Allostreptopyrroles A–E, β-alkylpyrrole derivatives from an actinomycete Allostreptomyces sp. RD068384

• Marwa Elsbaey,
• Naoya Oku,
• Mohamed S. A. Abdel-Mottaleb and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2024, 20, 1981–1987, doi:10.3762/bjoc.20.174

• : Allostreptomyces; β-alkylpyrrole; conformer; cytotoxic; DFT; 4-formylpyrrole-2-carboxylic acid; Introduction β-Alkylpyrroles are key structural motifs in biomolecules and functional organic materials [1]. For instance, β-alkylpyrroles are the main building blocks for the life-essential tetrapyrrole pigments

Solvent-dependent chemoselective synthesis of different isoquinolinones mediated by the hypervalent iodine(III) reagent PISA

• Ze-Nan Hu,
• Yan-Hui Wang,
• Jia-Bing Wu,
• Ze Chen,
• Dou Hong and
• Chi Zhang

Beilstein J. Org. Chem. 2024, 20, 1914–1921, doi:10.3762/bjoc.20.167

• activity and thus block cancer formation [2]. Alangiumkaloids A, an isoquinolinone alkaloid isolated from Alangium salviiforlium, was reported to exhibit cytotoxic activity against cancer cells [3]. In 2018, duvelisib, a dual inhibitor of phosphoinositide-3 kinases, was firstly approved by the FDA for the

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

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

• piperazinoquinazoline derivatives, a core found in fungal metabolites [25][26], systems with promising antitumour activity [27], as well as dipyrrolopiperazinone derivatives, substructure found in some alkaloids such as dibromophakellin or the palau’amine [28], which possess immunosuppressive and cytotoxic properties

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

• on androgen-sensitive Shionogi cells, with weak binding to the androgen receptor detected. This suggests that the antiproliferative property may be attributed to antiandrogenic and cytotoxic activities. Moreover, the spiro derivatives did not show affinity to other steroid receptors, indicating a

• their antiproliferative activity against a panel of cancer cells, in which the activity of some compounds was close to that of cis-platinum in some cell lines. It should be noted that N-propylamide derivatives showed low cytotoxicity on cancer cells. Additionally, 167c did not present cytotoxic activity

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

• proteusin family of RiPPs. They are produced by the tunicate symbiont Candidatus Entotheonella factor and exhibit membrane activity against Gram-positive bacteria and are highly cytotoxic. Cytotoxicity was tested with murine leukaemia cells; polytheonamide A, B, and C showed IC50 values between 68 and 78 pg

• member of the channel-forming, cytotoxic proteusins. It is biosynthesised by Microvirgula aerodenitrificans. Like polytheonamide B, aeronamide A shows cytotoxic activity against HeLa cells, with an IC50 of 1.48 nM. AerE, the PoyE homologue, installs five methylations on the amides of Asn25, Asn31, Asn37

• towards the C-terminus, named "axial amphipathicity". Thus, this methylation is thought to play an important role in correct target membrane insertion and the associated cytotoxic effect [125]. TsrM is another cob(II)alamin-dependent C-MT (Figure 10). This enzyme is involved in the biosynthesis of

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

• bioactivities including analgesic, sedative, and cytotoxic [12][13][14]. In order to identify new potential burpitides, we searched the NCBI Sequence Read Archive (SRA) for Streptophyta (all land plants and most green algae) transcriptomes that could be assembled and examined with a custom hidden Markov model

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

• ITC showed Kd values in the micromolar range with significant thermodynamic differences between E- and Z-azobenzene isomers, demonstrating the proof-of-concept of photomodulation of the ligand–lectin interactions. Results and Discussion Design of LecA photoswitchable ligands The cytotoxic LecA which

Synthesis of 4-functionalized pyrazoles via oxidative thio- or selenocyanation mediated by PhICl₂ and NH₄SCN/KSeCN

• Jialiang Wu,
• Haofeng Shi,
• Xuemin Li,
• Jiaxin He,
• Chen Zhang,
• Fengxia Sun and
• Yunfei Du

Beilstein J. Org. Chem. 2024, 20, 1453–1461, doi:10.3762/bjoc.20.128

• -inflammatory [6], antiviral [7], antibacterial [8], antifungal [9], cytotoxic [10], antioxidant [11], and analgesic [12] activities. For instance, celecoxib (I, Figure 1) (for treating rheumatoid arthritis and osteoarthritis), tepoxalin (II, Figure 1) (a veterinary painkiller used to relieve pain from muscle

• -ranging biological activities. Specifically, representative examples include fasicularin (IV, Figure 1), which possesses cytotoxic properties [21] and psammaplin B (V, Figure 1), which shows antimicrobial and mild tyrosine kinase inhibition activities [22]. In addition, Se-aspirin (VI, Figure 1) has been

Bismuth(III) triflate: an economical and environmentally friendly catalyst for the Nazarov reaction

