2-Heteroarylethylamines in medicinal chemistry: a review of 2-phenethylamine satellite chemical space

• Carlos Nieto,
• Alejandro Manchado,
• Ángel García-González,
• David Díez and
• Narciso M. Garrido

Beilstein J. Org. Chem. 2024, 20, 1880–1893, doi:10.3762/bjoc.20.163

• area of chemical space of biological importance) in medicinal chemistry is the 2-phenethyl moiety, a key component of diverse drug-like entities. Although the core 2-phenethylamine structure has been recognized by the drug discovery community, little attention has been given to the various ring-based

• De Esch et al. [55] and by Kazuta el al. [56]. The primary aim was the design of a new class of highly H3-selective agonists lacking H4 affinity by restricting the flexibility of the aminoethyl chain. Previous structure–activity exercises demonstrated an impact on selectivity upon introducing a

• systems reveals a conserved pattern: most of the changes are related to bioisostere structure–activity exploration of the chemical space from original phenyl hits. The results with the imidazole analogues are different, since the ʟ-histidine unit marks a non-phenyl-based scaffold hopping. The main goal of

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

• Cristina Martini,
• Muhammad Idham Darussalam Mardjan and
• Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

• nucleophilicity. In their second work about this topic, Prasad et al. synthesized 5-(3”-alkyl/arylamino-1”-azaindolizin-2”-yl)-2’-deoxyuridines 31 as new base-modified fluorescent nucleosides with high Stokes’ shift, potentially useful for investigating nucleic acid structure and functions. The authors

• compounds. Dömling et al. [50] also reported the synthesis of N-edited guanine derivatives. Different drugs display the guanine motif, fundamental for its biological activity is a triad HBA–HBD–HBD (HBA = hydrogen bond acceptor, HBD = hydrogen bond donor) included in its structure. The authors propose a one

• found to be compatible to the reaction conditions and a gram-scale synthesis was carried out to demonstrate the versatility of this methodology. 3.3 Post functionalization of GBB adducts The structural complexity of the original scaffolds of the GBB adducts can be increased by decorating the structure

A facile three-component route to powerful 5-aryldeazaalloxazine photocatalysts

• Ivana Weisheitelová,
• Radek Cibulka,
• Marek Sikorski and
• Tetiana Pavlovska

Beilstein J. Org. Chem. 2024, 20, 1831–1838, doi:10.3762/bjoc.20.161

• purification. Thus, it significantly improves existing approaches. Keywords: catalysis; deazaalloxazine; flavin; multicomponent approach; one-pot reaction; Introduction Heterocyclic compounds containing pyrimidine and quinoline motifs in their structure, both of natural and synthetic origin, find a wide set

• unexpected structure of product 6 was confirmed by 1H, 13C NMR and mass spectrometry. The main feature of the 1H NMR spectrum of compound 6 is the absence of the signals of the aromatic aldehyde moiety and the appearance of the singlet of the 5-CH methyne group at 9.56 ppm and the singlets of the protons of

Hetero-polycyclic aromatic systems: A data-driven investigation of structure–property relationships

• Sabyasachi Chakraborty,
• Eduardo Mayo Yanes and
• Renana Gershoni-Poranne

Beilstein J. Org. Chem. 2024, 20, 1817–1830, doi:10.3762/bjoc.20.160

• compounds that have a substantial impact in chemistry and materials science. Although their specific structure–property relationships hold the key to the design of new functional molecules, a detailed understanding of these relationships remains elusive. To elucidate these relationships, we performed a data

• PAS chemical space is with data-driven methods, which have proven in the last few years to be extremely successful at uncovering underlying structure–property relationships. To enable such exploration, we initiated the COMPAS Project (COMputational database of PASs), the first database dedicated to

• nature on the molecular properties of PASs. Our goal is to delineate specific structure–property relationships that may shed light on these prevalent, yet still mysterious, compounds and serve as design principles for future PASs. Data The molecules in COMPAS-2 contain 11 cyclic building blocks varying

Discovery of antimicrobial peptides clostrisin and cellulosin from Clostridium: insights into their structures, co-localized biosynthetic gene clusters, and antibiotic activity

