Two new lanostanoid glycosides isolated from a Kenyan polypore Fomitopsis carnea

• Winnie Chemutai Sum,
• Sherif S. Ebada,
• Didsanutda Gonkhom,
• Cony Decock,
• Rémy Bertrand Teponno,
• Josphat Clement Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2023, 19, 1161–1169, doi:10.3762/bjoc.19.84

• effects of compound 1 and related analogues could be realized by C-3 hydrolysis. In 2010, Liu et al. also demonstrated the major role played by changes at C-16 on antibacterial effects of F. pinicola steroids [33]. The acetylation at C-16 reduced the potency compared to the corresponding congener with a

Copper-catalyzed N-arylation of amines with aryliodonium ylides in water

• Kasturi U. Nabar,
• Bhalchandra M. Bhanage and
• Sudam G. Dawande

Beilstein J. Org. Chem. 2023, 19, 1008–1014, doi:10.3762/bjoc.19.76

• metabolism, cell growth and during pregnancy, ofloxacin (III) [7], an antibacterial agent, mefenamic acid (IV) [8], an anti-inflammatory agent used to treat mild pain, linezolid (V) [9], an antibacterial agent, repaglinide (VI) [10], used to treat diabetes mellitus type 2, and tolfenamic acid (VII) [11], an

Five new sesquiterpenoids from agarwood of Aquilaria sinensis

• Hong Zhou,
• Xu-Yang Li,
• Hong-Bin Fang,
• He-Zhong Jiang and
• Yong-Xian Cheng

Beilstein J. Org. Chem. 2023, 19, 998–1007, doi:10.3762/bjoc.19.75

• ]. Previous studies have shown that 2-(2-phenylethyl)chromones and sesquiterpenes are the characteristic and main bioactive components of agarwood [5][6]. Various bioactivities, including neuroactive [4], gastrointestinal modulation [7], cytotoxicity [8], antibacterial [9], antifungal, acetylcholinesterase

Aromatic C–H bond functionalization through organocatalyzed asymmetric intermolecular aza-Friedel–Crafts reaction: a recent update

• Anup Biswas

Beilstein J. Org. Chem. 2023, 19, 956–981, doi:10.3762/bjoc.19.72

• antibacterial acitivity against resistant S. aureus strains. It is also an inhibitor of the enzyme peptide deformylases (PDFs). The synthesis comprised the reaction between the highly substituted hydroquinone 142 and dehydroalanine 143 in the presence of chiral phosphoric acid P7 as catalyst to prepare

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

• Dileep Kumar Singh and
• Rajesh Kumar

Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71

• ], antiviral [11][12], antibacterial [13][14][15], antimalarial [16][17], anti-inflammatory [18][19], anti-oxidant [20][21][22], antifungal [23][24] and antibiotic [25][26] and as enzyme inhibitors [27][28]. Several pharmaceuticals, polymers and naturally occurring compounds, including heme, chlorophyll

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

• -chelating molecules, which are structurally and likely also biosynthetically linked to massiliachelin. However, these compounds are not related to the predicted lipopeptide siderophore. Herein, we describe their isolation, characterization and antibacterial activities, and we discuss their biosynthetic

• signal at δH 7.62 ppm characteristic for an amide. In vitro tests were conducted for all compounds to assess their antibacterial activities against three Gram-negative bacteria (Escherichia coli, Agrobacterium tumefaciens and Pseudomonas fluorescens) and one Gram-positive bacterium (Bacillus subtilis

• 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

Pyridine C(sp²)–H bond functionalization under transition-metal and rare earth metal catalysis

• Haritha Sindhe,
• Malladi Mounika Reddy,
• Karthikeyan Rajkumar,
• Akshay Kamble,
• Amardeep Singh,
• Anand Kumar and
• Satyasheel Sharma

Beilstein J. Org. Chem. 2023, 19, 820–863, doi:10.3762/bjoc.19.62

• tricyclic imidazonaphthyridinone derivative having antibacterial properties, with low catalyst loading (0.1 mol %) (Scheme 20b). Later, in 2014, the same authors, using an amide as directing group (DG), developed a protocol for the regioselective C3-alkenylation of pyridines through syn-addition of alkynes

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

• structures containing a substituted imidazo[1,2-a]pyridine fragment, such as anticancer [5], antibacterial [6], antifungal [7], antiviral [8], anti-inflammatory [9], antimalarial [10], antiparkinsonian [11] and antituberculous activities [12]. In addition, some derivatives show enzyme inhibition [13] and can

• 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

Cassane diterpenoids with α-glucosidase inhibitory activity from the fruits of Pterolobium macropterum

• Sarot Cheenpracha,
• Ratchanaporn Chokchaisiri,
• Lucksagoon Ganranoo,
• Sareeya Bureekaew,
• Thunwadee Limtharakul and
• Surat Laphookhieo

