Synthesis of 3,4,5-trisubstituted isoxazoles in water via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides

• Md Imran Hossain,
• Md Imdadul H. Khan,
• Seong Jong Kim and
• Hoang V. Le

Beilstein J. Org. Chem. 2022, 18, 446–458, doi:10.3762/bjoc.18.47

• and γ-amino alcohols [1]. Isoxazoles, appearing in 33 patents from the year 2016 to 2018 [3], are an important drug class due to their wide range of biological activities, such as anticancer [5], antibiotic [6][7], antimicrobial [8], antifungal [9], and anti-inflammatory [10]. Therefore, new methods

Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

• shown a wide range of biological activities of menadione, such as anticancer [15][16][17][18][19][20][21][22], antibacterial [23][24][25][26], antifungal [27][28], antimalarial [29][30][31][32], antichagasic [33], and anthelmintic [34] effects. In these cases, the redox cycle of menadione, followed by

A resorcin[4]arene hexameric capsule as a supramolecular catalyst in elimination and isomerization reactions

• Tommaso Lorenzetto,
• Fabrizio Fabris and
• Alessandro Scarso

Beilstein J. Org. Chem. 2022, 18, 337–349, doi:10.3762/bjoc.18.38

• , isolated from oils distilled from citronella plants, which is very effective as a repellent and antifungal. In the presence of Brønsted or Lewis acids (S)-citronellal undergoes an intramolecular carbonyl–ene cyclization reaction forming two new stereogenic centers, which turns out into four possible

New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence

• Long Zhao,
• Mao-Lin Yang,
• Min Liu and
• Ming-Wu Ding

Beilstein J. Org. Chem. 2022, 18, 286–292, doi:10.3762/bjoc.18.32

• the occurrence of these ring systems in various biologically important compounds (Figure 1). A number of 3,4-dihydroquinazolines were found to show remarkable anticancer [1], antiviral [2], antidepressant [3], antifungal [4], selective somatostatin 2 (ss2) agonistical [5], β-site amyloid precursor

• biological activities, including anticancer [9], neuroprotective [10], antiproliferative and antifungal activities [11]. Due to the significant bioactive properties of the 3,4-dihydroquinazoline and 4H-3,1-benzothiazine moieties, many preparation procedures have appeared in the literature for the synthesis

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

• . Keywords: antifungal activity; nucleophilic substitution; oxidative cyclization; [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines; Introduction Azolo-annulated azines can be regarded as purine isosteres and are of great interest for modern medicinal chemistry as potential biologically active compounds. In

• ]tetrazines [3], antibacterial, antifungal, and anti-infammatory activities of dihydro- and tetrahydro[1,2,4]triazolo[4,3-b][1,2,4,5]tetrazines [4][5][6], antituberculosis activity of [1,2,4]triazolo[4,3-b]- and imidazo[1,2-b][1,2,4,5]tetrazines [7][8][9], antibacterial and fungistatic action of thiazolo[3,2

• of [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazine fragment on antifungal activity of the synthesized compounds, we have tested the activity of their analogues, unannulated 1,2,4,5-tetrazines 2c,g, containing the amidine moiety, and isomeric [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazines. For a comparative

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

Efficient and regioselective synthesis of dihydroxy-substituted 2-aminocyclooctane-1-carboxylic acid and its bicyclic derivatives

• İlknur Polat,
• Selçuk Eşsiz,
• Uğur Bozkaya and
• Emine Salamci

Beilstein J. Org. Chem. 2022, 18, 77–85, doi:10.3762/bjoc.18.7

• β-amino acid derivatives have antibiotic (oryzoxymycin) and antifungal activities (Figure 1) [12][13]. Among the cyclic β-amino acids, the most widely investigated derivatives are the five- and six-membered derivatives [8][9][10][14][15], but only a few synthetic methods are available for the

Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins

• Jiang-Song Zhai and
• Da-Ming Du

Beilstein J. Org. Chem. 2022, 18, 25–36, doi:10.3762/bjoc.18.3

• biologically active natural products and pharmaceutical compounds with antipsychotic and antifungal activities, such as SB 209670, indatraline, tefludazine, mutisianthol, rasagiline, and ramelteon (Figure 1) [1][2][3][4][5]. Therefore, this structural motif has attracted great attention of researchers in the

• range of significant pharmacological and physiological activities in the medical and biological fields (Figure 2) [18][19][20][21]. For instance, compound A displays anticonvulsant activity and compound C can be used as an antifungal agent [22][23]. This impels the quest to develop a series of synthons

