Recent advances in the electrochemical synthesis of organophosphorus compounds

• Babak Kaboudin,
• Milad Behroozi,
• Sepideh Sadighi and
• Fatemeh Asgharzadeh

Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61

• that controls reaction selectivity by adjusting voltage or current [13]. Simple synthetic systems in electrochemical methods are limited to electrodes, cells, electrolytes, and power supplies. Today, in addition to the above, light, metallic, and organic catalysts are also used to increase the

• Electrochemical reaction cells When a redox reaction occurs indirectly, chemical energy is transformed into electrical energy. A device that facilitates this conversion is known as an electrochemical cell. Electrochemical reaction cells are divided into two primary categories: galvanic (voltaic) and electrolytic

• . They consist of two electrodes – anode (where oxidation occurs) and cathode (where reduction occurs) – immersed in an electrolyte. Galvanic cell The redox reaction occurs spontaneously in these cells, converting chemical energy into electrical energy. The potential difference between the two electrodes

Orthogonal photoswitching of heterobivalent azobenzene glycoclusters: the effect of glycoligand orientation in bacterial adhesion

• Leon M. Friedrich and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2025, 21, 736–748, doi:10.3762/bjoc.21.57

• protocol [41], the fluorescent GFP (green fluorescent protein)-expressing strain PKL1162 was applied to mannan-coated microtiter plates. In this assay, fluorescence intensity correlates with the number of adhered bacterial cells. The photoswitches 1–5 (cf. Figure 1) were used as inhibitors of bacterial

Synthesis of HBC fluorophores with an electrophilic handle for covalent attachment to Pepper RNA

• Raphael Bereiter and
• Ronald Micura

Beilstein J. Org. Chem. 2025, 21, 727–735, doi:10.3762/bjoc.21.56

• with an electrophilic handle for the covalent attachment of the surrogate to the RNA. The resulting irreversibly tethered dye–RNA complexes have opened up new avenues for RNA imaging in live cells. Here, we report the syntheses of such modified HBC530 ((4-((2-hydroxyethyl)(methyl)amino)benzylidene

• aptamer (FLAP) in the family of “RNA mimics of GFP”, called Spinach [3]. This aptamer was used to study intracellular RNA dynamics in living cells and was the starting point for a series of in vitro selected FLAPs, e.g., Corn [4], Chili [5], Mango [6], Pepper [7], Clivia [8], and Okra [9]. All known FLAPs

• (pulldown of circular Pepper RNA from total RNA of HEK 293T cells) see reference [11]. Supporting Information Supporting Information File 26: Experimental, characterization data and copies of NMR spectra. Funding This work was funded in part by the Austrian Science Fund FWF [P31691, F8011-B] and the

Origami with small molecules: exploiting the C–F bond as a conformational tool

• Patrick Ryan,
• Ramsha Iftikhar and
• Luke Hunter

Beilstein J. Org. Chem. 2025, 21, 680–716, doi:10.3762/bjoc.21.54

Photocatalyzed elaboration of antibody-based bioconjugates

• Marine Le Stum,
• Eugénie Romero and
• Gary A. Molander

Beilstein J. Org. Chem. 2025, 21, 616–629, doi:10.3762/bjoc.21.49

• designed in the context of cancer therapy [1], which combines the precision targeting of monoclonal antibodies (mAbs) with the therapeutic effects of cytotoxic drugs [2]. The ADCs are thus designed to deliver potent cytotoxic agents selectively and directly to cancer cells while minimizing damage to

• healthy tissues. Notably, ADCs have started to enter clinical trials for non-oncology applications as well [3]. The importance and value of ADCs are several fold: Precise targeting: ADCs specifically recognize their target cells because of their antibody component. This minimizes collateral damage to

• healthy tissues, reducing side effects compared to traditional chemotherapy. Enhanced potency: By delivering cytotoxic payloads directly to tumor or other target cells, ADCs achieve higher drug concentrations at the site of action. This potency enhances therapeutic efficacy. Treatment of refractory

Semisynthetic derivatives of massarilactone D with cytotoxic and nematicidal activities

• Rémy B. Teponno,
• Sara R. Noumeur and
• Marc Stadler

Beilstein J. Org. Chem. 2025, 21, 607–615, doi:10.3762/bjoc.21.48

• , epidermoid carcinoma A431, ovarian carcinoma SKOV-3, and breast cancer MCF-7 cell lines. Compounds 2 and 3 exhibited significant cytotoxicity against all the tested cells. Some of the semisynthetic derivatives were also tested for their nematicidal activity and compound 4 displayed significant and selective

