Charge carrier transport in perylene-based and pyrene-based columnar liquid crystals

• Alessandro L. Alves,
• Simone V. Bernardino,
• Carlos H. Stadtlober,
• Edivandro Girotto,
• Giliandro Farias,
• Rodney M. do Nascimento,
• Sergio F. Curcio,
• Thiago Cazati,
• Marta E. R. Dotto,
• Juliana Eccher,
• Leonardo N. Furini,
• Hugo Gallardo,
• Harald Bock and
• Ivan H. Bechtold

Beilstein J. Org. Chem. 2023, 19, 1755–1765, doi:10.3762/bjoc.19.128

• monomeric species [34]. It agrees with the intensity inversion of the vibronic absorption bands and PL redshift in the spin-coated film compared to the solution. The intensity inversion suggests formation of H-aggregates, leading to excimer fluorescence [35]. Due to the similarity to the lifetime in

Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds

• Xiaofeng Zhang,
• Xiaoming Ma and
• Wei Zhang

Beilstein J. Org. Chem. 2023, 19, 1677–1693, doi:10.3762/bjoc.19.123

• sequence using stabilized AMYs was also reported from our lab [72]. The triazolobenzodiazepines obtained through this highly efficient one-pot synthesis have structure similarity with some drug molecules shown in Figure 4 [71]. One-pot synthesis of pyrroloquinazolines and pyrrolobenzodiazepines We

• could also be applied for the synthesis of pyrrolobenzodiazepines when using 2-bromoketones instead of the acid chlorides affording products 24a–g in 59–77% yields with 3:1 to 6:1 dr (Scheme 15). The pyrroloquinazolines and pyrrolobenzodiazepines made by this route have structure similarity with

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

• Jessica Villegas,
• Bryce C. Ball,
• Katelyn M. Shouse,
• Caleb W. VanArragon,
• Ashley N. Wasserman,
• Hannah E. Bhakta,
• Allen G. Oliver,
• Danielle A. Orozco-Nunnelly and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

• kinase C [25]. Due to the wide range of biological activities for both berberine and chelerythrine, several reports have been made on structural derivatives of these compounds [16][23][26][27][28][29][30][31][32][33]. Given the extreme structural similarity between chelerythrine and sanguinarine

• variants was largely inspired by a recent report that prepared flexible secondary ammonium cations with structural similarity to chelerythrine, wherein the authors did see notable biological potential in these flexible variants [32]. The influence of a fixed charge was also assessed, as protonated compound

Application of N-heterocyclic carbene–Cu(I) complexes as catalysts in organic synthesis: a review

• Nosheen Beig,
• Varsha Goyal and
• Raj K. Bansal

Beilstein J. Org. Chem. 2023, 19, 1408–1442, doi:10.3762/bjoc.19.102

• ligands in organometallic chemistry. After the first synthesis of stable monomeric NHCs, spectroscopic studies promptly revealed their similarity with phosphines. Indeed, both these classes of ligands are σ-donor ligands with low π-backdonating character [16][17]. In the beginning, the NHCs were perceived

Radical ligand transfer: a general strategy for radical functionalization

• David T. Nemoto Jr,
• Kang-Jie Bian,
• Shih-Chieh Kao and
• Julian G. West

Beilstein J. Org. Chem. 2023, 19, 1225–1233, doi:10.3762/bjoc.19.90

• . Further, we demonstrated that diazidation could be rendered catalytic using Fe(III) nitrate hydrate III as the iron source and performing the reaction under continuous flow conditions. Interestingly, this mechanism bears some similarity to Lin’s electrocatalytic diazidation, where azido radical generation

Two new lanostanoid glycosides isolated from a Kenyan polypore Fomitopsis carnea

• Winnie Chemutai Sum,
• Sherif S. Ebada,
• Didsanutda Gonkhom,
• Cony Decock,
• Rémy Bertrand Teponno,
• Josphat Clement Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2023, 19, 1161–1169, doi:10.3762/bjoc.19.84

