Rapid, two-pot procedure for the synthesis of dihydropyridinones; total synthesis of aza-goniothalamin

• Thomas J. Cogswell,
• Craig S. Donald and
• Rodolfo Marquez

Beilstein J. Org. Chem. 2020, 16, 135–139, doi:10.3762/bjoc.16.15

• cell line, Figure 1). Thus, a path for the generation of a new class of potential anticancer agents based on the aza-goniothalamin framework was determined [17][18]. Results and Discussion Our approach to the synthesis of the dihydropyridinone framework was inspired by the work carried out by Veenstra

Reversible photoswitching of the DNA-binding properties of styrylquinolizinium derivatives through photochromic [2 + 2] cycloaddition and cycloreversion

• Sarah Kölsch,
• Heiko Ihmels,
• Jochen Mattay,
• Norbert Sewald and
• Brian O. Patrick

Beilstein J. Org. Chem. 2020, 16, 111–124, doi:10.3762/bjoc.16.13

• structural changes of the nucleic acid. In turn, both of these processes interfere with biologically relevant recognition processes between DNA and enzymes, e.g., topoisomerase [10]. Therefore, many potential lead structures of chemotherapeutic anticancer drugs exhibit DNA-binding properties [1][2][3][4][5

The interaction between cucurbit[8]uril and baicalein and the effect on baicalein properties

• Xiaodong Zhang,
• Jun Xie,
• Zhiling Xu,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2020, 16, 71–77, doi:10.3762/bjoc.16.9

• , anti-allergic, antispasmodic, diuretic and anticancer [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24]. For example, baicalein can play an antitumor effect on lung cancer by inducing cell apoptosis, blocking cell cycle and inhibiting metastasis of lung cancer, but it

Understanding the role of active site residues in CotB2 catalysis using a cluster model

• Keren Raz,
• Ronja Driller,
• Thomas Brück,
• Bernhard Loll and
• Dan T. Major

Beilstein J. Org. Chem. 2020, 16, 50–59, doi:10.3762/bjoc.16.7

• by featuring anticancer, antibacterial, anti-inflammatory, and antiretroviral activities [37]. Moreover, they are applied in the food industry as antioxidants and sweeteners [4]. CotB2 is a bacterial diterpene cyclase from S. melanosporofaciens, which catalyzes the formation of cyclooctat-9-en-7-ol

Light-controllable dithienylethene-modified cyclic peptides: photoswitching the in vivo toxicity in zebrafish embryos

• Sergii Afonin,
• Oleg Babii,
• Aline Reuter,
• Volker Middel,
• Masanari Takamiya,
• Uwe Strähle,
• Igor V. Komarov and
• Anne S. Ulrich

Beilstein J. Org. Chem. 2020, 16, 39–49, doi:10.3762/bjoc.16.6

• targets [2][7][8]. As a result, the market for peptide drugs (e.g., hormones, receptor antagonists, anticancer, or antibiotic agents) grows faster than that of many other chemotherapeutics [9]. Significant general disadvantages of peptides as pharmacological agents are their poor oral bioavailability, low

• photoswitchable analogue 2 in an allograft mouse model, the first in vivo photopharmacology application for a DAE-derived peptide as an anticancer agent has been demonstrated [29]. In order to optimize 2, we have recently performed a structure–activity relationship (SAR) study using a library of photoswitchable

• infectious diseases caused by Gram-positive or -negative bacteria, or for anticancer applications. We hypothesized that the lack of correlation between cell types might not only reflect different mechanisms of killing (possibly even within any pair of isomers), but that it may also be due to unique

Construction of trisubstituted chromone skeletons carrying electron-withdrawing groups via PhIO-mediated dehydrogenation and its application to the synthesis of frutinone A

• Qiao Li,
• Chen Zhuang,
• Donghua Wang,
• Wei Zhang,
• Rongxuan Jia,
• Fengxia Sun,
• Yilin Zhang and
• Yunfei Du

