New variochelins from soil-isolated Variovorax sp. H002

• Jabal Rahmat Haedar,
• Aya Yoshimura and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2024, 20, 692–700, doi:10.3762/bjoc.20.63

• draft genome sequence of the H002 strain identified the variochelin biosynthetic gene cluster (var), which encodes PKS (polyketide synthase) and NRPS (non-ribosomal peptide synthetase) genes. Finally, the siderophores isolated in this study exhibited antibacterial activity against several bacteria

Chemical and biosynthetic potential of Penicillium shentong XL-F41

• Ran Zou,
• Xin Li,
• Xiaochen Chen,
• Yue-Wei Guo and
• Baofu Xu

Beilstein J. Org. Chem. 2024, 20, 597–606, doi:10.3762/bjoc.20.52

• antibiotic mycophenolic acid originally isolated by Gosio in the 1890s [2], the important antibiotic penicillin was characterized more than one decade after Fleming discovered the antibacterial activity of a Penicillium extract, and since then, Penicillium has been an important target in drug development

Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors

• Yordanka Mollova-Sapundzhieva,
• Plamen Angelov,
• Danail Georgiev and
• Pavel Yanev

Beilstein J. Org. Chem. 2023, 19, 1804–1810, doi:10.3762/bjoc.19.132

•  2. Yields of 2-alkyl-4-quinolones 8, prepared according to Scheme 2: Yields of 1-hydroxy-2-alkyl-4-quinolone-3-carboxamides 4, prepared according to Scheme 2. Antibacterial activity of the synthesized quinolone derivatives 4, 5, and 8. Supporting Information Supporting Information File 25: Full

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

• (five Gram-positive and four Gram-negative bacteria, and three fungi). Additionally, the crystal structures of two berberine variants are described. Several berberine variants show enhanced antibacterial activity compared to the unaltered plant-derived molecule. We also report promising preliminary

• ]. Similar to berberine, results have demonstrated that the antibacterial activity of chelerythrine can be tied to DNA intercalation and disruption to cell membrane permeability [11][24]. One particular mechanism of action noted for chelerythrine’s antitumor bioactivity is through the inhibition of protein

• antibacterial activity, the structural changes in the chelerythrine variants had a dramatically negative impact when compared to the parent structure. Slight activity was observed for compound C1, though at this low dosage it was still deemed statistically insignificant compared to the blank. Screening these 20

Intermediates and shunt products of massiliachelin biosynthesis in Massilia sp. NR 4-1

• Till Steinmetz,
• Blaise Kimbadi Lombe and
• Markus Nett

Beilstein J. Org. Chem. 2023, 19, 909–917, doi:10.3762/bjoc.19.69

• paper assay The bacterial strains were acquired from the Leibniz Institute DSMZ (German Collection of Microorganisms and Cell Cultures GmbH). To test antibacterial activity, 0.1 mL of an overnight culture of each bacterial strain was plated on agar plates containing their preferred medium. The samples

• being tested were dissolved in methanol at a concentration of 50 µg/10 µL. Each compound was impregnated onto filter papers at a volume of 10 µL per disc. The inoculated plates were then incubated at 30 °C for 48 hours. The antibacterial activity was evaluated by measuring the zone of inhibition against

Synthesis of imidazo[1,2-a]pyridine-containing peptidomimetics by tandem of Groebke–Blackburn–Bienaymé and Ugi reactions

• Oleksandr V. Kolomiiets,
• Alexander V. Tsygankov,
• Maryna N. Kornet,
• Aleksander A. Brazhko,
• Vladimir I. Musatov and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2023, 19, 727–735, doi:10.3762/bjoc.19.53

• ]pyridine and peptidomimetic moieties as pharmacophores with four diversity points introduced from readily available starting materials, including scaffold diversity. A small focused compound library of 20 Ugi products was prepared and screened for antibacterial activity. Keywords: Groebke–Blackburn

• 8b is rather low in Ugi reactions. Antibacterial activity In the following experiment, we tested a specific group of compounds for their ability to act as antibacterial agents against Bacillus subtilis (strain 1211), Staphylococcus aureus (strain 2231) (Gram-positive), Escherichia coli (strain 1257

• the given concentration range. Despite the low level of antibacterial activity observed with the synthesized heterocycles, this could be beneficial for screening these compounds for other types of activity, such as anticancer or antidiabetic effects, since it would minimize any negative impact on the

Germacrene B – a central intermediate in sesquiterpene biosynthesis

• Houchao Xu and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 186–203, doi:10.3762/bjoc.19.18