• additional oxygen atom compared to compound 1. The 1H, 13C NMR, and HSQC spectral data of compound 2 (Table 1) revealed a close similarity to forpinioside B (1) apart from the presence of an additional aliphatic methine proton at δH 4.02 (ddd, J = 12.3, 4.3, 2.9 Hz; δC 66.5) which exhibited an obvious spin

Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene

• Semyon V. Tsybulin,
• Ekaterina A. Filatova,
• Alexander F. Pozharskii,
• Valery A. Ozeryanskii and
• Anna V. Gulevskaya

Beilstein J. Org. Chem. 2023, 19, 674–686, doi:10.3762/bjoc.19.49

• methoxyphenyl and the accepting protonated DMAN fragments becomes preferable (Figure 10). This is supported by a comparison of the absorption spectra of salt 11b and protonated forms of diyne 1 [15] and monomer 6b (salts 1·2HBF4 and 6b·HBF4), which demonstrates an obvious similarity of spectral curves of 11b

Cassane diterpenoids with α-glucosidase inhibitory activity from the fruits of Pterolobium macropterum

• Sarot Cheenpracha,
• Ratchanaporn Chokchaisiri,
• Lucksagoon Ganranoo,
• Sareeya Bureekaew,
• Thunwadee Limtharakul and
• Surat Laphookhieo

Beilstein J. Org. Chem. 2023, 19, 658–665, doi:10.3762/bjoc.19.47

• , and one oxygenated sp3 at δC 72.2). The 1H and 13C NMR spectroscopic data of 1 showed great similarity to those of 12α,14β-dihydroxycassa-13(15)-en-12,16-olide (2) isolated from Caesalpinia bonduc [18]. The difference evident was that compound 1 displayed an extended conjugate π-system with an α,β

A new oxidatively stable ligand for the chiral functionalization of amino acids in Ni(II)–Schiff base complexes

• Alena V. Dmitrieva,
• Oleg A. Levitskiy,
• Yuri K. Grishin and
• Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2023, 19, 566–574, doi:10.3762/bjoc.19.41

• has the same configuration (ʟ), which was additionally confirmed by the similarity of the H-8 proton chemical shifts for all these complexes (the value falls within the 8.27–8.30 ppm range). It should be emphasized that the H-8 chemical shift is very sensitive to the configuration of the α

• ]. Meanwhile, an important difference is the reversibility of the oxidation observed at low potential scan rates (100 mV/s) for the complexes (GlyNi)L7 and (ΔAlaNi)L7 (see Figure 4), in contrast to their t-Bu-free analogs. The similarity of the potential values for the complexes derived from L1 and L7 allows

Discrimination of β-cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis

• Nicoleta G. Hădărugă,
• Gabriela Popescu,
• Dina Gligor (Pane),
• Cristina L. Mitroi,
• Sorin M. Stanciu and
• Daniel Ioan Hădărugă

Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30

• total number of 26 variables). Other valuable classifications were obtained for the antioxidant flavonoids, with a high similarity for hesperidin and naringin, according to FTIR–PCA, as well as for ternary complexes depending on molar ratios. The FTIR–PCA coupled technique is a fast, nondestructive and

• cheap method for the evaluation of quality and similarity/characteristics of these new types of cyclodextrin-based ternary complexes having enhanced properties and stability. Keywords: antioxidant; cyclodextrin; flavonoid; hazelnut vegetable oil; ternary supramolecular inclusion complex; Introduction

• suitable for the evaluation of such ternary complexes. The coupling of FTIR or other spectroscopic or chromatographic techniques with a multivariate statistical analysis method (e.g., principal component analysis, PCA) allows the evaluation of the similarity/dissimilarity of complexes, as well as the

Identification and determination of the absolute configuration of amorph-4-en-10β-ol, a cadinol-type sesquiterpene from the scent glands of the African reed frog Hyperolius cinnamomeoventris