Beilstein J. Org. Chem. 2019, 15, 2958–2965, doi:10.3762/bjoc.15.291

• antibacterical [4], antifungal [5][6], anticancer [7], antioxidant [8], anti-HIV [9], antiulcer, immunostimulator [10], anti-inflammatory [11], as well as biocidal [12], wound-healing [13], and immune-stimulatory activities [14]. For instance, flavoxate [15][16] is a chromone derivative that was employed as an

Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering

• Eric J. N. Helfrich,
• Geng-Min Lin,
• Christopher A. Voigt and
• Jon Clardy

Beilstein J. Org. Chem. 2019, 15, 2889–2906, doi:10.3762/bjoc.15.283

• restricted members possess significant biological activities, like the anticancer agent taxol (1) [4] or the antimalarial agent artemisinin (2, Figure 1) [5][6]. The structural diversity and functional utility of this class of specialized metabolites have combined to encourage efforts to apply the tools of

• . Taxol (1), a plant-derived terpenoid, provides an illustrative example. Taxol was structurally characterized in 1971 [4] and approved by the FDA as an anticancer agent in 1992 [13]. Today, almost 50 years after its initial report, despite its blockbuster status in cancer therapy [14] and multiple

Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles

• Hoang Huy Do,
• Saif Ullah,
• Alexander Villinger,
• Joanna Lecka,
• Jean Sévigny,
• Peter Ehlers,
• Jamshed Iqbal and
• Peter Langer

Beilstein J. Org. Chem. 2019, 15, 2830–2839, doi:10.3762/bjoc.15.276

• reported to show potent antiallergic [1][2][3][4], anticancer [5][6], analgesic and anti-inflammatory activity [7] (Figure 1). Similarly, benzofuroindol has been studied intensively as a pharmacophore of calcium-activated potassium channel (BKCa) opening activity [8][9][10][11][12][13]. Hence

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

• promising activity shown by the compounds containing a thiazolidinedione nucleus cover numerous categories such as antihyperglycaemics [5], aldose reductase inhibitors (ARI) [6][7], anti-inflammatory [8][9], anti-arthritics [10], anticancer [11][12][13] and antimicrobial [14][15][16][17][18], etc., has made

• represent an important class of nitrogen-containing biologically active compounds which exhibit various biological properties, such as antiviral, antibacterial and anticancer, etc. [55][56][57][58]. Recently, the use of 1,2,3-triazole derivatives as drug candidates has been increased for clinical therapy of

• 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

• the maleimide group with its rich biological activity to the tetrapyrrole macrocycles with their unique photophysical properties may result in new conjugates with improved chemical, biological and anticancer characteristics [28]. Moreover, maleimide is a stable functionality that rapidly and

Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

• Heather J. Lacey,
• Cameron L. M. Gilchrist,
• Andrew Crombie,
• John A. Kalaitzis,
• Daniel Vuong,
• Peter J. Rutledge,
• Peter Turner,
• John I. Pitt,
• Ernest Lacey,
• Yit-Heng Chooi and
• Andrew M. Piggott

Beilstein J. Org. Chem. 2019, 15, 2631–2643, doi:10.3762/bjoc.15.256

• potential cancer target. Further structure–activity relationship studies are required to fully characterise this potential anticancer pharmacophore. This study again demonstrates how taxonomy-guided exploration of fungi is a highly effective strategy for identifying novel bioactive metabolites. Experimental

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

• the important anticancer drug suberoylanilide hydroxamic acid (SAHA) from its α,ß-didehydro derivative is described. The didehydro derivative is obtained through a cross metathesis reaction between a suitable terminal alkene and N-benzyloxyacrylamide. Some of the didehydro derivatives of SAHA were

• 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

• species (ROS) as some apoptotic features. Keywords: anticancer drug; cross metathesis; HDAC inhibition; hydroxamates; reactive oxygen species; Introduction Suberoylanilide hydroxamic acid (SAHA, 1, Figure 1, vorinostat [1][2], has now emerged as a FDA approved drug for the treatment of relapsed and

Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids

• Gerardo M. Ojeda,
• Prabhat Ranjan,
• Pavel Fedoseev,
• Lisandra Amable,
• Upendra K. Sharma,
• Daniel G. Rivera and
• Erik V. Van der Eycken

