Synthesis, structure, ionochromic and cytotoxic properties of new 2-(indolin-2-yl)-1,3-tropolones

• Yurii A. Sayapin,
• Eugeny A. Gusakov,
• Inna O. Tupaeva,
• Alexander D. Dubonosov,
• Igor V. Dorogan,
• Valery V. Tkachev,
• Anna S. Goncharova,
• Gennady V. Shilov,
• Natalia S. Kuznetsova,
• Svetlana Y. Filippova,
• Tatyana A. Krasnikova,
• Yanis A. Boumber,
• Alexey Y. Maksimov,
• Sergey M. Aldoshin and
• Vladimir I. Minkin

Beilstein J. Org. Chem. 2025, 21, 358–368, doi:10.3762/bjoc.21.26

• MTT assay was used to determine the anticancer activity of compound 7a against these cultures (Figure 6). The viability test is an important method to determine which new compounds are able to target cancer cells. The results of this test (IC50 value ± 95% confidence interval) allow us to evaluate the

Non-covalent organocatalyzed enantioselective cyclization reactions of α,β-unsaturated imines

• Sergio Torres-Oya and
• Mercedes Zurro

Beilstein J. Org. Chem. 2024, 20, 3221–3255, doi:10.3762/bjoc.20.268

• that some of the derivatives exhibit strong anticancer activity against Hela and MCF-7 cell lines. In early 2021, Mei, Lu and co-worker reported a chiral phosphoric acid-catalyzed asymmetric [4 + 2] cycloaddition of aurone-derived 1-azadienes 11 and 3-vinylindoles 61 (Scheme 23). This methodology

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

• anticancer activity of these compounds. Keywords: cancerostatic activity; carbohydrates; heterocycles; N-glycosides; indirubin; Introduction Indigo (1a), known for more than 6000 years and originally produced from indigo plants in India, represents a famous traditional blue pigment which was an expensive

• -rhamnosides α-17a and α-17c, respectively (Scheme 14) [23]. Water solubility plays an important role with regard to the pharmacological activity. It was previously shown that the water solubility and anticancer activity of non-glycosylated indirubins can be improved by conversion of the keto to an oxime group

• good activities were observed for both α-17a and β-17a. It is important to note that the anticancer activity of all indirubin-N-glycosides, in particular of rhamnosides α-17a and β-17a, was considerably higher as compared to the activities of previously reported non-glycosylated indirubins [23][24]. A

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

• Smoothened protein (Smo protein) [7]. The HH pathway, implicated in the development and progression of various human cancers (including colorectal, brain, gastrointestinal, lung, and breast cancers), drives tumorigenesis [8]. Consequently, HH pathway inhibitors have demonstrated significant anticancer

• activity. Synthesizing spiro heterocyclic steroids entails numerous methodologies. Although the inherent stereochemistry of steroids sometimes facilitates the production of a single diastereomer without the need for chiral auxiliaries, nevertheless, their synthesis remains challenging due to the creation

Chemo-enzymatic total synthesis: current approaches toward the integration of chemical and enzymatic transformations

• Ryo Tanifuji and
• Hiroki Oguri

Beilstein J. Org. Chem. 2024, 20, 1693–1712, doi:10.3762/bjoc.20.151

• hydroxy group of the aglycon. Cotylenin exhibits promising anticancer activity, and its diterpene aglycon, cotylenol (1), was isolated from the filamentous fungi such as Phomopsis amygdali and Cladosporium sp. 501-7W (Scheme 2A) [20][21][22]. Brassicicenes, differing in oxidation levels from 1, have been

Competing electrophilic substitution and oxidative polymerization of arylamines with selenium dioxide

• Vishnu Selladurai and
• Selvakumar Karuthapandi

Beilstein J. Org. Chem. 2024, 20, 1221–1235, doi:10.3762/bjoc.20.105

• as antioxidative [1][2], antimicrobial [3][4], and anticancer activity [5][6]. Several classes of organoselenium compounds are known to imitate the glutathione peroxidase [7][8][9][10][11]. Consequently, the development of new strategies for selenation of organic compounds has attracted considerable