• Moisés Alejandro Alejo Hernandez,
• Katia Pamela Villavicencio Sánchez,
• Rosendo Sánchez Morales,
• Karla Georgina Hernández-Magro Gil,
• David Silverio Moreno-Gutiérrez,
• Eddie Guillermo Sanchez-Rueda,
• Yanet Teresa-Cruz,
• Brian Choi,
• Armando Hernández Garcia,
• Alba Romero-Rodríguez,
• Oscar Juárez,
• Siseth Martínez-Caballero,
• Mario Figueroa and
• Corina-Diana Ceapă

Beilstein J. Org. Chem. 2024, 20, 1800–1816, doi:10.3762/bjoc.20.159

• function–structure relationships and how they impact biological activity. Since we have not found evidence of horizontal transfer of the cloA1 and cloA2 gene clusters, it is an interesting speculation that they could constitute the origin of this family and that, by duplicating one of these clusters, C

• liquenicidin VK21, and as the experimental results confirm, despite the in silico predictions, clostrisin does not form heterocycles. These differences in primary and secondary structure could be responsible for the divergent biological activities we encountered. In silico characterization of the post

• sequences from other clostridial species. A phylogenetic tree was made based on this sequence, showing various organisms within the same class (as detailed in Figure S5A in Supporting Information File 1). Additionally, structure models for CloPt1 and CloPt2 were generated using AlphaFold 2.0 [52] (Figure

Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides

• Samuel M. G. Dearman,
• Xiang Li,
• Yang Li,
• Kuldip Singh and
• Alison M. Stuart

Beilstein J. Org. Chem. 2024, 20, 1785–1793, doi:10.3762/bjoc.20.157

• (1–3 % spectroscopic yield) when BF3·OEt2 was added to the reaction mixture. X-ray crystallography and DFT calculations The solid-state structure of difluoroiodane 6 is shown in Figure 2 and displays the expected square pyramidal geometry around the iodine atom, with only minor distortion (τ5 = 0.191

• iodine(V) fluorides in good yields (72–90%). Unfortunately, none of the iodine(V) fluorides reacted with phenylmagnesium bromide to form fluorobenzene and we were never able to repeat Amey and Martin’s fluorination of phenylmagnesium bromide. A solid-state structure of 6 and DFT calculations on 6 and 20

• ) under a nitrogen atmosphere and the dichloromethane was removed in vacuo to afford difluoroiodane 6 as a pale orange solid (0.58 g, 90%). Bicyclic difluoro(aryl)-λ5-iodanes. Molecular structure of difluoroiodane 6 showing 50% displacement ellipsoids. Stability of difluoroiodane 6 in air in dry CD3CN

Ugi bisamides based on pyrrolyl-β-chlorovinylaldehyde and their unusual transformations

• Alexander V. Tsygankov,
• Vladyslav O. Vereshchak,
• Tetiana O. Savluk,
• Serhiy M. Desenko,
• Valeriia V. Ananieva,
• Oleksandr V. Buravov,
• Yana I. Sakhno,
• Svitlana V. Shishkina and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2024, 20, 1773–1784, doi:10.3762/bjoc.20.156

• presence of several alternative reaction centers in the structure of our substances, we sometimes encountered unexpected and intriguing results. Results and Discussion Synthesis of Ugi bisamides Four-component and three-component Ugi reactions The combination of pyrrole-containing α,β-unsaturated aldehyde

• reaction step for the synthesis and purification of the starting azomethines 9, we cannot propose the Ugi-3CR approach as more suitable compared to the Ugi-4CR approach. The structure of the Ugi bisamides 5–8 were proved by X-ray diffraction study on the example of substance 8c (Figure 2), according to

• which the Z-configuration of the chlorovinyl fragment was detected. Post-Ugi transformations As previously mentioned [32], the introduction of the convertible 2‑bromo-6-isocyanopyridine into the Ugi bisamide structure allows the conversion of the newly formed amide into a carboxylic acid fragment after

Harnessing unprotected deactivated amines and arylglyoxals in the Ugi reaction for the synthesis of fused complex nitrogen heterocycles

• Javier Gómez-Ayuso,
• Pablo Pertejo,
• Tomás Hermosilla,
• Israel Carreira-Barral,
• Roberto Quesada and
• María García-Valverde

Beilstein J. Org. Chem. 2024, 20, 1758–1766, doi:10.3762/bjoc.20.154

• , without purification, was treated with caesium carbonate (1 equiv) and heated to reflux for an hour. Gratefully, the dipyrrolopiperazinone derivatives 12 were obtained with high yields and complete diastereoselectivity in an efficient and simple way (Scheme 11, Table 6). The structure of these systems was

