Design of a novel tryptophan-rich membrane-active antimicrobial peptide from the membrane-proximal region of the HIV glycoprotein, gp41

• Evan F. Haney,
• Leonard T. Nguyen,
• David J. Schibli and
• Hans J. Vogel

Beilstein J. Org. Chem. 2012, 8, 1172–1184, doi:10.3762/bjoc.8.130

• , helical structure and phospholipid bilayer interactions [22]. The results obtained with the gp41w-derived peptides reveal a complex relationship between the structural factors that contribute to the antibacterial activity and the features that determine the hemolytic activity. A large proportion of AMPs

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

• vesicles in the absence of peptide, Ft = fluorescence intensity of vesicles at time t in the presence of peptide, and FT = total fluorescence intensity determined by disrupting the vesicles by the addition of 50 μL of a Triton X-100 solution. The experiments were stopped at 20 min. Antibacterial activity

• Peptide antibacterial activity was tested against Gram-positive and Gram-negative bacteria by the standardized disk diffusion Bauer–Kirby method [75] using the Müller–Hinton culture medium at pH 7.2–7.4 as recommended by the National Committee for Clinical Laboratory Standards [76]. The antibacterial

• 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

• . Some of the synthesized compounds were tested against an array of microorganisms and showed antibacterial activity against Bordetella bronchistepica, Micrococcus luteus, and Salmonella typhimurium. Keywords: antibacterial; cluster analysis; N-acylbenzotriazoles; peptidomimetics; similarity

• activity, with compounds 24 and 27 being the most active. The side-chain substitution clearly controls the antibacterial activity, as the cyclic scaffold is identical. The 18-membered ring scaffold 37, accessible through the benzotriazole route, provides an excellent opportunity for introducing

• bis(S-acylcysteine) 36 forming the pyridine–cysteine-containing macrocycle 40 in 70% yield (Scheme 3, see Supporting Information File 1 for experimental details). Bioassay Screening for antibacterial activity was performed for two cyclic peptidomimetics belonging to scaffold 37, namely 37a and 37b

Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step

• Dieter Enders,
• Jeanne Fronert,
• Tom Bisschops and
• Florian Boeck

Beilstein J. Org. Chem. 2012, 8, 1112–1117, doi:10.3762/bjoc.8.123

• used in the treatment of vitiligo, psoriasis and other skin diseases [3]. Some furocoumarins exhibit vasodilatory, antifungal and antibacterial activity [4][5]. Smyrindiol (1), also called (+)-(2’S,3’R)-3-hydroxymarmesin [7], is a linear dihydrofurocoumarin, which was isolated from the roots of

Chemistry of polyhalogenated nitrobutadienes, 10: Synthesis of highly functionalized heterocycles with a rigid 6-amino-3-azabicyclo[3.1.0]hexane moiety

• Viktor A. Zapol’skii,
• Jan C. Namyslo,
• Armin de Meijere and
• Dieter E. Kaufmann

Beilstein J. Org. Chem. 2012, 8, 621–628, doi:10.3762/bjoc.8.69

• (Scheme 5). These amides 20 and 21 are hot candidates for biological testing, as some known amides of 4-chloroisothiazol-3-carboxylic acid have been shown to exhibit high antibacterial activity [25][26][27]. The high number of heteroatoms in 20 and 21, accompanied by only a few hydrogen atoms, requires 1H

Phytoalexins of the Pyrinae: Biphenyls and dibenzofurans

• Cornelia Chizzali and
• Ludger Beerhues

Beilstein J. Org. Chem. 2012, 8, 613–620, doi:10.3762/bjoc.8.68

• dibenzofurans. The antibacterial activity of biphenyls and dibenzofurans is less well studied [24][25]. Recently, a number of the Pyrinae-specific phytoalexins were tested for in vitro antibacterial activity against E. amylovora, the fire-blight-causing agent [12]. 3,5-Dihydroxybiphenyl was the most active

• compound with a minimum inhibitory concentration (MIC) of 115 μg/mL. While this concentration was bactericidal, a concentration approximately ten times lower led to 50% growth inhibition (MIC50 = 17 μg/mL). Biphenyls exhibited somewhat stronger antibacterial activity than structurally related dibenzofurans

Mutational analysis of a phenazine biosynthetic gene cluster in Streptomyces anulatus 9663

• Orwah Saleh,
• Katrin Flinspach,
• Lucia Westrich,
• Andreas Kulik,
• Bertolt Gust,
• Hans-Peter Fiedler and
• Lutz Heide

Beilstein J. Org. Chem. 2012, 8, 501–513, doi:10.3762/bjoc.8.57

• as = +16.8 (c = 0.33, MeOH). Endophenazine E is a new natural product. The conjugation of a phenazine to N-acetylcysteine has been described previously [17]. In that case, conjugation occurred through the thiol group of cysteine and led to the loss of the antibacterial activity of the phenazine. A

Carbamate derivatives and sesquiterpenoids from the South China Sea gorgonian Melitodes squamata

• Li-Si Huang,
• Fei He,
• Hui Huang,
• Xiao-Yong Zhang and
• Shu-Hua Qi

Beilstein J. Org. Chem. 2012, 8, 170–176, doi:10.3762/bjoc.8.18

• rarely found in marine natural compounds, and 7 showed moderate antibacterial activity. The possible biosynthesis routes of 1–5 were conjectured. Keywords: carbamate; gorgonian; Melitodes squamata; sesquiterpenoid; Introduction Gorgonians are recognized to mainly produce acetogenins, sesquiterpenoids