A Diels–Alder probe for discovery of natural products containing furan moieties

• Alyssa S. Eggly,
• Namuunzul Otgontseren,
• Carson B. Roberts,
• Amir Y. Alwali,
• Haylie E. Hennigan and
• Elizabeth I. Parkinson

Beilstein J. Org. Chem. 2024, 20, 1001–1010, doi:10.3762/bjoc.20.88

• isolated from a sea sponge, Plakortis simplex [3][4]. Wortmannin, which also has a furan, was isolated from Penicillium wortmannin and shows anticancer activity via potent inhibition of phosphoinositide 3-kinase [5]. These are just a handful of the bioactive natural products containing furans that exist

Research progress on the pharmacological activity, biosynthetic pathways, and biosynthesis of crocins

• Zhongwei Hua,
• Nan Liu and
• Xiaohui Yan

Beilstein J. Org. Chem. 2024, 20, 741–752, doi:10.3762/bjoc.20.68

• -inflammatory properties, hepatorenal protection, and anticancer activity. They are often used as coloring and seasoning agents. Due to the limited content of crocins in plants and the high cost of chemical synthesis, the supply of crocins is insufficient to meet current demand. The biosynthetic pathways for

• alleviate gestational hypertension. Therefore, crocins have the potential to prevent pregnancy-induced hypertension [45]. Anticancer Crocins exhibit potent anticancer activity against various cancer cell lines. Jiang et al. found that crocins reduce the survival and activity of cervical cancer cells [46

• ]. Mollaei et al. observed an increased Bax/Bcl-2 ratio in crocin-treated cancer cells. Therefore, crocins are proposed to exert anticancer activity by promoting apoptosis of cancer cells [47]. This mechanism is consistent with the results of Hoshyar et al., who observed the apoptosis-promoting activity of

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

• these compounds in folk medicine for the treatment of different types of diseases, such as inflammatory processes, viral infections, metabolic disorders and some types of cancer [13][14][15][16][17][18][19]. The first biological studies of the combretastatin D series exploited their anticancer activity

An accelerated Rauhut–Currier dimerization enabled the synthesis of (±)-incarvilleatone and anticancer studies

• Tharun K. Kotammagari,
• Sweta Misra,
• Sayantan Paul,
• Sunita Kunte,
• Rajesh G. Gonnade,
• Manas K. Santra and
• Asish K. Bhattacharya

Beilstein J. Org. Chem. 2023, 19, 204–211, doi:10.3762/bjoc.19.19

• configuration of each enantiomer was determined by single-crystal X-ray analysis. In addition, a one-pot synthesis of (±)-incarviditone has been achieved from rac-rengyolone by using KHMDS as a base. We have also assessed the anticancer activity of all the synthesized compounds in breast cancer cells

• % yields, respectively, while Tang et al [4] furnished (±)-incarvilleatone (1) and (±)-incarviditone (2) from (±)-rengyolone (3) in 38% and 40% yields, respectively. A previous study [1] showed that (±)-incarviditone (2) has a limited anticancer activity. The anticancer activity is closely correlated with

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

• -loaded nanoparticle formulations had better anticancer activity than the drug solution (Figure 5b). Moreover, the group treated with blank CS-(6-O-capro-β-CD) nanoparticles + CPT solution showed a substantial reduction in cell viability. Cell viability in HT29 cells cultured with CPT solution alone was

• the blank poly-β-CD-C6 nanoparticles plus CPT solution treated group had higher anticancer activity than the only drug solution treated group at the end of 72 hours. Furthermore, the anticancer activity of blank poly-β-CD-C6 nanoparticles was shown to be greater than that of the drug solution. It was

• cells respond differently to the treated groups [61][62][63]. Evaluation of antitumoral efficiency of CPT-loaded CD nanoparticles on 3D cell cultures Anticancer activity of nanoparticles prepared from different CD derivatives was also investigated in a 3D cell culture method. Matrigel® was used as the

Combining the best of both worlds: radical-based divergent total synthesis

• Kyriaki Gennaiou,
• Antonios Kelesidis,
• Maria Kourgiantaki and
• Alexandros L. Zografos