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

• spectroscopic techniques. The biological properties of the freshly prepared compounds were screened against S. aureus, B. subtilis, A. hydrophila, E. coli, and A. baumannii bacteria and antituberculosis activity against M. tuberculosis H37Rv strains. Also, the antifungal activity was studied against C. albicans

• , 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

• . Antifungal activity of the novel compounds was also evaluated against Candida albicans, Candida tropicalis and Candida glabrata strains. Antibacterial and antituberculosis (TB) activities From the observed data (Table 1) it can be seen that the tested compounds showed moderate antibacterial activity, in the

Photophysical, photostability, and ROS generation properties of new trifluoromethylated quinoline-phenol Schiff bases

• Inaiá O. Rocha,
• Yuri G. Kappenberg,
• Wilian C. Rosa,
• Clarissa P. Frizzo,
• Nilo Zanatta,
• Marcos A. P. Martins,
• Isadora Tisoco,
• Bernardo A. Iglesias and
• Helio G. Bonacorso

Beilstein J. Org. Chem. 2021, 17, 2799–2811, doi:10.3762/bjoc.17.191

• imines, Schiff bases have the general organic function -C=N- [2], and are known to have a wide range of biological activities, including antioxidant [3], antitubercular [4], antibacterial [5], antimicrobial [6], and antifungal properties [7], in addition to their role as chemosensors [8] (Figure 1

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

Ligand-dependent stereoselective Suzuki–Miyaura cross-coupling reactions of β-enamido triflates

• Tomáš Chvojka,
• Athanasios Markos,
• Svatava Voltrová,
• Radek Pohl and
• Petr Beier

Beilstein J. Org. Chem. 2021, 17, 2657–2662, doi:10.3762/bjoc.17.179

• of cytotoxic, antifungal, or antibiotic properties [10][11][12]. Modern stereoselective syntheses leading to highly substituted enamides include cross-coupling of vinyl (pseudo)halides or organoboron compounds [13], hydroamidation of alkynes [14][15][16], ynamide functionalization [17][18][19], or

Cryogels: recent applications in 3D-bioprinting, injectable cryogels, drug delivery, and wound healing

• Luke O. Jones,
• Leah Williams,
• Tasmin Boam,
• Martin Kalmet,
• Chidubem Oguike and
• Fiona L. Hatton

Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171

• delivery, with different release profiles depending on the ratio of DMA/β-CD. The antifungal agent voriconazole was incorporated into a physically crosslinked cryogel comprising PVA and chitosan grafted with NIPAAm (CS-g-PNIPAM) for mucosal applications [98]. Cell culture assays confirmed that the cryogels

Strategies for the synthesis of brevipolides

• Yudhi D. Kurniawan and
• A'liyatur Rosyidah

Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157

• folk medicines [2][3][5][6][7][8][9][10] to pest management [2][3]. These traditional applications stimulated researchers to conduct biological studies with these plant extracts. A variety of bioactivities were then evidenced, such as antifungal, antibacterial [4][9] insecticidal [7], and radical

Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B

• Emmanuel T. Oluwabusola,
• Olusoji O. Adebisi,
• Fernando Reyes,
• Kojo S. Acquah,
• Mercedes De La Cruz,
• Larry L. Mweetwa,
• Joy E. Rajakulendran,
• Digby F. Warner,
• Deng Hai,
• Rainer Ebel and
• Marcel Jaspars

Beilstein J. Org. Chem. 2021, 17, 2390–2398, doi:10.3762/bjoc.17.156

• -spectrum biological functions which include antifungal [9][10][11] and antibacterial activities [12][13][14]. Natural product scaffolds isolated from species of this genus have contributed immensely as leads to drug discovery and development [15]. For instance, clofazimine [16], the antimycobacterial agent

Synthesis and antimicrobial activity of 1H-1,2,3-triazole and carboxylate analogues of metronidazole

• Satya Kumar Avula,
• Syed Raza Shah,
• Khdija Al-Hosni,
• Muhammad U. Anwar,
• Rene Csuk,
• Biswanath Das and
• Ahmed Al-Harrasi

Beilstein J. Org. Chem. 2021, 17, 2377–2384, doi:10.3762/bjoc.17.154

• metronidazole derivatives. The antimicrobial (antifungal and antibacterial) activity of the prepared compounds was studied. All compounds (except 2 and 3) showed a potent inhibition rate of fungal growth as compared to control and metronidazole. The synthetic compounds also showed higher bacterial growth

• elements (metronidazole core and triazole moiety) were considered as rigid motif with an alkyl/aryl group attached to the triazole unit. A diverse array of functional groups in the aromatic ring influencing the antimicrobial activity of the molecules have been utilized. Antifungal activity of compounds The

