Selective construction of dispiro[indoline-3,2'-quinoline-3',3''-indoline] and dispiro[indoline-3,2'-pyrrole-3',3''-indoline] via three-component reaction

• Ziying Xiao,
• Fengshun Xu,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 1234–1242, doi:10.3762/bjoc.19.91

• different reactivity to that of the adducts of 3-ethoxycarbonylmethyleneoxindoles. For confirming the chemical structures of dispirooxindoles 4a–i, the single crystal structure of compound 4a was determined by X-ray diffraction (Figure 2). In Figure 2, the two oxindole scaffolds are in trans-position. The

• -oxoindolin-3-ylidene)acetate with 5-chloro and 5-fluoro substituent gave the spiro compounds 3a–k in satisfactory yields. However, the dimedone adducts of ethyl 2-(2-oxoindolin-3-ylidene)acetate itself and its derivatives with 5-methyl group gave the products 3l and 3m in moderate yields. The chemical

• structures of the obtained dispiro compounds 3a–m were fully characterized by IR, HRMS, 1H and 13C NMR spectroscopy. Because of the three chiral carbon atoms in the product, several diastereomers might be formed in the reaction. However, TLC monitoring and 1H NMR spectra of the crude products clearly

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

• prostate cancer cells PC-3) were obtained from the DSMZ collection (Braunschweig, Germany). Chemical structures of compounds 1–4. Key 1H,1H COSY, HMBC, and ROESY correlations of compounds 1 and 2. 1H and 13C NMR data of compounds 1 and 2 in methanol-d4. Supporting Information Supporting Information File

The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition

• Xiu-Yu Chen,
• Hui Zheng,
• Ying Han,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 982–990, doi:10.3762/bjoc.19.73

• -dihydropyridines derived from the condensation of acetylacetone also afforded the expected product 4o in 65% yield. The chemical structures of the obtained isoquinoline[2,1-h][1,7]naphthyridines 4a–o were fully characterized by various spectroscopy methods and further confirmed by determination of the single

• ]pyrrole derivatives 6e, 6f, 6i, 6k, 6l, and 6m were isolated in 23–39% yield from the reaction mixture. In other cases, the corresponding 1,3a,4,6a-tetrahydrocyclopenta[b]pyrrole derivatives could not be isolated due to too low yields. By analyzing the chemical structures of the 1,3a,4,6a

• -tetrahydrocyclopenta[b]pyrrole derivatives 6, it was found that the 1,4-dihydropyridinyl ring of the substrate was converted to a fused pyrrole ring, which might be a result from a rearrangement process of the formed 2-azabicyclo[4.2.0]octa-3,7-diene-7,8-dicarboxylates 5a–o at elevated temperature. The chemical

Intermediates and shunt products of massiliachelin biosynthesis in Massilia sp. NR 4-1

• Till Steinmetz,
• Blaise Kimbadi Lombe and
• Markus Nett

Beilstein J. Org. Chem. 2023, 19, 909–917, doi:10.3762/bjoc.19.69

• the test organism. Ampicillin (Roth, Carl Roth GmbH + Co. KG, Germany), tetracycline (Fluka Honeywell International Inc., United States of America) and ciprofloxacin (Sigma, Sigma-Aldrich Chemie GmbH, Germany) were used as positive controls. Selected siderophores from β-proteobacteria. Chemical

• structures of compounds 1–6 isolated in this study and of the structurally related siderophores massiliachelin (7) and (S)-dihydroaeruginoic acid (8). 1H,1H-COSY and selected 1H,13C-HMBC correlations in 1. Proposed origin of the isolated compounds 1–6 as well as massiliachelin (7). Domain notation of the

Light-responsive rotaxane-based materials: inducing motion in the solid state

• Adrian Saura-Sanmartin

Beilstein J. Org. Chem. 2023, 19, 873–880, doi:10.3762/bjoc.19.64

• ) Chemical structure of polyrotaxane 2; and (b) cartoon representation of the light-triggered degradation of rotaxane polymer 2 [52]. The key colour of the cartoon representation is analogous to that of the chemical structures. a) Chemical structures of rotaxanes (E)-3 and (Z)-3; b) stick representation of

• atoms. The key colour of the cartoon representation is analogous to that of the chemical structures. Stick representations of the solid structures of: (a) U-CB[8]-MPyVB showing an interlocked ligand connected to two uranium clusters; and (b) the intertwined photodimerized product within the crystalline

