Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol

• Emine Salamci and
• Ayse Kilic Lafzi

Beilstein J. Org. Chem. 2022, 18, 1539–1543, doi:10.3762/bjoc.18.163

• antibiotic activities. Therefore, synthetic methodologies for the preparation of the aziridinyl system have attracted attention in recent decades. Opening of the aziridine ring by using different nucleophiles gives the corresponding amino alcohols, amino esters, azido amines, amines, and other derivatives [9

Synthesis of C6-modified mannose 1-phosphates and evaluation of derived sugar nucleotides against GDP-mannose dehydrogenase

• Sanaz Ahmadipour,
• Alice J. C. Wahart,
• Jonathan P. Dolan,
• Laura Beswick,
• Chris S. Hawes,
• Robert A. Field and
• Gavin J. Miller

Beilstein J. Org. Chem. 2022, 18, 1379–1384, doi:10.3762/bjoc.18.142

• of alginate overproduction contributes to the PA biofilm environment and the resultant and deleterious bacterial resistance to current antibiotic treatments [2]. Alginate production is therefore established as a major virulence factor within PA respiratory tract infections for CF sufferers, and

On drug discovery against infectious diseases and academic medicinal chemistry contributions

• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 1355–1378, doi:10.3762/bjoc.18.141

• targets [112]. History will judge the long-term wisdom of this choice although GSK has already reported gepotidacin (8) an antibiotic currently in phase 3 clinical trials [113][114]. Of importance is that, as depicted in Figure 3, the starting point of this new class of bacterial gyrases inhibitors [115

• consider the much less studied novobiocin (62) depicted in Figure 10. This compound is another naturally occurring antibiotic which was isolated in 1955 [311]. It turned out to be the first inhibitor of the bacterial ATP-ase function of gyrases found and it was actually instrumental in the discovery of

Understanding the competing pathways leading to hydropyrene and isoelisabethatriene

• Shani Zev,
• Marion Ringel,
• Ronja Driller,
• Bernhard Loll,
• Thomas Brück and
• Dan T. Major

Beilstein J. Org. Chem. 2022, 18, 972–978, doi:10.3762/bjoc.18.97

• , having antibiotic and anti-inflammatory activities, respectively [4][5]. Unexpectedly, a single active site mutation, M75L, significantly shifts the product distribution and IE A becomes the dominant product (44%) in this enzyme variant [6]. As suggested by Rinkel et al., both routes (HP and IE routes

Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa

• Shou-Mao Shen,
• Qing Yang,
• Yi Zang,
• Jia Li,
• Xueting Liu and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 916–925, doi:10.3762/bjoc.18.91

• antibiotic effects [3][5][6]. Acanthella sponges have thus attracted much attention from marine natural products chemists and pharmacologists. The title animal is the most chemically studied species among the Acanthella sponges. Till now, more than 100 secondary metabolites belonging to sesquiterpenoids and

Efficient production of clerodane and ent-kaurane diterpenes through truncated artificial pathways in Escherichia coli

• Fang-Ru Li,
• Xiaoxu Lin,
• Qian Yang,
• Ning-Hua Tan and
• Liao-Bin Dong

Beilstein J. Org. Chem. 2022, 18, 881–888, doi:10.3762/bjoc.18.89

• diterpenoids are two categories of diterpenoids that are widely distributed in terrestrial plants, fungi, and a few bacteria and possess broad pharmacological bioactivities [1][2][3]. Representative natural products containing these skeletons are terpentecin (cytotoxic and antibiotic), salvinorin A (kappa

• and biosynthetically constructed by two sequential DTSs from the common C20 linear allylic diphosphate GGDP [29]. Terpentetriene was the proposed biosynthetic intermediate of terpentecin, an anticancer and antibiotic natural product isolated from Kitasatospora griseolosporeus MF730-N6 in 1985 [24][30

• ent-CPP into the target tetracyclic skeleton, ent-kaurene (Figure 2). In this study, the ent-CPP synthase (eCDPS) gene was cloned from Streptomyces sp. NRRL S-1813, which was an alternative ent-kaurenol-derived antibiotic platensimycin producer [33][34][35], while the ent-kaurene synthase (BjKS) gene

Synthesis of 3,4,5-trisubstituted isoxazoles in water via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides

• Md Imran Hossain,
• Md Imdadul H. Khan,
• Seong Jong Kim and
• Hoang V. Le

Beilstein J. Org. Chem. 2022, 18, 446–458, doi:10.3762/bjoc.18.47

• and γ-amino alcohols [1]. Isoxazoles, appearing in 33 patents from the year 2016 to 2018 [3], are an important drug class due to their wide range of biological activities, such as anticancer [5], antibiotic [6][7], antimicrobial [8], antifungal [9], and anti-inflammatory [10]. Therefore, new methods

The asymmetric Henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxaban

• Martin Vrbický,
• Karel Macek,
• Jaroslav Pochobradský,
• Jan Svoboda,
• Miloš Sedlák and
• Pavel Drabina

Beilstein J. Org. Chem. 2022, 18, 438–445, doi:10.3762/bjoc.18.46

• antibiotic linezolid (1) and the anticoagulant rivaroxaban (2) – belong among modern pharmaceutics, which contain an oxazolidine-2-one moiety bearing a stereogenic center. The chirality of these drugs is a fundamental attribute for their biological activity. Herein, one of the efficient asymmetric syntheses

• difference between the de values of the starting amides 27 and 28 and the final drugs 1 and 2 was found. Conclusion In conclusion, the synthetic approach to the preparation of the antibiotic linezolid (1) and the anticoagulant rivaroxaban (2) based on the asymmetric Henry reaction was studied in detail. A

Efficient and regioselective synthesis of dihydroxy-substituted 2-aminocyclooctane-1-carboxylic acid and its bicyclic derivatives

• İlknur Polat,
• Selçuk Eşsiz,
• Uğur Bozkaya and
• Emine Salamci

Beilstein J. Org. Chem. 2022, 18, 77–85, doi:10.3762/bjoc.18.7

• β-amino acid derivatives have antibiotic (oryzoxymycin) and antifungal activities (Figure 1) [12][13]. Among the cyclic β-amino acids, the most widely investigated derivatives are the five- and six-membered derivatives [8][9][10][14][15], but only a few synthetic methods are available for the

Unsaturated fatty acids and a prenylated tryptophan derivative from a rare actinomycete of the genus Couchioplanes

• Shun Saito,
• Kanji Indo,
• Naoya Oku,
• Hisayuki Komaki,
• Masashi Kawasaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2021, 17, 2939–2949, doi:10.3762/bjoc.17.203

• Streptomyces, are especially noted, accounting for more than 800 metabolites of actinomycetes origin [11], which include the antiinfective aminoglycoside gentamicin [13], antidiabetic glycoside acarbose [14], glycopeptide antibiotic teicoplanin [15], enediyne antitumor component of drug-antibody conjugate

• previously [36]. The MIC of the reference antibiotic kanamycin was 0.31 μg/mL (against K. rhizophila). Structures of 1–6. COSY, key HMBC and NOESY correlations of 1–5. 1H NMR spectra and partial chemical shift assignments for MPA esters 4'a–4'd. Upper: (R)-MPA acylation products, Lower: (S)-MPA acylation

Total synthesis of the O-antigen repeating unit of Providencia stuartii O49 serotype through linear and one-pot assemblies

• Tanmoy Halder and
• Somnath Yadav

Beilstein J. Org. Chem. 2021, 17, 2915–2921, doi:10.3762/bjoc.17.199

• stuartii is a class of enterobacteria of the family Providencia that is responsible for several antibiotic resistant infections, particularly urinary tract infections of patients with prolonged catheterization in hospital settings. Towards the goal of development of vaccine candidates against this pathogen

• particularly responsible for antibiotic resistant infections in hospitalized patients with long term urinary catheters, particularly immuno-compromised patients [25]. A total 61% of urinary region specimens in the infected populace consist of either Providencia stuartii or Proteus mirabilis, and the infections

Host–guest interaction and properties of cucurbit[8]uril with chloramphenicol

• Lin Zhang,
• Jun Zheng,
• Guangyan Luo,
• Xiaoyue Li,
• Yunqian Zhang,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2021, 17, 2832–2839, doi:10.3762/bjoc.17.194

• inhibitory activity of CPE against E. coli. Keywords: antibacterial activity; chloramphenicol; cucurbit[8]uril; host–guest interaction; in vitro cumulative release; stability; Introduction Chloramphenicol (CPE, Figure 1A) is a broad-spectrum antibiotic resulting from the metabolism of chorismic acid in

