An efficient and concise access to 2-amino-4H-benzothiopyran-4-one derivatives

• Peng Li,
• Yongqi Wu,
• Tingting Zhang,
• Chen Ma,
• Ziyun Lin,
• Gang Li and
• Haihong Huang

Beilstein J. Org. Chem. 2019, 15, 703–709, doi:10.3762/bjoc.15.65

• due to their structural relationship with benzopyranones, which are known as one privileged scaffold in medicinal chemistry [1]. The corresponding 2-aminobenzothiopyranones are molecules of high interest as they have remarkable anticancer, antifungal and antitubercular activities [2][3][4][5

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

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

Synthesis of nonracemic hydroxyglutamic acids

• Dorota G. Piotrowska,
• Iwona E. Głowacka,
• Andrzej E. Wróblewski and
• Liwia Lubowiecka

Beilstein J. Org. Chem. 2019, 15, 236–255, doi:10.3762/bjoc.15.22

• and (2R,3R)-2 were found as components of antifungal and antimicrobial hexadepsipeptides called kutznerides isolated from the actinomycete Kutzneria sp. 744 [26][27]. And finally, threo-3-hydroxyglutamic acid was identified in the cell wall of Mycobacterium lacticum [28]. 4-Hydroxy-L-glutamic acid

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

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

Design and synthesis of C₃-symmetric molecules bearing propellane moieties via cyclotrimerization and a ring-closing metathesis sequence

• Sambasivarao Kotha,
• Saidulu Todeti and
• Vikas R. Aswar

Beilstein J. Org. Chem. 2018, 14, 2537–2544, doi:10.3762/bjoc.14.230

• units in bioactive natural products and pharmaceuticals. Some of these propellanes exhibit intresting properties like antibiotic, antifungal, anticancer, platelet-activating factor antagonistic and antibacterial activities. The propellane skeleton is present in many alkaloids such as aknadinine (1

Synthesis of dihydroquinazolines from 2-aminobenzylamine: N³-aryl derivatives with electron-withdrawing groups

• Nadia Gruber,
• Jimena E. Díaz and
• Liliana R. Orelli

Beilstein J. Org. Chem. 2018, 14, 2510–2519, doi:10.3762/bjoc.14.227

• antimicrobial [3] and antifungal properties [4]. In addition, antiparasitic activity has been studied for some members of this family as inhibitors of trypanothione reductase [5], an essential enzyme of the kinetoplastid Trypanosoma brucei. Their activity as selective T-type calcium channel blockers [6][7][8][9

Synthesis of a leopolic acid-inspired tetramic acid with antimicrobial activity against multidrug-resistant bacteria

• Luce Mattio,
• Loana Musso,
• Leonardo Scaglioni,
• Andrea Pinto,
• Piera Anna Martino and
• Sabrina Dallavalle

Beilstein J. Org. Chem. 2018, 14, 2482–2487, doi:10.3762/bjoc.14.224

• antibacterial, antiviral, antifungal and anticancer activities [13]. More than one hundred of them have been isolated from a variety of natural sources and numerous analogues have been synthesized and studied for their multiple biological activities [13]. For this reason, we planned the synthesis of a leopolic

Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetal

• Antonio Arcadi,
• Sandro Cacchi,
• Giancarlo Fabrizi,
• Francesca Ghirga,
• Antonella Goggiamani,
• Antonia Iazzetti and
• Fabio Marinelli

Beilstein J. Org. Chem. 2018, 14, 2411–2417, doi:10.3762/bjoc.14.218

• ]quinazolines were synthesized and exhibited good antimicrobial as well as notable antifungal activities [9][10][11]. Since the isolation of hinckdentine A, an unusual marine alkaloid from the bryozoan Hincksinoflustra denticulata collected off the eastern coast of Tasmania [12][13], indolo[1,2-c]quinazolines

Semi-synthesis and insecticidal activity of spinetoram J and its D-forosamine replacement analogues

• Kai Zhang,
• Jiarong Li,
• Honglin Liu,
• Haiyou Wang and
• Lamusi A

Beilstein J. Org. Chem. 2018, 14, 2321–2330, doi:10.3762/bjoc.14.207

• , these analogues may also have antibiotic, antifungal, anticancer, antiparasitic, and immunosuppressive properties. Conclusion This study demonstrated a viable approach to synthesize spinetoram J and its analogues. Compared with the previous semi-synthesis of spinetoram J, the improved semi-synthesis