• antifungal activity of all compounds were evaluated by inhibiting the growth of Didymella sp. (Figure 7 and Table 3). The fungal colony after 7 days of control treatment was noted to be 8.6 cm in diameter. Whereas, the growth of the fungal colony was detected maximum, i.e., 8.8 ± 0.2 and 9.0 ± 0.3 cm against

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

• -methyl-9-arylxanthenes 5a–l may be used in the pharmaceutical chemistry field as native and bioactive products, and their biochemical potentials and efficiencies will be investigated in the coming years because of their potential biological uses, such as antileukemic, antifungal, antimycobacterial

Asymmetric organocatalyzed synthesis of coumarin derivatives

• Natália M. Moreira,
• Lorena S. R. Martelli and
• Arlene G. Corrêa

Beilstein J. Org. Chem. 2021, 17, 1952–1980, doi:10.3762/bjoc.17.128

• plant constituents and display a wide range of pharmacological and biological activities, such as anticancer [1], antibacterial [2], and antifungal [3]. Moreover, coumarin derivatives have shown activity against neglected diseases as leishmaniasis [4], tuberculosis [5][6] and Chagas’ disease [7

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

Natural products in the predatory defence of the filamentous fungal pathogen Aspergillus fumigatus

• Jana M. Boysen,
• Nauman Saeed and
• Falk Hillmann

Beilstein J. Org. Chem. 2021, 17, 1814–1827, doi:10.3762/bjoc.17.124

• fungi also produce compounds with antibacterial, antifungal and insecticidal properties to ward of both competitors and predators. The mycotoxins aflatoxin B1 (1) from Aspergillus flavus and patulin (2), produced by Aspergillus and Penicillium species, exhibit insecticidal activity against Drosophila

• verruculogen to fumitremorgin A remains to be elucidated. Like several other clusters, the biosynthesis of fumitremorgins is dependent on LaeA [124]. Fumitremorgin B was shown to have antifungal properties against phytopathogenic fungi, antifeedant properties against army-worm larvae and toxic on brine shrimp

• and the 3-keto group are crucial for its antibacterial activity whereas, acetylation of the C-6 hydroxy group reduces the activity of HA [169]. Previous studies have also shown the antitrypanosomal, antifungal and cilioinhibitory properties of HA [72][83][86][87][88]. For these properties and little

Sustainable manganese catalysis for late-stage C–H functionalization of bioactive structural motifs

• Jongwoo Son

Beilstein J. Org. Chem. 2021, 17, 1733–1751, doi:10.3762/bjoc.17.122

• process facilitated the fluorination of sclareolide (1) and complex steroid 3. Sclareolide (1) is a naturally available terpenoid with antifungal and anticancer activities [23]. Under the optimized reaction conditions, sclareolide (1) is fluorinated at the C2 and C3 positions in 42% (see 2a) and 16% yield

Volatile emission and biosynthesis in endophytic fungi colonizing black poplar leaves

• Christin Walther,
• Pamela Baumann,
• Katrin Luck,
• Beate Rothe,
• Peter H. W. Biedermann,
• Jonathan Gershenzon,
• Tobias G. Köllner and
• Sybille B. Unsicker

Beilstein J. Org. Chem. 2021, 17, 1698–1711, doi:10.3762/bjoc.17.118

• work on this question is needed [63][75]. The volatiles found to be emitted from black poplar endophytic fungi in this study could have important biological activities. For instance, ethanol (17) and 2-phenylethanol (3) are known to have antifungal and phytotoxic activity and so could help the

• that are known to have antifungal and phytotoxic effects and may be produced to compete with other microbial species. Several also produce diverse mixtures of sesquiterpenes. Interestingly, several VOCs emitted from the endophytes were earlier reported to be emitted by black poplar. We characterized

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

Analogs of the carotane antibiotic fulvoferruginin from submerged cultures of a Thai Marasmius sp.

• Birthe Sandargo,
• Leon Kaysan,
• Rémy B. Teponno,
• Christian Richter,
• Benjarong Thongbai,
• Frank Surup and
• Marc Stadler

Beilstein J. Org. Chem. 2021, 17, 1385–1391, doi:10.3762/bjoc.17.97

• moderate antifungal activity. A recent find of a Marasmius species in Northern Thailand led, however, to the isolation and identification of five novel derivatives of this carotane-type sesquiterpenoid. The present study is dedicated to describing their isolation, and biological and physicochemical

• fulvoferruginins A–F (1–6), aside from the known antifungal activity of fulvoferruginin (1), no other antimicrobial activities were observed (Table S2 in Supporting Information File 1). All metabolites were also tested against the murine fibroblast cell line L929 and the cervix carcinoma cell line KB3.1. While all