The design and synthesis of an antibacterial phenothiazine–siderophore conjugate

• Abed Tarapdar,
• James K. S. Norris,
• Oliver Sampson,
• Galina Mukamolova and
• James T. Hodgkinson

Beilstein J. Org. Chem. 2018, 14, 2646–2650, doi:10.3762/bjoc.14.242

• Mycobacterium tuberculosis [9][10]. The emergence of MDR-TB has led to structure–activity studies to enhance the antitubercular activity of phenothiazines leading to the identification of chlorpromazine analogue 1 (Figure 1) which demonstrates MIC values comparable to first-line TB drugs in vitro [11]. However

Strategies toward protecting group-free glycosylation through selective activation of the anomeric center

• A. Michael Downey and
• Michal Hocek

Beilstein J. Org. Chem. 2017, 13, 1239–1279, doi:10.3762/bjoc.13.123

• saccharides. The interest in hexofuranoses is based on the arabinogalactan-rich membrane of Mycobacterium tuberculosis and other harmful microorganisms which consists of primarily Araf and Galf subunits [44]. One key step in the biosynthesis of these hexofuranoses is the isomerization of uridine 5′-diphospho

Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis

• Darcy J. Atkinson,
• Briar J. Naysmith,
• Daniel P. Furkert and
• Margaret A. Brimble

Beilstein J. Org. Chem. 2016, 12, 2325–2342, doi:10.3762/bjoc.12.226

• . Teixobactin (17) was isolated from the β-protobacterium, Eleftheria terrae that belongs to a new genus. Teixobactin (17) demonstrated potent activity against the resistant Gram-positive bacteria, MRSA and vancomycin-resistant Enterococci (VRE), as well as other bacterial species including, Mycobacterium

• tuberculosis (Mtb) and Clostridium difficile. Remarkably, no teixobactin-resistant mutants of Staphylococcus aureus or M. tuberculosis could be detected after sub-lethal dosing of the compound over a 27 day period [43]. This lack of resistance development may possibly be attributable to the mechanism of action

Antibiotics from predatory bacteria

• Juliane Korp,
• María S. Vela Gurovic and
• Markus Nett

Beilstein J. Org. Chem. 2016, 12, 594–607, doi:10.3762/bjoc.12.58

• , the enzymatic products of which exhibited high sequence similarity to proteins that are responsible for the biosynthesis of tuberculosinol and isotuberculosinol in Mycobacterium tuberculosis [128]. Following in vitro studies of the two Herpetosiphon enzymes as well as a reconstitution of the entire

Mycothiol synthesis by an anomerization reaction through endocyclic cleavage

• Shino Manabe and
• Yukishige Ito

Beilstein J. Org. Chem. 2016, 12, 328–333, doi:10.3762/bjoc.12.35

• ]. After cleavage, the N-acetylcysteine S-conjugate is transported out of the cell, while the inositol–glucosamine conjugate is recycled to afford MSH. MSH also plays an important role in the growth and survival of Mycobacterium tuberculosis. Because MSH-dependent pathways are not found in eukaryotes, the

Pyridinoacridine alkaloids of marine origin: NMR and MS spectral data, synthesis, biosynthesis and biological activity

• Louis P. Sandjo,
• Victor Kuete and
• Maique W. Biavatti

Beilstein J. Org. Chem. 2015, 11, 1667–1699, doi:10.3762/bjoc.11.183

• significant antituberculosis (TB) activity (MIC of 0.35 µM) against Mycobacterium tuberculosis H37Rv [70]. The 6H-pyrido[2,3,4-kl]acridin-6-one motif has been used as a core to develop other anti-TB compounds. In this way, the same activity has been observed with 4-(ethylthio)-6H-pyrido[2,3,4-kl]acridin-6-one

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

• 8 and 10 inhibited α-glucosidase with moderate to weak activities (Table 3). All isolated compounds were also evaluated for their inhibitory activity against Mycobacterium tuberculosis protein tyrosine phosphatase B (MptpB), of which were inactive (IC50 > 200 μM). Experimental General experimental

Synthesis of 1,2-cis-2-C-branched aryl-C-glucosides via desulfurization of carbohydrate based hemithioacetals

• Henok H. Kinfe,
• Fanuel M. Mebrahtu,
• Mandlenkosi M. Manana,
• Kagiso Madumo and
• Mokela S. Sokamisa

Beilstein J. Org. Chem. 2015, 11, 583–588, doi:10.3762/bjoc.11.64

• for the enzymes of Mycobacterium tuberculosis, in particular a deacetylase implicated in the biosynthesis of mycothiol, is under way and the results will be reported in the future. Single X-ray crystal structure of hemithioacetal 3a. (i) CAN, wet silica, KBr, CH2Cl2/CH3CN (1:1), rt, 30 min; (ii) a

Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo

• Alireza Shakoori,
• John B. Bremner,
• Mohammed K. Abdel-Hamid,
• Anthony C. Willis,
• Rachada Haritakun and
• Paul A. Keller

Beilstein J. Org. Chem. 2015, 11, 481–492, doi:10.3762/bjoc.11.54

• (Mycobacterium tuberculosis) [17] (Table 2). Promising antiplasmodial activity was seen with the spirocyclic compound 12 (IC50 2.65 µg/mL, 6.25 µM) and the related indoloazepinoindol-17-one 17 in which the allylic substituents are effectively merged (minus the ether oxygen) and embedded in the 7-membered ring

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

New highlights of the syntheses of pyrrolo[1,2-a]quinoxalin-4-ones

• Emilian Georgescu,
• Alina Nicolescu,
• Florentina Georgescu,
• Florina Teodorescu,
• Daniela Marinescu,
• Ana-Maria Macsim and
• Calin Deleanu

