Experimental and theoretical studies on the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-diones

• Nguyen Tran Nguyen,
• Vo Viet Dai,
• Nguyen Ngoc Tri,
• Luc Van Meervelt,
• Nguyen Tien Trung and
• Wim Dehaen

Beilstein J. Org. Chem. 2022, 18, 1140–1153, doi:10.3762/bjoc.18.118

• showed interesting antimicrobial and antibacterial activities [2][3][4]. (−)-Clausenamide was extracted and isolated from Clausena lansium which exhibited biological activities to enhance learning and memory capacities in amnesia animal models [5][6]. Doxapram, a non-natural compound, has been used to

• antibacterial and antifungal activities [39][40][41]. The presence of an acyl group at the 4-position enables these heterocycles to be functionalized via nucleophilic addition reactions between the carbonyl group and nucleophiles like hydroxylamine and semicarbazide [42]. Herein, we report the synthesis of 4

Scope of tetrazolo[1,5-a]quinoxalines in CuAAC reactions for the synthesis of triazoloquinoxalines, imidazoloquinoxalines, and rhenium complexes thereof

• Laura Holzhauer,
• Chloé Liagre,
• Olaf Fuhr,
• Nicole Jung and
• Stefan Bräse

Beilstein J. Org. Chem. 2022, 18, 1088–1099, doi:10.3762/bjoc.18.111

• possess antibacterial [2], antifungal [3], and antiviral properties [4] and form the core structure of commercially available drugs like brimonidine, varenicline, and quinacillin [5]. Quinoxalines can also be used in organic solar cell polymers [1][6] and have been described as donor moieties in many TADF

Synthesis of N-phenyl- and N-thiazolyl-1H-indazoles by copper-catalyzed intramolecular N-arylation of ortho-chlorinated arylhydrazones

• Yara Cristina Marchioro Barbosa,
• Guilherme Caneppele Paveglio,
• Claudio Martin Pereira de Pereira,
• Sidnei Moura,
• Cristiane Storck Schwalm,
• Gleison Antonio Casagrande and
• Lucas Pizzuti

Beilstein J. Org. Chem. 2022, 18, 1079–1087, doi:10.3762/bjoc.18.110

• anticancer [2], anti-HIV [3], anti-inflammatory [4], antiprotozoal [5], antifungal [6], antibacterial [7], antiplatelet [8], and antihypertensive [9] properties. The relevance to medicinal chemistry is also demonstrated by the presence of the 1H-indazole core in the structure of drugs. The anticataract agent

New azodyrecins identified by a genome mining-directed reactivity-based screening

• Atina Rizkiya Choirunnisa,
• Kuga Arima,
• Yo Abe,
• Noritaka Kagaya,
• Kei Kudo,
• Hikaru Suenaga,
• Junko Hashimoto,
• Manabu Fujie,
• Noriyuki Satoh,
• Kazuo Shin-ya,
• Kenichi Matsuda and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2022, 18, 1017–1025, doi:10.3762/bjoc.18.102

• of their biosynthetic mechanisms. Keywords: biosynthesis; methyltransferase; natural azoxides; reactivity-based screening; Streptomyces; Introduction Azoxy natural products are a rare yet intriguing class of natural products with various beneficial biological properties, such as antibacterial

Isolation and biosynthesis of daturamycins from Streptomyces sp. KIB-H1544

• Yin Chen,
• Jinqiu Ren,
• Ruimin Yang,
• Jie Li,
• Sheng-Xiong Huang and
• Yijun Yan

Beilstein J. Org. Chem. 2022, 18, 1009–1016, doi:10.3762/bjoc.18.101

• Streptomyces species [1][2][3][4]. Meanwhile, these types of compounds exhibit a broad spectrum of bioactivities, including antitumor [5][6], antibacterial [7][8], antioxidant [9][10][11][12], immunosuppressive [13], and antithrombotic activities [14]. The biosynthesis of the p-terphenyls has been studied

Morita–Baylis–Hillman reaction of 3-formyl-9H-pyrido[3,4-b]indoles and fluorescence studies of the products

• Nisha Devi and
• Virender Singh

Beilstein J. Org. Chem. 2022, 18, 926–934, doi:10.3762/bjoc.18.92

• activities is displayed by this pharmacologically rich nucleus which includes antibacterial, antifungal, anticancer, anxiolytic, antimalarial, antiviral, anti-HIV, anti-Alzheimer, and anticonvulsant activities etc. [18][19][20][21][22][23][24][25][26]. Potent anticancer activities are shown by the majority