• : (i) FAIR open data from X-ray structures and Mercury® 2020.1 Software (Cambridge Crystallographic Data Center) to create Figures 1b (CCDC number 1943103), 3b (CCDC number 2018646) and 4 (CCDC numbers 2090727 and 2090729); (ii) chemical structures employing ChemBioDraw® Ultra 12.0 (CambridgeSoft

Non-peptide compounds from Kronopolites svenhedini (Verhoeff) and their antitumor and iNOS inhibitory activities

• Yuan-Nan Yuan,
• Jin-Qiang Li,
• Hong-Bin Fang,
• Shao-Jun Xing,
• Yong-Ming Yan and
• Yong-Xian Cheng

Beilstein J. Org. Chem. 2023, 19, 789–799, doi:10.3762/bjoc.19.59

• . In our studies of arthropods over the years, we have found that non-peptide small molecules play a significant role in chemical structures and biological activities [11][12][13][14][15][16]. In examining the chemical constituents of the millipede K. svenhedini, the focus was directed toward non

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

• percent inhibition of activity was calculated as (A0 − A1)/A0 × 100, where A0 is the absorbance of control, and A1 is the absorbance with the sample. Acarbose was used as a standard drug and all experiments were evaluated in triplicate. Chemical structures of 1-3 isolated from P. macropterum. Key 1H,1H

Combretastatins D series and analogues: from isolation, synthetic challenges and biological activities

• Jorge de Lima Neto and
• Paulo Henrique Menezes

Beilstein J. Org. Chem. 2023, 19, 399–427, doi:10.3762/bjoc.19.31

• elucidate the chemical structures of the isolated compounds [19]. 2 Synthesis 2.1 Biosynthetic pathway In the literature, there are two possible biosynthetic pathways for the formation of these compounds. The first one was proposed by Pettit and co-workers [16][17] based on tyrosine as the starting material

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

Preparation of β-cyclodextrin/polysaccharide foams using saponin

• Max Petitjean and
• José Ramón Isasi

Beilstein J. Org. Chem. 2023, 19, 78–88, doi:10.3762/bjoc.19.7

• ]. The aglycone part is composed of steroid and triterpene molecules [3]. Not only present in plants [4][5], saponins have also been discovered in marine animals, such as sea cucumbers [6] or starfish [7]. Chemical structures of this family are varied [1], so they will show different properties [8

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

• atoms were included in the models. Thereafter, the structures were refined by full-matrix least-squares techniques with SHELXL-97 [53], implemented in the X-SEED [54] interface. Chemical structures of 17β-estradiol (top) and progesterone (bottom). The PXRD patterns of the β-CD·PRO complex produced via

Using UHPLC–MS profiling for the discovery of new sponge-derived metabolites and anthelmintic screening of the NatureBank bromotyrosine library

• Sasha Hayes,
• Aya C. Taki,
• Kah Yean Lum,
• Joseph J. Byrne,
• Merrick G. Ekins,
• Robin B. Gasser and
• Rohan A. Davis

Beilstein J. Org. Chem. 2022, 18, 1544–1552, doi:10.3762/bjoc.18.164

• . Chemical structures of 5-debromopurealidin H (1) and ianthesine E (2). Key COSY, HMBC and ROESY correlations for 5-debromopurealidin H (1). Chemical structures of the NatureBank bromotyrosine derivatives: psammaplysins F (3) and H (4), bastadins 4 (5), 8 (6) and 13 (7), aerothionin (8) and hexadellin A (9

Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells

• Merve Karaman,
• Abhishek Kumar Gupta,
• Subeesh Madayanad Suresh,
• Tomas Matulaitis,
• Lorenzo Mardegan,
• Daniel Tordera,
• Henk J. Bolink,
• Sen Wu,
• Stuart Warriner,
• Ifor D. Samuel and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2022, 18, 1311–1321, doi:10.3762/bjoc.18.136

• nm, ΦPL = 61%, τd = 242 μs, kRISC = 3.04 × 103 s−1, 1 wt % in mCP). Different strategies were explored to prepare LEECs based on DiKTa-OBuIm and DiKTa-DPA-OBuIm as emitters. The devices showed green and red emission, respectively. Chemical structures of (a) reported ionic TADF emitters for LEECs, (b

