Research progress on calixarene/pillararene-based controlled drug release systems

• Liu-Huan Yi,
• Jian Qin,
• Si-Ran Lu,
• Liu-Pan Yang,
• Li-Li Wang and
• Huan Yao

Beilstein J. Org. Chem. 2025, 21, 1757–1785, doi:10.3762/bjoc.21.139

• 2023, Zhang and colleagues [109] constructed a tumor microenvironment (TME)-activated supramolecular nanoplatform (Figure 8) which was consisted of a pillar[5]arene-based amphiphilic polymer (POPD), a phototherapeutic agent (Cy7-CN), an antimalarial drug with respiratory function (atovaquone, ATO), and

• -DM) or fingolimod (FTY720) in vitro. Upon local administration, the hypoxia-responsive self-assembling peptide hydrogel resulted in improved motor function and reduced inflammation in vivo. Recently, Geng and colleagues created additional binding sites by modifying the upper rim of CA4 with glucose

Preparation of a furfural-derived enantioenriched vinyloxazoline building block and exploring its reactivity

• Madara Darzina,
• Anna Lielpetere and
• Aigars Jirgensons

Beilstein J. Org. Chem. 2025, 21, 1737–1741, doi:10.3762/bjoc.21.136

• analogously from ester R-3d. Thus, Alloc was validated as non-expensive and relatively small N-protecting group, removal of which is compatible with double bond and acetal function of amides S-5 and R-5. The removal of the Pd catalyst at laboratory scale was done by chromatography. For large scale synthesis

Convenient alternative synthesis of the Malassezia-derived virulence factor malassezione and related compounds

• Karu Ramesh and
• Stephen L. Bearne

Beilstein J. Org. Chem. 2025, 21, 1730–1736, doi:10.3762/bjoc.21.135

• function [16][17]. Malassezione (1, also referred to as malathidone [18]) is an AHR agonist [19][20]. Recently, in an effort to identify compounds as glucokinase activators to treat type 2 diabetes, structure-based virtual screening identified malassezione as a potential glucokinase activator [21

Approaches to stereoselective 1,1'-glycosylation

• Daniele Zucchetta and
• Alla Zamyatina

Beilstein J. Org. Chem. 2025, 21, 1700–1718, doi:10.3762/bjoc.21.133

• ][12][13][14] and the nucleoside antibiotic tunicamycin [15][16][17], etc. These molecules play essential roles in cell signaling, host–pathogen interactions, and pathogenesis and, being the constituent of pathogen-associated molecular patterns (PAMPs), can function as critical virulence factor [7][18

• donors [65][66], care must be taken, and glycosylation conditions optimized to avoid the formation of oxocarbenium ions from TMS-glycosides intended to function as glycosyl acceptors. In this case, the ketoses 49 and 52 formed the oxocarbenium ions more readily due to stabilization by their alkyl

Continuous-flow-enabled intensification in nitration processes: a review of technological developments and practical applications over the past decade

• Feng Zhou,
• Chuansong Duanmu,
• Yanxing Li,
• Jin Li,
• Haiqing Xu,
• Pan Wang and
• Kai Zhu

Beilstein J. Org. Chem. 2025, 21, 1678–1699, doi:10.3762/bjoc.21.132

• literature reported by Marziano et al. [63], the introduction of the Mc function allows the activity coefficients-based rate equation to be reformulated as Mc function-correlated rate equation, explicitly linking sulfuric acid acidity to reaction rates. Therefore, the linearized integrated form for kinetics

• analysis can be obtained from the Mc function-correlated rate equation. The linearized equation requires prior determination of two key parameters: (i) the acidity function Mc and (ii) the concentration ratio of , to resolve the values of k* and n. According to the works of Marziano et al. [64][65][66

• ], quantitative correlations between the Mc function and both sulfuric acid concentration and temperature could be established. The values of are governed by both temperature and sulfuric acid concentration. The experimental determination of across varying temperature and H2SO4 concentrations has been widely

Structural analysis of stereoselective galactose pyruvylation toward the synthesis of bacterial capsular polysaccharides