• human cancer cells and evaluated for their nematicidal activity. Results and Discussion Semisynthesis of massarilactone D derivatives The reaction of massarilactone D with methacryloyl chloride in triethylamine in the presence of catalytic amounts of 4-dimethylaminopyridine afforded compound 2 (11

• prostate cancer PC-3, epidermoid carcinoma A431, ovarian carcinoma SKOV-3, and breast cancer MCF-7 cell lines. Although the parent compound was not active as previously described [15][16], compounds 2 and 3 exhibited a significant cytotoxic activity against all the tested cells lines with IC50 values

Cryptophycin unit B analogues

• Thomas Schachtsiek,
• Jona Voss,
• Maren Hamsen,
• Beate Neumann,
• Hans-Georg Stammler and
• Norbert Sewald

Beilstein J. Org. Chem. 2025, 21, 526–532, doi:10.3762/bjoc.21.40

• isolation from cyanobacteria [2], their extraordinarily high cytotoxicity was apparent and attracted attention, not least because of their still high efficacy against multidrug-resistant (MDR) cells [3]. Cryptophycin-52, a synthetic development candidate by Eli Lilly based on the initially discovered

• amines still show nanomolar activity against the MDR cell line KB-V1 (Table 1) with resistance factors FR (being the ratio between IC50 (KB-V1) and IC50 (KB-3-1)) of 25 (1) and 34 (2), thus being comparably much more potent against KB-V1 cells than for example the unit D analogues (FR ≈ 103) [19

Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye

• Metodej Dvoracek,
• Brendan Twamley,
• Mathias O. Senge and
• Mikhail A. Filatov

Beilstein J. Org. Chem. 2025, 21, 500–509, doi:10.3762/bjoc.21.37

• displacement parameter restraints. View of the packing of the unit cells of a) Me2B viewed normal to the c-axis and b) Me4B viewed normal to (110). Only the majority occupied moiety of the N–N bridge is shown in Me4B. UV–vis spectrum of Cl2B after irradiation in DCM. Proposed mechanism for the topochemical [2

Synthesis of electrophile-tethered preQ₁ analogs for covalent attachment to preQ₁ RNA

• Laurin Flemmich and
• Ronald Micura

Beilstein J. Org. Chem. 2025, 21, 483–489, doi:10.3762/bjoc.21.35

• vitro and in living cells using rationally designed electrophile-tethered derivatives of preQ1 (1) and its Watson–Crick diamino-faced counterpart DPQ1 (2, Scheme 1A). These ligands (compound classes 3 and 4, Scheme 1A) were tailored to target a conserved guanine nucleobase within a natural preQ1-binding

The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation

• Rituparna Das and
• Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27

• achieve better stereocontrol and to facilitate the formation of synthetically challenging glycosidic linkages. Keywords: chemical O-glycosylation; neighbouring group participation; remote group participation; solvent effect; stereocontrol; Introduction Cell surface glycans in living cells have

Synthesis, structure, ionochromic and cytotoxic properties of new 2-(indolin-2-yl)-1,3-tropolones

• Yurii A. Sayapin,
• Eugeny A. Gusakov,
• Inna O. Tupaeva,
• Alexander D. Dubonosov,
• Igor V. Dorogan,
• Valery V. Tkachev,
• Anna S. Goncharova,
• Gennady V. Shilov,
• Natalia S. Kuznetsova,
• Svetlana Y. Filippova,
• Tatyana A. Krasnikova,
• Yanis A. Boumber,
• Alexey Y. Maksimov,
• Sergey M. Aldoshin and
• Vladimir I. Minkin

Beilstein J. Org. Chem. 2025, 21, 358–368, doi:10.3762/bjoc.21.26

• MTT assay was used to determine the anticancer activity of compound 7a against these cultures (Figure 6). The viability test is an important method to determine which new compounds are able to target cancer cells. The results of this test (IC50 value ± 95% confidence interval) allow us to evaluate the

• cell culture, at which the number of live cells was reduced by 50%, was 0.172 ± 0.029 μM. For the H1299 culture, this value was 2.18 ± 0.7 μM. In comparison, the IC50 value of the standard anticancer drug cisplatin at 24 hour incubation is 137 ± 12 μM for the A431 culture [31] and 34.9 μM for the H1299

