Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

• Esteban P. Urriolabeitia,
• Pablo Sánchez,
• Alexandra Pop,
• Cristian Silvestru,
• Eduardo Laga,
• Ana I. Jiménez and
• Carlos Cativiela

Beilstein J. Org. Chem. 2020, 16, 1111–1123, doi:10.3762/bjoc.16.98

• different pharmacological targets. Among them, probably the most important is their remarkable intrinsic anti-inflammatory and antinociceptive action, for which some mechanisms have been postulated to explain this activity [2][3][4][5][6]. The interest in this type of compound has gained even more relevance

Suzuki–Miyaura cross coupling is not an informative reaction to demonstrate the performance of new solvents

• James Sherwood

Beilstein J. Org. Chem. 2020, 16, 1001–1005, doi:10.3762/bjoc.16.89

• . The highest conversion of 96% was obtained in DMI, but overall it is fair to conclude the reaction quickly reaches good conversions with little apparent influence from the solvent. The second case study transformed 4-bromophenylacetic acid into felbinac, a nonsteroidal anti-inflammatory drug (Scheme

Efficient synthesis of piperazinyl amides of 18β-glycyrrhetinic acid

• Dong Cai,
• ZhiHua Zhang,
• Yufan Meng,
• KaiLi Zhu,
• LiYi Chen,
• ChangXiang Yu,
• ChangWei Yu,
• ZiYi Fu,
• DianShen Yang and
• YiXia Gong

Beilstein J. Org. Chem. 2020, 16, 798–808, doi:10.3762/bjoc.16.73

• fisch root. 18β-glycyrrhetinic acid (1, Figure 1) was then obtained by hydrolysis of glycyrrhizin. 18β-glycyrrhetinic acid and its derivatives have been extensively investigated in medicinal chemistry for their various biological activities, including anti-inflammatory [1], antiulcer [2], antioxidative

Reaction of indoles with aromatic fluoromethyl ketones: an efficient synthesis of trifluoromethyl(indolyl)phenylmethanols using K₂CO₃/n-Bu₄PBr in water

• Thanigaimalai Pillaiyar,
• Masoud Sedaghati and
• Gregor Schnakenburg

Beilstein J. Org. Chem. 2020, 16, 778–790, doi:10.3762/bjoc.16.71

• variety of biological activities, including anti-inflammatory, and anticancer effects. Therefore, we decided to synthesize DIMs from 3a, which reacted with indole (1b) or 2-phenylindole (1k) in the presence of Ga(OTf)3 in ACN at room temperature or at 80 °C as reported by Y. Ling et al. [32]. As indicated

• preparation of 3,3'-, and 3,6'-DIMs, which are known to possess a wide variety of biological activities, including anti-inflammatory, and anticancer effects. Additionally, trifluoromethyl(indolyl)phenylmethanols itselft have various biological properties including anti-HIV activity. The developed new

Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds

• Vuyisa Mzozoyana,
• Fanie R. van Heerden and
• Craig Grimmer

Beilstein J. Org. Chem. 2020, 16, 190–199, doi:10.3762/bjoc.16.22

• coumarins have been identified from natural sources [1][2]. Coumarins have been reported to play a vital role as food and cosmetics constituents, cigarette additives, and dye-sensitized solar cells [3][4]. In addition, coumarins possess some biological activities such as anti-inflammatory [5], antitumor [6

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

• ; inclusion complex; properties; Introduction Baicalein (5,6,7-trihydroxyflavonoid) has a molecular formula of C15H10O5 (BALE, Figure 1) and is a natural flavonoid found in the roots of Scutellaria baicalensis Georgi [1]. The compound displays pharmacological activity such as antimicrobial, anti-inflammatory

• has a strong activity to eliminate superoxide radicals in cell-free systems [25]. It is also considered as an anti-inflammatory agent [26][27] that generally protects against oxidative stress [28], more specifically in cardiac cells [29], and in cisplatin-induced acute kidney injury [30]. However

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

• melanosporofaciens, which catalyzes the formation of cycloocta-9-en-7-ol, a precursor to the next-generation anti-inflammatory drug cyclooctatin. In this work, we present evidence for the significant role of the active site's residues in CotB2 on the reaction energetics using quantum mechanical calculations in an

• 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

• , representing the first committed step in the biosynthesis of the next-generation anti-inflammatory drug cyclooctatin. The intracellular target of cyclooctatin is an as of yet uncharacterized lysophospholipase, which is involved in early steps of the inflammatory signaling cascade [38][39][40]. In the last

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

• ⁹-tetrahydrocannabinol, better known as THC (3, Figure 1), is widely known as the principal psychoactive constituent of cannabis, cannabidiol (CBD, 4, Figure 1) for example, shows strongly diminished psychoactive properties but has promising anti-inflammatory [22], antischizophrenic [23], and anti-epileptic

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

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

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

• , sponges, molluscs and other fungi as well and possess a wide range of bioactivities [24]. The drimane sesquiterpenoids isolated from Aspergillus spp. have exhibited in vitro anti-inflammatory [5] and antiviral [22] activities as well as cytotoxicity against several mammalian cell lines [4][16][22

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

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

• [1][2][3]. Sesqui- and diterpenes are a diverse class of secondary metabolites derived predominantly from plants, marine invertebrates, fungi and some prokaryotes [4][5][6][7][8]. Properties of these natural products include antitumor, anti-oxidant, anti-inflammatory, antiviral, antimalarial