• Tsun-Yi Chiang,
• Mei-Huei Lin,
• Chun-Wei Chang,
• Jinq-Chyi Lee and
• Cheng-Chung Wang

Beilstein J. Org. Chem. 2025, 21, 1671–1677, doi:10.3762/bjoc.21.131

• function. Careful manipulation of reaction conditions such as solvent and temperature is necessary to achieve sufficient diastereomeric purity in pyruvate modification. This research contributes to the development in the field of polysaccharide synthesis and draws upon established methodologies, reflecting

Synthesis of optically active folded cyclic dimers and trimers

• Ena Kumamoto,
• Kana Ogawa,
• Kazunori Okamoto and
• Yasuhiro Morisaki

Beilstein J. Org. Chem. 2025, 21, 1603–1612, doi:10.3762/bjoc.21.124

• the PL decay curves (Figure S17, Supporting Information File 1) were fitted with the single exponential function. The lifetimes (τ) were estimated to be 1.6 ns and 1.0 ns, respectively. Circular dichroism (CD) and CPL spectra of (Sp)-6 and (Sp)-7 were obtained in CHCl3 solutions (1.0 × 10−5 M), and

Thermodynamic equilibrium between locally excited and charge transfer states in perylene–phenothiazine dyads

• Issei Fukunaga,
• Shunsuke Kobashi,
• Yuki Nagai,
• Hiroki Horita,
• Hiromitsu Maeda and
• Yoichi Kobayashi

Beilstein J. Org. Chem. 2025, 21, 1577–1586, doi:10.3762/bjoc.21.121

• band follow a single-exponential decay function in all compounds (Supporting Information File 1, Figure S23 and Figure S24). As a representative example, Figure 4 presents the emission decay profiles of Pe–PTZ(TPA)2, with overlaid decay curves monitored at 600 nm and 460 nm. The lifetimes of the CT

• states were 10.7, 10.3, 9.7, and 10.8 ns for Pe–PTZ, Pe–PTZ(PTA), Pe–PTZ(PTA)2, and Pe–Ph–PTZ(PTA)2, respectively. At the probe wavelength corresponding to the LE band of the Pe moiety (460 nm), a subnanosecond decay attributable to the LE state of the Pe moiety (within the instrumental response function

• the PTZ(TPA)2 moiety and the Pe radical anion almost instantaneously. The electron transfer occurs extremely rapidly (within the instrumental response function, <100 fs), likely via a direct CT transition. Subsequently, both signals showed growth components with time constants of 2.4 and 639 ps

General method for the synthesis of enaminones via photocatalysis

• Paula Pérez-Ramos,
• Raquel G. Soengas and
• Humberto Rodríguez-Solla

Beilstein J. Org. Chem. 2025, 21, 1535–1543, doi:10.3762/bjoc.21.116

• function (Scheme 4B). Furthermore, when the reaction of chromone 10 was carried out under standard conditions, the starting material was recovered unaltered, evidencing that the photocatalyzed dehalogenation step is crucial to enable the ring opening (Scheme 4C). In order to determine the role of Ni(II) in

Highly distinguishable isomeric states of a tripodal arylazopyrazole derivative on graphite through electron/hole-induced switching at ambient conditions

• Himani Malik,
• Sudha Devi,
• Debapriya Gupta,
• Ankit Kumar Gaur,
• Sugumar Venkataramani and
• Thiruvancheril G. Gopakumar

Beilstein J. Org. Chem. 2025, 21, 1496–1507, doi:10.3762/bjoc.21.112

• triggered through external stimuli to induce the switching and to modulate the function. Photo-triggerable molecular switches like azobenzene (AB) [10][11][12][13], spiropyran [14], diarylethene [15] and multifunctional AB [16] have attracted a lot of interest due to the distinct differences in the

• measurements obtained on two single FNAAP molecules. Additional I–V measurements are provided in Supporting Information File 1, section 7 for reference. Unlike the expected continuous variation of current as a function of voltage, we observed abrupt increases and decreases in the tunneling current, as