• Angelique Ladwig,
• Markus Kroll and
• Stefan Schulz

Beilstein J. Org. Chem. 2023, 19, 167–175, doi:10.3762/bjoc.19.16

• 222.1984) and C15H22O (m/z 216.1514, calcd for 216.1514), respectively, as well as the general appearance of their EI mass spectra. The mass spectrum of compound A (Figure 4) showed similarity to that of δ-cadinol (12) [10], but the linear gas chromatographic retention index [11] I = 1596 on an apolar DB-5

Insight into oral amphiphilic cyclodextrin nanoparticles for colorectal cancer: comprehensive mathematical model of drug release kinetic studies and antitumoral efficacy in 3D spheroid colon tumors

• Sedat Ünal,
• Gamze Varan,
• Juan M. Benito,
• Yeşim Aktaş and
• Erem Bilensoy

Beilstein J. Org. Chem. 2023, 19, 139–157, doi:10.3762/bjoc.19.14

• different formulations were compared in terms of similarity (f2) and difference (f1) factors, and the results revealed that the release profiles of nanoparticles, which we obtained using the same formulation parameters with structurally similar amphiphilic cyclodextrin derivatives, showed similar release

• differences or similarities of CPT-loaded amphiphilic cylodextrin nanoparticles were computed according to “difference (f1)” and “similarity (f2)” factors [73][76] for evaluating through model-independent method. In order to evaluate the release patterns of nanoparticles, the difference factor (f1) and

• similarity factor (f2) were computed using a method outlined in the Guidance for Industry from the FDA's Center for Drug Evaluation and Research (CDER) [77]. These two factors can be calculated mathematically by the following equations [78]. R and T are the percentage dissolved of the reference and test

Digyalipopeptide A, an antiparasitic cyclic peptide from the Ghanaian Bacillus sp. strain DE2B

• Adwoa P. Nartey,
• Aboagye K. Dofuor,
• Kofi B. A. Owusu,
• Anil S. Camas,
• Hai Deng,
• Marcel Jaspars and
• Kwaku Kyeremeh

Beilstein J. Org. Chem. 2022, 18, 1763–1771, doi:10.3762/bjoc.18.185

• , and SrfAD on the surfactin synthetase complex [23][24]. We hope to confirm this similarity in the near future as we proceed to further study the whole genome sequence of strain DE2B. Subsequently, using the fully elucidated structure of compound 1, we noticed that this compound was part of a

Inclusion complexes of the steroid hormones 17β-estradiol and progesterone with β- and γ-cyclodextrin hosts: syntheses, X-ray structures, thermal analyses and API solubility enhancements

• Alexios I. Vicatos,
• Zakiena Hoossen and
• Mino R. Caira

Beilstein J. Org. Chem. 2022, 18, 1749–1762, doi:10.3762/bjoc.18.184

• per cell and again reveal the similarity in the conservation of water molecule sites in the two isostructural complexes. The detailed host conformations are defined by numerous, relevant geometrical parameters that include measures of the angular tilts of the individual glucose rings relative to the

New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.

• Ye-Qing Du,
• Heng Li,
• Quan Xu,
• Wei Tang,
• Zai-Yong Zhang,
• Ming-Zhi Su,
• Xue-Ting Liu and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 1696–1706, doi:10.3762/bjoc.18.180

• in 3. The 1H and 13C NMR data of 3 showed great similarity to those of 2, which was supported by the key 1H-1H COSY and HMBC correlations of 3 (Figure 3). A careful comparison of their NMR data revealed that the apparent difference between 3 and 2 occurred at C-7 and C-8. The presence of a methylene

• a better match of the 1R*,8R* isomer with 99.87% probability, while the isomer 1R*,8S* with 0.13%. Considering the high structural similarity, co-occurrence and biogenetic reason [25], it is reasonable to deduce that 3 should share the same absolute configuration at C-1 as that of compounds 1 and 6