• lime peel oil [25]. Germacrene B is also one of the main constituents of the essential oils from different plants that have antibacterial activity [27][28][29]. Germacrene B synthases have been reported from Solanum habrochaites [30] and Cannabis sativa [31]. In addition, 1 is a minor product of the

Nostochopcerol, a new antibacterial monoacylglycerol from the edible cyanobacterium Nostochopsis lobatus

• Naoya Oku,
• Saki Hayashi,
• Yuji Yamaguchi,
• Hiroyuki Takenaka and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2023, 19, 133–138, doi:10.3762/bjoc.19.13

• -hexane. The resulting three layers were tested against four Gram-positive bacteria, five Gram-negative bacteria, six fungi, and two yeasts, which detected antibacterial activity against two Gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus, from the 90% aqueous MeOH layer. The

• responsible constituent, though prone to diffuse during chromatography, was purified with the guidance of antibacterial activity on ODS and Sephadex LH-20 and by reversed-phase HPLC on ODS and styrene-divinylbenzene copolymer to yield 0.7 mg of compound 1 from 113.3 mg of the solvent partition fraction. The

• , antifoamers, preservatives, antistatic agents, polymer lubricants, and mold-releasing agents for the production of foods, cosmetics, ointments, paints, and plastics [33]. Compound 1 exhibited antibacterial activity, evaluated by a microculture method, with MIC 50 μg/mL against B. subtilis ATCC6633 and 100 μg

Combining the best of both worlds: radical-based divergent total synthesis

• Kyriaki Gennaiou,
• Antonios Kelesidis,
• Maria Kourgiantaki and
• Alexandros L. Zografos

Beilstein J. Org. Chem. 2023, 19, 1–26, doi:10.3762/bjoc.19.1

• maydis in 2014 and were reported to possess antibacterial activity against a small panel of both gram-positive and -negative bacteria [89][90]. Interestingly, their chemical structure bears no resemblance to recognize antibiotics and their mechanism of action remains unknown. Based on the knowledge

Digyalipopeptide A, an antiparasitic cyclic peptide from the Ghanaian Bacillus sp. strain DE2B

• Adwoa P. Nartey,
• Aboagye K. Dofuor,
• Kofi B. A. Owusu,
• Anil S. Camas,
• Hai Deng,
• Marcel Jaspars and
• Kwaku Kyeremeh

Beilstein J. Org. Chem. 2022, 18, 1763–1771, doi:10.3762/bjoc.18.185

• data for compound 1 in DMSO-d6. Antiparasitic activity data for compound 1. Antibacterial activity data for compound 1. Cytotoxicity and selectivity profiles of compound 1 using normal macrophages. Supporting Information Supporting Information File 338: Experimental protocols, phylogenetic data

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

• -triazoquinoline derivatives, and the biological activity evaluation showed that most of the compounds had a higher antibacterial activity (the optimal MIC value was 6.25 mg/mL) against Gram-positive bacteria, Gram-negative bacteria and all tested fungi than the standard ciprofloxacin (Figure 1a). Bodke's group

• . In addition, Aravinda's group [11] prepared 3-(1,3-dioxolan-2-yl)benzo[h]quinolines containing thiol and selenol groups in one pot by microwave irradiation, and tested the antibacterial activity of the compounds. The results showed that the antibacterial effect of some compounds was better than

• secondary alcohols 2 that allowed for the efficient synthesis of a series of quinolines 3 (up to 95% yield and >99:1 selectivity) (Figure 2). A preliminary evaluation of the compounds’ potential antibacterial activity was also performed. Results and Discussion We started our research with the ADC reaction

Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites

• Houchao Xu,
• Anne Wochele,
• Minghe Luo,
• Gregor Schnakenburg,
• Yuhui Sun,
• Heike Brötz-Oesterhelt and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 1159–1165, doi:10.3762/bjoc.18.120

• ]. Another hangtaimycin co-metabolite in S. spectabilis [9] is tryptophan-dehydrobutyrine diketopiperazine (TDD, 4) that was already isolated several decades before the discovery of 1, and likewise reported to have no antibacterial activity [9]. The initially published structure was that of (E)-4 [9], but

• enantiomer can only lead to a chiral dimer that, if formed at all, may crystallise less efficiently. Bioactivity testing Previous reports have mentioned that TDD (4) exhibits no antibacterial activity, without providing information about the test organisms used [9]. For this reason, and because of the above