• ) are observed at both sample voltage polarities. The statistics of the number of states as a function of sample voltage are given in Figure 5b. The number of states increases as the voltage increases and reaches a maximum value of 8. We attribute the 8 distinguishable levels of current to the 8 states

Heterologous biosynthesis of cotylenol and concise synthesis of fusicoccane diterpenoids

• Ye Yuan,
• Zhenhua Guan,
• Xue-Jie Zhang,
• Nanyu Yao,
• Wenling Yuan,
• Yonghui Zhang,
• Ying Ye and
• Zheng Xiang

Beilstein J. Org. Chem. 2025, 21, 1489–1495, doi:10.3762/bjoc.21.111

• -inflammatory, antimicrobial, antiparasitic, and plant growth regulating activities. For instance, cotylenin A (1) and fusicoccin A (2) function as molecular glues to stabilize the interactions between 14-3-3 proteins and their binding partners in plant and animal cells [8][9][10][11][12]. It has been reported

Tautomerism and switching in 7-hydroxy-8-(azophenyl)quinoline and similar compounds

• Lidia Zaharieva,
• Vera Deneva,
• Fadhil S. Kamounah,
• Nikolay Vassilev,
• Ivan Angelov,
• Michael Pittelkow and
• Liudmil Antonov

Beilstein J. Org. Chem. 2025, 21, 1404–1421, doi:10.3762/bjoc.21.105

• makes possible to analyze the tautomerism in 1 as a function of (E+KE) and KK. The NMR spectra of 1 in acetonitrile-d3 are in agreement with the above analysis of tautomeric equilibration based on theoretical calculations and UV spectra. At room temperature the proton signals are very broad and

• the assignment of the carbon spectrum. The proton signal at 16.59 ppm seems to be a sum of two signals and a deconvolution with Lotenzian bandshape function was performed (Figure S5 in Supporting Information File 1). The obtained two signals have an integral intensity of 78 to 22, which is in

• corresponding state. The Franck–Condon states of the tautomers, existing in solution, are given in green. Changes of the absorbance of compound 1 at 465 nm in toluene upon turning on and off the irradiation source (365 nm). a) Change of ΔE(K-E) in kcal/mol as a function of the substitution on different

Recent advances in oxidative radical difunctionalization of N-arylacrylamides enabled by carbon radical reagents

• Jiangfei Chen,
• Yi-Lin Qu,
• Ming Yuan,
• Xiang-Mei Wu,
• Heng-Pei Jiang,
• Ying Fu and
• Shengrong Guo

Beilstein J. Org. Chem. 2025, 21, 1207–1271, doi:10.3762/bjoc.21.98

• the system. In 2024, Liang’s group reported the replacement of N-arylacrylamides with 7-fluoro-3-homoallylquinazolin-4-ones, which are tethered to an alkenyl group at the nitrogen atom and function as radical acceptors (Scheme 17). This approach effectively facilitated photoelectrocatalytic

Enhancing chemical synthesis planning: automated quantum mechanics-based regioselectivity prediction for C–H activation with directing groups

• Julius Seumer,
• Nicolai Ree and
• Jan H. Jensen

Beilstein J. Org. Chem. 2025, 21, 1171–1182, doi:10.3762/bjoc.21.94

• . The fraction of each prediction class (correct, semi-correct, wrong) as a function of the evaluation threshold is shown in Figure S1, Supporting Information File 1. Here, one can see that the number of wrong predictions is reduced by more than 30% when using an evaluation threshold of 1 kcal·mol−1

• , like meta or para functionalization. This can be done by using the workflow in the scoring function of a genetic algorithm, for example. Here, the absolute directing strength towards a specific site can be used to score different directing groups to each other and have the genetic algorithm design

Recent total synthesis of natural products leveraging a strategy of enamide cyclization

• Chun-Yu Mi,
• Jia-Yuan Zhai and
• Xiao-Ming Zhang

Beilstein J. Org. Chem. 2025, 21, 999–1009, doi:10.3762/bjoc.21.81

• the α-position of enamide to be an active cyclization site, with the alkyne tether acting as the nucleophile. Since it is well-established that alkynes, when activated by transition metals such as gold or platinum, can also function as electrophiles, modulating the reactivity of the decahydroquinoline

