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

• then elucidated as massarilactone D 4,7-di-O-crotonyl. Cytotoxic and nematicidal activities The antiproliferative properties of massarilactone D and the newly synthesized analogues were evaluated against the murine fibroblasts L929, human cervix carcinoma KB3-1, human lung carcinoma A549, human

• , as indicated by structure–activity relationship analysis. Conclusion In the present study, the use of various acylating reagents to modify massarilactone D introduces distinct functional groups, each with unique chemical properties. This approach led to the synthesis of seven previously undescribed

Total synthesis of (±)-simonsol C using dearomatization as key reaction under acidic conditions

• Xiao-Yang Bi,
• Xiao-Shuai Yang,
• Shan-Shan Chen,
• Jia-Jun Sui,
• Zhao-Nan Cai,
• Yong-Ming Chuan and
• Hong-Bo Qin

Beilstein J. Org. Chem. 2025, 21, 601–606, doi:10.3762/bjoc.21.47

• route. Keywords: acidic dearomazation; benzofuran; (±)-simonsol C; total synthesis; Introduction Star anise, derived from Illicium species cultivated in southeastern China [1] possesses significant economic, culinary, and medicinal value [2]. Particularly noteworthy are its medicinal properties

Sequential two-step, one-pot microwave-assisted Urech synthesis of 5-monosubstituted hydantoins from L-amino acids in water

• Wei-Jin Chang,
• Sook Yee Liew,
• Thomas Kurz and
• Siow-Ping Tan

Beilstein J. Org. Chem. 2025, 21, 596–600, doi:10.3762/bjoc.21.46

• accessibility of these bioactive compounds for pharmaceutical applications. Keywords: amino acids; hydantoin; microwave-assisted; one-pot reaction; Urech synthesis; Introduction The hydantoin moiety is a scaffold found in many biologically active compounds exhibiting a diverse range of properties, including

Formaldehyde surrogates in multicomponent reactions

• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Bernhard Westermann

Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45

• the oxazinane skeleton is an interesting scaffold for the design of synthetic routes for drug targets. The reaction works very well with a broad range of aromatic disulfides. Ortho, meta, and para-substituents with different electronic properties afford moderate to excellent yields. The reaction fails

Study of the interaction of 2H-furo[3,2-b]pyran-2-ones with nitrogen-containing nucleophiles

• Constantine V. Milyutin,
• Andrey N. Komogortsev and
• Boris V. Lichitsky

Beilstein J. Org. Chem. 2025, 21, 556–563, doi:10.3762/bjoc.21.44

• and allomaltol derivatives have the wide variety of biological activity [12][13][14][15][16]. This means that designing such hybrid products can significantly alter the pharmacological properties. Results and Discussion The starting compounds 1 were prepared from allomaltol employing a previously

Vinylogous functionalization of 4-alkylidene-5-aminopyrazoles with methyl trifluoropyruvates

• Judit Hostalet-Romero,
• Laura Carceller-Ferrer,
• Gonzalo Blay,
• Amparo Sanz-Marco,
• José R. Pedro and
• Carlos Vila

Beilstein J. Org. Chem. 2025, 21, 533–540, doi:10.3762/bjoc.21.41

• properties along a C=C double bond [1]. This effect has been established to be very advantageous to expand the range of reactions of different functional groups that can be coupled efficiently through a conjugated π-system. In this context, the addition reaction of vinylogous nucleophiles to carbonyl

• for the synthesis of tertiary trifluoromethyl carbinols [6][7]. In this context, trifluoromethyl carbinols constitute a key structural motif present in a wide range of molecules with important biological activities (Figure 1) [8][9][10], on account of the distinctive properties of organofluorine

Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene

• Long K. San,
• Sebastian Balser,
• Brian J. Reeves,
• Tyler T. Clikeman,
• Yu-Sheng Chen,
• Steven H. Strauss and
• Olga V. Boltalina

Beilstein J. Org. Chem. 2025, 21, 515–525, doi:10.3762/bjoc.21.39

• have promising applications in optoelectronics. For example, investigation of the photophysical and electronic properties of ANTH began in the 1960s [1][2][3], and since then many new ANTH derivatives have been synthesized and explored for their use as fluorescent probes, organic semiconductors, and

