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

• of this family, berberine (1a) is a natural product and may be isolated from different plants such as berberis vulgaris, hydrastis canadensis or coptidis rhizome [2]. Particularly, the latter is established in traditional Chinese medicine as source for anti-inflammatory extracts [2]. Berberine has

• 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

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

• (47) for prevention of influenza A and B. β-Lapachone (48) shows diverse biological activities like anticancer, antibacterial and anti-inflammatory activities [53]. Benzopyrans and naphthopyrans represent a class of fused pyrans that has been studied for antimicrobial effects (49 and 50, Figure 4) [54

• phenanthroline. 6 Pyrimidines/fused pyrimidines 6.1 Pyrimidines Pyrimidines are six-membered aromatic heterocycles containing two nitrogen atoms at positions 1 and 3. These are an important class of compounds depicting a wide range of biological activities such as COX inhibitors, anti-inflammatory, anticancer

• 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

• , antihypertensive, anti-Parkinson, anti-inflammatory, anticonvulsant, vasodilatory, antidiabetic, antitubercular, antifungal, and antibacterial activities [32][33][34][35][36][37][38], pH-sensing [39], OLEDs [40], chemiluminescent materials [41][42], metal complexes (Figure 1) [43][44][45][46], liquid crystal [47

Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols

• Marek Kõllo,
• Marje Kasari,
• Villu Kasari,
• Tõnis Pehk,
• Ivar Järving,
• Margus Lopp,
• Arvi Jõers and
• Tõnis Kanger

Beilstein J. Org. Chem. 2021, 17, 581–588, doi:10.3762/bjoc.17.52

• Pseudopterogorgia americana in 1972 (Figure 1B) [7], several others from the family have been reported [8][9][10][11][12][13][14]. The 9,11-secosterols exhibit diverse biological activities, including antihistaminic, antiproliferative, anti-inflammatory, cytotoxic and protein kinase C (PKC) inhibition activities [8

Breakdown of 3-(allylsulfonio)propanoates in bacteria from the Roseobacter group yields garlic oil constituents

• Anuj Kumar Chhalodia and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 569–580, doi:10.3762/bjoc.17.51

• antibacterial, antifungal, antioxidant, anti-inflammatory, and anticancer effects [4]. Later on, also heterocyclic compounds including 2-vinyl-4H-1,3-dithiine (6) and 3-vinyl-3,4-dihydro-1,2-dithiine (7) were discovered [5]. The formation of these volatile sulfur compounds starts from alliin (9) [6], a non

Amino- and polyaminophthalazin-1(2H)-ones: synthesis, coordination properties, and biological activity

• Zbigniew Malinowski,
• Emilia Fornal,
• Agata Sumara,
• Renata Kontek,
• Karol Bukowski,
• Beata Pasternak,
• Dariusz Sroczyński,
• Joachim Kusz,
• Magdalena Małecka and
• Monika Nowak

Beilstein J. Org. Chem. 2021, 17, 558–568, doi:10.3762/bjoc.17.50

• ][14] and PDE-10 [15] for a potential use in the treatment of chronic pain and neurodegenerative or psychiatric disorders. Some of these derivatives are known to possess anti-inflammatory (p38 MAP kinase inhibitors, Figure 1) [16], cardiotonic [17], and anticancer (Aurora-A kinase inhibitors

Hydrazides in the reaction with hydroxypyrrolines: less nucleophilicity – more diversity

• Dmitrii A. Shabalin,
• Evgeniya E. Ivanova,
• Igor A. Ushakov,
• Elena Yu. Schmidt and
• Boris A. Trofimov

Beilstein J. Org. Chem. 2021, 17, 319–324, doi:10.3762/bjoc.17.29

• fragments of influenza neuraminidase inhibitors [1], nonsteroidal progesterone receptor regulators [2][3], anti-inflammatory [4], antihypertensive and spasmolytic [5][6][7] agents (Figure 1). It is due to their prospects in drug design that a search for effective synthetic protocols to construct partially