• (right). The thermal ellipsoid plot (Olex2) is at the 40% probability level. X-ray diffraction structure of dipyrrolopiperazinone 12c. The thermal ellipsoid plot (Olex2) is at the 40 % probability level. Synthesis of benzodiazepinones 5 from anthranilic acid derivatives. Diastereoselective one-pot

Synthesis of polycyclic aromatic quinones by continuous flow electrochemical oxidation: anodic methoxylation of polycyclic aromatic phenols (PAPs)

• Hiwot M. Tiruye,
• Solon Economopoulos and
• Kåre B. Jørgensen

Beilstein J. Org. Chem. 2024, 20, 1746–1757, doi:10.3762/bjoc.20.153

• cation is formed with two resonance structures (not counting further movement into the other aromatic rings destroying the aromaticity of one more ring). Resonance structure A has the cation in a benzylic position and will be the preferred site for nucleophilic attack of methanol compared to resonance

• structure B, which is further destabilized by the neighbouring ketone. A similar resonance hybrid will be formed for molecules substituted in the 4-position, like 6b, explaining the selectivity towards p-quinones. Abstraction of a proton rearomatizes the molecule before another cation is formed in the

Syntheses and medicinal chemistry of spiro heterocyclic steroids

• Laura L. Romero-Hernández,
• Ana Isabel Ahuja-Casarín,
• Penélope Merino-Montiel,
• Sara Montiel-Smith,
• José Luis Vega-Báez and
• Jesús Sandoval-Ramírez

Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152

• . Remarkably, data indicate that at least 85% of all bioactive compounds incorporate a heterocyclic moiety into their structure [1][2]. Similarly, steroids are important structures due to their involvement in numerous therapeutic targets across various organisms. The significance of generating heterocyclic

• illustrate that a spirocycle can alter the stability, physicochemical, and pharmacokinetic properties of the structure [9]. In this review, we summarize recent synthetic procedures reported between 2000 and 2023 for synthesizing steroidal spiro heterocycles. The review categorizes the procedures based on the

• reaction times. Notably, 6-endo N-cyclization to form 2-piperidinones was not observed (Scheme 5). Using this protocol, a series of spiro-β-lactams were synthesized, with only the structure of the aryl moiety being varied. It is noteworthy to consider that the formation of two vicinal quaternary chiral

Chemo-enzymatic total synthesis: current approaches toward the integration of chemical and enzymatic transformations

• Ryo Tanifuji and
• Hiroki Oguri

Beilstein J. Org. Chem. 2024, 20, 1693–1712, doi:10.3762/bjoc.20.151

• intermolecular Diels–Alder reactions with 34 or other dienophiles, leading to a diverse array of bisorbicillinoids. Based on the crystal structure of TropB, a homologous enzyme of SorbC, Narayan and co-workers have intensively elucidated that the detailed mechanisms of the oxidative dearomatization catalyzed by

• subsequently overexpressed in insect cells and purified as soluble proteins, culminating in the elucidation of the X-ray crystallographic structure of MaDA (Scheme 5B, PDB: 6JQH). With these key enzymes in hand, Lei and co-workers conducted a chemo-enzymatic total synthesis of 3 and related natural products

• applications of chemo-enzymatic hybrid syntheses increases and we better understand the extent to which the structure of enzymes and the reactivity of synthetic substrates can be predicted, guidelines for the rational design of enzymes will likely be established, enabling the rapid identification of optimal

Oxidation of benzylic alcohols to carbonyls using N-heterocyclic stabilized λ³-iodanes

• Thomas J. Kuczmera,
• Pim Puylaert and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2024, 20, 1677–1683, doi:10.3762/bjoc.20.149

• ]. A crystal structure was additionally obtained for tetrazine 1c. Bond lengths and angles were similar to those of known five-membered NHIs [25], including a strong intramolecular interaction between the nitrogen of the tetrazine and the hypervalent iodine atom (I1–N1: 2.44(4) Å; the sum of VdW radii

• on silica. Overview of common non-iodine-based (left) and iodine-based (right) oxidizing reagents for the generation of carbonyls from the corresponding alcohols. NHIs investigated for the oxidation of benzylic alcohols and the crystal structure (ORTEP drawing) of 1c (CCDC 2321313), showing the

