Synthesis of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines and investigation of their fungistatic activity

• Anna V. Korotina,
• Svetlana G. Tolshchina,
• Rashida I. Ishmetova,
• Natalya P. Evstigneeva,
• Natalya A. Gerasimova,
• Natalya V. Zilberberg,
• Nikolay V. Kungurov,
• Gennady L. Rusinov,
• Oleg N. Chupakhin and
• Valery N. Charushin

Beilstein J. Org. Chem. 2022, 18, 243–250, doi:10.3762/bjoc.18.29

• particular, imidazo[1,2-a]pyridines and imidazo[1,2-a]pyrimidines exhibit a wide spectrum of biological activity, including antiviral and antibacterial ones [1][2]. A promising approach for the development of new drugs is the synthesis and bioscreening of high nitrogen-containing azoloazines, including azolo

Flow synthesis of oxadiazoles coupled with sequential in-line extraction and chromatography

• Kian Donnelly and
• Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 232–239, doi:10.3762/bjoc.18.27

• significant development in continuous flow platforms, particularly in industry [16][17][18][19][20]. 1,3,4-Oxadiazoles are biologically relevant 5-membered heterocyclic compounds with various favourable pharmacokinetic properties and have been investigated as potential candidates for antiviral, antifungal and

Chemical and chemoenzymatic routes to bridged homoarabinofuranosylpyrimidines: Bicyclic AZT analogues

• Sandeep Kumar,
• Jyotirmoy Maity,
• Banty Kumar,
• Sumit Kumar and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2022, 18, 95–101, doi:10.3762/bjoc.18.10

• AZT bicyclic analogues, 3′-azido-3′-deoxy-2′-O,5′-C-bridged-homoarabinofuranosylthymine and -uracil in excellent yields. These nucleosides were also accessed through the chemical methodology in good yields. The biological activity, particularly antiviral activity study of these compounds will be

1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

• Ruan Carlos B. Ribeiro,
• Patricia G. Ferreira,
• Amanda de A. Borges,
• Luana da S. M. Forezi,
• Fernando de Carvalho da Silva and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5

• with antibacterial, fungicidal, antimalarial, antiviral, trypanocidal, leishmanicidal, and antitumor activity serve as inspiration for the pharmaceutical industry [21][22][23][24]. However, they are considered as Pan Assay Interference compounds (PAINS) because they display biological activity in many

• ] developed the synthesis of naphtho[1,2-d]oxazole heterocycles from β-NQS as potential antiviral agents capable of inhibiting the HCV virus. Compound 45 was obtained from β-NQSNa (18) as shown above and reacted with substituted benzaldehyde or furfuryl aldehyde to form naphthoxazoles 51a–i and 53a–c

Biological properties and conformational studies of amphiphilic Pd(II) and Ni(II) complexes bearing functionalized aroylaminocarbo-N-thioylpyrrolinate units

• Samet Poyraz,
• Samet Belveren,
• Sabriye Aydınoğlu,
• Mahmut Ulger,
• Abel de Cózar,
• Maria de Gracia Retamosa,
• Jose M. Sansano and
• H. Ali Döndaş

Beilstein J. Org. Chem. 2021, 17, 2812–2821, doi:10.3762/bjoc.17.192

• , antitumoral, antimalarial, antifungal, or antiviral activities [14]. In this study, as a continuation of our work related to organometallic compounds with very low/modest amphiphilic character [15][16][17], we propose the incorporation of a 3-indolylmethyl group in the ligand and compare the bioactivity

Recent advances in the asymmetric phosphoric acid-catalyzed synthesis of axially chiral compounds

• Alemayehu Gashaw Woldegiorgis and
• Xufeng Lin

Beilstein J. Org. Chem. 2021, 17, 2729–2764, doi:10.3762/bjoc.17.185

• moderate yield with >90% enantioselectivity (Scheme 20c) and tolerable diastereoselectivity (4:1) [73]. The optically enriched benzimidazoles are N-heterocycles which are of great interest as drug-like molecules [75], and exhibit biological activities such as anticancer, antiviral, antifungal, and

The ethoxycarbonyl group as both activating and protective group in N-acyl-Pictet–Spengler reactions using methoxystyrenes. A short approach to racemic 1-benzyltetrahydroisoquinoline alkaloids

• Marco Keller,
• Karl Sauvageot-Witzku,
• Franz Geisslinger,
• Nicole Urban,
• Michael Schaefer,
• Karin Bartel and
• Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2716–2725, doi:10.3762/bjoc.17.183

• , antitumor, and antiviral effects [15]. Mechanistically, they have been shown to block two pore channel 2 (TPC2), an endolysosomal cation channel which is important for cellular migration and survival [6][15][46][47]. In our recent search for TPC2 blockers with antiproliferative potential we identified ring

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

• Umesh P. Aher,
• Dhananjai Srivastava,
• Girij P. Singh and
• Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