Selective synthesis of α-organylthio esters and α-organylthio ketones from β-keto esters and sodium S-organyl sulfurothioates under basic conditions

• Jean C. Kazmierczak,
• Roberta Cargnelutti,
• Thiago Barcellos,
• Claudio C. Silveira and
• Ricardo F. Schumacher

Beilstein J. Org. Chem. 2021, 17, 234–244, doi:10.3762/bjoc.17.24

• as antibiotic, analgesic, anti-inflammatory, antidepressant, and antidiabetic agents [19][20][21][22]. In this regard, special attention can be given to α-thiocarbonyl compounds, which have appeared as synthons in many organic transformations [23][24][25][26][27][28][29][30][31] and as a core present

Supramolecular polymerization of sulfated dendritic peptide amphiphiles into multivalent L-selectin binders

• David Straßburger,
• Svenja Herziger,
• Katharina Huth,
• Moritz Urschbach,
• Rainer Haag and
• Pol Besenius

Beilstein J. Org. Chem. 2021, 17, 97–104, doi:10.3762/bjoc.17.10

• applicable platform to prepare and evaluate anti-inflammatory materials using multicomponent and multifunctional supramolecular subunits. Analysis of the self-assembly behavior of I by A: CD-spectra of 5, 10, 25 or 50 µM aqueous solutions; B, and C: TEM micrographs of negatively stained 25 µM solutions in

Chemical constituents of Chaenomeles sinensis twigs and their biological activity

• Joon Min Cha,
• Dong Hyun Kim,
• Lalita Subedi,
• Zahra Khan,
• Sang Un Choi,
• Sun Yeou Kim and
• Chung Sub Kim

Beilstein J. Org. Chem. 2020, 16, 3078–3085, doi:10.3762/bjoc.16.257

• studies on this plant have reported triterpenoids [2][3][4][5][6][7][8] and phenolic compounds [2][9][10][11][12], and some of them showed anti-inflammatory and neuroprotective [13][14][15], antitumor [2], tissue factor inhibitory [5][9], antibacterial [8], antihemolytic [8], or antipruritic activities

• [14], lignans [15], and oxylipins [21] with cytotoxic, anti-inflammatory, or potential neuroprotective activities. In order to search for minor constituents of other structure classes in C. sinensis twigs, the MeOH extract and the four solvent-partitioned fractions were further investigated to afford

Metal-free nucleophilic trifluoromethylselenolation via an iodide-mediated umpolung reactivity of trifluoromethylselenotoluenesulfonate

• Kevin Grollier,
• Alexis Taponard,
• Arnaud De Zordo-Banliat,
• Emmanuel Magnier and
• Thierry Billard

Beilstein J. Org. Chem. 2020, 16, 3032–3037, doi:10.3762/bjoc.16.252

• agrochemistry. Even if, to date, there are no CF3Se-containing pharmaceuticals registered [15], a recent work has demonstrated the promising development of trifluoromethylselenolated nonsteroidal anti-inflammatory drugs as potential anticancer drugs [34]. Over the last years, trifluoromethylselenolation

Synthesis and investigation of quadruplex-DNA-binding, 9-O-substituted berberine derivatives

• Jonas Becher,
• Daria V. Berdnikova,
• Heiko Ihmels and
• Christopher Stremmel

Beilstein J. Org. Chem. 2020, 16, 2795–2806, doi:10.3762/bjoc.16.230

• successfully developed as G4-DNA ligands [17], the natural product berberine (1a) has attracted special attention. Berberine (1a) is an isoquinoline alkaloid with an exceptionally wide range of biological activities [23][24]. It has been shown that berberine (1a) and its derivatives act, for example, as anti

• -inflammatory [25], antibacterial [26][27], and anticancer reagents [28][29]. The latter property is mainly based on the binding interaction of berberine with nucleic acids and the resulting inhibition of topoisomerase and telomerase [2][30]. Most notably, berberine (1a) induces a strong growth inhibition in

Host–guest interaction of cucurbit[8]uril with oroxin A and its effect on the properties of oroxin A

