Efficient solid-phase synthesis and structural characterization of segetalins A–H, J and K

• Liangyu Liu,
• Wanqiu Lu,
• Quanping Guo and
• Zhaoqing Xu

Beilstein J. Org. Chem. 2025, 21, 2612–2617, doi:10.3762/bjoc.21.202

• (Caryophyllaceae), are head-to-tail cyclic oligopeptides comprising 5–9 amino acid residues [5][6][7][8][9][10][11][12][13]. These natural products exhibit a significant diversity of pharmacological activities [14][15][16], including estrogen-like activity (1, 2, 7, 8), antitumor effects (5), and antimicrobial

• evaluation and structure–activity relationship studies. The systematic investigation of the their key biological activities, including estrogenic activity (assessed via breast cell proliferation assays), antitumor activity (evaluated through HeLa cell inhibition assays), and antibacterial activity (evaluated

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

• class of interest in the search for new chemotherapeutic agents. They are known inhibitors of protein kinase C [40] and agonists of the GABA-type [41] and histamine-H3 receptors [42]. S-Allylic isothiouronium salts substituted with aliphatic groups have shown to combine high antitumor activity against

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

• attracted increasing interest as numerous TT-based compounds were proposed as promising candidates in medicinal chemistry due to their diverse pharmacological profiles including antitumor, antiviral, antimicrobial, enzymatic and phototherapeutic activities [15]. Among them, TT-2-carboxanilides exhibit

Transformation of the cyclohexane ring to the cyclopentane fragment of biologically active compounds

• Natalya Akhmetdinova,
• Ilgiz Biktagirov and
• Liliya Kh. Faizullina

Beilstein J. Org. Chem. 2025, 21, 2416–2446, doi:10.3762/bjoc.21.185

• ], the mechanism and factors controlling the selectivity of the oxidative ring contraction in cyclic α-formyl ketones under the action of H2O2 were studied in detail. Due to their complex architecture and diverse biological activities, including antiviral, antitumor, antimalarial, and antifungal activity

• ) (Scheme 20). Indanes (benzocyclopentanes) and their derivatives are widely used in materials science and nanotechnology and have important biological properties such as anti-allergic, antitumor, anticonvulsive, antihypercholesteremic, herbicidal, fungicidal and antimicrobial activity [60]. In [58], a

• 6,5,6-abeoabietane scaffold and impressive antitumor activity. α-Diazoketone 124 was synthesized from commercially available 1,2,4-trimethoxybenzene (123) [64] by a series of synthetic transformations, and converted by Wolff rearrangement to esters 125 and 126 with a trans-fused 6,5,6-ring system

An Fe(II)-catalyzed synthesis of spiro[indoline-3,2'-pyrrolidine] derivatives

• Elizaveta V. Gradova,
• Nikita A. Ozhegov,
• Roman O. Shcherbakov,
• Alexander G. Tkachenko,
• Larisa Y. Nesterova,
• Elena Y. Mendogralo and
• Maxim G. Uchuskin

Beilstein J. Org. Chem. 2025, 21, 2383–2388, doi:10.3762/bjoc.21.183

• bioactive molecules (Figure 1). This scaffold exhibits a broad range of pharmacological activities, including significant in vitro antimycobacterial properties [4], potent antitumor effects against melanoma cell lines [5], and antagonism of TH2 lymphocyte function [6]. Due to their wide-ranging biological

The application of desymmetric enantioselective reduction of cyclic 1,3-dicarbonyl compounds in the total synthesis of terpenoid and alkaloid natural products

• Dong-Xing Tan and
• Fu-She Han

Beilstein J. Org. Chem. 2025, 21, 2085–2102, doi:10.3762/bjoc.21.164

• : alkaloids; cyclic 1,3-dicarbonyl compounds; desymmetrization; enantioselective reduction; terpenoids; Introduction Terpenoids and alkaloids are two major classes of highly important natural products because they usually exhibit diverse and important biological activities, such as antitumor, anti