Studies towards the synthesis of hyperireflexolide A

• G. Hari Mangeswara Rao

Beilstein J. Org. Chem. 2018, 14, 2106–2111, doi:10.3762/bjoc.14.185

• antifungal [2] and cytotoxic activities [3]. γ-Lactone-fused cyclopentanes are of vital importance in organic synthesis and are the most abundant substructures found in various naturally occurring molecules [4][5]. A cis-cyclopentane ring-fused γ-lactone is the key structural unit of many complex and

Synthesis of spirocyclic scaffolds using hypervalent iodine reagents

• Fateh V. Singh,
• Priyanka B. Kole,
• Saeesh R. Mangaonkar and
• Samata E. Shetgaonkar

Beilstein J. Org. Chem. 2018, 14, 1778–1805, doi:10.3762/bjoc.14.152

• griseofulvum in 1939 [12]. In 1959, it was launched in the market as antifungal agent for the treatment of ringworm in human beings and animals [4][13]. Stepharine (3) is a member of the proaporphine alkaloid family and isolated from an angiosperm Stephania glabra [14]. Tofogliflozin (4) is a synthetic

Lanyamycin, a macrolide antibiotic from Sorangium cellulosum, strain Soce 481 (Myxobacteria)

• Lucky S. Mulwa,
• Rolf Jansen,
• Dimas F. Praditya,
• Kathrin I. Mohr,
• Patrick W. Okanya,
• Joachim Wink,
• Eike Steinmann and
• Marc Stadler

Beilstein J. Org. Chem. 2018, 14, 1554–1562, doi:10.3762/bjoc.14.132

• of which were found to exert anti-HIV activity while sorazolones, argyrins and tubulysins showed antitumor activity or cytotoxicity [4][5][6][7][8]. In our studies on the secondary metabolites of Sorangium cellulosum (strain Soce 481), we observed strong antifungal activity in the raw extract. On RP

• activity against bacteria and fungi and showed moderate antifungal activity in addition to a good inhibition of Micrococcus luteus (Table 3). When lanyamycin (1/2) was evaluated for cytotoxicity against growing primary cell lines, mouse fibroblasts (L929), and human cancer cell lines, nasopharyngeal cells

Two new 2-alkylquinolones, inhibitory to the fish skin ulcer pathogen Tenacibaculum maritimum, produced by a rhizobacterium of the genus Burkholderia sp.

• Dandan Li,
• Naoya Oku,
• Atsumi Hasada,
• Masafumi Shimizu and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2018, 14, 1446–1451, doi:10.3762/bjoc.14.122

• Pseudomonas aeruginosa. A series of chemoecological studies of P. aeruginosa has uncovered multifunctional roles of this quinolone class as antibacterial, antifungal, iron-chelating, and autoinducer agents to assist the survival of the producing organisms [32]. Additionally, drug discovery attempts have

• (23,200); IR ν max (ATR) cm−1: 2923, 2853, 1730, 1635, 1593, 1554, 1500, 1471, 1443, 1354, 1320, 1247, 1137, 1028, 965, 836, 759, 672; HRESIMS–TOF (m/z): [M + H]+ calcd for C18H24NO, 270.18524; found, 270.1855. Evaluation of antimicrobial activity The antibacterial and antifungal activity of 1–8 was

One hundred years of benzotropone chemistry

• Arif Dastan,
• Haydar Kilic and
• Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

• activity [14][15][16]. Troponoids 3–10 have been reported in the literature in a number of natural forms (Figure 1) [1][2][3][4][5][6][7][8]. These compounds have a structural class spacing from the simple monocyclic tropones, such as the potent antifungal and antibiotic monoterpene β-thujaplicin (4) [17

An overview of recent advances in duplex DNA recognition by small molecules

• Sayantan Bhaduri,
• Nihar Ranjan and
• Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

• order to probe their antifungal and antimycobacterial activity; several of these novel conjugates showed promising activity against the fungus C. neoformans (MIC80s ranging from 0.25–4 μg/mL) and the mycobacterium M. tuberculosis (MIC99s 3.1 μM) [62]. Since the last few decades, a plethora of synthetic

Fluorocyclisation via I(I)/I(III) catalysis: a concise route to fluorinated oxazolines

• Felix Scheidt,
• Christian Thiehoff,
• Gülay Yilmaz,
• Stephanie Meyer,
• Constantin G. Daniliuc,
• Gerald Kehr and
• Ryan Gilmour