Beilstein J. Org. Chem. 2014, 10, 2377–2387, doi:10.3762/bjoc.10.248

• constituent of several bioactive heterocyclic compounds that demonstrate interesting activity against Mycobacterium tuberculosis [1], anti-HIV [2], anticancer [3], and it modulates the estrogen receptor activity [4]. Synthetic methods towards pyrrolo[1,2-a]quinoxaline derivatives based on pyrroles [5], or

Conformation of dehydropentapeptides containing four achiral amino acid residues – controlling the role of L-valine

• Michał Jewgiński,
• Joanna Krzciuk-Gula,
• Maciej Makowski,
• Rafał Latajka and
• Paweł Kafarski

Beilstein J. Org. Chem. 2014, 10, 660–666, doi:10.3762/bjoc.10.58

• crucial for the biological activity of various peptide antibiotics [23], e.g., nisin (used as a food preservative [24]), epidermin (active against Gram positive bacteria [25]) and viomycin (used to fight infections of Mycobacterium tuberculosis [26]). As shown by Chauhan and co-workers, structure–activity

Synthesis of a derivative of α-D-Glcp(1->2)-D-Galf suitable for further glycosylation and of α-D-Glcp(1->2)-D-Gal, a disaccharide fragment obtained from varianose

• Carla Marino,
• Carlos Lima,
• Karina Mariño and
• Rosa M. de Lederkremer

Beilstein J. Org. Chem. 2012, 8, 2142–2148, doi:10.3762/bjoc.8.241

• products indicates an inverting mechanism. Also lately, galactofuranosyl transferases (GalfT) catalyzing β-Galf incorporation in glycans have been identified. Two bifunctional GalfTs are required for galactan biosynthesis in Mycobacterium tuberculosis, GalfT1 and GalfT2, able to construct both, β-Galf(1→5

The volatiles of pathogenic and nonpathogenic mycobacteria and related bacteria

• Thorben Nawrath,
• Georgies F. Mgode,
• Bart Weetjens,
• Stefan H. E. Kaufmann and
• Stefan Schulz

Beilstein J. Org. Chem. 2012, 8, 290–299, doi:10.3762/bjoc.8.31

• fatty-acid derivatives were released by pathogenic/nonpathogenic mycobacteria, while the two Nocardia spp. (N. asteroides and N. africana) emitted the sesquiterpene aciphyllene. Pathogenic Mycobacterium tuberculosis strains grown on agar plates produced a distinct bouquet with different volatiles, while

• allowed for only a rough approximation. Volatile compounds released by Mycobacterium tuberculosis and M. bovis identified in previous studies [9]. Total ion chromatogram of a headspace extract of a culture of Mycobacterium tuberculosis strain 2, grown on a 7H11 solid medium. Nonlabeled peaks originate

• from the nutrient medium. Volatiles released by mycobacteria and Nocardia spp. grown on a 7H11 solid medium. Volatiles released by M. tuberculosis grown in a 7H9 broth liquid medium. Volatiles released by Mycobacterium tuberculosis grown on a 7H11 solid medium.a Volatiles released by diverse

Marilones A–C, phthalides from the sponge-derived fungus Stachylidium sp.

• Celso Almeida,
• Stefan Kehraus,
• Miguel Prudêncio and
• Gabriele M. König

Beilstein J. Org. Chem. 2011, 7, 1636–1642, doi:10.3762/bjoc.7.192

• Hepatitis B virus was performed according to Sells et al. [32] and Korba and Gerin [33]. The activity assays against two strains of antibiotic resistant Mycobacterium tuberculosis were performed according to Bauer et al. [34]. The methodology for the inhibition of the NF-κB protein complex is described by

• serotonin receptors, and marilone B showed a specific antagonistic effect on the serotonin receptor 5-HT2B with a Ki value of 7.7 µM. Compounds 1–4 were further evaluated for antiviral activity, for inhibition of protein kinases and proteases, for growth inhibition of antibiotic-resistant Mycobacterium

• tuberculosis as well as further microbial pathogens, for activity in an antidiabetic activity assay panel, in a 3T3-L1 murine adipocyte assay, and in a NF-κB protein complex assay, but they exhibited no activity (see detailed description in Supporting Information File 1). Phthalide derivatives are compounds of

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

• also caused by multidrug-resistant tuberculosis strains, which are resistant to the most widely used agents, either Isoniazid or Rifampicin, and the need for new highly active compounds is increasing. Tuberculosis is caused by species of the genus Mycobacterium, for instance, Mycobacterium tuberculosis

Synthesis of glycoconjugate fragments of mycobacterial phosphatidylinositol mannosides and lipomannan

• Benjamin Cao,
• Jonathan M. White and
• Spencer J. Williams

Beilstein J. Org. Chem. 2011, 7, 369–377, doi:10.3762/bjoc.7.47

• Benjamin Cao Jonathan M. White Spencer J. Williams School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, Victoria, Australia, Fax: +61 3 9347 8124; Tel: +61 3 8344 2422 10.3762/bjoc.7.47 Abstract Mycobacterium tuberculosis, the causitive

An efficient synthesis of tetramic acid derivatives with extended conjugation from L-Ascorbic Acid

• Biswajit K. Singh,
• Surendra S. Bisht and
• Rama P. Tripathi

Beilstein J. Org. Chem. 2006, 2, No. 24, doi:10.1186/1860-5397-2-24

• synthesis of 5-hydroxyl tetramic acid derivatives without alkenyl substitutents at C-5, [36] but none of these compounds possesses significant activity against Mycobacterium tuberculosis. In continuation of this study tetramic acid derivatives with 5-alkenyl substitutents were synthesized starting from