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

• 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

• [2,1-b]quinazoline-6,12-dione) and its derivatives are particularly noteworthy as they demonstrate multiple biological activities, including antibacterial, antitumor, antifungal, antiviral, anti-inflammatory, antileishmanial, antiplasmodial, etc. [18][19]. The structurally isomeric class – pyrimido

Research progress on calixarene/pillararene-based controlled drug release systems

• Liu-Huan Yi,
• Jian Qin,
• Si-Ran Lu,
• Liu-Pan Yang,
• Li-Li Wang and
• Huan Yao

Beilstein J. Org. Chem. 2025, 21, 1757–1785, doi:10.3762/bjoc.21.139

• and azo linkages deepened the cavity and enhanced the interaction strength with drugs. The biotin on the upper rim endows biotin-SAC4A with the ability to actively target tumor cells based on the interaction between biotin and biotin receptors, thereby improving antitumor efficacy. DOX@biotin-SAC4A

3-Aryl-2H-azirines as annulation reagents in the Ni(II)-catalyzed synthesis of 1H-benzo[4,5]thieno[3,2-b]pyrroles

• Julia I. Pavlenko,
• Pavel A. Sakharov,
• Anastasiya V. Agafonova,
• Derenik A. Isadzhanyan,
• Alexander F. Khlebnikov and
• Mikhail S. Novikov

Beilstein J. Org. Chem. 2025, 21, 1595–1602, doi:10.3762/bjoc.21.123

• ester group. In our case, the demethoxycarbonylative annulation enables the formation of aromatic tricyclic benzo[4,5]thieno[3,2-b]pyrrole system which is encountered in compounds with antitumor activity [21][22] as well as in compounds exhibiting fluorescent properties [22][23]. Since general methods

Chemical synthesis of glycan motifs from the antitumor agent PI-88 through an orthogonal one-pot glycosylation strategy

• Shaokang Yang,
• Xingchun Sun,
• Hanyingzi Fan and
• Guozhi Xiao

Beilstein J. Org. Chem. 2025, 21, 1587–1594, doi:10.3762/bjoc.21.122

• Academy of Sciences, Kunming 650201, China 10.3762/bjoc.21.122 Abstract Chemical synthesis of monophosphorylated glycan motifs from the antitumor agent PI-88 has been achieved through an orthogonal one-pot glycosylation strategy on the basis of glycosyl ortho-(1-phenylvinyl)benzoates, which not only

• antitumor agent PI-88 (muparfostat), which retards tumor growth via inhibiting angiogenesis in two ways: 1) interaction with pro-angiogenic growth factors such as vascular endothelial growth factor (VEGF) and fibroblast growth factor (FGF) and 2) by prevention of the release of angiogenic growth factors

Facile synthesis of hydantoin/1,2,4-oxadiazoline spiro-compounds via 1,3-dipolar cycloaddition of nitrile oxides to 5-iminohydantoins

• Juliana V. Petrova,
• Varvara T. Tkachenko,
• Victor A. Tafeenko,
• Anna S. Pestretsova,
• Vadim S. Pokrovsky,
• Maxim E. Kukushkin and
• Elena K. Beloglazkina

Beilstein J. Org. Chem. 2025, 21, 1552–1560, doi:10.3762/bjoc.21.118

• pharmacophore, and molecules containing this group exhibit a wide range of biological activities, including antitumor, anti-HIV, anti-obesity, anti-inflammatory, antidiabetic, anticancer, and antitubercular properties [1][2]. Among these molecules, bicyclic compounds with the dihydrooxadiazole connected to

• oxindole [3][8][9], chrysenequinone [10], cycloheptatriene [11][12], thiazole [13], and matrine-type alkaloids [14]. The hybrid pharmacophore design is a frequently employed approach in the development of potential antitumor and other drugs [15][16]. This method involves the merging of two distinct

General method for the synthesis of enaminones via photocatalysis

• Paula Pérez-Ramos,
• Raquel G. Soengas and
• Humberto Rodríguez-Solla

Beilstein J. Org. Chem. 2025, 21, 1535–1543, doi:10.3762/bjoc.21.116

• acyclic compounds [19][20][21][22][23]. Furthermore, the enaminone structural moiety represents the key framework of many drug classes, including antibiotic (1) [24], anti-inflammatory (2) [25], antinociceptive (3) [26], anticonvulsant (4) [27], antitubercular (5) [28], and antitumor (6) [29] agents

