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

Diosgenyl 2-amino-2-deoxy-β-D-galactopyranoside: synthesis, derivatives and antimicrobial activity

• Henryk Myszka,
• Patrycja Sokołowska,
• Agnieszka Cieślińska,
• Andrzej Nowacki,
• Maciej Jaśkiewicz,
• Wojciech Kamysz and
• Beata Liberek

Beilstein J. Org. Chem. 2017, 13, 2310–2315, doi:10.3762/bjoc.13.227

• /bjoc.13.227 Abstract The synthesis of diosgenyl 2-amino-2-deoxy-β-D-galactopyranoside is presented for the first time. This synthetic saponin was transformed into its hydrochloride as well as N-acyl, 2-ureido, N-alkyl, and N,N-dialkyl derivatives. Antifungal and antibacterial studies show that some of

• , particularly antifungal [3][4][5][6] and antitumor [7][8][9]. The aglycone part of a saponin is termed sapogenin. Diosgenin, yamogenin, tigogenin, smilagenin and sarsapogenin are the most abundant sapogenins in nature [10]. They are linked via a glycosidic bond to a sugar unit, mainly D-glucose. Diosgenyl

• diosgenyl saponins are used in folk medicine in many countries. Such herbal medicines exhibit anti-inflammatory, antibacterial, antifungal, antiviral, diuretic and expectorant activities [2][11]. Importantly, these also help fight cancer cells [12][13][14]. Although saponins, in which D-galactose is

Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamine

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

Beilstein J. Org. Chem. 2017, 13, 1470–1477, doi:10.3762/bjoc.13.145

• analogues, dihydroquinazolines, also represent heterocyclic cores of pharmacological interest. Some derivatives containing this motif have shown antimicrobial [11] and antifungal properties [12]. Their activity as selective T-type calcium channel blockers [13][14][15] and as inhibitors of β-secretase (an

Sustainable synthesis of 3-substituted phthalides via a catalytic one-pot cascade strategy from 2-formylbenzoic acid with β-keto acids in glycerol

• Lina Jia and
• Fuzhong Han

Beilstein J. Org. Chem. 2017, 13, 1425–1429, doi:10.3762/bjoc.13.139

• [3][4][5], exhibit a broad spectrum of pharmacological activity, such as antibacterial, anti-HIV, antifungal, antibiotic, antitumor and immunosuppressive effects [6][7][8][9][10]. In addition, the one-pot cascade transformation has proven to be the key step in organic syntheses because of its broad

Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones

• Adesh Kumar Singh,
• Varsha Tiwari,
• Kunj Bihari Mishra,
• Surabhi Gupta and
• Jeyakumar Kandasamy

Beilstein J. Org. Chem. 2017, 13, 1139–1144, doi:10.3762/bjoc.13.113

• for the construction of highly functionalized natural products [1][2]. Sulfur moieties are found in several therapeutically important molecules that possess antibacterial, antifungal, anti-ulcer, anti-atherosclerotic, antihypertensive activities, etc. [3][4]. Sulfur compounds also play an important

Cycloheximide congeners produced by Streptomyces sp. SC0581 and photoinduced interconversion between (E)- and (Z)-2,3-dehydroanhydrocycloheximides

• Li Yang,
• Ping Wu,
• Jinghua Xue,
• Huitong Tan,
• Zheng Zhang and
• Xiaoyi Wei

Beilstein J. Org. Chem. 2017, 13, 1039–1049, doi:10.3762/bjoc.13.103

• 2 and 3 was observed and verified and the possible reaction path and mechanism were proposed by theoretical computations. The antifungal and cytotoxic activities of 1–6 were evaluated and suggested that 2,3-dehydrogenation results in the loss of the activities and supported that the OH-α is

• important to the activities of cycloheximide congeners. Keywords: antifungal activity; cycloheximide derivatives; E/Z photoisomerization; Streptomyces sp; theoretical conformational analysis; Introduction The glutarimide-containing antibiotics represent a fascinating class of natural products that exhibit

• without the toxic side-effects could provide a viable lead of therapeutic drugs or agricultural pesticides. During the course of our searching for bioactive microbial metabolites [8][9], a culture extract of Streptomyces sp. SC0581 was found to show antifungal activity against the phytopathogen

