Synthesis of 2H-furo[2,3-c]pyrazole ring systems through silver(I) ion-mediated ring-closure reaction

• Vaida Milišiūnaitė,
• Rūta Paulavičiūtė,
• Eglė Arbačiauskienė,
• Vytas Martynaitis,
• Wolfgang Holzer and
• Algirdas Šačkus

Beilstein J. Org. Chem. 2019, 15, 679–684, doi:10.3762/bjoc.15.62

• systems possessing a pyrazole ring fused to an oxygen-containing six-membered heterocycle are present in a wide variety of biologically active compounds. For example, the 1,4- and 2,4-dihydropyrano[2,3-c]pyrazole ring systems [1] often represent the main structural motifs of anticancer [2][3][4], anti

• -inflammatory [5], and antidiabetic agents [6]. The numerous known methods for the preparation of these compounds are generally based on multicomponent reactions of an aromatic aldehyde, a β-keto ester, a hydrazine and malononitrile [7]. In a similar reaction using a pyridinium ylide instead of malononitrile

Synthesis and biological investigation of (+)-3-hydroxymethylartemisinin

• Toni Smeilus,
• Farnoush Mousavizadeh,
• Johannes Krieger,
• Xingzhao Tu,
• Marcel Kaiser and
• Athanassios Giannis

Beilstein J. Org. Chem. 2019, 15, 567–570, doi:10.3762/bjoc.15.51

• sesquiterpene lactone is still unknown [5]. Whereas artemisinins are almost non-toxic to normal cells, several studies have confirmed their potent antitumor activity [6][7]. In addition, they have been reported to possess immunosuppressive, anti-inflammatory, antiviral, antifungal and antiparasitic activities

Reusable and highly enantioselective water-soluble Ru(II)-Amm-Pheox catalyst for intramolecular cyclopropanation of diazo compounds

• Hamada S. A. Mandour,
• Yoko Nakagawa,
• Masaya Tone,
• Hayato Inoue,
• Nansalmaa Otog,
• Ikuhide Fujisawa,
• Soda Chanthamath and
• Seiji Iwasa

Beilstein J. Org. Chem. 2019, 15, 357–363, doi:10.3762/bjoc.15.31

• nature and have excellent biological activity, including strong antibiotic, antihelmetic, antifungal, antitumor, antiviral and anti-inflammatory, which make them interesting lead structures for new drugs [34]. That is why a great deal of attention has been paid to the synthesis of the lactone ring [35

A novel and efficient synthesis of phenanthrene derivatives via palladium/norbornadiene-catalyzed domino one-pot reaction

• Yue Zhong,
• Wen-Yu Wu,
• Shao-Peng Yu,
• Tian-Yuan Fan,
• Hai-Tao Yu,
• Nian-Guang Li,
• Zhi-Hao Shi,
• Yu-Ping Tang and
• Jin-Ao Duan

Beilstein J. Org. Chem. 2019, 15, 291–298, doi:10.3762/bjoc.15.26

• ], antibacterial [6], anti-inflammatory [7] and so on. During the past decades, numerous methods for the preparation of phenanthrene derivatives have been developed. In 2003, Gabriel Tojo’s group reported a base-catalyzed photochemical synthesis of phenanthrene derivatives [8] through intramolecular aromatic

Metal-free C–H mercaptalization of benzothiazoles and benzoxazoles using 1,3-propanedithiol as thiol source

• Yan Xiao,
• Bing Jing,
• Xiaoxia Liu,
• Hongyu Xue and
• Yajun Liu

Beilstein J. Org. Chem. 2019, 15, 279–284, doi:10.3762/bjoc.15.24

• cancer cells [3][4][5]. 2-Mercapto-N-(substituted arylidine)benzoxazole-5-carbohydrazide derivatives have promising anti-inflammatory activities [6]. 2-Mercapto-5-nitro-1,3-benzoxazole and its derivatives shows strong anthelmintic activity [7]. 2-Mercapto-5-chloro-1,3-benzothiazoles possess antifungal

Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines

• Olga A. Storozhenko,
• Alexey A. Festa,
• Delphine R. Bella Ndoutoume,
• Alexander V. Aksenov,
• Alexey V. Varlamov and
• Leonid G. Voskressensky

Beilstein J. Org. Chem. 2018, 14, 3078–3087, doi:10.3762/bjoc.14.287

• may be found in crolibulin, an antitumor agent, undergoing phase II clinical trials [31], chromenotacrine CT-6, a potential anti-Alzheimer agent [32], and pranoprofen, a marketed anti-inflammatory drug [33]. Combination of chromene and imidazopyridine rings led to the discovery of compound A with