• , respectively. In this work, we explored the effects of the bulky and electron-withdrawing substituent perfluorobenzyl (BnF) on the photophysical properties and on the air- and photostability of ANTH for the first time. We hypothesized that the steric bulk of BnF and the flexibility of the –CF2– moiety between

• ANTH and the –C6F5 group might provide the desired spatial isolation of the ANTH (and other PAH) cores, and result in enhanced photoluminescence by disrupting close π–π stacking in the solid state. In addition, air- and photostability might also be improved due to the steric and electronic properties

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

• light irradiation, undergoing rearrangement and photodegradation, so there may be a risk of degradation if irradiation using UV light is tried. Alternatively, the lack of a [2 + 2] cycloaddition of Me2B, may be due to its photophysical properties not allowing for a reaction to occur, rather than the

• )bimane (DMOCDO10) and syn-(Me,Me)bimane (DXABIM10) [26], a room temperature structure of Me4B (TNZBCO10) [27], and a planar syn-(H,ethynyl)bimane (WAYHEJ) [28]. Optical properties The optical properties of the three bimanes were measured to investigate differences in their excited state properties, as

• shown in Table 2. These properties help to explain the variation in photoreactivity. Quantum yields were measured using Me2B as an internal reference, with a value of 33% in acetonitrile, as initially determined by Kosower [19]. While tentative, the low fluorescence quantum yields of these compounds may

Synthesis of N-acetyl diazocine derivatives via cross-coupling reaction

• Thomas Brandt,
• Pascal Lentes,
• Jeremy Rudtke,
• Michael Hösgen,
• Christian Näther and
• Rainer Herges

Beilstein J. Org. Chem. 2025, 21, 490–499, doi:10.3762/bjoc.21.36

• Abstract Diazocines are photoswitches derived from azobenzenes by bridging the two phenyl rings in ortho position with a CH2CH2 group forming an eight membered (diazocine) ring. Diazocine is superior to most azobenzenes in almost all photophysical properties (switching efficiency, quantum yield

• photoswitches with superior photophysical properties. The parent ethylene-bridged diazocine shows excellent switching photoconversion between the Z and the E configurations (Γ(Z → E)385nm = 92% and Γ(E → Z)520nm > 99% in n-hexane) due to well-separated n–π*-transitions in the visible part of the electromagnetic

• accumulation in the environment after excretion [1][6][7]. These superior properties of diazocines have been exploited in several applications such as the control of protein folding by implementation as cross-linkers between protein side chains [8] or in peptide backbones [9], as photoswitchable

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

• antibiotic properties, others expand the chemical diversity and thus the functional sophistication of ribonucleic acids, as in the case of Q [3]. In most bacteria, Q biosynthesis is tightly regulated by riboswitches, which are highly structured RNA elements located mostly in the 5’-leader of messenger RNA

• nucleoside queuosine (Q) occurring as natural tRNA modifications. Purine ring numbering is indicated in grey. The synthetic targets of this study are highlighted in grey: Natural riboswitch ligand pre-queuosine 1 (preQ1), a novel preQ1 analog with altered base-pairing properties (2,6-diamino-pre-queuosine 2

Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction

• James Guevara-Pulido,
• Fernando González-Pérez,
• José M. Andrés and
• Rafael Pedrosa

Beilstein J. Org. Chem. 2025, 21, 473–482, doi:10.3762/bjoc.21.34

• separated using chiral resolution. This involves separating the two enantiomers by converting the racemic mixture into a pair of diastereoisomers with the help of a chiral compound. The resulting diastereoisomers can be separated based on their physical properties using crystallization, distillation, or

Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions

• Francesco Mele,
• Ana M. Constantin,
• Andrea Porcheddu,
• Raimondo Maggi,
• Giovanni Maestri,
• Nicola Della Ca’ and
• Luca Capaldo

Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33

• light and promote mass transfer. As understanding of the methodology advances, the development of more complex synthetic strategies, including C–H, C–C, and C–heteroatom-bond formation, is expected [79]. Moreover, we anticipate that the difference in photophysical properties between organic molecules in

