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

p-Pyridinyl oxime carbamates: synthesis, DNA binding, DNA photocleaving activity and theoretical photodegradation studies

• Panagiotis S. Gritzapis,
• Panayiotis C. Varras,
• Nikolaos-Panagiotis Andreou,
• Katerina R. Katsani,
• Konstantinos Dafnopoulos,
• George Psomas,
• Zisis V. Peitsinis,
• Alexandros E. Koumbis and
• Konstantina C. Fylaktakidou

Beilstein J. Org. Chem. 2020, 16, 337–350, doi:10.3762/bjoc.16.33

• anticancer activity due to alteration of the structure and function of the genetic material. Amongst a plethora of such binders [1][2][3][4][5][6][7][8], various oxime derivatives were found to show affinity towards DNA [9][10][11][12], whereas others were found to cleave DNA as metal-free artificial

Diversity-oriented synthesis of spirothiazolidinediones and their biological evaluation

• Sambasivarao Kotha,
• Gaddamedi Sreevani,
• Lilya U. Dzhemileva,
• Milyausha M. Yunusbaeva,
• Usein M. Dzhemilev and
• Vladimir A. D’yakonov

Beilstein J. Org. Chem. 2019, 15, 2774–2781, doi:10.3762/bjoc.15.269

• strategy with propargyl halides. We have also shown the synthesis of linearly fused spirocyclic alcohol derivatives of thiazolidinedione using Wilkinson’s catalyst and these compounds were tested for their anticancer activity. We have shown for the first time that the new benzyl alcohol derivatives of

Fluorinated maleimide-substituted porphyrins and chlorins: synthesis and characterization

• Valentina A. Ol’shevskaya,
• Elena G. Kononova and
• Andrei V. Zaitsev

Beilstein J. Org. Chem. 2019, 15, 2704–2709, doi:10.3762/bjoc.15.263

• . Maleimides are considered as a biologically important scaffold that possess almost all types of biological activities including antibacterial and antifungal activity [24], anticancer activity [25], cox-2 inhibitor and anti-inflammatory, antidiabetic activity [26] and photodynamic activity [27]. Attaching of

α,ß-Didehydrosuberoylanilide hydroxamic acid (DDSAHA) as precursor and possible analogue of the anticancer drug SAHA

• Shital K. Chattopadhyay,
• Subhankar Ghosh,
• Sarita Sarkar and
• Kakali Bhadra

Beilstein J. Org. Chem. 2019, 15, 2524–2533, doi:10.3762/bjoc.15.245

• preliminarily evaluated for anticancer activity towards HeLa cells. The administration of the analogues caused a significant decrease in the proliferation of HeLa cells. Furthermore, one of the analogues showed a maximum cytotoxicity with a minimum GI50 value of 2.5 µg/mL and the generation of reactive oxygen

• refractory cutaneous T-cell lymphoma (CTCL) [3]. Moreover, it also shows anticancer activity against a large number of hematological and solid malignancies [4][5]. Its anticancer activity is related to inhibition of histone deacetylase inhibitor (HDACi) at nanomolar concentrations (IC50 < 86 nM). Although

• three steps. Biological studies Although approved for the treatment of CTCL, SAHA has been shown to display anticancer activity over a large range of other hematological and solid malignancies such as leukemia [24], lung cancer [25], cervical cancer (HeLa), breast cancer (MCF-7) [26], mesothelioma [27

Harnessing enzyme plasticity for the synthesis of oxygenated sesquiterpenoids

• Melodi Demiray,
• David J. Miller and
• Rudolf K. Allemann

Beilstein J. Org. Chem. 2019, 15, 2184–2190, doi:10.3762/bjoc.15.215

• as an attractant of aphids [10]. β-Sesquiphellandrene and α-curcumene are both found in turmeric (Curcuma longa) and have been shown to have anticancer activity [25][26]. The oxygenated α-curcumene and β-sesquiphellandrene derivatives α- and β-turmerone are reported to possess anticonvulsant

• -derived sesquiterpenes β-sesquiphellandrene [38][39][40] and zingiberene [40], a hydrocarbon with antifertility, antiviral and anticancer activity [41], suggested that the major compound was 12-methoxy-β-sesquiphellandrene (26), while the minor product was identified as 12-methoxyzingiberene (27). The two

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

• Iwona E. Głowacka,
• Aleksandra Trocha,
• Andrzej E. Wróblewski and
• Dorota G. Piotrowska

Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168

• formation of (1S,2S)-49 and provided a basis for the inversion of configuration at C2 by O-mesylation and intramolecular displacement to yield the 2-oxazoline (4S,5R)-54 readily hydrolyzed to florfenicol ((1R,2S)-49). Naturally occurring tyroscherin ((2S,3R,6E,8R,10R)-55) was recognized for its anticancer

• activity [56]. Alkylation of Weinreb amide (2S,1'S)-18 and stereoselective reduction of the corresponding ketone (2S,1'S)-56 with the NaBH4/ZnCl2 mixture gave the aziridine alcohol (2S,1'R,1''S)-57 already containing exact absolute configurations (2S and 3R) of the final product (Scheme 16) [57]. A two

Microwave-assisted synthesis of N,N-bis(phosphinoylmethyl)amines and N,N,N-tris(phosphinoylmethyl)amines bearing different substituents on the phosphorus atoms

• Erika Bálint,
• Anna Tripolszky,
• László Hegedűs and
• György Keglevich

Beilstein J. Org. Chem. 2019, 15, 469–473, doi:10.3762/bjoc.15.40

• ][3][4]. In addition, a few Pt, Ru and Au complexes incorporating phosphine ligands show significant anticancer activity [5][6]. One of the most common synthetic routes to α-aminophosphine oxides is the Kabachnik–Fields (phospha-Mannich) reaction, where an amine, an oxo compound (aldehyde or ketone