• , CN) (Aldrich) were used to prepare the solutions. Spectral fluorescent experiments were performed using quartz cells (lcuvette 1.0 cm, volume V 2 mL). Stock solutions of compounds 7 or 8 (c 5.0 × 10−5 mol L−1) and tetrabutylammonium salts (c 1.0 × 10−4 mol L−1) in acetonitrile were used. The

Synthesis, characterization, antimicrobial, cytotoxic and carbonic anhydrase inhibition activities of multifunctional pyrazolo-1,2-benzothiazine acetamides

• Ayesha Saeed,
• Shahana Ehsan,
• Muhammad Zia-ur-Rehman,
• Erin M. Marshall,
• Sandra Loesgen,
• Abdus Saleem,
• Simone Giovannuzzi and
• Claudiu T. Supuran

Beilstein J. Org. Chem. 2025, 21, 348–357, doi:10.3762/bjoc.21.25

• prepared in DMSO and cancer cells were treated with 10 μM doses of compounds using the apoptosis inducing standard mensacarcin (10 μM) as a positive control [56]. Only compound 7l decreased cell viability to 63%, while the rest of the compounds showed very low to no significant decrease in cell viability

• mammalian cells in vitro. Results of the microbroth single-dose assays revealed that two of the synthesized compounds have selective antibiotic activity against S. aureus. Subsequently, MIC90 values were calculated by performing microbroth dilution assays using serial dilutions of these two compounds

• against three different strains of S. aureus. Compound 7b has a MIC90 of 16 μg/mL, and 7h exhibited a MIC90 of 8 μg/mL against susceptible, methicillin-resistant, and multidrug-resistant S. aureus. So, it was observed that both of these compounds destroyed designated bacterial cells in a competitive

Antibiofilm and cytotoxic metabolites from the entomopathogenic fungus Samsoniella aurantia

• Rita Toshe,
• Syeda J. Khalid,
• Blondelle Matio Kemkuignou,
• Esteban Charria-Girón,
• Paul Eckhardt,
• Birthe Sandargo,
• Kunlapat Nuchthien,
• J. Jennifer Luangsa-ard,
• Till Opatz,
• Hedda Schrey,
• Sherif S. Ebada and
• Marc Stadler

Beilstein J. Org. Chem. 2025, 21, 327–339, doi:10.3762/bjoc.21.23

• activity, inhibiting approximately 70% of Staphylococcus aureus biofilms at concentrations as low as 3.9 µg/mL. Keywords: antibiofilm; antiproliferative; beauvericin; insect pathogen; Samsoniella; Introduction A microbial biofilm represents an assemblage of planktonic cells to overcome hostile living

• . aureus biofilms with farinosones D (1) and A (2). This distinction is pivotal in the evaluation of compounds for their antibiofilm efficacy, considering the potential scenario wherein a compound may affect the growth dynamics of cells without substantially disrupting the biofilm architecture or

• dispersing the encapsulated cells [16]. The results (Figure 6) yielded striking significance, revealing that the biomass remained metabolically inactive in biofilms treated with 1 and 2 low to concentrations of 3.9 and 1.9 µg/mL, respectively. It is worth noting here that both compounds followed a similar

Red light excitation: illuminating photocatalysis in a new spectrum

• Lucas Fortier,
• Corentin Lefebvre and
• Norbert Hoffmann

Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22

• -established for their use in organic photovoltaic cells and as efficient photosensitizers for singlet oxygen generation. In 2022, Goddard et al. have reported the groundbreaking use of squaraine derivatives as novel organic NIR photocatalysts for various chemical transformations, marking the first application

Synthesis and characterizations of highly luminescent 5-isopropoxybenzo[rst]pentaphene

• Islam S. Marae,
• Jingyun Tan,
• Rengo Yoshioka,
• Zakaria Ziadi,
• Eugene Khaskin,
• Serhii Vasylevskyi,
• Ryota Kabe,
• Xiushang Xu and
• Akimitsu Narita

Beilstein J. Org. Chem. 2025, 21, 270–276, doi:10.3762/bjoc.21.19

• improving the stability of inverted perovskite solar cells [23]. On the other hand, benzo[rst]pentaphene-5,8-dione (BPP-dione) is known as an oxidation product of BPP [24][25], but to the best of our knowledge, the detailed optical properties of this BPP derivative have not been previously described in the