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

• 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

• MCF7) [13]. In 2008, Muhi-eldeen et al, synthesized a hybrid compound with 1,3,4-oxadiazole moiety and pyrrolidine connected with propargylic moiety showed antibacterial activity against Staphylococcus aureus and E. coli [14]. On the other hand, the coupling of piperazine with heterocyclic compounds

• antibacterial activity against Escherichia coli was 4c, 4p, 4d, 4i, 4g, 4t, 4q, 4b, 4j, 4o, 4n, 4s, 4r, and 4l, respectively (Table 1). Moreover, compound 4i exhibited the highest activity against the pathogenic filamentous fungus Aspergillus fumigatus followed by compounds 4s, 4p, 4j, 4q, 4o, 4g, 4k, 4t, 4m

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

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

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

• 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

• sustained-release ability of drug molecules [31][33][34]. However, previous studies rarely reported the interaction between Q[8] and antibiotics, and did not explore the effect of Q[8] on antibacterial activity of antibiotics. Herein, Q[8] was selected as the host and the host–guest interaction between Q[8

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

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

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

• metronidazole derivatives. The antimicrobial (antifungal and antibacterial) activity of the prepared compounds was studied. All compounds (except 2 and 3) showed a potent inhibition rate of fungal growth as compared to control and metronidazole. The synthetic compounds also showed higher bacterial growth

• inhibition zones were recorded after 7 days of treatment and compared with growth area of fungi growing in control conditions. Antibacterial activity To determine the bacterial growth inhibiting effects of compounds, bacterial OD600 was measured at different time points i.e., 12, 24, 36 and 48 h (Figure 8

• 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

Natural products in the predatory defence of the filamentous fungal pathogen Aspergillus fumigatus

• Jana M. Boysen,
• Nauman Saeed and
• Falk Hillmann

Beilstein J. Org. Chem. 2021, 17, 1814–1827, doi:10.3762/bjoc.17.124

• and the 3-keto group are crucial for its antibacterial activity whereas, acetylation of the C-6 hydroxy group reduces the activity of HA [169]. Previous studies have also shown the antitrypanosomal, antifungal and cilioinhibitory properties of HA [72][83][86][87][88]. For these properties and little

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

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

Synthetic accesses to biguanide compounds

• Oleksandr Grytsai,
• Cyril Ronco and
• Rachid Benhida

Beilstein J. Org. Chem. 2021, 17, 1001–1040, doi:10.3762/bjoc.17.82

β-Lactamase inhibition profile of new amidine-substituted diazabicyclooctanes

• Zafar Iqbal,
• Lijuan Zhai,
• Yuanyu Gao,
• Dong Tang,
• Xueqin Ma,
• Jinbo Ji,
• Jian Sun,
• Jingwen Ji,
• Yuanbai Liu,
• Rui Jiang,
• Yangxiu Mu,
• Lili He,
• Haikang Yang and
• Zhixiang Yang

Beilstein J. Org. Chem. 2021, 17, 711–718, doi:10.3762/bjoc.17.60

• -lactamase inhibitors. As part of our efforts, we have synthesized a series of DBO derivatives A1–23 containing amidine substituents at the C2 position of the bicyclic ring. These compounds, alone and in combination with meropenem, were tested against ten bacterial strains for their antibacterial activity in

• vitro. All compounds did not show antibacterial activity when tested alone (MIC >64 mg/L), however, they exhibited a moderate inhibition activity in the presence of meropenem by lowering its MIC values. The compound A12 proved most potent among the other counterparts against all bacterial species with

• MIC from <0.125 mg/L to 2 mg/L, and is comparable to avibactam against both E. coli strains with a MIC value of <0.125 mg/L. Keywords: amidine; antibacterial activity; β-lactamase inhibitors; diazabicyclooctane; synthesis; Introduction Survival stress posed by antimicrobial agents triggers multiple

α,γ-Dioxygenated amides via tandem Brook rearrangement/radical oxygenation reactions and their application to syntheses of γ-lactams

• Mikhail K. Klychnikov,
• Radek Pohl,
• Ivana Císařová and
• Ullrich Jahn

Beilstein J. Org. Chem. 2021, 17, 688–704, doi:10.3762/bjoc.17.58

• -lactams are important lead compounds, e.g., derivatives with antibacterial activity were discovered, what gains importance with respect to the increasing bacterial resistance toward traditional β-lactam antibiotics [35][36][37][38][39]. Various synthetic pathways can be applied for the construction of the