New approach toward the synthesis of deuterated pyrazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]pyridines

• Aleksey Yu. Vorob’ev,
• Vyacheslav I. Supranovich,
• Gennady I. Borodkin and
• Vyacheslav G. Shubin

Beilstein J. Org. Chem. 2017, 13, 800–805, doi:10.3762/bjoc.13.80

• treating asthma and post-stroke patients [16]. 1,2,4-Triazolo[1,5-a]pyridines show antifungal [17], antitumor [18], and cytotoxic [19] activities. Both types of heterocyclic cores are readily available from N-aminopyridium salts and related pyridinium-N-imines via 1,3-cycloaddition reaction [20] or

N-Propargylamines: versatile building blocks in the construction of thiazole cores

• S. Arshadi,
• E. Vessally,
• L. Edjlali,
• R. Hosseinzadeh-Khanmiri and
• E. Ghorbani-Kalhor

Beilstein J. Org. Chem. 2017, 13, 625–638, doi:10.3762/bjoc.13.61

• pharmacological activities. For example, abafungin (Figure 1) is an antifungal drug marketed worldwide for the treatment of dermatomycoses. It works by inhibiting the enzyme sterol 24-C-methyltransferase [1][2][3][4]. Febuxostat, also known by its brand name adenuric is a xanthine oxidase inhibitor that helps to

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

• antibacterial activity against Escherichia coli and Bacillus subtilis, and antifungal activity against Aspergillus niger and Penicillium notatum. Among the synthesized series of 1-indanone derivatives 64, the highest antibacterial activity was exhibited by derivatives 64k and 64l, whereas the most potent

• antifungal activity was revealed for derivatives 64h and 64j. The authors have also studied anti-inflammatory properties of these derivatives using the carrageenan induced paw edema method in rats. The anti-inflammatory activity of the synthesized compounds was compared with standard indomethacin (a non

• antiviral and antifungal molecule produced by bacteria. Because of its interesting biological activity, Mitchell and Liebeskind have decided to synthesize abicoviromycin (168) derivatives [78]. In spite of the potent biological activity, abicoviromycin (168) is extremely heat- and acid-sensitive. Moreover

Biosynthetic origin of butyrolactol A, an antifungal polyketide produced by a marine-derived Streptomyces

• Enjuro Harunari,
• Hisayuki Komaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2017, 13, 441–450, doi:10.3762/bjoc.13.47

• , Kisarazu, Chiba 292-0818, Japan 10.3762/bjoc.13.47 Abstract Butyrolactol A is an antifungal polyketide of Streptomyces bearing an uncommon tert-butyl starter unit and a polyol system in which eight hydroxy/acyloxy carbons are contiguously connected. Except for its congener butyrolactol B, there exist no

• -like structures [4][5][6][7][8]. Butyrolactol A (1) is an antifungal polyketide first isolated from Streptomyces rochei S785-16 [9] (Figure 1). The left half of 1 is the hydrophobic unconjugated tetraene system including one Z-olefin with a terminal tert-butyl group, whereas the hydrophilic polyol

• structure and the antifungal potency, no further research has been reported for 1. There are two interesting aspects in the structure of butyrolactol A (1). First, among the polyketides, a tert-butyl group has been found exclusively in metabolites of marine cyanobacteria except for 1 [11][12][13][14

Brønsted acid-mediated cyclization–dehydrosulfonylation/reduction sequences: An easy access to pyrazinoisoquinolines and pyridopyrazines

• Ramana Sreenivasa Rao and
• Chinnasamy Ramaraj Ramanathan

Beilstein J. Org. Chem. 2017, 13, 428–440, doi:10.3762/bjoc.13.46

• anticancer [2][3], antifungal [4], amoebiasis, trypanosomiasis, bilharziasis [5][6], and schistosomiasis [7][8]. Some are cell adhesion inhibitors [9] brandykinin receptor antagonists [10][11] and chymase inhibitors [12]. Quinoxaline derivatives are known to act as aldose reductase (ALR2) inhibitors and are

Computational methods in drug discovery

• Sumudu P. Leelananda and
• Steffen Lindert

Beilstein J. Org. Chem. 2016, 12, 2694–2718, doi:10.3762/bjoc.12.267