Ligand-dependent stereoselective Suzuki–Miyaura cross-coupling reactions of β-enamido triflates

• Tomáš Chvojka,
• Athanasios Markos,
• Svatava Voltrová,
• Radek Pohl and
• Petr Beier

Beilstein J. Org. Chem. 2021, 17, 2657–2662, doi:10.3762/bjoc.17.179

• of cytotoxic, antifungal, or antibiotic properties [10][11][12]. Modern stereoselective syntheses leading to highly substituted enamides include cross-coupling of vinyl (pseudo)halides or organoboron compounds [13], hydroamidation of alkynes [14][15][16], ynamide functionalization [17][18][19], or

Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B

• Emmanuel T. Oluwabusola,
• Olusoji O. Adebisi,
• Fernando Reyes,
• Kojo S. Acquah,
• Mercedes De La Cruz,
• Larry L. Mweetwa,
• Joy E. Rajakulendran,
• Digby F. Warner,
• Deng Hai,
• Rainer Ebel and
• Marcel Jaspars

Beilstein J. Org. Chem. 2021, 17, 2390–2398, doi:10.3762/bjoc.17.156

• pseudomonine [28] are produced under iron deficiency by various Pseudomonas species to acquire iron which is essential for cell metabolism and growth [29][30]. Studies show that siderophore–antibiotic complexes may be used as a Trojan horse strategy in which the antibiotics utilize the iron-siderophore

Synthesis and antimicrobial activity of 1H-1,2,3-triazole and carboxylate analogues of metronidazole

• Satya Kumar Avula,
• Syed Raza Shah,
• Khdija Al-Hosni,
• Muhammad U. Anwar,
• Rene Csuk,
• Biswanath Das and
• Ahmed Al-Harrasi

Beilstein J. Org. Chem. 2021, 17, 2377–2384, doi:10.3762/bjoc.17.154

• cost-effective drug. Due to its impressive antimicrobial activity and limited adverse effect metronidazole (1) has been considered as a “Gold Standard” antibiotic (Figure 1). However, to avoid the problem related to clinical resistance to this antimicrobial agent some novel and improved analogues of

(Phenylamino)pyrimidine-1,2,3-triazole derivatives as analogs of imatinib: searching for novel compounds against chronic myeloid leukemia

• Luiz Claudio Ferreira Pimentel,
• Lucas Villas Boas Hoelz,
• Henayle Fernandes Canzian,
• Frederico Silva Castelo Branco,
• Andressa Paula de Oliveira,
• Vinicius Rangel Campos,
• Floriano Paes Silva Júnior,
• Rafael Ferreira Dantas,
• Jackson Antônio Lamounier Camargos Resende,
• Anna Claudia Cunha,
• Nubia Boechat and
• Mônica Macedo Bastos

Beilstein J. Org. Chem. 2021, 17, 2260–2269, doi:10.3762/bjoc.17.144

• the antibiotic gentamicin, and all cell lines were grown in a cell culture bottle, which had a 0.22 µm pore membrane filter on the lid, allowing the circulation of CO2. WSS-1 cells grew adherently, while cells of the K562 strain grew in suspension. All strains were maintained at 35 °C, at 5% CO2. Cell

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

• ligands but also to the diene R5 and R6 substituents. With this innovative method in hands, the authors explored the synthetic applicability in the preparation of a core unit from lasalocid A (124), a known antibiotic drug [194] that, along with its four analogues 120–123 (Scheme 37A), were extracted from

• ), a known biosynthetic antibiotic drug that presents a highly complex chemical structure [197] (Scheme 38A). The activation exclusively occurs at one of the hydrogen atoms of the dehydroalanine (Dha) portions Dha1 and Dha2, towards the formation of the Z-stereoisomer (Scheme 38A). No reaction was

Natural products in the predatory defence of the filamentous fungal pathogen Aspergillus fumigatus

• Jana M. Boysen,
• Nauman Saeed and
• Falk Hillmann

Beilstein J. Org. Chem. 2021, 17, 1814–1827, doi:10.3762/bjoc.17.124

• ][133]. A. fumigatus possesses an additional MetAP-2 gene in the fma cluster that protects itself against its own toxin [134]. Fumagillin has therapeutic potential for the treatment of intestinal microsporidiosis and nosemiasis in honey bees [58][135]. Overall, antibiotic, immunosuppressive, antitumor

