(Bio)isosteres of ortho- and meta-substituted benzenes

• H. Erik Diepers and
• Johannes C. L. Walker

Beilstein J. Org. Chem. 2024, 20, 859–890, doi:10.3762/bjoc.20.78

• increased by bioisosteric replacement of ortho-benzene with 1,2-BCHs, the metabolic stability as determined by intrinsic clearance rate in human liver microsomes (Clint) and half-time of metabolic decomposition (t1/2) decreased. Mykhailiuk and co-workers also reported the antifungal activity of fluxapyroxad

• and boscalid biosisosteres (±)-55 and (±)-56 (Figure 6) [36]. The comparison of the antifungal activity over a wide range of concentrations showed that while biological activity is preserved upon incorporation of the 1,2-BCH scaffold, it is significantly reduced. This was also the case for the

• clearance rate in human liver microsomes (CLint) than fluxapyroxad (lower metabolic stability) but boscalid bioisostere (±)-71 had a lower CLint and was more metabolically stable than boscalid. Importantly, Mykhailiuk and co-workers also compared the antifungal activity of fluxapyroxad, boscalid and the

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

• Jessica Villegas,
• Bryce C. Ball,
• Katelyn M. Shouse,
• Caleb W. VanArragon,
• Ashley N. Wasserman,
• Hannah E. Bhakta,
• Allen G. Oliver,
• Danielle A. Orozco-Nunnelly and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

• against all Gram-positive strains, with exceptional activity against S. epidermidis. This variant further enhanced the bacterial selectivity, as its heightened antibacterial levels were coupled with notable decreases in antifungal activity as compared to berberine. A graph showing a complete comparison of

Cyclometalated iridium complexes-catalyzed acceptorless dehydrogenative coupling reaction: construction of quinoline derivatives and evaluation of their antimicrobial activities

• Hongling Shui,
• Yuhong Zhong,
• Renshi Luo,
• Zhanyi Zhang,
• Jiuzhong Huang,
• Ping Yang and
• Nianhua Luo

Beilstein J. Org. Chem. 2022, 18, 1507–1517, doi:10.3762/bjoc.18.159

• Gram-positive bacteria. In particular, the antibacterial activity of compound 3ad against Staphylococcus aureus (MIC = 2 μg/mL) was much higher than that of the positive control norfloxacin. Meanwhile, the antifungal activity of compound 3ck (MIC = 64 μg/mL) was stronger than norfloxacin. However, 3an

• and other compounds showed similar or lower antifungal activity than norfloxacin. Unfortunately, all compounds were less effective against Gram-negative bacteria (MIC > 128 μg/mL) than the parent drug norfloxacin. To sum up, the synthesized compounds exhibited enhanced antibacterial activity against

The stereochemical course of 2-methylisoborneol biosynthesis

• Binbin Gu,
• Anwei Hou and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 818–824, doi:10.3762/bjoc.18.82

• in other foodstuff such as fish and coffee contaminations with 1 are perceived as unpleasant flavor constituents [15][16][17][18]. Despite its occurrence in fungi, 1 also has moderate antifungal activity as observed for its inhibition of mycelial growth and sporulation in Fusarium moniliforme [19

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

• for their in vitro antibacterial potential against Staphylococcus aureus and Bacillus subtilis as examples of Gram-positive bacteria as well as against Escherichia coli and Proteus vulgaris as examples of Gram-negative bacteria [35]. They were also evaluated for their in vitro antifungal activity

• , 4p and 4c, respectively. Besides, the order of antifungal activity against the pathogenic yeast Candida albicans was 4g, 4i, 4q, 4j, 4o, 4p, 4m, 4k, 4s, 4t, 4n, 4v, 4d, 4e, 4h, 4l, 4c and 4r, respectively (Table 1). Likewise, no antimicrobial activities could be detected for compound 4f under these