• Manoel T. Rodrigues Jr.,
• Aline S. B. de Oliveira,
• Ralph C. Gomes,
• Amanda Soares Hirata,
• Lucas A. Zeoly,
• Hugo Santos,
• João Arantes,
• Catarina Sofia Mateus Reis-Silva,
• João Agostinho Machado-Neto,
• Leticia Veras Costa-Lotufo and
• Fernando Coelho

Beilstein J. Org. Chem. 2024, 20, 1167–1178, doi:10.3762/bjoc.20.99

• achieved. Under both conditions, virtually no product mixtures were observed. Preliminary biological evaluation To investigate the cytotoxic activity of the indanone derivatives, in total 20 compounds were tested at a concentration of 5 and 50 μg/mL for 72 h in a panel of four histologically unrelated

Mild and efficient synthesis and base-promoted rearrangement of novel isoxazolo[4,5-b]pyridines

• Vladislav V. Nikol’skiy,
• Mikhail E. Minyaev,
• Maxim A. Bastrakov and
• Alexey M. Starosotnikov

Beilstein J. Org. Chem. 2024, 20, 1069–1075, doi:10.3762/bjoc.20.94

• -oriented heterocyclic systems. Some examples of biologically active isoxazolo[4,5-b]pyridines with antibacterial [8], anticancer [12] and cytotoxic [10][13] acitivities. Biologically active analogs of compounds 13. X-ray crystal structures of compounds 12c (top left; the second crystallographically unique

Entry to new spiroheterocycles via tandem Rh(II)-catalyzed O–H insertion/base-promoted cyclization involving diazoarylidene succinimides

• Alexander Yanovich,
• Anastasia Vepreva,
• Ksenia Malkova,
• Grigory Kantin and
• Dmitry Dar’in

Beilstein J. Org. Chem. 2024, 20, 561–569, doi:10.3762/bjoc.20.48

• activity) [16], ramariolide A (antitubercular) [17], (+)-massarinolin A (antibacterial) [18], anemonin (antiparasitic) [19], (+)-pyrenolide D (cytotoxic) [20], and (+)-crassalactone D (antitumor) [21]. Synthetic or semisynthetic spiro Δα,β-butenolides have also shown a range of biological properties

Pseudallenes A and B, new sulfur-containing ovalicin sesquiterpenoid derivatives with antimicrobial activity from the deep-sea cold seep sediment-derived fungus Pseudallescheria boydii CS-793

• Zhen Ying,
• Xiao-Ming Li,
• Sui-Qun Yang,
• Hong-Lei Li,
• Xin Li,
• Bin-Gui Wang and
• Ling-Hong Meng

Beilstein J. Org. Chem. 2024, 20, 470–478, doi:10.3762/bjoc.20.42

• our attention. Several meroterpenoids, alkaloids, polyketides, and sesquiterpenoids from the species displayed various biological properties including anti-inflammatory, antimicrobial, and cytotoxic activities [7][8][9]. In the present work, two rare new examples of sulfur-containing ovalicin

Cycloaddition reactions of heterocyclic azides with 2-cyanoacetamidines as a new route to C,N-diheteroarylcarbamidines

• Pavel S. Silaichev,
• Tetyana V. Beryozkina,
• Vsevolod V. Melekhin,
• Valeriy O. Filimonov,
• Andrey N. Maslivets,
• Vladimir G. Ilkin,
• Wim Dehaen and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2024, 20, 17–24, doi:10.3762/bjoc.20.3

• experimentally observed. The base-catalyzed cycloaddition of 3,3-diaminoacrylonitriles 1 to azides 2, thus proceeds in a Cornforth-type fashion, which involves a triazole–triazole isomerization through ring opening, rotation of the amidine substituent around the single bond, and cyclization. Cytotoxic activity

• The cytotoxic activity of seven synthesized compounds 3b,d,e,g,h,l,m was studied. According to the results of the MTT test, IC50 values were calculated for these compounds (Table 2). The results obtained indicated that compounds 3b,e,g,h did not have a pronounced effect on the viability of cultured

• and elaboration of a novel tandem process, synthesis of starting building blocks and 21-st target compounds was made by chemistry team and founded by Russian Science Foundation, project number 23-13-00248. The study of cytotoxic effect of 7 compounds was financially supported by the Ministry of

Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect

• Ken-ichi Nakashima,
• Naohito Abe,
• Masayoshi Oyama,
• Hiroko Murata and
• Makoto Inoue

Beilstein J. Org. Chem. 2023, 19, 1604–1614, doi:10.3762/bjoc.19.117

• revealed that compound 7 was cytotoxic to RAW 264.7 cells at concentrations above 25 μM (Figure 6d). Furthermore, 7 suppressed the LPS-induced increases in IL-1β and IL-6 transcriptional levels in a concentration-dependent manner from 1 or 2.5 μM (Figure 6e). Thus, while cytotoxicity was likely involved in

Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration

• Ghenwa Nasr,
• Hélène Greige-Gerges,
• Sophie Fourmentin,
• Abdelhamid Elaissari and
• Nathalie Khreich

Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115

• can subsequently achieve the highest solubilization of CHOL [27], while the low-substituted derivatives (CRYSMEB in our case) were less cytotoxic and maintained the integrity of endothelial cells assuming a lower affinity to CHOL membrane compared to the other derivatives [23]. Furthermore, the

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

• berberine variants displayed promising preliminary results for cytotoxic effects against tumor cells. Zones of inhibition for 1 mg of evaporated methanolic (MeOH) extracts from various parts of the A. mexicana plant against a panel of 12 microorganisms. The mean zone of inhibition in millimeters is shown

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

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

• ). The structures of the isolated compounds were established based on HRESIMS and extensive 1D and 2D NMR experiments. All the isolated compounds were assessed for their antimicrobial and cytotoxic activities. Among the tested compounds, forpinioside B (1) exhibited significant antimicrobial activity

• medicine (TCM) [6]. Studies on other Ganoderma species have also reported antidiabetic [7] and cytotoxic [8] effects of these compounds. Another widely used oriental medicine polypore Wolfiporia (also referred to under the synonym ‘Poria’ in the literature) cocos, has proved to a beneficial source of

• ) exhibited nitric oxide (NO) and/or cytotoxic effects, respectively [12][13]. The genus Fomitopsis was first coined by Karsten typified by F. pinicola [14]. Our current study fungus F. carnea was reported for the first time from Japan in 1943 by Blume and Nees [15]. Later, Ryvarden and Johansen in 1980 [16

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

• compounds, cytotoxic and anti-inflammatory properties were evaluated. In particular, a mouse pancreatic cancer cell line (Panc02-h7-GP-GFP) was used to determine cytotoxicity. Additionally, LPS-induced pro-inflammatory expression of iNOS and COX-2 in RAW264.7 cells was evaluated. Antitumor activity of

Nucleophile-induced ring contraction in pyrrolo[2,1-c][1,4]benzothiazines: access to pyrrolo[2,1-b][1,3]benzothiazoles

• Ekaterina A. Lystsova,
• Maksim V. Dmitriev,
• Andrey N. Maslivets and
• Ekaterina E. Khramtsova

Beilstein J. Org. Chem. 2023, 19, 646–657, doi:10.3762/bjoc.19.46

• anticonvulsant agents had been developed based on PBTA derivatives (Figure 1) [2]. In addition, series of PBTAs (Figure 1) were found to exhibit antibacterial, antifungal, antioxidant, and cytotoxic activities [3][4]. Several strategies have been developed for the synthesis of PBTA derivatives [2][3][4][5][6][7

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

• with the drug solution. As in 2D cell culture results, it was observed that CT26 cells were more sensitive than HT29 cells in cell culture studies with 3D spheroids. It is known that cells in 3D multicellular tumor spheroids typically have lower sensitivity to cytotoxic drugs compared to 2D cultured

Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr₄/PPh₃ and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior

• Christian Schumacher,
• Jas S. Ward,
• Kari Rissanen,
• Carsten Bolm and
• Mohamed Ramadan El Sayed Aly

Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9

• propargylated, coupled with azido quinoline, and then functionalized with glucose as part of random designs to discover new antimicrobial and cytotoxic candidates. From these studies, conjugates I [9] and II [10] were identified to display an excellent preliminary antibacterial impact, and congener III [10

• ] showed a good cytotoxic effect against the prostate cancer cell line PC-3 (Figure 2). When the spacer of I was increased from C6 to C11, the antimicrobial potential dramatically decreased [11]. In order to extend the compound platform, the synthesis of 3-azidocholest-5-ene was addressed [10]. Starting

• signal is attributed to the H-3 of (15%) byproduct 3β-azidocholest-5-ene; **denotes to two protons of the 3β-azidocholest-5-ene epimer [12]. Chemical structure of three isomeric cholesterols. Selected previously described cholesterol derivatives with interesting antibacterial and cytotoxic activities [9

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

• , since it promotes the ability of these ubiquitous cyclic lipopeptides to be effective and biologically active across different organism types. Hence, cyclic lipopeptides have been previously reported to possess antimicrobial, antifungal, antiviral, anticancer, and cytotoxic biological activities, but

Total synthesis of grayanane natural products

• Nicolas Fay,
• Rémi Blieck,
• Cyrille Kouklovsky and
• Aurélien de la Torre

Beilstein J. Org. Chem. 2022, 18, 1707–1719, doi:10.3762/bjoc.18.181

• ], antifeedant [7][8][9], antituberculosis [10], cytotoxic [11] and antioxidant [12] properties. The grayanane family comprises more than 160 natural products, and new members are isolated every year. For instance, 13 new grayanane natural products were reported since 2020 [13][14][15][16]. Grayanane