Reactions of 3-(p-substituted-phenyl)-5-chloromethyl-1,2,4-oxadiazoles with KCN leading to acetonitriles and alkanes via a non-reductive decyanation pathway

• Akın Sağırlı and
• Yaşar Dürüst

Beilstein J. Org. Chem. 2018, 14, 3011–3017, doi:10.3762/bjoc.14.280

• bioactivities, such as anticancer [1], antimicrobial [2], antifungal [3], anti-inflammatory [4], tyrosine kinase inhibition [5] and histamine H3 antagonism properties [6]. In addition, these five-membered heterocycles were widely used as components of organic light emitting diodes (OLEDs), polymers, liquid

Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium

• Nadia Bouzayani,
• Jamil Kraїem,
• Sylvain Marque,
• Yakdhane Kacem,
• Abel Carlin-Sinclair,
• Jérôme Marrot and
• Béchir Ben Hassine

Beilstein J. Org. Chem. 2018, 14, 2923–2930, doi:10.3762/bjoc.14.271

• widely distributed in nature and possess several biological activities. In 1967, Geigy described the preparation of 1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones I which are recognized as anti-inflammatory and analgesic agents [1]. Other compounds, such as 1H-imidazo[2,1-a]isoindole-2,5-diones II

Synthesis of indole–cycloalkyl[b]pyridine hybrids via a four-component six-step tandem process

• Muthumani Muthu,
• Rakkappan Vishnu Priya,
• Abdulrahman I. Almansour,
• Raju Suresh Kumar and
• Raju Ranjith Kumar

Beilstein J. Org. Chem. 2018, 14, 2907–2915, doi:10.3762/bjoc.14.269

• [62][63][64][65][66][67]. For example, the synthetic drug sumatriptan used for the treatment of migraine and cluster headaches belongs to the triptan class, whereas indomethacin is a non-steroidal anti-inflammatory drug used to relieve pain, swelling and joint stiffness caused by arthritis [68][69

Protein–protein interactions in bacteria: a promising and challenging avenue towards the discovery of new antibiotics

• Laura Carro

Beilstein J. Org. Chem. 2018, 14, 2881–2896, doi:10.3762/bjoc.14.267

• (bromodomain and extra terminal) molibresib (4, Figure 2), developed by GSK and currently in phase I for the treatment of several carcinomas [30]. It is also worth highlighting two PPI inhibitors that have recently been approved: lifitegrast (5, Figure 2) is an anti-inflammatory integrin antagonist that

• (Figure 3) which displayed a >4-fold increase in its affinity for E. coli SC [63]. Recent evidence suggests that non-steroidal anti-inflammatory drugs (NSAIDs) have antimicrobial activity. Oakley et al. studied the E. coli β-clamp binding affinity of commercially available NSAIDs with the help of a FP

Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4-(arylselanyl)-1H-pyrazoles

• Camila S. Pires,
• Daniela H. de Oliveira,
• Maria R. B. Pontel,
• Jean C. Kazmierczak,
• Roberta Cargnelutti,
• Diego Alves,
• Raquel G. Jacob and
• Ricardo F. Schumacher

Beilstein J. Org. Chem. 2018, 14, 2789–2798, doi:10.3762/bjoc.14.256

• commercially available drugs such as celecoxib, lonazolac, rimonabant and sildenafil [12][13]. In special, 5-amino-1H-pyrazoles are valuable compounds that present several biological and pharmaceutical activities including antiviral, anticancer, antituberculosis, anti-inflammatory, antifungal and

Gold-catalyzed post-Ugi alkyne hydroarylation for the synthesis of 2-quinolones

• Xiaochen Du,
• Jianjun Huang,
• Anton A. Nechaev,
• Ruwei Yao,
• Jing Gong,
• Erik V. Van der Eycken,
• Olga P. Pereshivko and
• Vsevolod A. Peshkov

Beilstein J. Org. Chem. 2018, 14, 2572–2579, doi:10.3762/bjoc.14.234

• derivatives, 2-quinolone and 4-quinolone, are the core structural elements of many natural products and pharmaceutical agents [1][2][3]. In particular, 2-quinolone derivatives show a broad range of biological activities including antiviral [4][5][6][7], antimicrobial [8][9], antiparasitic [10][11], anti

• -inflammatory [12][13] and anticancer [9][13][14][15][16][17][18][19]. In addition, 2-quinolones were identified as promising entities for the treatment of neuropathic pain [20][21][22] and erectile dysfunction [23]. Therefore, the elaboration of practical methodologies for the synthesis [24] and