• synthesis of various natural and synthetic products. MBH adducts itself display diverse biological activities like antifungal, antibacterial, herbicide, antiparasitic and antitumor as reviewed by Lima-Junior et al. (2012) [45]. It was envisaged that in comparison to the traditional methods like Pictet

Synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexane via cyclopropene cycloadditions to the stable azomethine ylide derived from Ruhemann's purple

• Alexander S. Filatov,
• Olesya V. Khoroshilova,
• Anna G. Larina,
• Vitali M. Boitsov and
• Alexander V. Stepakov

Beilstein J. Org. Chem. 2022, 18, 769–780, doi:10.3762/bjoc.18.77

• ], anticancer [4], antidiabetic [5], and antibacterial [6] properties. It is also worth noting that spiro compounds have found application in agriculture as fungicides [7], as well as in materials science as organic semiconductors [8]. The 3-azabicyclo[3.1.0]hexane framework is a valuable structural fragment

DDQ in mechanochemical C–N coupling reactions

• Shyamal Kanti Bera,
• Rosalin Bhanja and
• Prasenjit Mal

Beilstein J. Org. Chem. 2022, 18, 639–646, doi:10.3762/bjoc.18.64

• established from the X-ray crystallography data. Various methodologies are available in the literature toward constructing quinazolin-4(3H)-one derivatives [40][45][46]. Quinazolin-4(3H)-ones and its derivatives possess several biological activities such as antibacterial [47], antiviral [48], antitumor [49

Cholyl 1,3,4-oxadiazole hybrid compounds: design, synthesis and antimicrobial assessment

• Anas J. Rasras,
• Mohamed El-Naggar,
• Nesreen A. Safwat and
• Raed A. Al-Qawasmeh

Beilstein J. Org. Chem. 2022, 18, 631–638, doi:10.3762/bjoc.18.63

• exhibited selective activity against fungi only. Keywords: antibacterial; cholic acid; heterocyclic; Mannich reaction; oxadiazole; Introduction Microbial infections caused by Gram-negative and Gram-positive bacteria embarrass the health care system worldwide [1]. Pathogens such as Escherichia coli

• , Staphylococcus aureus, Klebsiella pneumoniae, and Staphylococcus pneumoniae were responsible for most of bacteremia deaths related to antimicrobial resistance in 2019 [2]. Current antibacterial drugs are facing various challenges, due to the inability to accumulate inside human cells made them inactive [3] and

• biological activities such as anti-COVID-19 [5], anticancer [6][7][8], antibacterial activity against Staphylococcus aureus and Bacillus subtilis [9][10], antifungal agents against Candida albicans and phytopathogenic fungi [11][12], and antiproliferative against different cell lines (e.g., PC3, HCT-116, and

Chemistry of polyhalogenated nitrobutadienes, 17: Efficient synthesis of persubstituted chloroquinolinyl-1H-pyrazoles and evaluation of their antimalarial, anti-SARS-CoV-2, antibacterial, and cytotoxic activities

• Viktor A. Zapol’skii,
• Isabell Berneburg,
• Ursula Bilitewski,
• Melissa Dillenberger,
• Katja Becker,
• Stefan Jungwirth,
• Aditya Shekhar,
• Bastian Krueger and
• Dieter E. Kaufmann

Beilstein J. Org. Chem. 2022, 18, 524–532, doi:10.3762/bjoc.18.54

• ± 0.04 µM (100 ng/mL, 200 nM), respectively. Two compounds (3b and 10d) have also been tested for anti-SARS-CoV-2, antibacterial, and cytotoxic activity. Keywords: antimalarial activity; anti-SARS-CoV-2 activity; chloroquine; 2-nitroperchlorobutadiene; nucleophilic vinylic substitution; 1H-pyrazoles

• falciparum strain [19]. Certain 7-chloroquinolinyl-pyrazole derivatives have also shown antibacterial [20], hypoglycemic as well as antioxidant activity [21] or can be used as selective nonpeptide neurotensin receptor type 2 compounds [22]. Some azolylquinolines have been used as agrochemical fungicides

• persubstituted pyrazoles were unknown until now. In addition, it is known that polyhalogenated nitrobutadienes are versatile synthetic precursors for many bioactive heterocycles such as insecticidal neonicotinoids [34]. Evaluation of biological properties Antibacterial and cytotoxic properties The general

