Thiazolidinones: novel insights from microwave synthesis, computational studies, and potentially bioactive hybrids

• Luan A. Martinho,
• Victor H. J. G. Praciano,
• Guilherme D. R. Matos,
• Claudia C. Gatto and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2025, 21, 2618–2636, doi:10.3762/bjoc.21.203

• ], antioxidant [34], cytotoxic [35], and antiproliferative [36]. The structures of these compounds allow the synthesis of a large collection of bioactive molecules due to their nucleophilic and electrophilic properties [37]. One of the forms of modifications is at the methylene group, particularly in the 5

Synthesis and characterization of a isothiouronium-calix[4]arene derivative: self-assembly and anticancer activity

• Giuseppe Granata,
• Loredana Ferreri,
• Claudia Giovanna Leotta,
• Giovanni Mario Pitari and
• Grazia Maria Letizia Consoli

Beilstein J. Org. Chem. 2025, 21, 2535–2541, doi:10.3762/bjoc.21.195

• (786-O cells) and compared with that in non-malignant fibroblast cells (SW1 cells). Compound 3 showed a significantly greater antiproliferative effect on cancer cells (IC50 37.4 µM) than on normal fibroblasts (517 µM). The importance of the isothiouronium moieties in the observed cytoxic effect was

• confirmed by comparison with the calix[4]arene precursor (1) lacking these functional units. The selective antiproliferative profile of compound 3 highlights its potential as a lead anticancer agent. Moreover, compound 3 holds promise for further development in combination multidrug therapy due to the

• renal carcinoma cells (786O) and normal human fibroblasts (SW1), and the tumor cells selectivity was evaluated. To elucidate the role of the isothiouronium groups, antiproliferative effects were also estimated on calix[4]arene precursor 1 lacking these functional groups. Results and Discussion Synthesis

Assembly strategy for thieno[3,2-b]thiophenes via a disulfide intermediate derived from 3-nitrothiophene-2,5-dicarboxylate

• Roman A. Irgashev

Beilstein J. Org. Chem. 2025, 21, 2489–2497, doi:10.3762/bjoc.21.191

• notable DNA intercalation and antiproliferative effects [16][17], while TT–BODIPY derivatives were shown to efficiently generate singlet oxygen and demonstrate light-induced cytotoxicity, highlighting their promise as photodynamic therapeutic agents [18]. Near-infrared TT–DPP-based dyes have also been

Discovery of cytotoxic indolo[1,2-c]quinazoline derivatives through scaffold-based design

• Daniil V. Khabarov,
• Valeria A. Litvinova,
• Lyubov G. Dezhenkova,
• Dmitry N. Kaluzhny,
• Alexander S. Tikhomirov and
• Andrey E. Shchekotikhin

Beilstein J. Org. Chem. 2025, 21, 2062–2071, doi:10.3762/bjoc.21.161

• biological evaluation of novel indolo[1,2-c]quinazoline derivatives, with a particular focus on their antiproliferative potential against human cancer cells. We introduced structural modifications at positions 5, 6, and 12 of the indolo[1,2-c]quinazoline core to explore the structure–activity relationships

• polycyclic structures, DNA was not the primary target for their antiproliferative effects, as confirmed by FID assay and fluorescence titration studies. This study represents the first comprehensive evaluation of indolo[1,2-c]quinazolines as potential scaffold for the development of antitumor agents

• , offering valuable insights into their SAR and paving the way for a future evaluation of these compounds as anticancer therapeutics. Keywords: antiproliferative activity; antitumor agents; indolo[1,2-c]quinazoline; modification; structure–activity relationship; Introduction Organic compounds featuring

Synthesis, biological and electrochemical evaluation of glycidyl esters of phosphorus acids as potential anticancer drugs

• Almaz A. Zagidullin,
• Emil R. Bulatov,
• Mikhail N. Khrizanforov,
• Damir R. Davletshin,
• Elvina M. Gilyazova,
• Ivan A. Strelkov and
• Vasily A. Miluykov