• Zhishu Zeng,
• Jun Xie,
• Guangyan Luo,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2020, 16, 2332–2337, doi:10.3762/bjoc.16.194

• beneficial biological effects of OA, which include antioxidant, antidiabetic, anticancer, antibacterial, anti-inflammatory and antiviral properties [25][26][27][28][29][30]. Herein, we selected Q[8] as a host molecule and investigated its host–guest interactions with OA, as well as its effect on the

Access to highly substituted oxazoles by the reaction of α-azidochalcone with potassium thiocyanate

• Mysore Bhyrappa Harisha,
• Pandi Dhanalakshmi,
• Rajendran Suresh,
• Raju Ranjith Kumar and
• Shanmugam Muthusubramanian

Beilstein J. Org. Chem. 2020, 16, 2108–2118, doi:10.3762/bjoc.16.178

• ][22][23][24][25][26]. Some oxazoles play a significant role in biological properties such as TRPV1 antagonistical activity, antifungal, analgesic, anti-inflammatory, antiproliferative, antileukemia, anticancer [27][28][29][30][31][32] and enzyme inhibitory activities [33][34][35][36][37][38][39][40

• , anti-inflammatory, antimicrobial, anitubercular, psychotropic and anticancer [54][55][56][57][58][59][60]. The marketed cancer drug dasatinib [61] continues to prove its worth. In this work, it is shown that highly substituted oxazoles and aminothiazoles could be accessed directly from the reaction of

Muyocopronones A and B: azaphilones from the endophytic fungus Muyocopron laterale

• Ken-ichi Nakashima,
• Junko Tomida,
• Tomoe Tsuboi,
• Yoshiaki Kawamura and
• Makoto Inoue

Beilstein J. Org. Chem. 2020, 16, 2100–2107, doi:10.3762/bjoc.16.177

• ], tau aggression [3], and heat shock protein 90 [4], in addition to their antimicrobial, cytotoxic, anticancer, and anti-inflammatory effects [5]. To date, over 400 azaphilones have been reported from various fungal strains, the majority of which have been produced by ascomycetes belonging to the

Synthesis of 3(2)-phosphonylated thiazolo[3,2-a]oxopyrimidines

• Ksenia I. Kaskevich,
• Anastasia A. Babushkina,
• Vladislav V. Gurzhiy,
• Dmitrij M. Egorov,
• Nataly I. Svintsitskaya and
• Albina V. Dogadina

Beilstein J. Org. Chem. 2020, 16, 1947–1954, doi:10.3762/bjoc.16.161

• ], anti-inflammatory [8][9], and antiviral [10][11]. The best known methods for the preparation of thiazolopyrimidines are based on condensation reactions. The most commonly used synthesis is the three-component condensation of 2-aminothiazoline, aromatic aldehyde, and ethyl cyanoacetate, which leads to

Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

• Paola Vitale,
• Luciana Cicco,
• Ilaria Cellamare,
• Filippo M. Perna,
• Antonio Salomone and
• Vito Capriati

Beilstein J. Org. Chem. 2020, 16, 1915–1923, doi:10.3762/bjoc.16.158

• , anti-inflammatory, antitubercular, antihypertensive, antihistaminic, anti-obesity, antiviral, and other medicinal agents [21][22][23][24][25][26][27]. Herein, we wish to report that either 2-aroylimidazoles (B) (Scheme 1, path b) or 2,4-diaroylpyrimidines (C) (Scheme 1, path c) can regioselectively be

Stereoselective Biginelli-like reaction catalyzed by a chiral phosphoric acid bearing two hydroxy groups

• Xiaoyun Hu,
• Jianxin Guo,
• Cui Wang,
• Rui Zhang and
• Victor Borovkov

Beilstein J. Org. Chem. 2020, 16, 1875–1880, doi:10.3762/bjoc.16.155

• ][2][3][4]. In the last decade, chiral DHPMs showed valuable pharmacological properties such as antiviral, antitumor, antibacterial, anti-inflammatory, and antihypertensive effects [5][6]. However, the individual enantiomers of DHPMs were found to exhibit different or even opposite pharmaceutical