Sesquiterpenes from the soil-derived fungus Trichoderma citrinoviride PSU-SPSF346

• Wiriya Yaosanit,
• Vatcharin Rukachaisirikul,
• Souwalak Phongpaichit,
• Sita Preedanon and
• Jariya Sakayaroj

Beilstein J. Org. Chem. 2022, 18, 479–485, doi:10.3762/bjoc.18.50

• Trichoderma citrinoviride produces structurally diverse secondary metabolites including diterpenes [1][2], alkaloids [3], sorbicillinoids [4][5], long chain alcohols [6], and cyclonerane sesquiterpenes [7]. Some of them display antibacterial [1][2][7], cytotoxic [3], anti-inflammatory [4], and antimicroalgal

• amount were evaluated for their antibacterial activity against S. aureus ATCC25923 and methicillin-resistant S. aureus SK1, antifungal activity against C. neoformans ATCC90113 as well as cytotoxic activity against KB, MCF-7, and noncancerous Vero (African green monkey kidney fibroblast) cells. None of

Tosylhydrazine-promoted self-conjugate reduction–Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives

• Sayan Pramanik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 469–478, doi:10.3762/bjoc.18.49

• , antitubercular, antidiabetic, antibacterial as well as cholinesterase inhibition (Figure 1) [3][4][5][6][7]. These unique chemical and biological characteristics of bispirooxindoles have stimulated the concentration of the synthetic community on developing new synthetic strategies towards their synthesis [8][9

Cs₂CO₃-Promoted reaction of tertiary bromopropargylic alcohols and phenols in DMF: a novel approach to α-phenoxyketones

• Ol'ga G. Volostnykh,
• Olesya A. Shemyakina,
• Anton V. Stepanov and
• Igor' A. Ushakov

Beilstein J. Org. Chem. 2022, 18, 420–428, doi:10.3762/bjoc.18.44

• ], amyloid-β protein production inhibitory [52], urease inhibitory [53], farnesyl transferase inhibitory (kurasoin A and B) [54][55], antitumor and antibacterial (doxorubicin, olivomycin A, chromomycin A3, carminomycin I, epothilones) [56][57][58] activities. Experimental General information 1Н and 13С NMR

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

Four bioactive new steroids from the soft coral Lobophytum pauciflorum collected in South China Sea

• Di Zhang,
• Zhe Wang,
• Xiao Han,
• Xiao-Lei Li,
• Zhong-Yu Lu,
• Bei-Bei Dou,
• Wen-Ze Zhang,
• Xu-Li Tang,
• Ping-Lin Li and
• Guo-Qiang Li

Beilstein J. Org. Chem. 2022, 18, 374–380, doi:10.3762/bjoc.18.42

• containing side chains with 23,24-dimethyl groups and (17)20E double bond, have been reported to be frequently isolated from soft corals of this genus, some of them exhibited anti-inflammatory [4], cytotoxic [5][6], and antibacterial activities [7]. To search for bioactive natural products, we have

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

• ]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

• -b][1,2,4,5]tetrazines [10], fungistatic activity of imidazo[1,2-b][1,2,4,5]tetrazines [11], antibacterial and antiglycation activity of imidazo[1,2-b]- and [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazines [12][13][14] as well as antitumor activity of [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazines [15][16] and

Glycosylated coumarins, flavonoids, lignans and phenylpropanoids from Wikstroemia nutans and their biological activities

• Meifang Wu,
• Xiangdong Su,
• Yichuang Wu,
• Yuanjing Luo,
• Ying Guo and
• Yongbo Xue

Beilstein J. Org. Chem. 2022, 18, 200–207, doi:10.3762/bjoc.18.23

• for the first time. All co-isolates were evaluated for their in vitro inhibitory effects on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in murine RAW264.7 macrophage cells. The antibacterial activity of the selected compounds was also tested. Our work enriches the structure

• large quantity of phenolic substances found in plants and microorganisms [5]. These naturally occurring coumarins were well documented due to their diverse chemical structures and promising biological properties, such as anticancer, antitubercular, anti-inflammatory, anticoagulant, antibacterial, and

• against nitric oxide (NO) production in LPS-stimulated RAW 264.7 mouse macrophages. The antibacterial activities of compounds 1–4 against Escherichia coli, Staphylococcus aureus subsp. aureus, Salmonella enterica subsp. enterica, and Pseudomonas aeruginosa were also tested, however, none of them showed