Electrochemical synthesis of cyclic biaryl λ³-bromanes from 2,2’-dibromobiphenyls

• Andrejs Savkins and
• Igors Sokolovs

Beilstein J. Org. Chem. 2025, 21, 451–457, doi:10.3762/bjoc.21.32

• to 2.88 V) and unsuccessful substrates 4i–m, S9a, S9b (from 1.73 V to 2.54 V) (Table S2 in Supporting Information File 1) span similar potential regimes suggesting that the success of the anodic oxidation likely depends on the structural rather than the electrochemical properties of the starting 2,2

Beyond symmetric self-assembly and effective molarity: unlocking functional enzyme mimics with robust organic cages

• Keith G. Andrews

Beilstein J. Org. Chem. 2025, 21, 421–443, doi:10.3762/bjoc.21.30

• zeolites [28][29][30][31][32]. Undoubtedly property changes can occur in cavities, but those properties not covered by organization must be explicable: I would argue (for typical ground-state reactions) they are covered by the concept of polarization. Modern descriptions of enzyme active sites speak of

• a size-selective space [105][126][129][130][132][134]. A key advantage is that these capsules have been made on multi-hundred-gram scales and can be recycled [132]. Additionally, control of structural or bound water by the capsule [105] and properties such as a lowered pKa inside [125] demonstrate a

• instance, the window[1]resorcin[3]arene capsule type [135] demonstrates that the symmetry and properties of traditional symmetric capsules can be modulated, although precise control over the assembly remains difficult. Finally, we must mention the recently reported cavitand capsules of Gibb, who has

Unraveling aromaticity: the dual worlds of pyrazole, pyrazoline, and 3D carborane

• Zahra Noori,
• Miquel Solà,
• Clara Viñas,
• Francesc Teixidor and
• Jordi Poater

Beilstein J. Org. Chem. 2025, 21, 412–420, doi:10.3762/bjoc.21.29

• photoinduced electron transfer [8][9]. Thanks to their notable photophysical properties, pyrazoles are applied in OLED technology [10]. Noticeably, in its ground state, pyrazole (C3H4N2) is an aromatic molecule that follows Hückel's rule, with two formal double bonds and a lone pair on one nitrogen generating

• therefore non-aromatic. Even when fused with benzene via a C–C bond, pyrazoline remains non-aromatic, which is the case of indazoline. Icosahedral carboranes are globular molecular clusters made of carbon and boron, displaying 3D aromaticity [12][13][14][15]. Their unique properties – such as aromaticity

• ], offering enhanced properties and efficacy [28][30][33][34][35]. Therefore, the advancement of simple, efficient methodologies for synthesizing o-carborane-fused heterocycles is critically needed. However, the limited number of synthetic strategies for carborane functionalization [36] continues to constrain

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

• the neighbouring C-2 position have been devised, formulated and standardised providing the neighbouring group assistance to form 1,2-trans glycosides [77][78]. However, acyl groups with electron-withdrawing properties in the neighbouring position have been observed to be disarming in nature in most of

• protection: The pivaloyl (OPiv) ester is another such participating ester protection with decreased migratory properties. Moreover, the intrinsic neopentyl property of the ester significantly reduces the probability of nucleophilic attack at the oxocarbenium centre instead of the anomeric carbon, thereby

• in machine-assisted oligosaccharide synthesis. 4-Acetoxy-2,2-dimethylbutanoyl (ADMB) esters were reported by Ensley and co-workers [108] having similar properties with the pivalate group. The facile removal of the C-2-ADMB group with a catalytic quantity of diazabicycloundecane (DBU) in methanol at

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

• properties towards CN− and Hg2+ ions and evaluation of in vitro cytotoxic activity against A431 skin cancer and H1299 lung cancer cell lines. Results and Discussion We found that boiling of equimolar amounts of benzannelated 2,3,3-trimethylindolenines 2a,b and o-chloranil (3) (method A) in dioxane leads to

• represent molecular switches of optical and fluorescent properties under sequential addition of CN− and Hg2+ ions and the transformation cycle presented in Scheme 3 can be repeated at least 5–6 times. The resulting compounds 7b and 8a,b have extremely low water solubility, which makes it impossible to