Beilstein J. Org. Chem. 2023, 19, 658–665, doi:10.3762/bjoc.19.47

• exhibit diverse biological properties, including anti-inflammatory [12], antimalarial [13], antitumor [14], antiviral [15], antibacterial [16], antiproliferative [13], and immunomodulatory [17] activities. As part of our studies on Thai medicinal plants, an investigation of the fruits of P. macropterum

Nucleophile-induced ring contraction in pyrrolo[2,1-c][1,4]benzothiazines: access to pyrrolo[2,1-b][1,3]benzothiazoles

• Ekaterina A. Lystsova,
• Maksim V. Dmitriev,
• Andrey N. Maslivets and
• Ekaterina E. Khramtsova

Beilstein J. Org. Chem. 2023, 19, 646–657, doi:10.3762/bjoc.19.46

• anticonvulsant agents had been developed based on PBTA derivatives (Figure 1) [2]. In addition, series of PBTAs (Figure 1) were found to exhibit antibacterial, antifungal, antioxidant, and cytotoxic activities [3][4]. Several strategies have been developed for the synthesis of PBTA derivatives [2][3][4][5][6][7

Combretastatins D series and analogues: from isolation, synthetic challenges and biological activities

• Jorge de Lima Neto and
• Paulo Henrique Menezes

Beilstein J. Org. Chem. 2023, 19, 399–427, doi:10.3762/bjoc.19.31

• antibacterial or antifungal activities were observed [55]. Ponnapalli and co-workers tested in an agar diffusion assay the isolated compounds corniculatolide A (4), 11-O-methylcorniculatolide A (5), 12-hydroxy-11-O-methylcorniculatolide A (6), isocorniculatolide A (7), and 11-O-methylisocorniculatolide A (8

An efficient metal-free and catalyst-free C–S/C–O bond-formation strategy: synthesis of pyrazole-conjugated thioamides and amides

• Shubham Sharma,
• Dharmender Singh,
• Sunit Kumar,
• Vaishali,
• Rahul Jamra,
• Naveen Banyal,
• Deepika,
• Chandi C. Malakar and
• Virender Singh

Beilstein J. Org. Chem. 2023, 19, 231–244, doi:10.3762/bjoc.19.22

• [7], estrogen receptor ligands [8], A2A receptor antagonists [9], and DNA intercalating agents [10]. Importantly, pyrazole derivatives can be traced in a spectrum of well-established drug candidates of various categories with diverse therapeutic properties such as antipyretic [11], antibacterial [12

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

• , Japan 10.3762/bjoc.19.13 Abstract A new antibacterial 3-monoacyl-sn-glycerol, nostochopcerol (1), was isolated from a cultured algal mass of the edible cyanobacterium Nostochopsis lobatus MAC0804NAN. The structure of compound 1 was established by the analysis of NMR and MS data while its chirality was

• established by comparison of optical rotation values with synthetically prepared authentics. Compound 1 inhibited the growth of Bacillus subtilis and Staphylococcus aureus at MIC of 50 μg/mL and 100 μg/mL, respectively. Keywords: antibacterial; cyanobacterium; edible; monoacylglycerol; Nostochopsis lobatus

• limited number of attempts include an antifungal lipopeptide nostofungicidine [4] and an antioxidant nostocionone [5] from Nostoc commune, an unusual antibacterial n−1 fatty acid from N. verrucosum [2], and the sacrolides, antimicrobial oxylipin macrolactones from Aphanothece sacrum [6][7]. Nostochopsis

Practical synthesis of isocoumarins via Rh(III)-catalyzed C–H activation/annulation cascade

• Qian-Ci Gao,
• Yi-Fei Li,
• Jun Xuan and
• Xiao-Qiang Hu

Beilstein J. Org. Chem. 2023, 19, 100–106, doi:10.3762/bjoc.19.10

• occurring lactones isolated from bacterial strains, molds, and plants, exhibiting a wide range of pharmacological properties such as antibacterial, antitumor, and anti-HIV activities (Scheme 1a) [1][2][3][4][5]. Fascinated by their versatile properties, researchers were prompted to develop efficient methods

Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr₄/PPh₃ and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior

• Christian Schumacher,
• Jas S. Ward,
• Kari Rissanen,
• Carsten Bolm and
• Mohamed Ramadan El Sayed Aly

Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9

• propargylated, coupled with azido quinoline, and then functionalized with glucose as part of random designs to discover new antimicrobial and cytotoxic candidates. From these studies, conjugates I [9] and II [10] were identified to display an excellent preliminary antibacterial impact, and congener III [10

• signal is attributed to the H-3 of (15%) byproduct 3β-azidocholest-5-ene; **denotes to two protons of the 3β-azidocholest-5-ene epimer [12]. Chemical structure of three isomeric cholesterols. Selected previously described cholesterol derivatives with interesting antibacterial and cytotoxic activities [9