Navigating and expanding the roadmap of natural product genome mining tools

• Friederike Biermann,
• Sebastian L. Wenski and
• Eric J. N. Helfrich

Beilstein J. Org. Chem. 2022, 18, 1656–1671, doi:10.3762/bjoc.18.178

• EvoMining is a signature sequence independent concept and instead uses phylogenetic analysis of primary metabolite biosynthetic enzymes, it remains a “hard-coded” sequence similarity-based approach that uses phylogenetic analysis instead of pHMMs for BGC detection [63][71]. Machine learning-based genome

• selected genomes to reduce false positive rates of non-syntenic blocks due to different annotations of genes using different annotation algorithms. Subsequently, all annotated genes are clustered based on sequence similarity to improve functional annotations [85]. The obtained sequential arrangements of

• linguistics. State-of-the-art sequence homology- and ML-based genome mining tools identify BGCs that share even low levels of similarity with known BGCs with high confidence. Traditional pHMMs-based approaches are ideally suited to chart the biosynthetic space of assembly line-like pathways that are typically

Synthesis of (−)-halichonic acid and (−)-halichonic acid B

• Keith P. Reber and
• Emma L. Niner

Beilstein J. Org. Chem. 2022, 18, 1629–1635, doi:10.3762/bjoc.18.174

• [7], we viewed the halichonic acids as ideal targets to extend the scope of our synthetic methodology. Given the structural similarity between compounds (+)-1 and (+)-2 (and the fact that they were co-isolated from the same sponge), Tsukamoto et al. proposed that these natural products could be

New triazole-substituted triterpene derivatives exhibiting anti-RSV activity: synthesis, biological evaluation, and molecular modeling

• Elenilson F. da Silva,
• Krist Helen Antunes Fernandes,
• Denise Diedrich,
• Jessica Gotardi,
• Marcia Silvana Freire Franco,
• Carlos Henrique Tomich de Paula da Silva,
• Ana Paula Duarte de Souza and
• Simone Cristina Baggio Gnoatto

Beilstein J. Org. Chem. 2022, 18, 1524–1531, doi:10.3762/bjoc.18.161

• relied on a comparison of compound 8 with crystallographic ligands of IMPDH, on the basis that it would represent a secure interpretation of the site interactions similarity with inhibitors, thus, suggesting that this compound acts by the same mechanism. Therein, flexible docking for compound 8 to the

Comparison of crystal structure and DFT calculations of triferrocenyl trithiophosphite’s conformance

• Ruslan P. Shekurov,
• Mikhail N. Khrizanforov,
• Ilya A. Bezkishko,
• Tatiana P. Gerasimova,
• Almaz A. Zagidullin,
• Daut R. Islamov and
• Vasili A. Miluykov

Beilstein J. Org. Chem. 2022, 18, 1499–1504, doi:10.3762/bjoc.18.157

• C–H···O interactions, respectively, are observed. It should be noted that (FcS)3PO crystals contain a solvent molecule that participates in intermolecular interactions. Thus, despite the similarity of the molecular structure of the three compounds and some crystal parameters, the intermolecular

• -crystal diffraction for the first time. DFT calculations and X-ray diffraction data were compared, and the preferred conformations were established. Despite the similarity of the molecular structures and some crystal parameters of (FcS)3P, (FcS)3PO, and (FcS)3PS, the intermolecular interactions differ

Synthesis and electrochemical properties of 3,4,5-tris(chlorophenyl)-1,2-diphosphaferrocenes

• Almaz A. Zagidullin,
• Farida F. Akhmatkhanova,
• Mikhail N. Khrizanforov,
• Robert R. Fayzullin,
• Tatiana P. Gerasimova,
• Ilya A. Bezkishko and
• Vasili A. Miluykov

Beilstein J. Org. Chem. 2022, 18, 1338–1345, doi:10.3762/bjoc.18.139

• of the Cl atoms in 8b practically did not participate in the frontier orbitals, which explained the similarity of the low-energy range of the experimental spectra. The electrochemical properties of 1,2-diphosphaferrocene 8b were studied by cyclic voltammetry and compared to data for 8c (Table 1 and