• incorporated into the growing DNA strand. However, the absence of a 3'-hydroxy group prevents further strand elongation. The anticancer and antiviral activity of 2’,3’-dideoxynucleosides is mainly based on inhibition of DNA synthesis, either through the chain termination process or by competitive inhibition [3

• nucleic acid components. Therefore, it was assumed until recently that effective inhibition of the metabolic enzyme is only possible by ᴅ-nucleoside analogues, which have the stereochemistry of natural nucleosides. This was proved to be untrue when the antiviral activity of 1,3-oxathiolane nucleosides

• with ʟ-configuration was discovered, and this led to the approval of 3TC (lamivudine, (−)-BCH-189, 1) as an antiviral drug and, among many others, to the use of FTC (emtricitabine, 2) and ʟ-FMAU (clevudine). ʟ-Nucleosides can have a comparable and often greater antiviral efficacy than the ᴅ

Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

• Ilya A. P. Jourjine,
• Lukas Zeisel,
• Jürgen Krauß and
• Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2668–2679, doi:10.3762/bjoc.17.181

• of caulophine (1e) [7], and anti-HIV activity of gramniphenol D (1g) and related gramniphenol E (1h) [8]. For synthetic fluorenones antitumoral [9], antiviral [10], and trypanocidal [11] activities have been reported, and tilorone (1i), an antiviral fluorenone launched about 50 years ago, is

Transition-metal-free intramolecular Friedel–Crafts reaction by alkene activation: A method for the synthesis of some novel xanthene derivatives

• Tülay Yıldız,
• İrem Baştaş and
• Hatice Başpınar Küçük

Beilstein J. Org. Chem. 2021, 17, 2203–2208, doi:10.3762/bjoc.17.142

• anticarcinogenic [1][2], antiviral [3], antibacterial [4][5], and anti-inflammatory [6]. Because of their pharmaceutical activity, they are used in photodynamic therapy [7][8][9]. In addition, they have an important place in the dye industry due to their photochemical and photophysical properties. They are also

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

• ], antiviral in general (6) [49], antituberculotic (7), and antimalarial (8) [50] (Scheme 3A). Using 2-phenylquinoline derivatives as substrates includes some intrinsic challenges, since there are two sites in the molecule where the C–H activation can take place. The authors were able to selectively obtain the

• free amine derivative was produced in 43% overall yield. The 2,8-dioxabicyclo[3.3.1]nonane skeleton is contained in biflavonoids and was shown to exhibit many medicinal activities like antiviral, anti-inflammatory and antitumor properties. The bicyclic compound 49 was aminated at the benzylic position

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

Double-headed nucleosides: Synthesis and applications

• Vineet Verma,
• Jyotirmoy Maity,
• Vipin K. Maikhuri,
• Ritika Sharma,
• Himal K. Ganguly and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98

Antiviral therapy in shrimp through plant virus VLP containing VP28 dsRNA against WSSV

• Santiago Ramos-Carreño,
• Ivone Giffard-Mena,
• Jose N. Zamudio-Ocadiz,
• Alfredo Nuñez-Rivera,
• Ricardo Valencia-Yañez,
• Jaime Ruiz-Garcia,
• Maria Teresa Viana and
• Ruben D. Cadena-Nava

Beilstein J. Org. Chem. 2021, 17, 1360–1373, doi:10.3762/bjoc.17.95

• California (UABC), Carretera Transpeninsular Ensenada-Tijuana No. 3917, Colonia Playitas, C.P. 22860 Ensenada, B.C., México 10.3762/bjoc.17.95 Abstract The white spot syndrome virus (WSSV), currently affecting cultured shrimp, causes substantial economic losses to the worldwide shrimp industry. An antiviral

• degradation of antiviral RNA molecules. The present work demonstrates that VLPs (virus-like particles) allow efficient delivery of dsRNAi as antiviral therapy in shrimp. In particular, VLPs derived from a virus that infects plants, such as cowpea chlorotic mottle virus (CCMV), in which the capsid protein (CP

• applied to pathogen control in shrimp and also other organisms, widening the application window in nanomedicine. Keywords: antiviral therapy; CCMV; oral administration; P. vannamei; plant VLPs; RNAi; VP28; white spot syndrome virus; Introduction The white spot syndrome virus (WSSV) is recognized as one

Synthesis of functionalized imidazo[4,5-e]thiazolo[3,2-b]triazines by condensation of imidazo[4,5-e]triazinethiones with DMAD or DEAD and rearrangement to imidazo[4,5-e]thiazolo[2,3-c]triazines

• Alexei N. Izmest’ev,
• Dmitry B. Vinogradov,
• Natalya G. Kolotyrkina,
• Angelina N. Kravchenko and
• Galina A. Gazieva

Beilstein J. Org. Chem. 2021, 17, 1141–1148, doi:10.3762/bjoc.17.87

• ], antituberculosis [2], anti-inflammatory [3][4], anticancer [5], antidiabetic [6][7], and antiviral activities [8]. A significant number of biologically active thiazolidines amount to their heteroannelated derivatives, namely, condensed thiazolo[3,2-a]pyrimidines [9] and thiazolo[3,2-b]-1,2,4-triazoles [10], as