• . Compounds 4g and 4i showed good antifungal activity against C. albicans. Compounds 4t, 4i, 4p, and 4c were the most active derivatives against S. aureus with MIC values between 31 and 70 µg/mL, while compound 4p showed good activity against Bacillus subtilis with a MIC value of 70 µg/mL. Further development

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

• 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

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

• 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

• analysis of antifungal activity, the previously described [37] 3-methyl- and 3-phenyltriazolo[4,3-b][1,2,4,5]tetrazines 10a,b were used as structural analogues of compounds 3a,b. Furthermore, in the reactions of compound 10a with methanol, heptylamine and morpholine, new derivatives 11a–c have been

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

• . 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

• tested against the M. tuberculosis H37Rv strain with 3.90 μg/mL. It seems that the presence of the indole ring has enhanced the activity of complex L3-Ni when comparing with other Ni complexes such as L1-Ni and L2-Ni. Antifungal activity The screened complexes showed antifungal activity, in the range of

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

• 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

• codes: carbon = grey, nitrogen = blue, oxygen = red, hydrogen = white. General structural feature of the synthesized molecules 5. The graph representing the antifungal activity of Didymella sp. against compounds 5a–i and 7a–e. The graph representing the antibacterial activity of E. coli against

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

Progress in the total synthesis of inthomycins

• Bidyut Kumar Senapati

Beilstein J. Org. Chem. 2021, 17, 58–82, doi:10.3762/bjoc.17.7

• Omura’s group in 1995 [3]. Inthomycin A ((+)-1) displays moderate antifungal activity against cellulose-containing Phytophthora parasitica and Phytophthora capsici [4]. Inthomycins were reported to possess many interesting biological properties, which include the specific inhibition of the cellular

Copper-catalyzed O-alkenylation of phosphonates

• Nuria Vázquez-Galiñanes,
• Mariña Andón-Rodríguez,
• Patricia Gómez-Roibás and
• Martín Fañanás-Mastral

Beilstein J. Org. Chem. 2020, 16, 611–615, doi:10.3762/bjoc.16.56

• chemistry [1][2][3]. In particular, O-alkenyl phosphonate esters (i.e., enol phosphonates) have been described as potent insecticides and show antifungal activity [4]. While several methods are available for the preparation of cyclic enol phosphonates [5][6][7][8][9][10], the synthesis of the acyclic

Fluorinated maleimide-substituted porphyrins and chlorins: synthesis and characterization

• Valentina A. Ol’shevskaya,
• Elena G. Kononova and
• Andrei V. Zaitsev

Beilstein J. Org. Chem. 2019, 15, 2704–2709, doi:10.3762/bjoc.15.263

• . Maleimides are considered as a biologically important scaffold that possess almost all types of biological activities including antibacterial and antifungal activity [24], anticancer activity [25], cox-2 inhibitor and anti-inflammatory, antidiabetic activity [26] and photodynamic activity [27]. Attaching of

Synthesis of pyrrolo[1,2-a]quinolines by formal 1,3-dipolar cycloaddition reactions of quinolinium salts

• Anthony Choi,
• Rebecca M. Morley and
• Iain Coldham

Beilstein J. Org. Chem. 2019, 15, 1480–1484, doi:10.3762/bjoc.15.149

• with a quinoline. Pyrroloquinolines have been found to show antibacterial and antifungal activity, to be ligands for the NK1 receptor, and to be effective against the Hif hypoxia pathway in cancer cell lines [36][37][38]. Almost all of the examples of dipolar cycloaddition reactions involving

Steroid diversification by multicomponent reactions

• Leslie Reguera,
• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

• library of androstanic derivatives 21 (Figure 2B) and their reduced analogues bearing the 3β-hydroxy group were biologically tested showing antifungal activity against Fusarium virguliforme and Fusarium solani. The generation of this compound library suffered from the formation of the Passerini reaction