Beilstein J. Org. Chem. 2023, 19, 1–26, doi:10.3762/bjoc.19.1

• -fused tetracycle instead, were reported to possess NF-kB-inhibitory activity and anticancer activity against NCI H-929 cancer cell lines (Scheme 6) [39]. In 2021 Lu’s group reported the total synthesis of members of both meroterpenoid families based on a highly chemoselective α-alkylation in the

Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group

• Chuanhua Qu,
• Run Huang,
• Yong Li,
• Tong Liu,
• Yuan Chen and
• Guiting Song

Beilstein J. Org. Chem. 2021, 17, 2822–2831, doi:10.3762/bjoc.17.193

• , antimicrobial, antimalarial, and anticancer activities [1][2]. Diarylmethane motifs are widely present in natural products and pharmaceuticals that exhibit extraordinary biological activity [3][4] (Figure 1). Among them, their anticancer activity is particularly attractive, demonstrated by drugs such as

• letrozole [5] and entrectinib [6], with especially entrectinib showing a potent anticancer activity against a broad spectrum of human cancer cell lines. In recent decades, the construction of a hybrid system with varied biological and pharmaceutical activities has received extensive attention from medicinal

Highly stereocontrolled total synthesis of racemic codonopsinol B through isoxazolidine-4,5-diol vinylation

• Lukáš Ďurina,
• Anna Ďurinová,
• František Trejtnar,
• Ľuboš Janotka,
• Lucia Messingerová,
• Jana Doháňošová,
• Ján Moncol and
• Róbert Fischer

Beilstein J. Org. Chem. 2021, 17, 2781–2786, doi:10.3762/bjoc.17.188

• human cancer cell lines has never been described. In view of this, we have developed an efficient and highly diastereoselective approach towards codonopsinol B (1) and its N-nor-methyl analogue 2 from achiral starting materials and evaluated their anticancer activity using four different cancer cell

Silica gel and microwave-promoted synthesis of dihydropyrrolizines and tetrahydroindolizines from enaminones

• Robin Klintworth,
• Garreth L. Morgans,
• Stefania M. Scalzullo,
• Charles B. de Koning,
• Willem A. L. van Otterlo and
• Joseph P. Michael

Beilstein J. Org. Chem. 2021, 17, 2543–2552, doi:10.3762/bjoc.17.170

• pomegranate alkaloid punicagranine (5) (Figure 1) [5]. The 2,3-dihydro-1H-pyrrolizine motif is also a structural component of potential drugs with a variety of pharmacological effects [6], including anticancer activity [7]. Relevant examples include (−)-ketorolac (6) [8], which has reached the market as a

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

• using nonprecious Fe and Cu catalysis have been described by Sutherland and co-workers in 2020 (Scheme 32B and C) [165]. Benzofurans are important scaffolds present in several bioactive compounds, such as balsaminone A (91, antipruritic activity), xylarianaphthol-1 (92, anticancer activity), and

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

• Joseane A. Mendes,
• Paulo R. R. Costa,
• Miguel Yus,
• Francisco Foubelo and
• Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

Synthetic accesses to biguanide compounds

• Oleksandr Grytsai,
• Cyril Ronco and
• Rachid Benhida

Beilstein J. Org. Chem. 2021, 17, 1001–1040, doi:10.3762/bjoc.17.82

• [1] such as antidiabetics, antimalaria, disinfectants, and antivirals. After a period of dormancy, the discovery of the anticancer activity of metformin has reignited a growing interest in biguanides. Indeed, in biological media, the biguanide group is highly prone to interaction with biomolecules

• dicyanamide in refluxing butanol with modest yields (36–54%) [54]. The resulting compounds were tested as proton-conducting materials (Scheme 23A). Another example was reported by Pietras et al. who prepared a series of cyclic amines in order to access new metformin analogs with anticancer activity against

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

• Shivani Gulati,
• Stephy Elza John and
• Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

• approach delivered the desired product in 62% yield after 6 h which reveals the efficiency of microwaves in increasing the yield and reducing the reaction time. The studies for the anticancer activity of the synthesized molecules revealed them to be more potent than the standard doxorubicin against AGS