• and antiangiogenic properties have been attributed to fumagillin [129][136][137][138][139][140]. Specific antibiotic activities were demonstrated against the pathogen Entamoeba histolytica and later against eukaryotic parasites such as Trypanosoma and Plasmodium the causative agent of malaria [141

• treatment [75][164]. Helvolic acid Helvolic acid (HA) (23) is a fusidane-type antibiotic that belongs to the triterpenoid class of secondary metabolites. Originally, it was discovered from A. fumigatus but later several other members of the sub phylum Pezizomycotina were also found to be HA producers [165

Sustainable manganese catalysis for late-stage C–H functionalization of bioactive structural motifs

• Jongwoo Son

Beilstein J. Org. Chem. 2021, 17, 1733–1751, doi:10.3762/bjoc.17.122

• candidates with tailored physical and biological properties [47]. For example, ampicillin, an analogue of benzylpenicillin (penicillin G), also used as an antibiotic, contains an amine group at the benzylic position [48]. Likewise, other commercially available small-molecule drugs, such as Plavix

• ® (antiplatelet), Gleevec® (anticancer), and augmentin (antibiotic), also contain the benzylic amine motif. Therefore, C–H amination is synthetically important for the diversification of biologically active molecules. Transition metal catalysis has set the stage for C–H amination processes in organic syntheses

• late-stage methylation of complex drug derivatives, such as of indoprofen (anti-inflammatory), tedizolid (antibiotic), and celecoxib (anti-inflammatory), successfully delivered methylated drug candidates 22f–h, respectively. In addition, methylation of proline-containing multipeptides was achieved via

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center

• Thanigaimalai Pillaiyar,
• Masoud Sedaghati,
• Andhika B. Mahardhika,
• Lukas L. Wendt and
• Christa E. Müller

Beilstein J. Org. Chem. 2021, 17, 1464–1475, doi:10.3762/bjoc.17.102

• treatment of prostate cancer [16] and showed promise for the treatment of cervical dysplasia [17]. The related trisindoline (II) was reported to possess antibiotic activity [18], while DIM derivatives III and IV also showed anticancer activities (Figure 1). Owing to their exciting biological activities, DIM

Double-headed nucleosides: Synthesis and applications

• Vineet Verma,
• Jyotirmoy Maity,
• Vipin K. Maikhuri,
• Ritika Sharma,
• Himal K. Ganguly and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98

Analogs of the carotane antibiotic fulvoferruginin from submerged cultures of a Thai Marasmius sp.

• Birthe Sandargo,
• Leon Kaysan,
• Rémy B. Teponno,
• Christian Richter,
• Benjarong Thongbai,
• Frank Surup and
• Marc Stadler

Beilstein J. Org. Chem. 2021, 17, 1385–1391, doi:10.3762/bjoc.17.97

• antibiotic fulvoferruginin (1), fulvoferruginins B–F (2–6). The structures of these sesquiterpenoids were elucidated using HRESIMS, 1D and 2D NMR, as well as CD spectroscopy. Assessing the bioactivity, fulvoferruginin emerged as a potent cytotoxic agent of potential pharmaceutical interest. Keywords

• Marasmius spp. include the cryptoporic acids [4], marasmals, marasmones, and oreadones [5][6], the caryophyllane hebelophyllene C [7], and the carotane fulvoferruginin (1) [8] (Figure 1). The latter is the only known secondary metabolite from M. fulvoferrugineus Gilliam and displays a modest antibiotic and

Icilio Guareschi and his amazing “1897 reaction”

• Gian Cesare Tron,
• Alberto Minassi,
• Giovanni Sorba,
• Mara Fausone and
• Giovanni Appendino

Beilstein J. Org. Chem. 2021, 17, 1335–1351, doi:10.3762/bjoc.17.93

• Academy and is of great relevance to chemistry, being where, downtown the capital of the Kingdom of Sardinia (sic!), Ascanio Sobrero synthesized nitroglycerin in 1849 [24] and where Bartolomeo Gosio (1863–1944) reported the purification of the first antibiotic (mycophenolic acid) in 1899 [27]. Guareschi

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

• Guido Gambacorta,
• James S. Sharley and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90