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

• activity against Candida albicans and Candida tropicalis [8] and 2-mercapto-1,3-benzothiol and its derivatives exhibit inhibitory effects against thyroid peroxidase [9]. (Hetero)aryl thiols are often prepared from the corresponding halides through direct nucleophilic substitution [10][11][12] or metal

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

• (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

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

• 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

• path and mechanism were proposed by theoretical computations. All the isolated compounds were evaluated for antifungal activity and cancer cell toxicity. Herein are reported the isolation, structural elucidation, and biological activities of these compounds and the interconversion between 2 and 3

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

Synthesis of the C8’-epimeric thymine pyranosyl amino acid core of amipurimycin

• Pramod R. Markad,
• Navanath Kumbhar and
• Dilip D. Dhavale

Beilstein J. Org. Chem. 2016, 12, 1765–1771, doi:10.3762/bjoc.12.165

• miharamycin that are known as antifungal agents [2]. Amipurimycin (1) isolated from Streptomyces novoguineensis sp. nov., displays antifungal activity against pyricularia oryzae – a causative agent in rice blast disease [3][4]. Goto and co-workers have proposed the primary structure of amipurimycin (1, Figure

• configurations at the C6’, C2” and C3” of the cis-pentacin are still undefined. Thus, the partially unresolved structure, a potent antifungal activity, the unexplored mode of action and the limited synthetic study make amipurimycin (1) an attractive target for futher investigation. As of now, a total synthesis

Modular synthesis of the pyrimidine core of the manzacidins by divergent Tsuji–Trost coupling

• Sebastian Bretzke,
• Stephan Scheeff,
• Felicitas Vollmeyer,
• Friederike Eberhagen,
• Frank Rominger and
• Dirk Menche

Beilstein J. Org. Chem. 2016, 12, 1111–1121, doi:10.3762/bjoc.12.107

• last century [2]. The compounds have demonstrated potent antifungal activity [3], and acted as α-adrenoceptor blockers, antagonists of the serotonergic receptor and/or actomyosin ATPase activators [23][24][25]. As shown in Figure 1 for the most prominent representatives, manzacidins A (1) and C (2

Marine-derived myxobacteria of the suborder Nannocystineae: An underexplored source of structurally intriguing and biologically active metabolites

• Antonio Dávila-Céspedes,
• Peter Hufendiek,
• Max Crüsemann,
• Till F. Schäberle and
• Gabriele M. König

Beilstein J. Org. Chem. 2016, 12, 969–984, doi:10.3762/bjoc.12.96

• strain Na a174, is supposed to be a result of degradation processes due to long-time cultivation. Additionally, the known compound 1,6-dihydroxyphenazin (19) and its arabinofuranoside 20 were obtained. To date, 14 has shown marginal antifungal activity towards Mucor hiemalis (DSM 2656, MIC: 33.3 μg/mL

• testing, revealed that the lactone moiety and the configuration of the methoxyacrylate partial structure are crucial for antifungal activity. The latter structural motif is well known from a range of antifungal compounds produced by fungi and myxobacteria, e.g., the strobilurins and the melithiazols [67

Biosynthesis of α-pyrones

• Till F. Schäberle

Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56

• (29) showed antifungal activity against Rhizoctonia cerealis, Gaeumannomyces graminis and Botrytis cinerea (Figure 6) [34]. The structural related trichopyrone (30) instead showed no antimicrobial activity [35]. For compound 29 it was further revealed that it represents the prominent headspace

• kill their prey [45][46]. Fusapyrone (32) and the derivative deoxyfusapyrone (33) had been isolated from Fusarium semitectum [39]. These compounds show considerable antifungal activity, e.g., a minimum inhibitory concentration against Botrytis cinerea, Aspergillus parasiticus, and Penicillium brevi

• been used against skin diseases due to its mutagenic effect [71]. Bacterial monobenzo-α-pyrones were isolated from the myxobacterium Stigmatella aurantiaca MYX-030. Myxocoumarins A (65) and B (66) were identified, and 65 was tested for antifungal activity [72]. It showed a promising activity against