Beilstein J. Org. Chem. 2025, 21, 1909–1916, doi:10.3762/bjoc.21.148

• electrochemical behavior. The compounds were efficiently obtained via the condensation of chlorophosphine oxides and phosphorus oxychloride with glycidol, affording high-purity products in moderate to good yields. Cytotoxicity studies revealed that all three compounds possess antiproliferative activity against

Studies on the syntheses of β-carboline alkaloids brevicarine and brevicolline

• Benedek Batizi,
• Patrik Pollák,
• András Dancsó,
• Péter Keglevich,
• Gyula Simig,
• Balázs Volk and
• Mátyás Milen

Beilstein J. Org. Chem. 2025, 21, 955–963, doi:10.3762/bjoc.21.79

• : it acts as an antioxidant [28], shows antibacterial activity against Mycobacterium tuberculosis [31], has antiproliferative effects against triple-negative breast cancer [32], serves as an agent against Parkinson's disease [29], and possesses skin anti-inflammatory properties [33]. Notably, the

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

• then elucidated as massarilactone D 4,7-di-O-crotonyl. Cytotoxic and nematicidal activities The antiproliferative properties of massarilactone D and the newly synthesized analogues were evaluated against the murine fibroblasts L929, human cervix carcinoma KB3-1, human lung carcinoma A549, human

• with cinnamoyl chloride suggests that these two polyketides can interconvert from each other and could be artifacts and vice versa formed during extraction and isolation. This finding suggests that, to improve the antiproliferative efficacy of these derivatives, the exo-methylene group should be

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

Antibiofilm and cytotoxic metabolites from the entomopathogenic fungus Samsoniella aurantia

• Rita Toshe,
• Syeda J. Khalid,
• Blondelle Matio Kemkuignou,
• Esteban Charria-Girón,
• Paul Eckhardt,
• Birthe Sandargo,
• Kunlapat Nuchthien,
• J. Jennifer Luangsa-ard,
• Till Opatz,
• Hedda Schrey,
• Sherif S. Ebada and
• Marc Stadler

Beilstein J. Org. Chem. 2025, 21, 327–339, doi:10.3762/bjoc.21.23

• activity, inhibiting approximately 70% of Staphylococcus aureus biofilms at concentrations as low as 3.9 µg/mL. Keywords: antibiofilm; antiproliferative; beauvericin; insect pathogen; Samsoniella; Introduction A microbial biofilm represents an assemblage of planktonic cells to overcome hostile living

N-Glycosides of indigo, indirubin, and isoindigo: blue, red, and yellow sugars and their cancerostatic activity

• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2840–2869, doi:10.3762/bjoc.20.240

• sodium tert-butanolate afforded the desired deprotected indigo-N-rhamnoside 5d (α/β = 2:1). In contrast to the antiproliferative properties of the akashins, 5d showed no significant activity against human cancer cell lines. The glycosylation of 13 can be explained as follows (Scheme 9): Reaction of tetra

• collaboration with Michael Lalk and Patrick Bednarski (University of Greifswald), the antiproliferative activities of indirubin-N-rhamnosides 17a–c,f, indirubin-N-glucoside β-18a, indirubin-N-galactoside β-20a, and indirubin-N-mannoside β-21a were studied. In this context, four human cancer cell lines were

• substituent. The carbohydrate moiety also has an influence on the antiproliferative activity. The best activities were observed for rhamnosides, while the lowest activity was observed for galactoside β-20a. The configuration of the anomeric carbon atom of the rhamnoside did not show a major influence as very

Synthesis, electrochemical properties, and antioxidant activity of sterically hindered catechols with 1,3,4-oxadiazole, 1,2,4-triazole, thiazole or pyridine fragments

• Daria A. Burmistrova,
• Andrey Galustyan,
• Nadezhda P. Pomortseva,
• Kristina D. Pashaeva,
• Maxim V. Arsenyev,
• Oleg P. Demidov,
• Mikhail A. Kiskin,
• Andrey I. Poddel’sky,
• Nadezhda T. Berberova and
• Ivan V. Smolyaninov