Recent advances in organocatalytic atroposelective reactions

• Henrich Szabados and
• Radovan Šebesta

Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6

• enantiopurity at 130 °C for 48 h in toluene. Investigating the biological activity for a number of compounds, good cytotoxicity was reported for five kinds of cancer cells. The mechanistic study suggests that the indole ring of the substrate is having a crucial role in the reaction mechanism because replacing

Hot shape transformation: the role of PSar dehydration in stomatocyte morphogenesis

• Remi Peters,
• Levy A. Charleston,
• Karinan van Eck,
• Teun van Berlo and
• Daniela A. Wilson

Beilstein J. Org. Chem. 2025, 21, 47–54, doi:10.3762/bjoc.21.5

• , which results in more rigid domains. The anomalous shapes observed, with bending starting from seemingly random positions, support this hypothesis (Supporting Information File 1, Figure S36). These irregular shapes are reminiscent of some anomalous shapes observed in red blood cells [25]. It was also

Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade

• Merve Yence,
• Dilgam Ahmadli,
• Damla Surmeli,
• Umut Mert Karacaoğlu,
• Sujit Pal and
• Yunus Emre Türkmen

Beilstein J. Org. Chem. 2024, 20, 3290–3298, doi:10.3762/bjoc.20.273

• fluorescent chemosensors and probes [4][5][6], as well as materials for applications in organic light-emitting diodes (OLEDs) [7][8][9], organic field-effect transistors (OFETs) [10], and perovskite solar cells [11]. In this respect, replacing either one or more of the carbons or rings of a fluoranthene with

Ceratinadin G, a new psammaplysin derivative possessing a cyano group from a sponge of the genus Pseudoceratina

• Shin-ichiro Kurimoto,
• Kouta Inoue,
• Taito Ohno and
• Takaaki Kubota

Beilstein J. Org. Chem. 2024, 20, 3215–3220, doi:10.3762/bjoc.20.267

• cytotoxicity against L1210 murine leukemia cells and KB epidermoid carcinoma cells. Keywords: ceratinadin; cytotoxicity; marine sponge; psammaplysin; Pseudoceratina sp.; Introduction Marine sponges are widely recognized as a rich source of unique bioactive natural products. For instance, marine sponges

• ceratinadin G (1) was evaluated against L1210 murine leukemia cells and KB epidermoid carcinoma cells. Ceratinadin G (1) showed moderate cytotoxic activity against L1210 cells (IC50 = 4.7 μM) and KB cells (IC50 = 15.1 μM). Conclusion Ceratinadin G (1) is the first psammaplysin derivative identified to contain

• -1500 spectropolarimeter. 1H and 13C NMR spectra were acquired on a Bruker Avance II 600 MHz NMR spectrometer equipped with a cryoplatform, using 3.0 mm micro cells (Shigemi Co., Ltd.) for CD3OD. The 1H NMR chemical shift of residual CD2HOD in CD3OD at 3.35 ppm and the 13C NMR chemical shift of CD3OD at

Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D

• Sasha Hayes,
• Yaoying Lu,
• Bernd H. A. Rehm and
• Rohan A. Davis

Beilstein J. Org. Chem. 2024, 20, 3205–3214, doi:10.3762/bjoc.20.266

• cultures at 37 °C in LB medium were washed once with sterile saline 0.9% (w/v) and adjusted to an OD600 of 0.05. Then, 1% inoculum was transferred into fresh LB medium. Following the incubation at 37 °C, 200 rpm for 5–6 h to reach the mid-log phase, the cells were washed once with sterile saline 0.9% (w/v

Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies

• Lucía Campos-Prieto,
• Aitor García-Rey,
• Eddy Sotelo and
• Ana Mallo-Abreu

Beilstein J. Org. Chem. 2024, 20, 3151–3173, doi:10.3762/bjoc.20.261

• cells containing the Nrf2/antioxidant response element (ARE). The melatonin–lipoic acid (LA) hybrids 3a and 3b emerged as potent antioxidants, successfully inducing the Nrf2 transcriptional pathway at concentrations of 10, 30, and 100 μM (Figure 5). Notably, these hybrids exhibited lower CD values (28.1

• donepezil, employing a widely accepted tauopathy model in SH-SY5Y cells. Notably, compound 7a was identified as the most promising multitarget-directed ligand in the study, exhibiting superior neuroprotection compared to both MK-886 and the commercial drug donepezil in a cell viability MTT assay. These