Methyltransferases from RiPP pathways: shaping the landscape of natural product chemistry

• Maria-Paula Schröder,
• Isabel P.-M. Pfeiffer and
• Silja Mordhorst

Beilstein J. Org. Chem. 2024, 20, 1652–1670, doi:10.3762/bjoc.20.147

• sections. Myxococcus xanthus DK1622 and other strains of M. xanthus produce the peptide cittilin A (Figure 4). The novel RiPP class of cittilins was established based on its unique bicyclic structure. Experimental evidence suggests that O-methylation occurs in the last biosynthetic step by the MT CitC [65

• biocatalytic applications. The co-crystallisation of LahSB with bound SAH provides important details about the structure–function relationship, the substrate–enzyme interaction, and the cofactor binding site (Figure 5). This structural information, including the residues involved in binding, is essential for

• cyclised core peptide to exert its effects on the precursor peptide. Furthermore, SAM was shown to be an obligate co-substrate for OlvSA [71]. Crystallographic data of OlvSA is not yet available. The predicted three-dimensional structure displays substantial differences from the crystal structure of LahSB

Polymer degrading marine Microbulbifer bacteria: an un(der)utilized source of chemical and biocatalytic novelty

• Weimao Zhong and
• Vinayak Agarwal

Beilstein J. Org. Chem. 2024, 20, 1635–1651, doi:10.3762/bjoc.20.146

• barriers to natural product discovery; high rediscovery rates, reliance on largely serendipitous response in bioactivity assays, and the resources and expertise required for their structure determination being the primary impediments [1][2]. With this background, accessing biological sources that have not

• and cloned from deep-sea-derived Microbulbifer sp. JAMB-A94 with pH and temperature optima being 7.0 and 55 °C, respectively [26]. The recombinant enzyme was likewise produced using a B. subtilis host. The crystal structure of the catalytic domain was determined to show a β-jelly roll fold with

• structural similarity to two other β-agarases, ZgAgaA and ZgAgaB, from Zobellia galactanivorans, which is a model marine bacterium for the bioconversion of algal biomass [29][107][108][109]. The crystal structure suggested that the thermostability of rAgaA likely derives from the numerous surface salt

New triazinephosphonate dopants for Nafion proton exchange membranes (PEM)

• Fátima C. Teixeira,
• António P. S. Teixeira and
• C. M. Rangel

Beilstein J. Org. Chem. 2024, 20, 1623–1634, doi:10.3762/bjoc.20.145

• been shown to be dependent of the chemical structure of the dopant. Triazines are a class of heteroaromatic compounds with three nitrogen atoms on a six-membered ring, with the general formula C3N3H3. According to the position of the nitrogen atoms in the ring, they constitute 1,2,3-, 1,2,4- and 1,3,5

• that these dopants can act both as a source of protons and proton acceptors, facilitating the intermolecular proton conduction. The rational of the strategy behind the use of amino- and hydroxyphenyl spacers is twofold: i) their inclusion in the structure separates the bulky phosphonate groups from the

• ), in low yield, with a chlorine atom remaining bonded to the triazine ring (Scheme 5). The spectroscopic data of the isolated compound are in accordance with the proposed structure for compound TP1. The MS spectrum confirms the presence of a chlorine atom, with a molecular ion MH+ and a MH+ + 2 peak

pKalculator: A pK_a predictor for C–H bonds

• Rasmus M. Borup,
• Nicolai Ree and
• Jan H. Jensen

Beilstein J. Org. Chem. 2024, 20, 1614–1622, doi:10.3762/bjoc.20.144

• solvation models. CAM-B3LYP is chosen as the optimal functional based on a benchmark study that evaluates the accuracy of different levels of theory, ranging from semiempirical methods (xTB) [21] over composite electronic structure methods (r2SCAN-3c) [29] to DFT methods (CAM-B3LYP) [24][25]. All these

• produce 20 random conformers from a SMILES string and optimize the structure with molecular mechanics force fields [38] using RDKit [16]. The CM5 atomic charges of the lowest-energy conformer are then used to generate atomic descriptors based on sorting the CM5 charges for a given atom of the input SMILES

Supramolecular assemblies of amphiphilic donor–acceptor Stenhouse adducts as macroscopic soft scaffolds

• Ka-Lung Hung,
• Leong-Hung Cheung,
• Yikun Ren,
• Ming-Hin Chau,
• Yan-Yi Lam,
• Takashi Kajitani and
• Franco King-Chi Leung