Beilstein J. Org. Chem. 2018, 14, 1021–1027, doi:10.3762/bjoc.14.88

• siderophore antibiotic D-fluviabactin, the cytotoxic agent westiellamide, the antifungal macrodiolide leupyrrin A1 and the antitumour compound BE-70016 (Figure 1). In addition, synthetic polymers based on the 2-oxazoline building block constitute versatile platforms for a range of biomedical applications

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

• Pyrazolo[3,4-b]pyrazines have received great attention because of their interesting biological activities such as inhibition of protein kinases [137], blood platelet aggregation [138], bone metabolism improvers [139] as well as antifungal [140], antibacterial [141], antiparasitic [142] and antiviral [143

Volatiles from the tropical ascomycete Daldinia clavata (Hypoxylaceae, Xylariales)

• Tao Wang,
• Kathrin I. Mohr,
• Marc Stadler and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2018, 14, 135–147, doi:10.3762/bjoc.14.9

• -pyrone 17 exhibited a moderate antifungal and weak antibacterial effect, while the lactone 9 was moderately cytotoxic, but devoid of significant antimicrobial activity. The chlorinated aromatic compound 14 only weakly inhibited the sensitive test organisms Chromobacterium violaceum and Mucor hiemalis

• -5,6-dihydro-2H-pyran-2-one (9) and 6-nonyl-2H-pyran-2-one (17). Volatiles from Daldinia clavata MUCL 47436. 13C NMR data (chemical shifts in ppm) for 11a–d (125 MHz, C6D6). In vitro antibacterial, antifungal and cytotoxic activity of compounds 9, 14 and 17 in comparison with positive controls

Vinylphosphonium and 2-aminovinylphosphonium salts – preparation and applications in organic synthesis

• Anna Kuźnik,
• Roman Mazurkiewicz and
• Beata Fryczkowska

Beilstein J. Org. Chem. 2017, 13, 2710–2738, doi:10.3762/bjoc.13.269

• with aldehydes and ketones in THF in the presence of K2CO3 leading to allylamines 61, which are an important class of compounds due to their biological activities (Scheme 40) [56]. They are used, inter alia, as chemotherapeutic agents, enzyme inhibitors, and antifungal compounds [57][58][59]. The

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

• achieve a controlled release of biologically active copper ions and it has shown to be an effective antifungal agent against representative yeast and mold [135]. Friščić et al. also reported the synthesis of coordination polymers and BioMOFs using LAG by grinding together zinc oxide and fumaric acid. In

Sulfation and amidinohydrolysis in the biosynthesis of giant linear polyenes

• Hui Hong,
• Markiyan Samborskyy,
• Katsiaryna Usachova,
• Katharina Schnatz and
• Peter F. Leadlay

Beilstein J. Org. Chem. 2017, 13, 2408–2415, doi:10.3762/bjoc.13.238

• polyene clethramycin (1a, Scheme 1), originally isolated as an antifungal and as an inhibitor of pollen tube outgrowth from a plant-associated Streptomyces hygroscopicus strain [5]. Clethramycin (together with desulfoclethramycin (1b)) is also a product of the prolific strain Streptomyces malaysiensis

• DSM4137 (formerly Streptomyces violaceusniger DSM4137) [6] and it co-occurs with the closely-related antifungal mediomycins A (1c) and B (1d, Scheme 1) in Streptomyces mediocidicus ATCC 23936 [7]. Mediomycins are also produced by Streptomyces blastmyceticus [8]. The genes for the assembly-line PKS for

• mediomycin from S. blastmyceticus have been recently reported, encoding a separate extension module for all 27 cycles of chain extension [8]. These systems are attractive targets for knowledge-based engineering to produce novel antifungal compounds. A member of this class of polyketides, tetrafibricin from

Fluorination of some highly functionalized cycloalkanes: chemoselectivity and substrate dependence

• Attila Márió Remete,
• Melinda Nonn,
• Santos Fustero,
• Matti Haukka,
• Ferenc Fülöp and
• Loránd Kiss

Beilstein J. Org. Chem. 2017, 13, 2364–2371, doi:10.3762/bjoc.13.233

• , cispentacin) are relevant antifungal agents [19]. Therefore we have selected some five and six-membered alicyclic dihydroxylated β-amino ester stereo- and regioisomers as model compounds [23][24][25][26], derived from cyclopentene or cyclohexene β-amino acids. These were used in order to evaluate their