Synthesis of 10-O-aryl-substituted berberine derivatives by Chan–Evans–Lam coupling and investigation of their DNA-binding properties

• Peter Jonas Wickhorst,
• Mathilda Blachnik,
• Denisa Lagumdzija and
• Heiko Ihmels

Beilstein J. Org. Chem. 2021, 17, 991–1000, doi:10.3762/bjoc.17.81

• also been employed in modern medicine because of its antimicrobial [3], antiprotozoal [4], antiviral [5], and anti-inflammatory [6] activity, and it is used in the treatment of tuberculosis [7], diarrhea [8], diabetes [9], cardiovascular diseases [10] or high cholesterol levels [11]. Most interestingly

Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications

• Christopher Liczner,
• Kieran Duke,
• Gabrielle Juneau,
• Martin Egli and
• Christopher J. Wilds

Beilstein J. Org. Chem. 2021, 17, 908–931, doi:10.3762/bjoc.17.76

• acids (ANA) are analogs of RNA where the hydroxy group at C2' is inverted (Figure 1G). In fluoroarabino nucleic acids (FANA) this C2' hydroxy group is replaced by fluorine. Arabino- and fluoroarabino nucleosides have demonstrated anticancer and antiviral activities (as reviewed in [173]). β-ᴅ

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

• . Tacrine (1) is an acridine derivative used in the treatment of Alzheimer’s disease. A plethora of acridine derivatives have been synthesized and clinically proved with various biological activities such as ethacridine (antibacterial drug; 2), acranil (antiviral drug; 3) and quinacrine (antimalarial agent

• , analgesic, etc. They form a major structural constituent of biomolecules like DNA and significant drugs like fluorouracil (65), zidovudine (66), lamivudine (67), risperidone (68), and buspirone (69, Figure 6) [65]. The biological importance of pyrimidinones like anticonvulsant (70), antiviral (71) and

• 78 (Scheme 29). 6.2 Fused pyrimidines Fused pyrimidines represent an important class of heterocycles with potential biological activities such as antidiabetic (79), antiviral (80), anti-inflammatory (81, 82), anticancer (83), antibacterial (84) and antiplatelet (85) [75][76][77][78][79] with an

Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles

• Soumyaranjan Pati,
• Renata G. Almeida,
• Eufrânio N. da Silva Júnior and
• Irishi N. N. Namboothiri

Beilstein J. Org. Chem. 2021, 17, 762–770, doi:10.3762/bjoc.17.66

• class of heterocycles presents important biological properties, such as antiviral, anti-inflammatory, antimicrobial etc. and are considered as key building blocks in pharmaceutical industry [6][7][8][9]. Thus, they marked their presence as prominent scaffolds in many drug molecules such as tazobactam

Synthesis of dibenzosuberenone-based novel polycyclic π-conjugated dihydropyridazines, pyridazines and pyrroles

• Ramazan Koçak and
• Arif Daştan

Beilstein J. Org. Chem. 2021, 17, 719–729, doi:10.3762/bjoc.17.61

• commonly used for the synthesis of biologically active compounds having enzyme inhibition and antiviral activity [1][2], and are found in the structures of many commercially available antidepressant drugs [3][4][5][6][7][8][9][10][11][12]. In addition, dibenzosuberenone (1) and polyconjugated derivatives

[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

Valorisation of plastic waste via metal-catalysed depolymerisation

• Francesca Liguori,
• Carmen Moreno-Marrodán and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

1,2,3-Triazoles as leaving groups: S_NAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles

• Dace Cīrule,
• Irina Novosjolova,
• Ērika Bizdēna and
• Māris Turks

Beilstein J. Org. Chem. 2021, 17, 410–419, doi:10.3762/bjoc.17.37

• ][3][4][5][6]. They are often used as antiviral, anticancer and antibacterial agents. Such intensive medicinal chemistry applications demand for constant development of novel synthetic methodologies. Frequently, the purine structure is modified in SNAr reactions with N- [7][8][9][10][11] and S

The preparation and properties of 1,1-difluorocyclopropane derivatives

• Kymbat S. Adekenova,
• Peter B. Wyatt and
• Sergazy M. Adekenov

Beilstein J. Org. Chem. 2021, 17, 245–272, doi:10.3762/bjoc.17.25

1,2,3-Triazoles as leaving groups in S_NAr–Arbuzov reactions: synthesis of C6-phosphonated purine derivatives

• Kārlis-Ēriks Kriķis,
• Irina Novosjolova,
• Anatoly Mishnev and
• Māris Turks

Beilstein J. Org. Chem. 2021, 17, 193–202, doi:10.3762/bjoc.17.19

• side chain are well known as antiviral agents, such as adefovir, tenofovir, and cidofovir [7]. Lately, it was found that ANPs possess inhibitory activity against hypoxanthine-guanine-xanthine phosphoribosyltransferase of the parasite Plasmodium falciparum, and several research groups are focused on the