• properties under sequential addition of CN− and Hg2+ ions. 2-(1,1-Dimethyl-1H-benzo[e]indolin-2-yl)-5,6,7-trichloro-1,3-tropolone (7a) was found to exhibit high in vitro cytotoxic activity against A431 skin cancer and H1299 lung cancer cell lines. In addition, the IC50 values of compound 7a are significantly

Synthesis of new condensed naphthoquinone, pyran and pyrimidine furancarboxylates

• Kirill A. Gomonov,
• Vasilii V. Pelipko,
• Igor A. Litvinov,
• Ilya A. Pilipenko,
• Anna M. Stepanova,
• Nikolai A. Lapatin,
• Ruslan I. Baichurin and
• Sergei V. Makarenko

Beilstein J. Org. Chem. 2025, 21, 340–347, doi:10.3762/bjoc.21.24

• heterocyclic structures leads to the production of new types of heterocyclic compounds with practical useful properties [1][2][3][4][5][6]. Representatives of the naphthofuran series exhibit anticancer [7] and antiinfectious activity [8]. Anticancer properties have also been found in representatives of the

• ethyl esters 5b and 6b is −15.6(2) and −11.5(2)°, respectively, indicating that in the case of methyl esters, the alkoxycarbonyl fragment is less out of plane, causing a greater conjugation with the furan fragment. The possibility of exhibiting fluorescent properties was investigated for tetracyclic

• , λMo Kα = 0.71073 Å, ω and φ scanning in 0.5° steps) at the distributed spectral-analytical center of shared facilities for study of structure, composition and properties of substances and materials of FRC Kazan scientific center of Russian academy of sciences. Crystals of compounds suitable for X-ray

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

• anticancer properties [6]. With concerns about biofilm formation and resistance escalating in the medical field, entomopathogenic fungi have emerged as a promising source of novel bioactive compounds [5]. Our recent exploration of B. neobassiana highlighted this growing interest, affording one tetramic acid

• screening assays were conducted to explore their antibiofilm properties. According to the crystal violet (CV) assay, both compounds exhibited significant activity in the S. aureus biofilm inhibition assay. Farinosone A (2) (Figure 5A) displayed activity at a concentration as low as 3.9 µg/mL, resulting in

• activity trend, reflecting the results from CV biofilm inhibition assay, where compound 2 was found to be more effective than compound 1. The genetic and molecular basis of biofilm formation in staphylococci are complex. This process involves at least two key properties: planktonic cell adherence to

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

• advantageous for large-scale applications, offering enhanced safety and operational simplicity. Traditionally, research in this field has focused on metal-based photocatalysts, particularly those based on transition metals like ruthenium and osmium due to their intrinsic photophysical properties. However, with

• , which exploits the properties of red-light excitation while addressing the energy constraints posed by low-energy photons. Whereas multiple works addressing the upconversion phenomenon involving heavy metals like palladium, platinum [23][24] or osmium [25], grafted ruthenium complexes over ytterbium and

•  4d) [30]. In a continuation of this trend, a recent study by O. S. Wenger et al. further expands the frontiers of red-light photoredox catalysis with first-row transition metals by introducing Cr(0) luminophores that exhibit photophysical properties competitive with Ru(II) and Os(II) complexes [31

Oxidation of [3]naphthylenes to cations and dications converts local paratropicity into global diatropicity

• Abel Cárdenas,
• Zexin Jin,
• Yong Ni,
• Jishan Wu,
• Yan Xia,
• Francisco Javier Ramírez and
• Juan Casado

Beilstein J. Org. Chem. 2025, 21, 277–285, doi:10.3762/bjoc.21.20

• , National University of Singapore, 3 Science Drive 3, Singapore, Singapore 10.3762/bjoc.21.20 Abstract Oxidized states of polycyclic aromatic hydrocarbons are of importance as they represent charged conductive species in organic semiconductor substrates. In this work, we investigated the properties of

• , all of which lead to conductive and photoactive species [9][12]. Given the inherent instability of neutral antiaromatic systems, including those systems containing fragments or moieties with local antiaromaticity, the detailed structural properties of the charged species formed from neutral