Beilstein J. Org. Chem. 2019, 15, 2447–2457, doi:10.3762/bjoc.15.237

• variety of pharmacological and antimicrobial properties [5][6], including analgesic, antihypertensive, anti-inflammatory, anticancer, antifungal and antimalarial activity (Figure 1). A key feature of the tetrazole ring is its bioisosteric character with the carboxylic acid and amide functional groups

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

• Irina G. Tkachenko,
• Sergey A. Komykhov,
• Vladimir I. Musatov,
• Svitlana V. Shishkina,
• Viktoriya V. Dyakonenko,
• Vladimir N. Shvets,
• Mikhail V. Diachkov,
• Valentyn A. Chebanov and
• Sergey M. Desenko

Beilstein J. Org. Chem. 2019, 15, 2390–2397, doi:10.3762/bjoc.15.231

• biological properties. They have been reported to have anticancer [1], antimicrobial [2][3] and antioxidant [3] activities and to act as inhibitors of hepatitis B virus [4]. The dihydro derivatives of tetrazolo[1,5-a]pyrimidines belong to a bit special kind of dihydropyrimidines due to the strong electron

Current understanding and biotechnological application of the bacterial diterpene synthase CotB2

• Ronja Driller,
• Daniel Garbe,
• Norbert Mehlmer,
• Monika Fuchs,
• Keren Raz,
• Dan Thomas Major,
• Thomas Brück and
• Bernhard Loll

Beilstein J. Org. Chem. 2019, 15, 2355–2368, doi:10.3762/bjoc.15.228

• inexpensive carbon sources. Prominent examples of optimized terpene production pathways in E. coli are taxadiene, a precursor of the anticancer drug taxol [28], amorpha‐4,11‐diene, an antimalarial drug precursor [29], and cyclooctatin [30]. The scope of this review encompasses a detailed consideration of the

• isolated in 1985 from cigarette smoke condensate and identified as anticancer agents [76]. With quite similar potency (α-CBT: 25.2 µM and β-CBT: 21.9 µM [77]), they showed inhibition of the induction of Epstein–Barr virus early antigen by lymphoblastoid cancer cells. In the tobacco plant itself, both

Fluorescent phosphorus dendrimers excited by two photons: synthesis, two-photon absorption properties and biological uses

• Anne-Marie Caminade,
• Artem Zibarov,
• Eduardo Cueto Diaz,
• Aurélien Hameau,
• Maxime Klausen,
• Kathleen Moineau-Chane Ching,
• Jean-Pierre Majoral,
• Jean-Baptiste Verlhac,
• Olivier Mongin and
• Mireille Blanchard-Desce

Beilstein J. Org. Chem. 2019, 15, 2287–2303, doi:10.3762/bjoc.15.221

• the mechanism of action of anticancer compounds, and for safer photodynamic therapy. Keywords: bioimaging; dendrimer; fluorescence; phosphorus; two-photon absorption; Introduction Natural luminescence phenomena such as the bioluminescence of fireflies or of certain marine microorganisms, or the

• ). This dendrimer retains some fluorescence as well as very high TPA cross-sections in a broad range of the NIR (near infra-red) biological spectral window. Furthermore, it displays significant singlet oxygen production, thus this dendrimer combines unique properties for bioimaging and anticancer therapy

• deciphering mechanism of action of anticancer compounds, and recently for safer photodynamic therapy. In view of the results already obtained, there is no doubt that other biological properties of these fully organic “nanodots” can be foreseen, thanks to their low toxicity, large color modularity, and high

Isolation of fungi using the diffusion chamber device FIND technology

• Benjamin Libor,
• Henrik Harms,
• Stefan Kehraus,
• Ekaterina Egereva,
• Max Crüsemann and
• Gabriele M. König

Beilstein J. Org. Chem. 2019, 15, 2191–2203, doi:10.3762/bjoc.15.216

• -stimulating, and anticancer activities [2]. Since the World Health Organization (WHO) declared antibiotic resistance a global threat and urged the search for new antibiotics, the interest in fungal metabolites increased recently. In order to find new structural types, novel source organisms have to be