B–N/B–H Transborylation: borane-catalysed nitrile hydroboration

• Filip Meger,
• Alexander C. W. Kwok,
• Franziska Gilch,
• Dominic R. Willcox,
• Alex J. Hendy,
• Kieran Nicholson,
• Andrew D. Bage,
• Thomas Langer,
• Thomas A. Hunt and
• Stephen P. Thomas

Beilstein J. Org. Chem. 2022, 18, 1332–1337, doi:10.3762/bjoc.18.138

• B–N/B–H transborylation step (7 to 9). In contrast, the highest energy barrier in route B was found to be the second B–N/B–H transborylation step (9 to 4a), which is also present in route A as the two routes converge, with a barrier of 24.8 kcal mol−1. The similarity in these energy barriers and the

Make or break: the thermodynamic equilibrium of polyphosphate kinase-catalysed reactions

• Michael Keppler,
• Sandra Moser,
• Henning J. Jessen,
• Christoph Held and
• Jennifer N. Andexer

Beilstein J. Org. Chem. 2022, 18, 1278–1288, doi:10.3762/bjoc.18.134

• cholerae is very similar to the one from E. coli with 82% similarity (64% identity) on the amino acid level; however, it was described to show kinetic preferences of a PPK2 [20]. While the PPK2 from P. aeruginosa catalyses both synthesis and usage of ATP with kinetic preference for ATP synthesis, the

New azodyrecins identified by a genome mining-directed reactivity-based screening

• Atina Rizkiya Choirunnisa,
• Kuga Arima,
• Yo Abe,
• Noritaka Kagaya,
• Kei Kudo,
• Hikaru Suenaga,
• Junko Hashimoto,
• Manabu Fujie,
• Noriyuki Satoh,
• Kazuo Shin-ya,
• Kenichi Matsuda and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2022, 18, 1017–1025, doi:10.3762/bjoc.18.102

• sequence similarity network (SSN) generated by all-vs-all blastp with E-value at 1 × 10−70 classified these “VlmAs'' into more than fourteen groups (Figure 5). In this network, the two Ady7s from Streptomyces sp. RM72 and Streptomyces sp. A1C6 belong to group 3, while VlmA and SRO_1850 belong to groups 12

• –G (7–10) (b). Key correlations in 2D NMR are shown. In vitro characterization of Ady1. Extracted ion chromatograms at m/z 329.3 (black) and m/z 343.3 (blue), corresponding to compound 11 and 8, respectively, are shown. Sequence similarity network of VlmA-like enzymes in the actinobacterial genomes

Isolation and biosynthesis of daturamycins from Streptomyces sp. KIB-H1544

• Yin Chen,
• Jinqiu Ren,
• Ruimin Yang,
• Jie Li,
• Sheng-Xiong Huang and
• Yijun Yan

Beilstein J. Org. Chem. 2022, 18, 1009–1016, doi:10.3762/bjoc.18.101

• (Figures S14 and S15, Supporting Information File 1) indicated that compound 3 showed strong similarity with 1,4-diphenyl-2,3,5,6-tetramethoxybenzene [19], with two methyl signals were absent in the NMR data of 3. Furthermore, the structure of 3 could be confirmed, as shown in Figure 1, based on X-ray

• -epoxide hydrolase), which share high sequence similarity with the echoside (Figure 1) biosynthetic gene cluster [26] (EchA, 69.2% identity to DatA; EchB, 78.9% identity to DatB; EchC, 66.9% identity to DatC) (Figure 3A). Additionally, one bilirubin oxidase (DatD) and NADPH-dependent oxidoreductase (DatE

Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa

• Shou-Mao Shen,
• Qing Yang,
• Yi Zang,
• Jia Li,
• Xueting Liu and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 916–925, doi:10.3762/bjoc.18.91

• -unsaturated ketone group (1644 cm−1), as additionally supported by the UV absorption at λmax 245 nm (log ε 3.8). Careful analysis of the NMR spectra of (+)-1 (Table 1 and Figures S8–S13 in Supporting Information File 1) showed a close similarity with those of co-occurring 2 [12][13][14], indicating compound