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

• consecutive all-carbon quaternary carbon atoms [54][55][56]. Preliminary biological screening of this family revealed notable antibacterial and anticancer activities due to the α-methylene lactone moiety they bear [57]. Recently, in order to synthesize the common core present in crinipellins, Xie and Ding’s

• 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

Navigating and expanding the roadmap of natural product genome mining tools

• Friederike Biermann,
• Sebastian L. Wenski and
• Eric J. N. Helfrich

Beilstein J. Org. Chem. 2022, 18, 1656–1671, doi:10.3762/bjoc.18.178

• ., bongkrekic acid (4) [11]), antibacterial (e.g., vancomycin (5) [12]) or antifungal compounds (e.g., amphotericin B (6) [13]) (Figure 1). The identification of almost all clinically relevant antibiotics using bioactivity-guided fractionation approaches long before the beginning of the post-genomic era

Using UHPLC–MS profiling for the discovery of new sponge-derived metabolites and anthelmintic screening of the NatureBank bromotyrosine library

• Sasha Hayes,
• Aya C. Taki,
• Kah Yean Lum,
• Joseph J. Byrne,
• Merrick G. Ekins,
• Robin B. Gasser and
• Rohan A. Davis

Beilstein J. Org. Chem. 2022, 18, 1544–1552, doi:10.3762/bjoc.18.164

• ], antibacterial [7][8], antimalarial [9], anti-HIV [10] and antifouling activities [11]. Due to our continuing interest in the identification of new secondary metabolites from Australian marine sources, in addition to further expanding the NatureBank [12] open access compound library, we have recently embarked on

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

• loading offers the potential to access the aryl/heteroaryl quinolones in suitable amounts. In addition, the antibacterial and antifungal activities of the synthesized quinolines were evaluated in vitro, and the experimental results showed that the antibacterial activities of compounds 3ab, 3ad, and 3ah

• against Gram-positive bacteria and compound 3ck against C. albicans were better than the reference drug norfloxacin. Keywords: acceptorless dehydrogenative coupling reaction; antibacterial; cyclometalated iridium complexes; quinolines; Introduction As an important class of heterocyclic compounds

• , quinoline and its derivatives widely exist in natural products. They have a wide range of biological activities, such as antibacterial [1], anti-inflammatory [2], antitumor [3], antihepatitis C (HCV) [4], antituberculosis (TB) [5], antimalarial [6], and anti-Alzheimer's disease (AD) [7]. Among these

On drug discovery against infectious diseases and academic medicinal chemistry contributions

• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 1355–1378, doi:10.3762/bjoc.18.141

• -bearing substances, endowed with an antibacterial effect [58]. However, this compound was originally patented for a fungicide effect [59] and then found to also inhibit mammalian c-Jun N-terminal kinase [60]. Unsurprisingly, it was also reported in 2022 as a covalent inhibitor for the SARS-CoV-2 main

• antibacterial research department of GSK reported the results of their genome-driven seven-year long quest for original antibiotics. This target-based approach actually failed although 300 bacterial genes had been considered and 70 high-throughput screening campaigns, focusing on the corresponding proteins, had

• second original class of bacterial gyrases inhibitors. In 2004, the nitro-bearing derivative 11, resulting from a high-throughput phenotypic-based screening, was patented by Pharmacia/Pfizer for its antibacterial properties [122][123]. Even if this compound was also effective in vivo, many synthesis and

Ferrocenoyl-adenines: substituent effects on regioselective acylation

• Mateja Toma,
• Gabrijel Zubčić,
• Jasmina Lapić,
• Senka Djaković,
• Davor Šakić and
• Valerije Vrček

Beilstein J. Org. Chem. 2022, 18, 1270–1277, doi:10.3762/bjoc.18.133

• ferrocene–nucleobase conjugates [4], which are known to exhibit anticancer [5][6][7], antibacterial [8][9][10], or antitrypanosomal activity [11], but also may serve as electrochemical biosensors [12][13], self-assembled molecular materials [14][15], decorations of carbon tubes and nanomaterials [16][17

Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates

• Péter Kisszékelyi,
• Tibor Peňaška,
• Klára Stankovianska,
• Mária Mečiarová and
• Radovan Šebesta

Beilstein J. Org. Chem. 2022, 18, 1195–1202, doi:10.3762/bjoc.18.124

• hydrogenation; Introduction Heterocyclic compounds with a benzothiazine moiety are attractive building blocks in medicinal chemistry. Benzo-1,4-thiazine derivatives possess a wide range of biological and pharmacological properties, such as anticancer and antitumor, antioxidant, antimicrobial, antibacterial

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

• well as the previously synthesised HTM222 (2) and 1 isolated from S. spectabilis. Neither 2 nor any of the stereoisomers of 4 showed antibacterial effects against a panel of Gram-positive and Gram-negative organisms (Supporting Information File 1, Table S2). Only 1 exhibited concentration-dependent