• 1, 2, 6, and 7 have not been previously reported. The cytotoxicity of 1–9 against human malignant melanoma A735 and cervical carcinoma HeLa cell lines, and the antibacterial activity of 1–5 and 7 towards bacteria Escherichia coli, Bacillus subtilis and Micrococcus luteus were evaluated. The possible

• by MTT assay. The results show that 1–9 does not exhibit cytotoxicity against A735 and HeLa cell lines with IC50 > 200 μg/mL. Antibacterial activity of compounds 1–5 at a concentration of 25 μg/disc (diameter 6 mm) was measured against bacteria Escherichia coli, Bacillus subtilis, and Micrococcus

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

• ampicillin (30 µg mL−1) as the standard antibiotic reference for antibacterial activity, and calforan (30 µg mL−1) was used as a reference antifungal activity. The tested compounds were dissolved in N,N-dimethylformamide (DMF) to give a solution of 1 mg mL−1. The inhibition zones (diameter of the hole) were

• presence of diiodocoumarin-3-carboxamides decreased the antimicrobial activity. Graphical representation of the antibacterial activity of tested compounds compared to ampicillin. Graphical representation of antifungal activity of tested compounds, compared to calforan. Synthesis of 6,8-diiodocoumarin

• structures of all newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR and mass spectrometry. The inhibitory effects of the synthetic compounds against these organisms are given in Table 1, Figure 1 and Figure 2. Among the series tested, compounds 12–14a,b exhibited excellent antibacterial

Toward an integrated route to the vernonia allenes and related sesquiterpenoids

• Da Xu,
• Michael A. Drahl and
• Lawrence J. Williams

Beilstein J. Org. Chem. 2011, 7, 937–943, doi:10.3762/bjoc.7.104

• promyelocytic leukemia cell line in a dose-dependent manner [26], and ester derivatives of salonitenolide 12 show promising antibacterial activity [27]. We have initiated a study that aims to integrate the chemical syntheses of compounds in this structure space into a single, late-stage-divergent, route [28]. A

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

• previously mentioned compounds were synthesized in order to evaluate their antiviral and cytotoxic activity. Moreover, antibacterial activity of some of these derivatives has also been studied. Some of the tested compounds have shown interesting results and a brief survey is given in the following section

• reference carboplatin or 6-thioguanine, interesting relationships between activity and length of alkyl chain were observed. Antibacterial activity The recurrence of the chronic infectious disease tuberculosis has initiated research on new classes of antimycobacterial agents. The exigency of new drugs was

An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

• Marcus Baumann,
• Ian R. Baxendale,
• Steven V. Ley and
• Nikzad Nikbin

Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57

Application of the diastereoselective photodeconjugation of α,β-unsaturated esters to the synthesis of gymnastatin H

• Ludovic Raffier and
• Olivier Piva

Beilstein J. Org. Chem. 2011, 7, 151–155, doi:10.3762/bjoc.7.21

• exhibit antibacterial activity and cytotoxities against cultured P388 cancer cells. Interestingly, the same acid chain with an R-configuration has been identified in other structures like dankastatins [11] isolated from the same source, aranorosin (11) isolated from Pseudoarachniotus roseus [12] and

Pyridinium based amphiphilic hydrogelators as potential antibacterial agents

• Sayanti Brahmachari,
• Sisir Debnath,
• Sounak Dutta and
• Prasanta Kumar Das

Beilstein J. Org. Chem. 2010, 6, 859–868, doi:10.3762/bjoc.6.101

• antibacterial activity against both Gram-positive and Gram-negative bacteria with minimum inhibitory concentration (MIC) values as low as 0.4 μg/mL. Cytotoxicity tests using MTT assay showed 50% NIH3T3 cell viability with hydrogelating amphiphile 2 up to 100 μg/mL. Keywords: antibacterial; bilayer structure

• fluorescence spectroscopy. The topographical features of the soft matter were visualized using different microscopic techniques (scanning electron microscopy (SEM), atomic force microscopy (AFM)). Interestingly, these compounds were found to show excellent antibacterial activity against Gram-positive and Gram

• killing bacteria with MIC values of 0.4–2.0 μg/mL for Gram-positive bacteria and 5.0–20.0 μg/mL for Gram-negative bacteria. However, 2 was found to have slightly better antibacterial activity than 1 with MIC values of only 0.4 μg/mL for Gram-positive Micrococcus luteus and 10 μg/mL for Gram-negative

New acylides: synthesis of 3-O-[γ-(4-oxo-2-aryl- thiazolidin- 3-yl)butyryl]erythromycin A derivatives

• Deepa Pandey,
• Wahajul Haq and
• Seturam B. Katti

Beilstein J. Org. Chem. 2008, 4, No. 14, doi:10.3762/bjoc.4.14

• molecule may be advantageous for antibacterial activity in view of similar system having been reported as antibacterials [10][11]. The thiazolidin-4-ones can be generated under very mild conditions using the DCC mediated one-pot synthesis reported by us [12]. Results and Discussion Decladinosyl-6-O