• 1700 cm−1 Raman band) and in NAP for m-2 (marked by the triplet in the 1500–1600 cm−1 region). Nucleus-independent chemical shifts (NICS) Among the different criteria to evaluate aromaticity, magnetic properties are the most confident, as they are directly connected with the ring currents associated to

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

• properties were investigated by UV–vis absorption and fluorescence spectroscopy in compassion to pristine BPP and its oxidation product, benzo[rst]pentaphene-5,8-dione (BPP-dione). BPP-OiPr exhibited a significantly enhanced photoluminescence quantum yield (PLQY), reaching 73% in comparison to pristine BPP

• by scanning electron microscopy. The intriguing optical properties of BPP and its derivatives may lead to their application as fluorophores. Keywords: benzo[rst]pentaphene; intramolecular charge transfer; nanocrystals; photoluminescence; polycyclic aromatic hydrocarbon; Introduction Polycyclic

• aromatic hydrocarbons (PAHs) have attracted increasing attention in view of their fascinating optical and electronic properties, which strongly depend on their size, shape, and edge structures, e.g., armchair and zigzag [1][2][3][4][5][6]. Benzo[rst]pentaphene (BPP) is an intriguing PAH with a combination

Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory

• Misato Suganuma,
• Daichi Kitagawa,
• Shota Hamatani and
• Seiya Kobatake

Beilstein J. Org. Chem. 2025, 21, 242–252, doi:10.3762/bjoc.21.16

• family of photochromic compounds. This study explores the photochromic properties and thermal back reactivities of various aza-diarylethene regioisomers (N1–N4 and I1–I4) in n-hexane. These molecules exhibit fast thermally reversible photochromic reactions driven by 6π aza-electrocyclization. Kinetic

• Molecular photoswitches have been studied for a long time because their physicochemical properties such as refractive index [1][2], dipole moment [3][4], conductivity [5][6], magnetism [7][8], and fluorescence [9][10][11] can be spatiotemporally modulated by light without physical contact. Therefore

• ][26][27], photomechanical materials [28][29][30][31][32], and so on. As seen in these representative application examples, the thermal stability of the colorless and colored isomers is one of the essential properties of molecular photoswitches. For example, the photochemically reversible-type (P-type

Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles

• Yujun Pang,
• Jinglan Yan,
• Nawaf Al-Maharik,
• Qian Zhang,
• Zeguo Fang and
• Dong Li

Beilstein J. Org. Chem. 2025, 21, 234–241, doi:10.3762/bjoc.21.15

• pharmaceuticals and agrochemicals nowadays, largely due to the unique ability of fluorinated groups to influence the physicochemical and biochemical properties of molecules [1][2][3]. Among the various fluorinated functionalities, the difluoromethyl (CF2H) group and its aryl-substituted derivative, the benzylic

• properties that can modify the activity and pharmacokinetic profiles of drugs [7]. Prominent examples include pantoprazole, a widely used proton-pump inhibitor (PPI) featuring a CF2H group; deracoxib, another drug that also incorporates a CF2H moiety in its structure; and a MET inhibitor specifically

• designed with a PhCF2 group (Figure 1a) [8][9][10]. As a result, there is a pressing need for the development of efficient methods for incorporating both the CF2H and PhCF2 groups into diverse molecular frameworks, particularly those with bioactivity properties. The benzimidazole core is widely recognized

Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization

• Asahi Kanno,
• Ryo Tanifuji,
• Satoshi Yoshida,
• Sota Sato,
• Saori Maki-Yonekura,
• Kiyofumi Takaba,
• Jungmin Kang,
• Kensuke Tono,
• Koji Yonekura and
• Hiroki Oguri

Beilstein J. Org. Chem. 2025, 21, 226–233, doi:10.3762/bjoc.21.14

• the optical properties of 18 in CHCl3 (c = 100 μM) by measuring its UV–vis absorption spectrum as well as its excitation and emission spectra. The UV–vis spectrum of 18 showed two absorption peaks at 334 nm and around 375 nm (gray solid line). When excited at 375 nm, the emission spectra of 18