Molecular diversity of the base-promoted reaction of phenacylmalononitriles with dialkyl but-2-ynedioates

• Hui Zheng,
• Ying Han,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 991–998, doi:10.3762/bjoc.18.99

• in the reaction. Because there is only one chiral carbon atom in the molecule, there are no diastereoisomers in the obtained products 3a–l. The chemical structures of compounds 3a–l were fully characterized by IR, HRMS, 1H and 13C NMR spectra. As for an example, the 1H NMR spectrum of compound 3i

• clearly indicated that only one diastereoisomer was actually produced in the reaction. The chemical structures of the compounds 4a–k were established by various spectroscopy methods. Additionally, the single crystal structures of compounds 4a and 4c were successfully determined (Figure 2 and Figure 3

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

• following the manufacturer’s instructions. β-ACTIN was used as the normalization control. All reactions were performed in triplicate. The NF-κB inhibitor Bay 11-7082 (5 μM) was used as a positive control. Chemical structures of compounds 1–8. ORTEP drawing of 2 (displacement ellipsoids are drawn at the 50

Efficient production of clerodane and ent-kaurane diterpenes through truncated artificial pathways in Escherichia coli

• Fang-Ru Li,
• Xiaoxu Lin,
• Qian Yang,
• Ning-Hua Tan and
• Liao-Bin Dong

Beilstein J. Org. Chem. 2022, 18, 881–888, doi:10.3762/bjoc.18.89

• ), have attracted great attention from chemists and biologists due to their intriguing chemical structures and broad pharmacological functions [1][2][3][4]. The vast structural diversity of diterpenoids arise biosynthetically from the following two stages: i) diterpene synthase (DTS, also called diterpene

• produced new peaks in the HPLC profiles after a 3-day fermentation. Larger scale (3 L) fermentations of DL10004 and DL10006 led to the isolation of 45 mg and 90 mg of terpentetriene and ent-kaurene, respectively, whose 1H and 13C NMR spectra supported their chemical structures (Figures S4–S7 in Supporting

Post-synthesis from Lewis acid–base interaction: an alternative way to generate light and harvest triplet excitons

• Hengjia Liu and
• Guohua Xie

Beilstein J. Org. Chem. 2022, 18, 825–836, doi:10.3762/bjoc.18.83

• nitrogen-containing heterocycles, resulting in the change of energy levels and spectra. The following will illustrate Lewis acids used in the exploration of luminescent materials and mechanisms due to Lewis acid–base interactions. The chemical structures of some candidate Lewis acids are shown in Figure 1

• ][32], e.g., organic thin-film transistors [45][46], organic photovoltaics [47], and chemical sensing [48]. Chemical structures of Lewis acid examples. Chemical structures of Lewis basic fluorescent polymer poly{2,5-pyridylene-co-1,4-[2,5-bis(2-ethylhexyloxy)]phenylene} 1 and D–A–D compound 2,5-bis((N

• vapor-treated device and the macroscopic gradation emissive pattern of polymer films on a glass plate after treatment and excited by 365 nm UV light. Figure 4 was reproduced from [31] with permission from The Royal Society of Chemistry. This content is not subject to CC BY 4.0. Chemical structures of

Terpenoids from Glechoma hederacea var. longituba and their biological activities

• Dong Hyun Kim,
• Song Lim Ham,
• Zahra Khan,
• Sun Yeou Kim,
• Sang Un Choi,
• Chung Sub Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2022, 18, 555–566, doi:10.3762/bjoc.18.58

• + probability using an Excel sheet [25]. Chemical structures of compounds 1–9. Structure elucidation of 1. (A) Key COSY, HMBC, and NOE correlations of 1. (B) Comparison of calculated ECD data of 1a and experimental ECD spectrum of 1. Structure elucidation of 2. (A) Key COSY, HMBC, and NOE correlations of 2. (B

Comparative study of thermally activated delayed fluorescent properties of donor–acceptor and donor–acceptor–donor architectures based on phenoxazine and dibenzo[a,j]phenazine

• Saika Izumi,
• Prasannamani Govindharaj,
• Anna Drewniak,
• Paola Zimmermann Crocomo,
• Satoshi Minakata,
• Leonardo Evaristo de Sousa,
• Piotr de Silva,
• Przemyslaw Data and
• Youhei Takeda

