Five new sesquiterpenoids from agarwood of Aquilaria sinensis

• Hong Zhou,
• Xu-Yang Li,
• Hong-Bin Fang,
• He-Zhong Jiang and
• Yong-Xian Cheng

Beilstein J. Org. Chem. 2023, 19, 998–1007, doi:10.3762/bjoc.19.75

• absolute configurations, were identified by comprehensive spectroscopic analyses and computational methods. Inspired by our previous study on the same kinds of skeletons, we speculated that the new compounds have anticancer and anti-inflammatory activities. The results did not show any activity, but they

• studies, the components from A. sinensis possess various attractive bioactivities, such as anti-inflammatory, anticancer, antirenal fibrosis, and acetylcholinesterase inhibitory effects, which motivate us to assume that compounds with similar skeletons may have the same bioactivities. Therefore, the new

• compounds were evaluated for their anti-inflammatory and anticancer potential using the same method as described previously [16][22][23], and the cell viability was determined by CCK-8 assays (Figures A and B, Supporting Information File 1). Unfortunately, we could not distinguish any one of these

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

• Dileep Kumar Singh and
• Rajesh Kumar

Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71

• many natural products [1][2][3] and biologically active molecules [4][5][6][7]. Pyrroles are a significant class of five-membered aromatic nitrogen-containing heterocyclic skeletons that have attracted much attention due to their broad spectrum of biological activity, such as anticancer [8][9][10

Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones

• Ksenia Malkova,
• Andrey Bubyrev,
• Stanislav Kalinin and
• Dmitry Dar’in

Beilstein J. Org. Chem. 2023, 19, 800–807, doi:10.3762/bjoc.19.60

• derivatives have been recently reported to possess intriguing pharmacological activities [3] including antiprotozoal [4][5][6][7], antitubercular [8][9], anticancer [10][11], anti-inflammatory [12], antioxidant [13], anti-HIV [14], antifungal [15], and an antineurodegenerative effect [16]. Hence, designing

Synthesis of imidazo[1,2-a]pyridine-containing peptidomimetics by tandem of Groebke–Blackburn–Bienaymé and Ugi reactions

• Oleksandr V. Kolomiiets,
• Alexander V. Tsygankov,
• Maryna N. Kornet,
• Aleksander A. Brazhko,
• Vladimir I. Musatov and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2023, 19, 727–735, doi:10.3762/bjoc.19.53

• structures containing a substituted imidazo[1,2-a]pyridine fragment, such as anticancer [5], antibacterial [6], antifungal [7], antiviral [8], anti-inflammatory [9], antimalarial [10], antiparkinsonian [11] and antituberculous activities [12]. In addition, some derivatives show enzyme inhibition [13] and can

• the given concentration range. Despite the low level of antibacterial activity observed with the synthesized heterocycles, this could be beneficial for screening these compounds for other types of activity, such as anticancer or antidiabetic effects, since it would minimize any negative impact on the

Dipeptide analogues of fluorinated aminophosphonic acid sodium salts as moderate competitive inhibitors of cathepsin C

• Karolina Wątroba,
• Małgorzata Pawełczak and
• Marcin Kaźmierczak

Beilstein J. Org. Chem. 2023, 19, 434–439, doi:10.3762/bjoc.19.33

• , F, H, K, L, O, S, V, W, and X) [1]. Cathepsin C is considered a good target for designing new anticancer agents with broad substrate specificity [2]. Cathepsin C, which affects the processing of keratin, is of great importance in maintaining the structural organization of the epidermis, primarily

• in chemotherapies to support traditional anticancer drugs. Moreover, there is a growing interest in the topic of cathepsin C inhibition, which directly affects serine protease activity [5][6]. Inhibitors of cathepsin C can be cystatins that show activity against a large group of cysteine proteases [7

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

• , since Pettit and co-workers, in a program from U.S. National Cancer Institute for the discovery of new anticancer agents, initially showed that combretastatins D-1 (1) and D-2 (2) isolated from the bark of the Combretum caffrum tree inhibited the growth of the murine lymphocytic leukemia cell line P388

Strategies to access the [5-8] bicyclic core encountered in the sesquiterpene, diterpene and sesterterpene series