Recent total synthesis of natural products leveraging a strategy of enamide cyclization

• Chun-Yu Mi,
• Jia-Yuan Zhai and
• Xiao-Ming Zhang

Beilstein J. Org. Chem. 2025, 21, 999–1009, doi:10.3762/bjoc.21.81

• antitumor, antibacterial, antiviral, and antioxidizing properties. Previous synthetic strategies for these molecules typically rely on multi-step procedures to assemble the tricyclic core. However, the direct catalytic enantioselective formation of this scaffold from a linear precursor remains underexplored

4-(1-Methylamino)ethylidene-1,5-disubstituted pyrrolidine-2,3-diones: synthesis, anti-inflammatory effect and in silico approaches

• Nguyen Tran Nguyen,
• Vo Viet Dai,
• Luc Van Meervelt,
• Do Thi Thao and
• Nguyen Minh Thong

Beilstein J. Org. Chem. 2025, 21, 817–829, doi:10.3762/bjoc.21.65

• pyrrolidine-2,3-dione derivatives could inhibit biomacromolecules (DNA, BSA, mPGES-1 or CDKs) and consequently, enable them to be candidates for Alzheimer's disease [11], anti-inflammatory [12][13][14][15][16][17], and antitumor drug discovery [12]. Furthermore, pyrrolidine-2,3-diones are also important

Synthesis, characterization, antimicrobial, cytotoxic and carbonic anhydrase inhibition activities of multifunctional pyrazolo-1,2-benzothiazine acetamides

• Ayesha Saeed,
• Shahana Ehsan,
• Muhammad Zia-ur-Rehman,
• Erin M. Marshall,
• Sandra Loesgen,
• Abdus Saleem,
• Simone Giovannuzzi and
• Claudiu T. Supuran

Beilstein J. Org. Chem. 2025, 21, 348–357, doi:10.3762/bjoc.21.25

• ][15], antiviral [16], antifungal [14][17], antirheumatic [18], antiparasitic [19], insecticidal [20], antituberculous [21][22][23][24], antitumor [25], antileukemic [26], antidiabetic [27], and antifertility therapeutics [28]. Some 1,2-benzothiazine derivatives have been explored in the treatment of

Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization

• Asahi Kanno,
• Ryo Tanifuji,
• Satoshi Yoshida,
• Sota Sato,
• Saori Maki-Yonekura,
• Kiyofumi Takaba,
• Jungmin Kang,
• Kensuke Tono,
• Koji Yonekura and
• Hiroki Oguri

Beilstein J. Org. Chem. 2025, 21, 226–233, doi:10.3762/bjoc.21.14

• antitumor activity, triggered by DNA alkylation [6][7][8]. The aminonitrile/hemiaminal at C21 generates an iminium cation while releasing a cyanide or a hydroxy group under physiological conditions. This iminium cation facilitates nucleophilic attack by guanine residues in the minor groove of the GC-rich

Heteroannulations of cyanoacetamide-based MCR scaffolds utilizing formamide

• Marios Zingiridis,
• Danae Papachristodoulou,
• Despoina Menegaki,
• Konstantinos G. Froudas and
• Constantinos G. Neochoritis

Beilstein J. Org. Chem. 2025, 21, 217–225, doi:10.3762/bjoc.21.13

• activities, including antimalarial, antitumor, anthelmintic, antibacterial, antiasthmatic, and antiplatelet effects [61][62][63]. In particular, quinolinopyrimidine and pyrimidone derivatives have attracted a great interest due to their biological profile [64][65][66][67][68][69]. After some optimization, we

Reactivity of hypervalent iodine(III) reagents bearing a benzylamine with sulfenate salts

• Beatriz Dedeiras,
• Catarina S. Caldeira,
• José C. Cunha,
• Clara S. B. Gomes and
• M. Manuel B. Marques