• were limited to mycotoxins [34] where in the other cases the isolated structures showed remarkable activities in the field of anticancer and antimicrobial agents [35][36][37][38][39][40]. H. alpina is one of only six species known from the less examined genus Heydenia, and was mistaken for a member of

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

Genome mining in Trichoderma viride J1-030: discovery and identification of novel sesquiterpene synthase and its products

• Xiang Sun,
• You-Sheng Cai,
• Yujie Yuan,
• Guangkai Bian,
• Ziling Ye,
• Zixin Deng and
• Tiangang Liu

Beilstein J. Org. Chem. 2019, 15, 2052–2058, doi:10.3762/bjoc.15.202

• structurally diverse (poly)cyclic core skeletons [3][12]. A set of post-modification enzymes can transform core sesquiterpene skeletons into different kinds of sesquiterpenoids with potential anticancer, cytotoxic and antibiotic functions [13]. More than 121 skeleton structures derived from the sesquiterpene

A review of the total syntheses of triptolide

• Xiang Zhang,
• Zaozao Xiao and
• Hongtao Xu

Beilstein J. Org. Chem. 2019, 15, 1984–1995, doi:10.3762/bjoc.15.194

• cross-talk network amongst these targets and signaling pathways are considered to be responsible for the multiple anticancer activities of triptolide [18][19][20][21][22][23][24]. Triptolide could also suppress inflammation and stimulate cytoprotection by regulating pro-inflammatory cytokines and

Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkyl-substituted benzimidazoles with arenes in the superacid CF₃SO₃H. NMR and DFT studies of dicationic electrophilic species

• Dmitry S. Ryabukhin,
• Alexey N. Turdakov,
• Natalia S. Soldatova,
• Mikhail O. Kompanets,
• Alexander Yu. Ivanov,
• Irina A. Boyarskaya and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2019, 15, 1962–1973, doi:10.3762/bjoc.15.191

• biological activities including antiparasitic (albendazole, mebendazole), antiulcer (omeprazole), antihypertensive (candesartan, telmisartan, azilsartan, medoxomil, mebefradil), anticancer (bendamustine), antiemetic/antipsychotic (droperidole), antihistaminic (astemizole, emedastine) and many others (Figure

Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica

• Silvie Rimpelová,
• Michal Jurášek,
• Lucie Peterková,
• Jiří Bejček,
• Vojtěch Spiwok,
• Miloš Majdl,
• Michal Jirásko,
• Miloš Buděšínský,
• Juraj Harmatha,
• Eva Kmoníčková,
• Pavel Drašar and
• Tomáš Ruml

Beilstein J. Org. Chem. 2019, 15, 1933–1944, doi:10.3762/bjoc.15.189

• archangelica Wulfen using supercritical CO2 extraction. We show that dansyl-archangelolide localizes in the endoplasmic reticulum of living cells similarly to trilobolide; localization in mitochondria was also detected. This led us to a more detailed study of the anticancer potential of archangelolide

• fluorescent conjugate; sarco/endoplasmic reticulum calcium ATPase; sesquiterpene lactone; trilobolide analogue; Introduction Sesquiterpene lactones (SLs) have been attracting interest already for some time due to the plethora of biological effects they elicit. Various SLs show anticancer, antimicrobial

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

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

• Gagandeep Kour Reen,
• Ashok Kumar and
• Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165

• ., anti-inflammatory, anticancer, antibacterial, anxioselective and antiprotozoal [3][4][5]. Furthermore, a number of drugs embracing the imidazopyridine (IP) skeleton have been commercially marketed with their trade names as minodronic acid (for the treatment of osteoporosis), olprinone (for acute heart

A heteroditopic macrocycle as organocatalytic nanoreactor for pyrroloacridinone synthesis in water

• Piyali Sarkar,
• Sayan Sarkar and
• Pradyut Ghosh

Beilstein J. Org. Chem. 2019, 15, 1505–1514, doi:10.3762/bjoc.15.152

• antitumor, antifungal, anthelmintic, anticancer activities, etc. [5][6][7]. Although a few syntheses of these molecules have been reported in the literature, these generally consist of multistep protocols and require harsh acidic catalysts [5][8][9][10][11][12]. Moreover, only in a very few cases, the