On the photoluminescence in triarylmethyl-centered mono-, di-, and multiradicals

• Daniel Straub,
• Markus Gross,
• Mona E. Arnold,
• Julia Zolg and
• Alexander J. C. Kuehne

Beilstein J. Org. Chem. 2025, 21, 964–998, doi:10.3762/bjoc.21.80

Study of tribenzo[b,d,f]azepine as donor in D–A photocatalysts

• Katy Medrano-Uribe,
• Jorge Humbrías-Martín and
• Luca Dell’Amico

Beilstein J. Org. Chem. 2025, 21, 935–944, doi:10.3762/bjoc.21.76

• promising redox potentials in their excited states, indicating their potential to function as effective bimodal photocatalysts. Additionally, our photophysical characterization provided essential insights into their behavior in the excited state and stability. We initiated the study of the photocatalytic

Dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion–π interactions

• Wen-Hui Mi,
• Teng-Yu Huang,
• Xu-Dong Wang,
• Yu-Fei Ao,
• Qi-Qiang Wang and
• De-Xian Wang

Beilstein J. Org. Chem. 2025, 21, 884–889, doi:10.3762/bjoc.21.72

• Wen-Hui Mi Teng-Yu Huang Xu-Dong Wang Yu-Fei Ao Qi-Qiang Wang De-Xian Wang Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China University of Chinese Academy of

Chitosan-supported CuI-catalyzed cascade reaction of 2-halobenzoic acids and amidines for the synthesis of quinazolinones

• Xuhong Zhao,
• Weishuang Li,
• Mengli Yang,
• Bojie Li,
• Yaoyao Zhang,
• Lizhen Huang and
• Lei Zhu

Beilstein J. Org. Chem. 2025, 21, 839–844, doi:10.3762/bjoc.21.67

• efficient, reusable heterogeneous catalyst for this cascade reaction, achieving good to excellent yields without any loss of activity even after ten cycles of simple filtration-based recovery [12]. Moreover, a copper catalyst has been shown to function effectively in both organic and aqueous media [13][14

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

• -orientation of one glycoligand in the presence of another glycoligand that remains unaffected. It seems to be obvious that an “optoglycomics” approach in the glycosciences in order to investigate carbohydrate function by light can lead to new insights into carbohydrate recognition. However, complex systems

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

• cyclic amines. Next, we will examine some important derivatives of amines, such as amides and sulfonamides. Throughout, the emphasis will mostly be on bioactive molecules, but finally this section will conclude by examining a different type of molecular function, namely, organocatalysis. When fluorine is

Asymmetric synthesis of fluorinated derivatives of aromatic and γ-branched amino acids via a chiral Ni(II) complex

• Maurizio Iannuzzi,
• Thomas Hohmann,
• Michael Dyrks,
• Kilian Haoues,
• Katarzyna Salamon-Krokosz and
• Beate Koksch

Beilstein J. Org. Chem. 2025, 21, 659–669, doi:10.3762/bjoc.21.52

• , interaction and function. Furthermore, the synthesis of both isomers of trifluoroleucine was described. (2S,4R)-Trifluoroleucine could be isolated on a milligram-scale in good yields and excellent enantiomeric purities, representing a viable synthetic route for these building blocks adding another strategy to

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

• function. Their chemical modification has been developed using iminoxyl radicals [28]. Although numerous methods exist for the functionalization of Trp in proteins, their application in the elaboration of ADCs is limited [29]. Given the many challenges in antibody modification as outlined above, it is

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

• cytotoxic activity of natural products by increasing the hydrophobicity, enhancing cell membrane permeability and binding affinity with intracellular targets [26]. Structure–activity relationships analysis of both hemisynthetic products 2 and 3 revealed a shared conjugated methylene olefinic function that

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

• function as aldehyde equivalent in reactions where iminium species are involved. In this case, the C–X bond of the dihaloalkanes can be activated by metal catalysis, allowing the incorporation of the C1 building block by a mechanism that does not involve the preformation of an imine/enamine intermediate