Beilstein J. Org. Chem. 2024, 20, 3281–3289, doi:10.3762/bjoc.20.272

• , commonly referred to as sulfa drugs. These include top seller drugs, e.g., antimicrobials, anti-inflammatories, antihypertensives, and antitumor agents [24][25][26]. Particularly, the sulfonamide motif can act as a bioisostere of carboxylic acids, establishing a set of hydrogen bonds similar to those

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

• moiety. It was demonstrated that 3-alkylideneoxindole-N-glycosides 46 show a significant antitumor activity against melanoma human cell lines SK-Mel-147 and A-375 [46]. As mentioned above, the death ligand TRAIL is a promising strategy for cancer treatment. Unfortunately, melanoma cells show both

• antitumor effects were related to the inhibition of the survival pathway of c-Jun and JNK2 (Jun N-terminal kinase). In an additional study, it was shown that treatment with derivative E-β-46b results in an increase of melanoma cell sensitivity for death ligands and allows to overcome resistance against

• worth to be noted that all these activation steps were stopped by the presence of antioxidants which indicates that ROS act as key regulators of the antitumor effects of 3-alkylideneoxindole-N-glycosides 48. In the last decades, we have witnessed an increasing incidence of cutaneous T-cell lymphoma

Synthesis of benzo[f]quinazoline-1,3(2H,4H)-diones

• Ruben Manuel Figueira de Abreu,
• Peter Ehlers and
• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2708–2719, doi:10.3762/bjoc.20.228

• reactions (Figure 1). Polycondensed heterocycles containing a uracil moiety have also been studied in recent years. For example, compound A exhibits antitumor and antimicrobial properties (Figure 2) [66][67]. Compounds A and B are used as starting materials for the synthesis of polyaromatic derivatives of

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

• neuroprotective, antihypoxic effects, act as antiparkinsonian agents [3][4][5], exhibit antitumor and antibacterial activity [6][7][8], possess antioxidant properties for regulating free radical processes [9][10][11]. The functionalization of polyphenolic compounds by introducing various substituents or

• heterocycles are classified as privileged medicinal scaffolds being components of many drugs [13][14]. Thiazole derivatives and their reduced forms exhibit antitumor (thiazofurin, ixabepilone), antibacterial (cefotaxime, ceftaroline, cefiderocol), antifungal (isavuconazole, fosravuconazole), antiviral

• derivatives are used as ligands in the synthesis of metal complexes (Ni(II), Pd(II), Pt(II), Cu(I), Ag(I) etc.) exhibiting antibacterial and antitumor activity [34]. In most cases, polyfunctional catechol thioethers were obtained by Michael reaction via the interaction of o-, p-benzoquinone and the

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

• is 1,2,3-triazin-4-one. Such compounds exhibit a wide variety of biological activities including antitumor, anticonvulsant, diuretic, anesthetic and sedative effects [33][34][35][36]. Also, several commercially available pharmaceuticals used as herbicidal, antibacterial, fungicidal and insecticidal

Natural resorcylic lactones derived from alternariol

• Joachim Podlech

Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187

Regioselective alkylation of a versatile indazole: Electrophile scope and mechanistic insights from density functional theory calculations

• Pengcheng Lu,
• Luis Juarez,
• Paul A. Wiget,
• Weihe Zhang,
• Krishnan Raman and
• Pravin L. Kotian

Beilstein J. Org. Chem. 2024, 20, 1940–1954, doi:10.3762/bjoc.20.170

• wide range of pharmacological activities, such as anti-inflammatory, anti-arrhythmic, antitumor, antifungal, antibacterial, and anti-HIV activities [7][8][9][10][11][12][13]. For example, two N1-substituted bioactive indazoles are found in Figure 1, danicopan (1), a complement factor D inhibitor for

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

• artificial systems. Additionally, 5-deazaflavins have emerged as prospective antitumor agents [9][10]. Surprisingly, among the broad family of flavin derivatives, 5-deazaalloxazines have received less attention regarding their photophysical properties, despite their close similarity to the above-mentioned 5