• , inspired by natural alkaloids such as deoxyvasicinone and evodiamine with promising inhibition of ChEs and antioxidant and neuroprotective effects against glutamate-induced OS in HT-22 cells [41]. In 2016, Dgachi et al. [42] applied a Knoevenagel-based multicomponent approach to further explore the

Advances in the use of metal-free tetrapyrrolic macrocycles as catalysts

• Mandeep K. Chahal

Beilstein J. Org. Chem. 2024, 20, 3085–3112, doi:10.3762/bjoc.20.257

• applied in various fields, including organometallic catalysis, dye-sensitized solar cells, sensing, artificial olfactory systems, photodynamic therapy (PDT), anticancer drugs, biochemical probes, and electrochemical devices. Relevant examples of these two pyrrolic macrocycles as metal-free organocatalysts

• , cyclam (tetraazacyclotetradecane), phthalocyanines, corroles and their supramolecular frameworks have been widely used as both homogeneous and heterogeneous electrocatalysts for various energy conversion and storage techniques, such as fuel cells, water splitting devices, and rechargeable metal–air

Synthesis of the 1,5-disubstituted tetrazole-methanesulfonylindole hybrid system via high-order multicomponent reaction

• Cesia M. Aguilar-Morales,
• América A. Frías-López,
• Nadia V. Emilio-Velázquez,
• Alejandro Islas-Jácome,
• Angelica Judith Granados-López,
• Jorge Gustavo Araujo-Huitrado,
• Yamilé López-Hernández,
• Hiram Hernández-López,
• Luis Chacón-García,
• Jesús Adrián López and
• Carlos J. Cortés-García

Beilstein J. Org. Chem. 2024, 20, 3077–3084, doi:10.3762/bjoc.20.256

• efficiency and creating six new bonds (two C–C, three C–N, and one N–N). Additionally, the products were evaluated against breast cancer MCF-7 cells, finding moderate activity in the compounds substituted with fluorine and chlorine. Keywords: 1,5-disubstituted tetrazoles; high-order multicomponent reaction

• cytotoxic compounds. For example, a cytotoxic effect was found in CAL 27 cells, presumably through a mechanism of TNF-α inhibition in vitro, which could be related to the anti-inflammatory effect identified in several studies of NSAIDs that inhibit cancer cell viability in vitro [37][38]. In another study

• aimed at inhibiting tubulin assembly, N-mesyl-2-(1-phenylvinyl)indoles were active against HCT-116 cells on the order of a GI50 of 10 mM, although the mechanism originally sought was not demonstrated [39]. Therefore, in this work, the cytotoxic activity of methanesulfonylindoles 18a–j was explored

Tunable full-color dual-state (solution and solid) emission of push–pull molecules containing the 1-pyrindane moiety

• Anastasia I. Ershova,
• Sergey V. Fedoseev,
• Konstantin V. Lipin,
• Mikhail Yu. Ievlev,
• Oleg E. Nasakin and
• Oleg V. Ershov

Beilstein J. Org. Chem. 2024, 20, 3016–3025, doi:10.3762/bjoc.20.251

• materials [14][20][21][22][23][24][25][26][27][28][29][30][31][32][33]. For example, organic π-systems whose main structural unit is stilbazole are used as active compounds in organic light-emitting diodes (OLEDs) [20], dye-sensitized solar cells (DSSCs) [21], nonlinear optics (NLO) materials [22][23

• ], positron emission tomography (PET) imaging [24], fluorescent probes and labels [25][26][27] detecting H2S in foodstuff, water, and living cells [28], Fe3+ ions [29], Hg2+ ions [30], and cyanide anions [31], for acid–base vapor sensing [32], and as candidate material for photonics devices, optical switches

Synthesis of pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives via isocyanide-based multicomponent reactions

• Marzieh Norouzi,
• Mohammad Taghi Nazeri,
• Ahmad Shaabani and
• Behrouz Notash

Beilstein J. Org. Chem. 2024, 20, 2870–2882, doi:10.3762/bjoc.20.241

• numerous reports, quantum yield is one of the most important photophysical parameters for describing luminescent molecules and materials since high quantum efficiency is important for a wide range of applications, including displays, lasers, bio-imaging, solar cells, and accurate measurement of the quantum