Et₃N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties

• Dharmender Singh,
• Vipin Kumar and
• Virender Singh

Beilstein J. Org. Chem. 2020, 16, 1740–1753, doi:10.3762/bjoc.16.146

• products [1][2][3][4] and pharmacologically active compounds endowed with anticancer [5][6][7][8][9], anti-inflammatory, antioxidant, antimalarial, antifungal, and antileishmanial activities (Figure 1) [10][11][12][13]. Notably, this privileged scaffold is incorporated in several marketed drugs such as

Tuneable access to indole, indolone, and cinnoline derivatives from a common 1,4-diketone Michael acceptor

• Dalel El-Marrouki,
• Sabrina Touchet,
• Abderrahmen Abdelli,
• Hédi M’Rabet,
• Mohamed Lotfi Efrit and
• Philippe C. Gros

Beilstein J. Org. Chem. 2020, 16, 1722–1731, doi:10.3762/bjoc.16.144

• drugs used as anticancer, antiemetic, antihypertensive, antidepressant, anti-inflammatory, or anti-HIV agents, among others [9]. In contrast, concerning indolone and cinnoline derivatives, there are very few marketed drugs, but many molecules are under investigations for their activities as

• antibacterial, antifungal, anticancer, or anti-inflammatory agents or even on the central nervous system [7][12][13]. Several routes have been reported to access these key compounds, the most developed being for the indole [14] derivatives using the Fischer indole synthesis involving sigmatropic rearrangements

Microwave-assisted efficient one-pot synthesis of N²-(tetrazol-5-yl)-6-aryl/heteroaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines

• Moustafa Sherief Moustafa,
• Ramadan Ahmed Mekheimer,
• Saleh Mohammed Al-Mousawi,
• Mohamed Abd-Elmonem,
• Hesham El-Zorba,
• Afaf Mohamed Abdel Hameed,
• Tahany Mahmoud Mohamed and
• Kamal Usef Sadek

Beilstein J. Org. Chem. 2020, 16, 1706–1712, doi:10.3762/bjoc.16.142

• ]. Tetrazole derivatives exhibit a wide spectrum of biological activities as antibacterial [14], anticancer [15], anti-inflammatory [16], antidiabetic [17], antitubercular [18], and analgesic [19] agents. It is well established that many medical disorders can be caused as a result of defects at more than one

Synthesis of new dihydroberberine and tetrahydroberberine analogues and evaluation of their antiproliferative activity on NCI-H1975 cells

• Giacomo Mari,
• Lucia De Crescentini,
• Serena Benedetti,
• Francesco Palma,
• Stefania Santeusanio and
• Fabio Mantellini

Beilstein J. Org. Chem. 2020, 16, 1606–1616, doi:10.3762/bjoc.16.133

• various inflammatory diseases. The main component of this rhizome is berberine (BER), an alkaloid with numerous pharmacological properties, which include anticancer and anti-inflammatory activities [1]. However, the low bioavailability, poor solubility, and moderate nucleic acid binding affinity

• , or induce the manifestation of new features. The choice to insert an hydrazonic function on the DHBER skeleton was suggested by its wide range of interesting biological activities like antimicrobial [43], antioxidant [44], analgesic [45], anti-inflammatory [45], antiplatelet [45], anticonvulsant [46

[3 + 2] Cycloaddition with photogenerated azomethine ylides in β-cyclodextrin

• Margareta Sohora,
• Leo Mandić and
• Nikola Basarić

Beilstein J. Org. Chem. 2020, 16, 1296–1304, doi:10.3762/bjoc.16.110

• ]. Photodecarboxylations were also intensively investigated in a series of nonsteroidal anti-inflammatory drugs [22][23][24] such as ketoprofen [25][26][27][28][29][30][31][32][33][34], due to photoallergic responses initiated by photodecarboxylation of these drugs [35]. Stereoselectivity in photochemical reactions can be