Beilstein J. Org. Chem. 2022, 18, 459–468, doi:10.3762/bjoc.18.48

• theoretical calculations, the role of the additional donor unit in the TADF mechanism is boosting the rISC process by balancing the singlet–triplet energy gap and spin–orbit coupling. The results showcased herein would allow for designing efficient TADF emitters more flexibly in the future. Chemical

• structures of 1 and POZ-DBPHZ. Steady-state UV–vis absorption (Abs) and photoluminescence (PL) spectra of dilute solutions (c ≈ 10−5 M) of compound 1. The PL spectra were acquired with λex = 340 nm for the cyclohexane solution and λex = 360 nm for solutions in the other solvents. Time-resolved PL decay

Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

Amamistatins isolated from Nocardia altamirensis

• Till Steinmetz,
• Wolf Hiller and
• Markus Nett

Beilstein J. Org. Chem. 2022, 18, 360–367, doi:10.3762/bjoc.18.40

• at 630 nm in a microplate reader. The values were plotted and the DC50 values were calculated. All tests were run in triplicate. Chemical structures of amamistatins (1–5) and a putative biosynthetic shunt product (6) isolated in this study. 1: R1 = CHO, R2 = H, R3 = H; 2: R1 = CHO, R2 = H, R3 = OH; 3

Synthesis of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines and investigation of their fungistatic activity

• Anna V. Korotina,
• Svetlana G. Tolshchina,
• Rashida I. Ishmetova,
• Natalya P. Evstigneeva,
• Natalya A. Gerasimova,
• Natalya V. Zilberberg,
• Nikolay V. Kungurov,
• Gennady L. Rusinov,
• Oleg N. Chupakhin and
• Valery N. Charushin

Beilstein J. Org. Chem. 2022, 18, 243–250, doi:10.3762/bjoc.18.29

• been found. All the above-mentioned results demonstrate good prospects for finding new antifungal drugs in this class of compounds. X-ray structure of N-(6-(4-bromo-3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazin-3-yl)benzamide. Chemical structures of [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine (a), [1,2,4

Anomeric 1,2,3-triazole-linked sialic acid derivatives show selective inhibition towards a bacterial neuraminidase over a trypanosome trans-sialidase

• Peterson de Andrade,
• Sanaz Ahmadipour and
• Robert A. Field

Beilstein J. Org. Chem. 2022, 18, 208–216, doi:10.3762/bjoc.18.24

• the deprotection step with CH3OH/triethylamine/H2O 4:1:5 [26], triethylammonium ions were exchanged upon treatment with Amberlite IR 120 (Na+ form) and compounds 3a–h were obtained in excellent yield and purity without further purification. Chemical structures and reported activities of viral (A

Glycosylated coumarins, flavonoids, lignans and phenylpropanoids from Wikstroemia nutans and their biological activities

• Meifang Wu,
• Xiangdong Su,
• Yichuang Wu,
• Yuanjing Luo,
• Ying Guo and
• Yongbo Xue

Beilstein J. Org. Chem. 2022, 18, 200–207, doi:10.3762/bjoc.18.23

• large quantity of phenolic substances found in plants and microorganisms [5]. These naturally occurring coumarins were well documented due to their diverse chemical structures and promising biological properties, such as anticancer, antitubercular, anti-inflammatory, anticoagulant, antibacterial, and

• ) at 35 °C with isocratic elution of 25% CH3CN in 0.1% H3PO4 for 40 min and subsequent washing of the column with 90% CH3CN at a flow rate 0.8 mL/min. Peaks at 16.54 and 19.64 min have coincided with derivatives of ᴅ-glucose and ᴅ-xylose [30]. Chemical structures of compounds 1–17 from W. nutans. The

Mechanistic studies of the solvolysis of alkanesulfonyl and arenesulfonyl halides

• Malcolm J. D’Souza and
• Dennis N. Kevill

Beilstein J. Org. Chem. 2022, 18, 120–132, doi:10.3762/bjoc.18.13

• values are from [56] and [62]. Organic reactions where the breaking of a C–X bond involves the formation of a high energy ion-pair intermediate. The chemical structures for the 1-adamantyl substrate, 2-adamantyl substrate, and the S-methyldibenzothiophenium ion (MeDBTh+). In the 1- and 2-substituted