Investigation of the electrophilic reactivity of the biologically active marine sesquiterpenoid onchidal and model compounds

• Melissa M. Cadelis and
• Brent R. Copp

Beilstein J. Org. Chem. 2018, 14, 2229–2235, doi:10.3762/bjoc.14.197

• terpenoid natural products containing the 1,4-dialdehyde moiety have been isolated from sources such as fungi, algae, sponges and molluscs [1]. Many of these natural products exhibit biological activity, ranging from anti-inflammatory to antimicrobial and antifeedant activities [1]. The prototypical

Anomeric modification of carbohydrates using the Mitsunobu reaction

• Julia Hain,
• Patrick Rollin,
• Werner Klaffke and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1619–1636, doi:10.3762/bjoc.14.138

• with complex acids like 16 (Scheme 4) [36]. The same approach was chosen in the Stachulski group for the anomeric modification of glucuronides with the anti-inflammatory drug diclofenac (17) to give the respective product 23 (Scheme 4) [37]. Bourhim et al. reported that the Mitsunobu reaction with

Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins

• Robby Vroemans,
• Fante Bamba,
• Jonas Winters,
• Joice Thomas,
• Jeroen Jacobs,
• Luc Van Meervelt,
• Jubi John and
• Wim Dehaen

Beilstein J. Org. Chem. 2018, 14, 626–633, doi:10.3762/bjoc.14.49

• withdrawal, etc. [26][27][28][29][30][31][32][33][34]. In addition, these azaheterocycles also exhibit anti-inflammatory, antitumor, antiparasitic and anxiolytic activities [35][36][37][38][39][40][41][42]. In particular, 1,4-benzodiazepine derivatives are proposed to serve as a structural mimic of peptide β

High-yielding continuous-flow synthesis of antimalarial drug hydroxychloroquine

• Eric Yu,
• Hari P. R. Mangunuru,
• Nakul S. Telang,
• Caleb J. Kong,
• Jenson Verghese,
• Stanley E. Gilliland III,
• Saeed Ahmad,
• Raymond N. Dominey and
• B. Frank Gupton

Beilstein J. Org. Chem. 2018, 14, 583–592, doi:10.3762/bjoc.14.45

• -steroidal drug with anti-inflammatory activity for the treatment of rheumatoid arthritis (RA) in patients with cardiovascular disease [7][8][9]. The World Health Organization has identified HCQ (1) as an essential antimalarial medication for a basic healthcare system, but global access to HCQ (1) has been

Continuous multistep synthesis of 2-(azidomethyl)oxazoles

• Thaís A. Rossa,
• Nícolas S. Suveges,
• Marcus M. Sá,
• David Cantillo and
• C. Oliver Kappe

Beilstein J. Org. Chem. 2018, 14, 506–514, doi:10.3762/bjoc.14.36

• antibiotic or antimicrobial properties such as pimprinine [4] or phenoxan [5] (Figure 1a). Also many synthetic active pharmaceutical ingredients (API) contain the oxazole as an active moiety [1][2][3]. Oxaprozin, for example, is an important non-narcotic, non-steroidal anti-inflammatory drug [6][7

One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na₂S₂O₈

• Teppei Sasaki,
• Katsuhiko Moriyama and
• Hideo Togo

Beilstein J. Org. Chem. 2018, 14, 345–353, doi:10.3762/bjoc.14.22

• coumarins arises from the fact that the coumarin skeleton is present in many natural products extracted from plants [1][2][3] and some of them show potent pharmacological activities, such as antidepressant [4], antimicrobial [5][6], antioxidants [7][8], anti-inflammatory [9][10], antinociceptive [11

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

• Ranjana Aggarwal and
• Suresh Kumar

Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15

• pharmacological activities such as: anticancer [1][2], anti-inflammatory [3][4], antioxidant [5], antibacterial [6][7][8], analgesic [9], antiviral [10][11], antimicrobial [12][13], antifungal [6], antiglycemic [14], antiamoebic [15] and antidepressive [16][17]. Considering the immense biological properties

• -trifluoromethylpyrazolo[1,5-a]pyrimidine derivative 124 by dehydration on refluxing with acetic anhydride (Scheme 34). All the synthesized compounds were screened for their anti-inflammatory activity. Mulakayala and co-workers [91] synthesized 7-trifluoromethylpyrazolo[1,5-a]pyrimidine carboxylates 127 by the reaction of

