Evaluation of the enantioselectivity of new chiral ligands based on imidazolidin-4-one derivatives

• Jan Bartáček,
• Karel Chlumský,
• Jan Mrkvička,
• Lucie Paloušová,
• Miloš Sedlák and
• Pavel Drabina

Beilstein J. Org. Chem. 2024, 20, 684–691, doi:10.3762/bjoc.20.62

• enhanced economic efficiency, eco-friendly practices, and reduced waste. Catalysts with the highest enantioselectivity have been employed in the synthesis of essential chiral intermediates for drug production, such as amprenavir [12], rivaroxaban [13][14], linezolid [13] and salmeterol [7]. Therefore

Copper-catalyzed N-arylation of amines with aryliodonium ylides in water

• Kasturi U. Nabar,
• Bhalchandra M. Bhanage and
• Sudam G. Dawande

Beilstein J. Org. Chem. 2023, 19, 1008–1014, doi:10.3762/bjoc.19.76

• metabolism, cell growth and during pregnancy, ofloxacin (III) [7], an antibacterial agent, mefenamic acid (IV) [8], an anti-inflammatory agent used to treat mild pain, linezolid (V) [9], an antibacterial agent, repaglinide (VI) [10], used to treat diabetes mellitus type 2, and tolfenamic acid (VII) [11], an

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

• syntheses of these drugs were obtained in high yields and enantiomeric excesses of up to 91% ee. Keywords: asymmetric Henry reaction; enantioselective catalysis; linezolid; oxazolidine-2-one derivatives; rivaroxaban; Introduction Oxazolidine-2-one derivatives represent an important branch of

• pharmaceutical substances [1][2][3]. This class includes for instance oxazolidine-type antibiotics [3], e.g., linezolid (1) [4] (sold under the trade name Zyvox® (Figure 1) or tedizolid [5] (sold under the trade name Sivextro®), and the anticoagulant rivaroxaban (2) [6][7] (Figure 1), a member of DOACs (direct

A complementary approach to conjugated N-acyliminium formation through photoredox-catalyzed intermolecular radical addition to allenamides and allencarbamates

• Olusesan K. Koleoso,
• Matthew Turner,
• Felix Plasser and
• Marc C. Kimber

Beilstein J. Org. Chem. 2020, 16, 1983–1990, doi:10.3762/bjoc.16.165

• (32 to 35) in moderate to good isolated yields. 4-Bromo-2-fluoroaniline was also examined as a nucleophile, as we had previously shown this to be an effective aniline platform for developing linezolid analogues, and this delivered two N,N’-allylaminals 36 and 37, respectively. Masson had previously

One-pot synthesis of oxazolidinones and five-membered cyclic carbonates from epoxides and chlorosulfonyl isocyanate: theoretical evidence for an asynchronous concerted pathway

• Esra Demir,
• Ozlem Sari,
• Yasin Çetinkaya,
• Ufuk Atmaca,
• Safiye Sağ Erdem and
• Murat Çelik

Beilstein J. Org. Chem. 2020, 16, 1805–1819, doi:10.3762/bjoc.16.148

• considerable use as antibiotics [1], immunomodulators [2], antibacterials [3], as well as synthetic intermediates and chiral auxiliaries for various organic conversions [4][5][6][7]. Linezolid [1][2][3] (3) and cytoxazone [8][9] (4) are oxazolidinone derivatives having significant biological activities

• . Linezolid (3) is the first oxazolidinone drug approved in 2000 by the Food and Drug Administration (FDA) for the treatment of multidrug resistant Gram-positive bacterial infections (Scheme 1) [10]. Cytoxazone is a microbial metabolite exhibiting potent cytokine-modulating activity. Tedizolid phosphate

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

• Iwona E. Głowacka,
• Aleksandra Trocha,
• Andrzej E. Wróblewski and
• Dorota G. Piotrowska

Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168

• )-105 (Scheme 27) [78]. Application of other organometallics paved the way to synthesis of a variety of 3-substituted 2-amino-1,3-propanodiols. 1,3-Diamino-2-hydroxy derivatives Linezolid ((S)-107) represents a new class of 1,3-oxazolidin-2-one antibiotics and contains the (2S)-1,3-diamino-2

• debenzylation followed by acylation provided enantiomerically pure (S)-linezolid ((S)-107). 2-Amino-1,3,4-triols ᴅ-ribo-Phytosphingosine ((2S,3S,4R)-2-aminooctadecane-1,3,4-triol, (2S,3S,4R)-110) appears to be the most common from other stereoisomeric phytosphingosines which are present in many species and show

Targeting the Pseudomonas quinolone signal quorum sensing system for the discovery of novel anti-infective pathoblockers

• Christian Schütz and
• Martin Empting

Beilstein J. Org. Chem. 2018, 14, 2627–2645, doi:10.3762/bjoc.14.241

• facilitated the discovery of novel PqsD-targeting compounds through CuAAC-mediated conjugation of a fluorescent dye (Figure 9) [62]. Finally, Sangshetti et al. reported the discovery of linezolid-like Schiff bases, which showed promising anti-biofilm activity in the double-digit micromolar range [63]. Notably

• , their potency in attenuating biofilm formation was more pronounced than ciprofloxacin and linezolid itself. A docking study suggested PqsD to be the target of these compounds like 23 (Figure 10), although this remains speculative. PqsE inhibitors The pathway-specific thioesterase PqsE is not only

• substrate tunnel is indicated by a mesh. Structures and characteristics of hits against PqsD identified through different methods. HHQ and PQS analogues as PqsD inhibitors and chemical probe used for screening. Structure of PqsD-targeting biofilm inhibitor derived from linezolid. Fragment-based PqsE

Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity

• Atul A. Dhavan,
• Rahul D. Kaduskar,
• Loana Musso,
• Leonardo Scaglioni,
• Piera Anna Martino and
• Sabrina Dallavalle

Beilstein J. Org. Chem. 2016, 12, 1624–1628, doi:10.3762/bjoc.12.159

• derivative [16][17][22][23]. The oxazolidinone ring is rare among natural products, but there are successful examples in medicinal chemistry of drugs containing this skeleton, such as the antibiotic linezolid [24]. As the core structure of compound 14 represents a new scaffold, never isolated or synthesized

Correction: Effective in silico prediction of new oxazolidinone antibiotics: force field simulations of the antibiotic–ribosome complex supervised by experiment and electronic structure methods

• Jörg Grunenberg and
• Giuseppe Licari

Beilstein J. Org. Chem. 2016, 12, 608–610, doi:10.3762/bjoc.12.59

• ; computational chemistry; drug design; molecular recognition; relaxed force constants; Our original publication contains an erratic number of predicted antibiotic structures in Scheme 2. With this Erratum we provide the corrected Scheme 2. Scheme 2 in the original article: Predicted new linezolid-like

Effective in silico prediction of new oxazolidinone antibiotics: force field simulations of the antibiotic–ribosome complex supervised by experiment and electronic structure methods

• Jörg Grunenberg and
• Giuseppe Licari

Beilstein J. Org. Chem. 2016, 12, 415–428, doi:10.3762/bjoc.12.45

• experimentally known MIC values of eight linezolid analogues were used in order to crosscheck the robustness of our model. In a final step, this benchmarking led to the prediction of several new and promising lead compounds. Synthesis and biological evaluation of the new compounds are on the way. Keywords

• serious Gram-positive infections, linezolid, was introduced in the markets in the year 2000. While also binding to the 50S subunit, it seems to unfold its inhibiting activity in a unique and early stage [13][14]. The nomenclature of the linezolid structure is shown in Figure 1 along with the pharmacophore

• portion displayed in blue [15]. While only the S-enantiomer seems to be potent, linezolid shows activity against a wide range of Gram-positive bacteria such as vancomycin-resistant Enterococcus (VRE), methicillin-resistant Staphylococcus aureus (MRSA) and penicillin-resistant Streptococcus pneumoniae