• Cécile Alleman,
• Charlène Gadais,
• Laurent Legentil and
• François-Hugues Porée

Beilstein J. Org. Chem. 2023, 19, 245–281, doi:10.3762/bjoc.19.23

• to anticancer properties [21][24][25]. Indeed, access to the ophiobolin structure is crucial to study their biological activities in detail. Many synthetic approaches have emerged for the synthesis of ophiobolins and total syntheses of some congeners have also been reported [21][24]. Nakada and co

An efficient metal-free and catalyst-free C–S/C–O bond-formation strategy: synthesis of pyrazole-conjugated thioamides and amides

• Shubham Sharma,
• Dharmender Singh,
• Sunit Kumar,
• Vaishali,
• Rahul Jamra,
• Naveen Banyal,
• Deepika,
• Chandi C. Malakar and
• Virender Singh

Beilstein J. Org. Chem. 2023, 19, 231–244, doi:10.3762/bjoc.19.22

• ], anticancer [13][14][15], antiviral [16], analgesic [17], antioxidants, antimicrobial [18], antidiabetic, anticonvulsant [19], antihelminthic [20], and antiarrhythmic activities. The pyrazole nucleus is a core unit in several FDA-approved marketed drugs such as sildenafil [21][22][23], celebrex [24][25

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

• mathematically by release kinetic modeling for the first time. The overall findings indicated that the strategy of orally targeting anticancer drugs such as CPT with positively charged poly-β-CD-C6 nanoparticles to colon tumors for local and/or systemic efficacy is a promising approach. Keywords: colorectal

• is possible, chemotherapeutic treatment is still one of the most researched approaches in terms of tumor recurrence and the progression of the disease. In CRC chemotherapy, the most common approach is mainly an intravenous administration of anticancer drugs such as camptothecin (CPT) analogs

• the physicochemical properties and poor bioavailability of many widely used anticancer drugs. Specifically in the treatment of CRC, since the colon is the most distant part of the gastrointestinal (GI) tract, the ability of oral delivery of anticancer drugs to reach the colon in a stable and effective

Preparation of β-cyclodextrin/polysaccharide foams using saponin

• Max Petitjean and
• José Ramón Isasi

Beilstein J. Org. Chem. 2023, 19, 78–88, doi:10.3762/bjoc.19.7

• that saponins possess anticancer properties, by limiting proliferation and metastasis. This has been tested on different cancers such as leukemia [16], breast cancer [17] or prostate cancer to cite only a few of them [18]. They also present antimicrobial, antioxidant, anti-inflammatory, antidiabetic

• dressings. This saponin possesses two large hydrophilic parts, surrounding the aglycone [30]. The association chitosan–saponin can show other functions for medicinal purposes, and anticancer nanoparticles made of chitosan loaded with saponins have been prepared by Nair and Jayakumar [31], and even

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

• meroterpenoids. This class of compounds possesses versatile bioactivities, ranging from anticancer and anti-HIV to antifungal properties, with minor modifications on the decoration of either the hydroquinone or the terpene part of the secondary metabolite [34]. The group applied a semisynthetic plan starting

• 2021) [37]: Dysideanone B (75), isolated from the South China Sea sponge Dysidea avara, possesses an unprecedented 6/6/6/6-fused tetracycle with interesting anticancer properties against HeLa and HepG2 cancer cell lines (Scheme 6) [38]. The structurally similar dysiherbols 79 and 80, bearing a 6/6/5/6

• -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

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

Inclusion complexes of the steroid hormones 17β-estradiol and progesterone with β- and γ-cyclodextrin hosts: syntheses, X-ray structures, thermal analyses and API solubility enhancements

• Alexios I. Vicatos,
• Zakiena Hoossen and
• Mino R. Caira

Beilstein J. Org. Chem. 2022, 18, 1749–1762, doi:10.3762/bjoc.18.184

• . Furthermore, no previous structure determinations via SCXRD analysis of CD complexes of BES and PRO have been reported. Many studies involved phase solubility analyses to determine CD complex formation and association constants. Our previous study of the complexation of the steroidal anticancer agent 2

