 7, 1688–1696, doi:10.3762/bjoc.7.199

• activity, better than the standard ampicillin, against two species of Gram-positive bacteria, Staphylococcus aureus (NCTC-7447), Bacillus cereus (ATCC-14579) and two Gram-negative bacteria, Escherichia coli (NCTC-10410) and Serratia marcescens (IMRU-70), while the same compounds showed moderate antifungal

• bacteria, namely Staphylococcus aureus (NCTC-7447), Bacillus cereus (ATCC-14579), and two Gram-negative bacteria, namely Escherichia coli (NCTC-10410), Serratia marcescens (IMRU-70); and against two species of fungi, namely Aspergillus fumigatus (MTCC-3008) and Candida albicans (MTCC-227). The tested

Scalable synthesis of (1-cyclopropyl)cyclopropylamine hydrochloride

• Sergei I. Kozhushkov,
• Alexander F. Khlebnikov,
• Rafael R. Kostikov,
• Dmitrii S. Yufit and
• Armin de Meijere

Beilstein J. Org. Chem. 2011, 7, 1003–1006, doi:10.3762/bjoc.7.113

• )cyclopropylamine (4) have been found to be useful variously for the treatment of hepatitis C [3][4], as pest control agents [5], as inhibitors of methicillin-resistant Staphylococcus aureus [5], as pesticides, insecticides and acaricides [7][8][9][10][11][12][13] and more. This amine has been prepared from

Synthesis, reactivity and biological activity of 5-alkoxymethyluracil analogues

• Lucie Brulikova and
• Jan Hlavac

Beilstein J. Org. Chem. 2011, 7, 678–698, doi:10.3762/bjoc.7.80

• tested for their antimicrobial activity against standard reference gram-positive and gram-negative bacterial strains such as Enterococcus faecalis CCM 4224, Staphylococcus aureus CCM 3953, Escherichia coli CCM 3954 and Pseudomonas aeruginosa CCM 3955 and against gram-positive and gram-negative bacteria

• obtained from clinical material of patients treated at the University Hospital in Olomouc (methicillin resistant Staphylococcus aureus - MRSA, Staphylococcus haemolyticus, Escherichia coli and Pseudomonas aeruginosa) with resistance to currently used fluoroquinolones. Only the octyl and nonyl derivatives

• 126h, 127h and 126i, 127i showed slight activity against Enterococcus faecalis CCM 4224, Staphylococcus aureus CCM 3953, Staphylococcus aureus (MRSA) and Staphylococcus haemolyticus. Conclusion This review was an attempt to summarize all available information on the synthesis and biological activity of