Beilstein J. Org. Chem. 2024, 20, 2378–2391, doi:10.3762/bjoc.20.202

• properties [28]. Anti-tuberculosis activity was identified for 5-substituted 2-mercapto-1,3,4-oxadiazoles [29], 5-substituted-2-[(3,5-dinitrobenzyl)-sulfanyl]-1,3,4-oxadiazoles and 1,3,4-thiadiazoles [30]. Some derivatives of 5-(4-tert-butylphenyl)-1,3,4-oxadiazole-2(3H)-thione showed antiproliferative

Tandem diazotization/cyclization approach for the synthesis of a fused 1,2,3-triazinone-furazan/furoxan heterocyclic system

• Yuri A. Sidunets,
• Valeriya G. Melekhina and
• Leonid L. Fershtat

Beilstein J. Org. Chem. 2024, 20, 2342–2348, doi:10.3762/bjoc.20.200

• high-energy materials [8][9][10][11][12][13]. Moreover, furazan derivatives possess antiproliferative, antibacterial, antiparasitic and antiviral activity [14][15][16]. On the other hand, furoxans referred to as unique heterocyclic compounds that exhibit NO-releasing properties under physiological

Access to 2-oxoazetidine-3-carboxylic acid derivatives via thermal microwave-assisted Wolff rearrangement of 3-diazotetramic acids in the presence of nucleophiles

• Ivan Lyutin,
• Vasilisa Krivovicheva,
• Grigory Kantin and
• Dmitry Dar’in

Beilstein J. Org. Chem. 2024, 20, 1894–1899, doi:10.3762/bjoc.20.164

• derivatives (mainly amides) exhibit various types of biological activity, among which the following can be highlighted: inhibition of β-lactamases [4][5], antitubercular properties [6], antiproliferative and antibacterial activity [7], herbicidal properties [8][9], inhibition of neutral amino acid transporter

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

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

• heterocyclic moieties containing three or more (hetero)cycles. Moreover, many compounds are accompanied by data on their biological activities, such as antiproliferative, antimalarial, antimicrobial, antifungal, steroid antagonist, and enzyme inhibition, among others, aimed at furnishing pertinent insights for

• et al. reported the synthesis of cycloadducts 47 from reaction of (E)-16-arylidene derivatives 46 and azomethine ylides generated in situ from substituted isatins and sarcosine [27] (Scheme 14). The resulting spiro compounds proved to be potent antiproliferative agents against human cancer cell lines

• promoted by mercury(II) oxide, yielding spiro 2-substituted amino-4,5-dihydro-1,3-oxazoles 72a,b in moderate to good yields (Scheme 21). All spiro derivatives exhibited potent antiproliferative activity when tested on six human cancer cell lines (GI50 = 0.34–18 µM). Structure–activity relationships

The Ugi4CR as effective tool to access promising anticancer isatin-based α-acetamide carboxamide oxindole hybrids

• Carolina S. Marques,
• Aday González-Bakker and
• José M. Padrón

Beilstein J. Org. Chem. 2024, 20, 1213–1220, doi:10.3762/bjoc.20.104

• , aliphatic chain on the acid component and small aliphatic chain on the aldehyde component to increase the antiproliferative activity. Also, benzyl isocyanide was favored over the aliphatic one (Scheme 1A) [16]. Considering the value of amide groups in drug discovery [19], the feasibility of running the

• . Compounds 5ib and 5hb, with N-Boc protected-heterocycle units in the 5-amide position of the oxindole ring (Scheme 2) failed to afford the corresponding 3-deprotected isatin hybrids, since only decomposition byproducts (not identified) were obtained. Antiproliferative activity Considering the potential

• antiproliferative activity of these compounds, we screened 14 α-acetamide carboxamide isatin hybrids against six human solid tumor cell lines. The panel of cell lines comprised non-small cell lung carcinoma A549 and SW1573, cervical adenocarcinoma HeLa, breast cancer HBL-100 and T-47D, and colon adenocarcinoma WiDr