Beilstein J. Org. Chem. 2024, 20, 1590–1603, doi:10.3762/bjoc.20.142

• systematically by visible light irradiation. On a macroscopic length scale, the soft DAn scaffolds were able to perform macroscopic structure disassembly upon visible-light irradiation. The biocompatibility of the macroscopic soft DAn scaffolds was investigated, revealing limited cytotoxicity. The current work

• micelle structures 3–4 nm in diameter (Figure 3b and Figure S8b, Supporting Information File 1). The supramolecular structure of DA11 and the supramolecular transformation were similar to those observed in DA10 [37]. This subtle increase in alkyl linker length in DA11 gave an essentially identical

• %) formed lamellar structures ≈200 nm in length and ≈40 nm in width (Figure 3c and Figure S8c, Supporting Information File 1), as observed by TEM. A similar lamellar structure was found in an aqueous solution of DA6 (Figure 3e and Figure S8e, Supporting Information File 1). More significant structural

Regio- and stereochemical stability induced by anomeric and gauche effects in difluorinated pyrrolidines

• Ana Flávia Candida Silva,
• Francisco A. Martins and
• Matheus P. Freitas

Beilstein J. Org. Chem. 2024, 20, 1572–1579, doi:10.3762/bjoc.20.140

• of the pyrrolidine ring in proline motifs has been found to induce significant conformational changes that impact the structure and biological roles of modified peptides and proteins. Vicinal difluorination of fluoroproline, for example, in (3S,4R)-3,4-difluoroproline, serves to mitigate the inherent

• Lewis interactions from a natural bond orbital perspective. Keywords: anomeric effect; fluoropyrrolidine; gauche effect; stereochemistry; Introduction The pyrrolidine ring structure is prevalent in numerous natural alkaloids and is an important feature of the proline and hydroxyproline residues that

• , and a stability landscape covering all optimized structures may be obtained from this analysis. Among these structures, only six were found to be significantly stable (<3 kcal⋅mol−1) in either the gas phase or DMSO. Remarkably, structure 19 was the most stable, followed by structure 17, as shown in

Mining raw plant transcriptomic data for new cyclopeptide alkaloids

• Draco Kriger,
• Michael A. Pasquale,
• Brigitte G. Ampolini and
• Jonathan R. Chekan

Beilstein J. Org. Chem. 2024, 20, 1548–1559, doi:10.3762/bjoc.20.138

• matched the structure of moroidin (Figure 4). Furthermore, manually searching for the “QLLVWRGH” core sequence in the full transcriptome only revealed the stand-alone precursor peptides, further suggesting the biosynthetic pathways contain split burpitide cyclases in these plants. This seems to suggest

• , Figures S16–S26, Table S1). Indeed, our results support the proposed structure of ceanothine B while also assigning absolute stereochemistry consistent with all ʟ-amino acids (Figure 5). We next explored the GNPS network for new cyclopeptide alkaloids from C. americanus. We previously noted the presence

• analysis, which confirmed the presence of all ʟ-Phe in the structure (Supporting Information File 1, Figure S27). Beyond this, multiple other features in the GNPS network appeared to represent new molecules for C. americanus (Supporting Information File 1, Figures S4–S11). Xylopyrine-C was previously

Primary amine-catalyzed enantioselective 1,4-Michael addition reaction of pyrazolin-5-ones to α,β-unsaturated ketones

• Pooja Goyal,
• Akhil K. Dubey,
• Raghunath Chowdhury and
• Amey Wadawale

Beilstein J. Org. Chem. 2024, 20, 1518–1526, doi:10.3762/bjoc.20.136

• temperature. The crude reaction mixture was purified by silica gel (230–400 mesh) column chromatography (petroleum ether/EtOAc as the eluent) to give the product 3 or ent-3. Selected examples of drugs and bioactive molecules bearing a pyrazole core. Single crystal X-ray structure of ent-3ba (CCDC 2234286

Photoswitchable glycoligands targeting Pseudomonas aeruginosa LecA

• Yu Fan,
• Ahmed El Rhaz,
• Stéphane Maisonneuve,
• Emilie Gillon,
• Maha Fatthalla,
• Franck Le Bideau,
• Guillaume Laurent,
• Samir Messaoudi,
• Anne Imberty and
• Juan Xie