Formal total synthesis of macarpine via a Au(I)-catalyzed 6-endo-dig cycloisomerization strategy

• Jiayue Fu,
• Bingbing Li,
• Zefang Zhou,
• Maosheng Cheng,
• Lu Yang and
• Yongxiang Liu

Beilstein J. Org. Chem. 2022, 18, 1589–1595, doi:10.3762/bjoc.18.169

• hydrogenated base and fully aromatized base, in which natural fully aromatic alkaloids can be further classified into three subclasses: O4-base, O5-base, and O6-base [3]. Among these alkaloids macarpine is the most oxidized tetracyclic alkaloid with many bioactivities, including anesthesia, anticancer, anti

Functionalization of imidazole N-oxide: a recent discovery in organic transformations

• Koustav Singha,
• Imran Habib and
• Mossaraf Hossain

Beilstein J. Org. Chem. 2022, 18, 1575–1588, doi:10.3762/bjoc.18.168

• compounds exhibit various bioactivities, such as antimicrobial [4], antidiabetic [5], antiviral [6], antihypertensive, anticancer [7], anti-inflammatory [8], analgesic [9], antimicrobial and so on (Figure 1). For the synthesis of imidazole derivatives, there are several interesting methodologies available

A facile approach to spiro[dihydrofuran-2,3'-oxindoles] via formal [4 + 1] annulation reaction of fused 1H-pyrrole-2,3-diones with diazooxindoles

• Pavel A. Topanov,
• Anna A. Maslivets,
• Maksim V. Dmitriev,
• Irina V. Mashevskaya,
• Yurii V. Shklyaev and
• Andrey N. Maslivets

Beilstein J. Org. Chem. 2022, 18, 1532–1538, doi:10.3762/bjoc.18.162

• and J [16] were also isolated from the fungus Penicillium commune and contain a furan fragment spiro-annulated by 2-oxindole. These compounds exhibit anticancer [13] and antimicrobial [17] activities. One of the expeditious methods for obtaining dihydrofurans is the cycloaddition reaction of diazo

Synthesis of the biologically important dideuterium-labelled adenosine triphosphate analogue ApppI(d₂)

• Petri A. Turhanen

Beilstein J. Org. Chem. 2022, 18, 1466–1470, doi:10.3762/bjoc.18.153

• already in clinical use as antiviral or anticancer drugs [2][5][6]. Bisphosphonates (BPs), the stable analogues of the natural pyrophosphate (Figure 1) found in cells, have been used for decades in the treatment of bone-related diseases, such as osteoporosis [7][8]. BPs can be categorized by the chemical

• known to be involved in the induction of cell death [14]. The mechanism of action related to the antiresorptive and anticancer effects of NBPs has been proposed to be attributable to the metabolites formed in the mevalonate pathway induced by NBPs [15]. In 2020 in Finland, the wholesaling of BPs has

On drug discovery against infectious diseases and academic medicinal chemistry contributions

• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 1355–1378, doi:10.3762/bjoc.18.141

• chemistry culture caused by this lack of academic support. Indeed, virtual docking has yet to demonstrate that it was instrumental in preselecting a really successful hit out of chemical libraries and considering, for instance, anticancer drugs as potential antivirals is barely more relevant than assaying

• combinatorial approach [232][233] appeared to have only led to one anticancer drug [234], major progresses in the design, selection, generation and purification of libraries have since then turned this type of chemistry into a central tool for drug discovery [235][236][237] along with more recent success

• [288][289][290][291][292][293]. Moreover, the use/design of new chemical reactions may lead to hard-to-get and original analogues possibly better than the one reported. One example, depicted in Scheme 2, would be the fluorination, under superacid conditions [294], of the highly elaborated anticancer

Ferrocenoyl-adenines: substituent effects on regioselective acylation

• Mateja Toma,
• Gabrijel Zubčić,
• Jasmina Lapić,
• Senka Djaković,
• Davor Šakić and
• Valerije Vrček

Beilstein J. Org. Chem. 2022, 18, 1270–1277, doi:10.3762/bjoc.18.133

• ferrocene–nucleobase conjugates [4], which are known to exhibit anticancer [5][6][7], antibacterial [8][9][10], or antitrypanosomal activity [11], but also may serve as electrochemical biosensors [12][13], self-assembled molecular materials [14][15], decorations of carbon tubes and nanomaterials [16][17

Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates

• Péter Kisszékelyi,
• Tibor Peňaška,
• Klára Stankovianska,
• Mária Mečiarová and
• Radovan Šebesta

Beilstein J. Org. Chem. 2022, 18, 1195–1202, doi:10.3762/bjoc.18.124

• hydrogenation; Introduction Heterocyclic compounds with a benzothiazine moiety are attractive building blocks in medicinal chemistry. Benzo-1,4-thiazine derivatives possess a wide range of biological and pharmacological properties, such as anticancer and antitumor, antioxidant, antimicrobial, antibacterial

Scope of tetrazolo[1,5-a]quinoxalines in CuAAC reactions for the synthesis of triazoloquinoxalines, imidazoloquinoxalines, and rhenium complexes thereof

• Laura Holzhauer,
• Chloé Liagre,
• Olaf Fuhr,
• Nicole Jung and
• Stefan Bräse

Beilstein J. Org. Chem. 2022, 18, 1088–1099, doi:10.3762/bjoc.18.111

• formation from tetrazolo[1,5-a]quinoxalines 1 is still limited. Triazole-linked N-heterocycles like pyridotriazoles and quinolinotriazoles exert a variety of favorable biological properties like anticancer and antimicrobial activities as well as protein kinase inhibition [10][13][14][15]. Moreover, a vast

• of a metal complex with an inverse triazoloquinoxaline ligand [12]. Imidazo[1,2-a]quinoxalines have been reported to possess anticancer and antitumor properties [27][28] and show activity as adenosine receptor antagonists [29] as well as PDE4 inhibitors [30]. The reaction of ring-fused tetrazoles to

Synthesis of N-phenyl- and N-thiazolyl-1H-indazoles by copper-catalyzed intramolecular N-arylation of ortho-chlorinated arylhydrazones

• Yara Cristina Marchioro Barbosa,
• Guilherme Caneppele Paveglio,
• Claudio Martin Pereira de Pereira,
• Sidnei Moura,
• Cristiane Storck Schwalm,
• Gleison Antonio Casagrande and
• Lucas Pizzuti

Beilstein J. Org. Chem. 2022, 18, 1079–1087, doi:10.3762/bjoc.18.110

• anticancer [2], anti-HIV [3], anti-inflammatory [4], antiprotozoal [5], antifungal [6], antibacterial [7], antiplatelet [8], and antihypertensive [9] properties. The relevance to medicinal chemistry is also demonstrated by the presence of the 1H-indazole core in the structure of drugs. The anticataract agent

Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold

• Dmitry Dar’in,
• Grigory Kantin,
• Alexander Bunev and
• Mikhail Krasavin

Beilstein J. Org. Chem. 2022, 18, 1070–1078, doi:10.3762/bjoc.18.109

• readily available 3(2H)-isoquinolones followed by TfOH-promoted hydroarylation by an arene molecule. Screening of the novel 1,2,4-trisubstituted 1,4-DHIQs against cancer cell lines confirmed high cytotoxicity of selected analogs, which validates this new chemotype for further investigations as anticancer

• anticancer cytotoxic agents. Diverse bioactive compounds based on the privileged 1,4-DHIQ scaffold. Strategy investigated in this work. Preparation of 3(2H)-isoquinolones 11. aObtained as a 10:1 mixture of regioisomers; purified by crystallization. bEmployed in the next step without purification (not

Morita–Baylis–Hillman reaction of 3-formyl-9H-pyrido[3,4-b]indoles and fluorescence studies of the products

• Nisha Devi and
• Virender Singh

Beilstein J. Org. Chem. 2022, 18, 926–934, doi:10.3762/bjoc.18.92

• activities is displayed by this pharmacologically rich nucleus which includes antibacterial, antifungal, anticancer, anxiolytic, antimalarial, antiviral, anti-HIV, anti-Alzheimer, and anticonvulsant activities etc. [18][19][20][21][22][23][24][25][26]. Potent anticancer activities are shown by the majority