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

• activity, such as antibacterial [8], anticancer [9] or antiproliferative [10]. In addition, isoxazolo[4,5-b]pyridines were found to inhibit cytochrome P450 CYP17 responsible for the biosynthesis of androgens and estrogen precursors [11]. Some biologically active isoxazolo[4,5-b]pyridines are shown on

Methodology for awakening the potential secondary metabolic capacity in actinomycetes

• Shun Saito and
• Midori A. Arai

Beilstein J. Org. Chem. 2024, 20, 753–766, doi:10.3762/bjoc.20.69

• undecylprodigiosin (21) is always triggered in the dying zone of the mycelial network of Streptomyces coelicolor M145 prior to morphological differentiation, right after an initial round of cell death [98]. They hypothesized that under certain circumstances, production of antiproliferative agents could play a role

Construction of diazepine-containing spiroindolines via annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates

• Xing Liu,
• Wenjing Shi,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 1923–1932, doi:10.3762/bjoc.19.143

• motif, which is frequently found in natural products, bioactive molecules, and pharmaceuticals [1][2][3][4]. 1,2-Diazepine derivatives exhibit promising biological activities such as anticonvulsant, antibacterial, and antiproliferative effects [5][6][7][8][9][10][11][12][13]. Thus, the development of

Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups

• Dayanne Martins,
• Roberta Lamosa,
• Talis Uelisson da Silva,
• Carolina B. P. Ligiero,
• Sérgio de Paula Machado,
• Daphne S. Cukierman and
• Nicolás A. Rey

Beilstein J. Org. Chem. 2023, 19, 1713–1727, doi:10.3762/bjoc.19.125

• thus less side-effects in therapy [23]. In this sense, we have reported dicopper(II) complexes from different N-acylhydrazonic binucleating ligands with potent antiproliferative activity against a panel of cancer cell lines [24][25][26]. On the field of neurodegeneration, our research group was the

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

• ) that exhibit promising anticancer properties renew the interest in this class of compounds. Indeed, ether lipid represent a new and promising class of compounds featuring the capacity to modulate selectively the activity of some membrane proteins or, for other compounds, feature antiproliferative

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

• bioactive lanostane triterpenoids [9][10]. In addition, the edible European fungus Macrolepiota procera also produced antiproliferative and anti-inflammatory lanostanoid derivatives [11]. Furthermore, triterpenes from Tricholoma pardinum and Fomitopsis betulina (previously known as Piptoporus betulinus

Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines

• Dmitry B. Vinogradov,
• Alexei N. Izmest’ev,
• Angelina N. Kravchenko,
• Yuri A. Strelenko and
• Galina A. Gazieva

Beilstein J. Org. Chem. 2023, 19, 1047–1054, doi:10.3762/bjoc.19.80

• [16][17]. Recent studies of the antitumor activity of imidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazines revealed a number of compounds with a high antiproliferative effect towards a large number of human cancer cell lines (Figure 1) [18][19]. Therefore, the synthesis of new imidazothiazolotriazines and

• synthetic bioactive 1,3-thiazine and imidazothiazolotriazine derivatives with high antiproliferative activity. 1H NMR spectra of the starting compound 1d (a) and the reaction mixture after 1.5 (b) and 4 (c) hours in DMSO-d6 (the colored signals correspond to the protons shown in red in Scheme 4). 1H NMR

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

• exhibit diverse biological properties, including anti-inflammatory [12], antimalarial [13], antitumor [14], antiviral [15], antibacterial [16], antiproliferative [13], and immunomodulatory [17] activities. As part of our studies on Thai medicinal plants, an investigation of the fruits of P. macropterum

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

• μM) [54]. O-Methylcombretastatin D-2, 28 was also evaluated for its antiproliferative activity against MCF-7 human breast carcinoma, RKO human colon carcinoma, and CRL 1730 human umbilical endothelial cells. It exhibited activity in all cell lines with IC50 values around 5–10 mM [50]. Aiming to