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

• antibiotics (e.g., cephalosporins), immunosuppressants (e.g., mycophenolic acid) and immunomodulators (e.g., fingolimod), as well as cholesterol lowering agents (statins). Generally, fungal metabolites were shown to have antiviral, cytotoxic, antineoplastic, cardiovascular, anti-inflammatory, immune

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

• [2][3][4], such as antiproliferative, antifertility [5], anti-osteoporosis [6], immunosuppressive and anti-inflammatory activities [7]. Reports have indicated that triptolide induces apoptosis, triggers autophagy [8], and arrests cell cycle progression through modulating the relevant signaling

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

• , archangelolide did not bind into the sarco/endoplasmic reticular calcium ATPase cavity utilized by thapsigargin. Last, but not least, archangelolide exhibited anti-inflammatory activity, which makes it promising compound for medicinal purposes. Keywords: anti-inflammatory properties; archangelolide; dansyl

• anti-inflammatory activity of compound 1 using rat macrophages. Results and Discussion L. archangelica metabolite isolation and identification For isolation of the major metabolites of L. archangelica, we used 100 g of fine ground seeds (Supporting Information File 1, Figure S2) and the method of

• to 75% (statistically not significant) was also recorded when rat primary macrophages were incubated with 1000 pg·mL−1 LPS + 40 µM compound 5. However, no toxicity was observed for the combination of LPS + dansyl amide at the same concentration. Immunomodulatory [26] and anti-inflammatory [27

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

Introduction of an isoxazoline unit to the β-position of porphyrin via regioselective 1,3-dipolar cycloaddition reaction

• Xiujun Liu,
• Xiang Ma and
• Yaqing Feng

Beilstein J. Org. Chem. 2019, 15, 1434–1440, doi:10.3762/bjoc.15.143

• ], but also have a broad spectrum of interesting bioactivities, e.g., anti-inflammatory [40][41]. In addition, a few porphyrin-based dipoles have been also reported [42]. Recently, a 1,3-dipolar cycloaddition reaction was performed between the vinyl group at methyl pheophorbide A and the in-situ

One-pot activation–alkynylation–cyclization synthesis of 1,5-diacyl-5-hydroxypyrazolines in a consecutive three-component fashion

• Christina Görgen,
• Katharina Boden,
• Guido J. Reiss,
• Walter Frank and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2019, 15, 1360–1370, doi:10.3762/bjoc.15.136

• ingredients [8][9][10][11], as ligands [12][13], and as chromophores [14][15][16], the partially unsaturated 2H-pyrazolines have particularly attracted attention for instance as antibacterial [17], anti-inflammatory [18], antidiabetic [19], and antidepressive [20] agents. Especially, 1-acylpyrazolines have

Steroid diversification by multicomponent reactions

• Leslie Reguera,
• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

• displaying biological activities such as antimicrobial, antiviral and anti-inflammatory, among others. Scheme 3 exemplifies the reaction of cholestan-6-one 7 with 2-aminopyridine and phenyl isocyanide to afford the heterocycle–steroid hybrid 8 in good yield and diastereoselectivity, whereas different

• androstanic steroids. Such heterocyclic moieties are of interest because of their pharmacological activity, for example, as anti-inflammatory agents. Employing epiandrosterone and benzaldehyde as oxo components, ammonium acetate and malononitrile as C-nucleophile, the authors produced 2-amino-3-cyano-1,4

Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams

• Edorta Martínez de Marigorta,
• Jesús M. de Los Santos,
• Ana M. Ochoa de Retana,
• Javier Vicario and
• Francisco Palacios

Beilstein J. Org. Chem. 2019, 15, 1065–1085, doi:10.3762/bjoc.15.104

• compounds. Molecules containing the isoindolinone moiety are of pharmaceutical interest as anxiolytic (pazinaclone [15], pagoclone [16], and JM1232 [17]), anticancer (lenalidomide) [18], anti-inflammatory (indoprofen) [19] and antibiotic agents (lactonamycin) [20] (Figure 4). In addition, some isoindolinone

• , nintedanib is employed against pulmonary fibrosis [32], tenidap [33] is a nonsteroidal anti-inflammatory drug (NSAID), while indolidan [34] and adibendan [35] are potent long-acting cardiotonic agents and SM-130686 is a GHSR agonist [36] (Figure 5). Other kinase inhibitors such as sunitinib [37] and

Efficient synthesis of 4-substituted-ortho-phthalaldehyde analogues: toward the emergence of new building blocks

• Clémence Moitessier,
• Ahmad Rifai,
• Pierre-Edouard Danjou,
• Isabelle Mallard and
• Francine Cazier-Dennin

Beilstein J. Org. Chem. 2019, 15, 721–726, doi:10.3762/bjoc.15.67

• as well for the preparation of hydantoin derivatives to treat anti-inflammatory disorders [16]. More recently, in a study of Cao et al. [17] 4-HO-OPA was synthesized, once again in a low yield (4%) in order to produce the cucurbit[n]uril core. As shown by literature, the poor efficiency of 4

New sesquiterpenoids from the South China Sea soft corals Clavularia viridis and Lemnalia flava

• Qihao Wu,
• Yuan Gao,
• Meng-Meng Zhang,
• Li Sheng,
• Jia Li,
• Xu-Wen Li,
• Hong Wang and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2019, 15, 695–702, doi:10.3762/bjoc.15.64

• , cytotoxic, to anti-inflammatory properties [10]. In the framework of our ongoing research for the bioactive metabolites from South China Sea soft corals [11][12], we made the collection of the title samples Clavularia viridis and Lemnalia flava off the Xisha Islands, Hainan Province, China. The chemical