Beilstein J. Org. Chem. 2024, 20, 1486–1496, doi:10.3762/bjoc.20.132

• deactivation of biological function. It also offers the potential to change the properties of defined molecules in biological systems with minimal disturbance to the rest of the system. Photoswitchable ligands, i.e., the incorporation of light-responsive moieties into a drug-like molecular structure, allow

• has a tetrameric structure, displays a high affinity for ᴅ-galactose (ᴅ-Gal, with Kd = 34 μM) and galactosides. The 3- and 4-hydroxy function on the ᴅ-Gal unit are involved in the coordination of Ca2+ in the binding site [5][6][7][8][32]. A large range of galactosyl conjugates have been synthetized

• were observed for the first injection, followed by titration corresponding to stoichiometry of 1, in agreement with known structure (Figure 4). Control experiment with injection of compounds in buffer only did not show significant heat of dilution. Affinity values, as well as thermodynamics

Bioinformatic prediction of the stereoselectivity of modular polyketide synthase: an update of the sequence motifs in ketoreductase domain

• Changjun Xiang,
• Shunyu Yao,
• Ruoyu Wang and
• Lihan Zhang

Beilstein J. Org. Chem. 2024, 20, 1476–1485, doi:10.3762/bjoc.20.131

• cannot be directly inferred from the final product structure, and we discuss these KRs separately based on their module types. The curated 1,762 KR sequences were grouped into different types based on their product structure and the taxonomy of their host strains (Figure 2a). Among the KR sequences we

• the sequence of both KR subdomains [13]. This suggests a strong domain–domain interaction between KR and DH, as observed in the structure of KR-DH-ER tridomain (Figure 2c) [24], and indicates that KRs in β-modules and γ/δ-modules may not be generally interchangeable for domain swapping. However, the

• KRC, the N-terminal helix αB and the lid region αFG located at the C-terminal of KRC (Figure 2d). Indeed, this lid region exhibits a direct interaction with the DH and DH-KR linker (Figure 2c). However, such interaction was not observed between the N-terminal helix αB and DH in the crystal structure

Synthesis of 2-benzyl N-substituted anilines via imine condensation–isoaromatization of (E)-2-arylidene-3-cyclohexenones and primary amines

• Lu Li,
• Na Li,
• Xiao-Tian Mo,
• Ming-Wei Yuan,
• Lin Jiang and
• Ming-Long Yuan

Beilstein J. Org. Chem. 2024, 20, 1468–1475, doi:10.3762/bjoc.20.130

• % yields. Finally, when we switched our attention to the generality of primary aromatic amines such as aniline or secondary amines such as dibenzylamine, it was found that only the starting materials were recovered after work-up of the reaction mixture. The structure of 2-benzyl N-substituted anilines 4

Selectfluor and alcohol-mediated synthesis of bicyclic oxyfluorination compounds by Wagner–Meerwein rearrangement

• Ziya Dağalan,
• Muhammed Hanifi Çelikoğlu,
• Saffet Çelik,
• Ramazan Koçak and
• Bilal Nişancı

Beilstein J. Org. Chem. 2024, 20, 1462–1467, doi:10.3762/bjoc.20.129

• rearrangement using benzonorbornadiene and the chiral natural compound (+)-camphene as bicyclic alkenes, selectfluor as an electrophilic fluorine source, and water and various alcohols as nucleophile sources. The structure of bicyclic oxy- and alkoxyfluorine compounds was determined by NMR and QTOF-MS analyses

• compounds by changing their metabolic stability, hydrogen bonding ability, lipophilicity, solubility, bioavailability, conformation and general structure [1][2][3][4]. About 20% of commercially available drugs contain fluorine, and this ratio is estimated to increase further [5][6]. Among organofluorines

Predicting bond dissociation energies of cyclic hypervalent halogen reagents using DFT calculations and graph attention network model

• Yingbo Shao,
• Zhiyuan Ren,
• Zhihui Han,
• Li Chen,
• Yao Li and
• Xiao-Song Xue

Beilstein J. Org. Chem. 2024, 20, 1444–1452, doi:10.3762/bjoc.20.127

• the core framework, incorporating ten selected atomic descriptors as local information within the graph structure. Effective molecular transformations into molecular graphs (Figure 4b) were achieved using the RDKit and Deep Graph Library [87]. The dataset was randomly divided into training and testing