• successively added one after the other in toluene/ethanol (9:1) at reflux temperature in presence of p-TSA. The reaction carried out in pure ethanol provided a mixture of 5-aminopyrazoles (Scheme 42). The synthesized 7-aminopyrazolo[1,5-a]pyrimidines 148 were found to be good anti-inflammatory agents. Tian et

Consecutive hydrazino-Ugi-azide reactions: synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles

• Angélica de Fátima S. Barreto,
• Veronica Alves dos Santos and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2017, 13, 2596–2602, doi:10.3762/bjoc.13.256

• and, in particular, it displays a wide range of biological properties such as analgesic, anti-inflammatory, antiviral, anticancer, among others [3][4][5]. The tetrazole nucleus most widely described in the literature is the 1,5-disubstituted tetrazole [6][7] because it presents a wide range of

• pharmacological activities. For instance, cilostazol (anti-inflammatory), pentylenetetrazol (circulatory and respiratory stimulant) and nojiritetrazole (antidiabetic) are drugs containing the 1,5-disubstituted tetrazole nucleus, along with the pharmaceutically important tetrazoles losartan and valsartan, which

Exploring mechanochemistry to turn organic bio-relevant molecules into metal-organic frameworks: a short review

• Vânia André,
• Sílvia Quaresma,
• João Luís Ferreira da Silva and
• M. Teresa Duarte

Beilstein J. Org. Chem. 2017, 13, 2416–2427, doi:10.3762/bjoc.13.239

• biomedical applications [128]. Having in mind the synthesis of BioMOFs involving the excipient magnesium oxide initially proposed by Byrn et al. [129], Chow et al. and Friščić et al. developed new BioMOFs by LAG, grinding together MgO with the non-steroidal anti-inflammatory drugs (NSAIDS) ibuprofen (S and

Diosgenyl 2-amino-2-deoxy-β-D-galactopyranoside: synthesis, derivatives and antimicrobial activity

• Henryk Myszka,
• Patrycja Sokołowska,
• Agnieszka Cieślińska,
• Andrzej Nowacki,
• Maciej Jaśkiewicz,
• Wojciech Kamysz and
• Beata Liberek

Beilstein J. Org. Chem. 2017, 13, 2310–2315, doi:10.3762/bjoc.13.227

• diosgenyl saponins are used in folk medicine in many countries. Such herbal medicines exhibit anti-inflammatory, antibacterial, antifungal, antiviral, diuretic and expectorant activities [2][11]. Importantly, these also help fight cancer cells [12][13][14]. Although saponins, in which D-galactose is

Curcuminoid–BF₂ complexes: Synthesis, fluorescence and optimization of BF₂ group cleavage

• Henning Weiss,
• Jeannine Reichel,
• Helmar Görls,
• Kilian Rolf Anton Schneider,
• Mathias Micheel,
• Michael Pröhl,
• Michael Gottschaldt,
• Benjamin Dietzek and
• Wolfgang Weigand

Beilstein J. Org. Chem. 2017, 13, 2264–2272, doi:10.3762/bjoc.13.223

• curcuma longa, and its analogues, the curcuminoids, have attracted much attention regarding their biological activities [1]. These include antioxidant [2] and radical scavenging [3], antitumor [4] and anti-inflammatory [5] activities, as well as HIV inhibition [6]. Despite showing activity against several

Solid-state studies and antioxidant properties of the γ-cyclodextrin·fisetin inclusion compound

• Joana M. Pais,
• Maria João Barroca,
• Maria Paula M. Marques,
• Filipe A. Almeida Paz and
• Susana S. Braga

Beilstein J. Org. Chem. 2017, 13, 2138–2145, doi:10.3762/bjoc.13.212

• compound is evaluated by the DPPH assay. Keywords: antioxidant activity; co-lyophilization; fisetin; gamma-cyclodextrin; molecular encapsulation; solid-state analysis; Introduction Flavonoids, natural compounds with numerous beneficial actions on human health, including antioxidant [1], anti-inflammatory

Preparation of imidazo[1,2-a]-N-heterocyclic derivatives with gem-difluorinated side chains

• Layal Hariss,
• Kamal Bou Hadir,
• Mirvat El-Masri,
• Thierry Roisnel,
• René Grée and
• Ali Hachem

Beilstein J. Org. Chem. 2017, 13, 2115–2121, doi:10.3762/bjoc.13.208

• compounds are frequently found in bioactive naturally occurring compounds, as well as in the synthetic pharmacopeia. Imidazo[1,2-a]pyridine is an important heterocyclic system present in many molecules featuring diverse biological activities, such as antiviral, antimicrobial, antitumor, anti-inflammatory