[2 + 1] Cycloaddition reactions of fullerene C₆₀ based on diazo compounds

• Yuliya N. Biglova

Beilstein J. Org. Chem. 2021, 17, 630–670, doi:10.3762/bjoc.17.55

• ]. Fullerene-containing compounds with antiviral (various forms of influenza, herpes, HIV) [28][29][30], antibacterial [31][32][33], and anticancer activity [34][35] have been found among them. An important approach in this area involves the synthesis of complex- and covalent-bound fullerene derivatives with

• first gave ester 181 and then acid 182 (Scheme 31), the sodium and potassium salts of which are well soluble in water. The compound has antiviral and anticancer activity as well as pronounced antioxidant properties combined with low toxicity. Diarylmethanofullerene 183 was synthesized according to

Progress in the total synthesis of inthomycins

• Bidyut Kumar Senapati

Beilstein J. Org. Chem. 2021, 17, 58–82, doi:10.3762/bjoc.17.7

• biosynthesis [1][4], in vitro antimicrobial activity [4][5], and anticancer activity against human prostate cancer cell lines [6][7]. A recent study suggested that the close analogue (+)-11 of inthomycin C was found to exhibit proteasome inhibition activity [8]. The skeletal structures of inthomycins A–C (1–3

Styryl-based new organic chromophores bearing free amino and azomethine groups: synthesis, photophysical, NLO, and thermal properties

• Anka Utama Putra,
• Deniz Çakmaz,
• Nurgül Seferoğlu,
• Alberto Barsella and
• Zeynel Seferoğlu

Beilstein J. Org. Chem. 2020, 16, 2282–2296, doi:10.3762/bjoc.16.189

• anticancer activity, to name a few. Moreover, Schiff bases bearing a salicylidene moiety are also used as chemosensors for sensing of specific ions. In addition, some derivatives also show NLO activity [25][34][35][36][37]. Herein, we report on the synthesis and full photophysical characterization of a

Synthesis of new dihydroberberine and tetrahydroberberine analogues and evaluation of their antiproliferative activity on NCI-H1975 cells

• Giacomo Mari,
• Lucia De Crescentini,
• Serena Benedetti,
• Francesco Palma,
• Stefania Santeusanio and
• Fabio Mantellini

Beilstein J. Org. Chem. 2020, 16, 1606–1616, doi:10.3762/bjoc.16.133

• to position 13 of the BER skeleton, usually causes a geometric propensity for additional stacking-type, noncovalent aromatic interactions with cellular targets forming stronger complexes with nucleic acids than BER [9][10][11][12]. In fact, the so obtained functionalized BER shows better anticancer

• activity [13][14][15][16][17][18][19], and an increased DNA and RNA binding efficacy [4][6][9], due to its aromatic interactions with the biological macromolecules [20]. Another interesting and promising derivative is dihydroberberine (DHBER), the reduced form of BER. The enaminic function of this alkaloid

Synthesis and anticancer activity of bis(2-arylimidazo[1,2-a]pyridin-3-yl) selenides and diselenides: the copper-catalyzed tandem C–H selenation of 2-arylimidazo[1,2-a]pyridine with selenium

• Mio Matsumura,
• Tsutomu Takahashi,
• Hikari Yamauchi,
• Shunsuke Sakuma,
• Yukako Hayashi,
• Tadashi Hyodo,
• Tohru Obata,
• Kentaro Yamaguchi,
• Yasuyuki Fujiwara and
• Shuji Yasuike

Beilstein J. Org. Chem. 2020, 16, 1075–1083, doi:10.3762/bjoc.16.94

• anticancer activity are described. The double C–H selenation of imidazo[1,2-a]pyridine with Se powder was catalyzed by CuI (10 mol %) ligated with 1,10-phenanthroline (10 mol %) at 130 °C under aerobic conditions. The selenides or diselenides were prepared almost selectively using selenium powder in an

• ]pyridin-3-yl] diselenide showed an excellent anticancer activity and low cytotoxicity toward noncancer cells, suggesting that this diselenide is a potential lead compound for anticancer therapy. Keywords: anticancer activity; copper catalyst; diselenide; imidazopyridine; selenide; selenium; Introduction

• presented herein. This reaction was used to selectively synthesize selenides and diselenides bearing two imidazopyridine rings by simply controlling the amount of selenium added. Furthermore, we also report the anticancer activity of the prepared compounds. Results and Discussion We previously reported that