Synthesis and bioactivity of pyrrole-conjugated phosphopeptides

• Qiuxin Zhang,
• Weiyi Tan and
• Bing Xu

Beilstein J. Org. Chem. 2022, 18, 159–166, doi:10.3762/bjoc.18.17

• ][11], collagen mimic [12], antibacterial [13][14], biomineralization [15][16], mimicry of amyloids [17], cell cultures [18], and tissue engineering [19]. Particularly, the use of enzyme-instructed self-assembly (EISA) [20][21] of peptide assemblies has expanded the applications of peptide assemblies

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

• oxidative processes in aerobic metabolism, photosynthesis, oxidative phosphorylation, blood clotting, and other electron transport reactions [7][8]. These biochemical functions give them several biological activities, such as antibacterial, fungicidal, antimalarial, trypanocidal, and antitumor. For this

• 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

Host–guest interaction and properties of cucurbit[8]uril with chloramphenicol

• Lin Zhang,
• Jun Zheng,
• Guangyan Luo,
• Xiaoyue Li,
• Yunqian Zhang,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2021, 17, 2832–2839, doi:10.3762/bjoc.17.194

• (CPE) was investigated using single-crystal X-ray diffraction spectroscopy, isothermal titration calorimetry (ITC) and UV–vis, NMR and IR spectroscopy. The effects of Q[8] on the stability, in vitro release performance and antibacterial activity of CPE were also studied. The results showed that CPE and

• antibacterial results showed that the minimum inhibitory concentration (MIC) of CPE and CPE@Q[8] toward Escherichia coli (E. coli) was 1.5 × 10–3 and 1.0 × 10–3 mol/L, respectively, and toward Staphylococcus aureus (S. aureus), the MIC was 2.0 × 10–3 mol/L for both CPE and CPE@Q[8]. Therefore, Q[8] enhanced the

• inhibitory activity of CPE against E. coli. Keywords: antibacterial activity; chloramphenicol; cucurbit[8]uril; host–guest interaction; in vitro cumulative release; stability; Introduction Chloramphenicol (CPE, Figure 1A) is a broad-spectrum antibiotic resulting from the metabolism of chorismic acid in

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

• organometallic compounds were screened for their antibacterial activity against a range of Gram-positive (Staphylococcus aureus, Bacillus subtilis) and Gram-negative (Aeromonas hydrophila, Escherichia coli, Acinetobacter baumannii) bacteria and antimycobacterial activity against M. tuberculosis H37Rv strains

• . 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

• %), 1287.2101 (67.1%), 1286.2068 (100.0%), 1285.2084 (81.7%), 1284.2073 (40.8%); anal. calcd for C62H58Cl2N6O10PdS2: C, 57.9; H, 4.5; N, 6.5; S, 5.0%; found: C, 58.4; H, 4.3; N, 6.6; S, 5.1. Biological tests The antibacterial activity of the complexes against standard bacterial strains (Staphylococcus aureus

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

• ). Quinolines are another important class of compounds and have numerous medicinal chemistry applications due to their biological applicability [9] and promising antimycobacterial [10], antimalarial [11][12], and antibacterial [13] activities. On the other hand, 6-aminoquinoline compounds demonstrate

The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3H)-ones – an efficient approach to 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones

• Alla I. Vaskevych,
• Nataliia O. Savinchuk,
• Ruslan I. Vaskevych,
• Eduard B. Rusanov,
• Oleksandr O. Grygorenko and
• Mykhailo V. Vovk

Beilstein J. Org. Chem. 2021, 17, 2787–2794, doi:10.3762/bjoc.17.189

• anti-inflammatory [9], antibacterial [10], antiarrythmic [11] activity; some representatives are CNS suppressors and poly-ADP ribose polymerase (PARP) inhibitors [12] (see Figure 1). Several approaches to obtain 2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one derivatives of type 1 are known in the

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

• antibacterial effects [76]. In this context, Miller and co-workers reported the performance of C2-symmetric chiral phosphoric acids (C2-type) and phosphothreonine-embedded, peptidic phosphoric acids (pThr-type CPAs) to catalyze a wide range of atroposelective cyclodehydration reactions for the synthesis of

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

• -counterparts, with more favorable toxicological profiles and a greater stability [10]. A variety of nucleoside analogues as possible antiviral agents has appeared, possessing the unusual β-ʟ-configuration. Work has been motivated by the fact that, while retaining strong antiviral and/or antibacterial activity