Beilstein Journal of Organic Chemistry最新文献

{"title":"Synthesis and acaricidal activity against <i>Varroa destructor</i> of α- and γ-costic acid dimers.","authors":"Alessandro Santarsiere, Ernesto Santoro, Maria Letizia Ciavatta, Marianna Carbone, Sonia Ganassi, Cosimo Tedino, Antonio De Cristofaro, Antonio Evidente, Stefano Superchi","doi":"10.3762/bjoc.22.87","DOIUrl":"10.3762/bjoc.22.87","url":null,"abstract":"<p><p>α-Costic acid is a natural sesquiterpene possessing diverse biological activities. Among these, the most promising property for practical application is its acaricidal activity against <i>Varroa destructor</i>, considered the most important and dangerous parasite of the honeybee (<i>Apis mellifera</i> L.). Infestations of <i>V. destructor</i> can decimate bee populations in just a few years, resulting in substantial environmental and economic losses. This study reports the synthesis of α- and γ-costic acid diesters with ethylene glycol and evaluates their acaricidal efficacy against <i>V. destructor</i> in comparison with their parent acids. Although the resulting dimers were approximately 50% less active than the parent costic acids, they exhibited higher potency than the previously reported α-costic acid methyl ester. Among all, γ-costic acid, whose acaricidal activity is reported here for the first time, shows the highest activity with mortality higher than 90%, thus emerging as the most promising candidate for the development of effective and environmentally friendly strategies for the control of <i>V. destructor</i>. Furthermore, it may hold potential for the biocontrol of other mite pests affecting economically important crops such as legumes and cereals, which are currently associated with significant yield losses and extensive reliance on synthetic pesticides.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1088-1096"},"PeriodicalIF":2.7,"publicationDate":"2026-07-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13402994/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148598568","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Retraction: α,ß-Didehydrosuberoylanilide hydroxamic acid (DDSAHA) as precursor and possible analogue of the anticancer drug SAHA.","authors":"Shital K Chattopadhyay, Subhankar Ghosh, Sarita Sarkar, Kakali Bhadra","doi":"10.3762/bjoc.22.86","DOIUrl":"10.3762/bjoc.22.86","url":null,"abstract":"<p><p>[This retracts the article DOI: 10.3762/bjoc.15.245.].</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1086-1087"},"PeriodicalIF":2.7,"publicationDate":"2026-07-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13402992/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148598599","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Amino acid-based surfactants: sustainable synthesis and antimicrobial mechanisms.","authors":"Rafaela Gomes Bezerra, Lourdes Pérez, Francisco Fábio Oliveira de Sousa","doi":"10.3762/bjoc.22.85","DOIUrl":"10.3762/bjoc.22.85","url":null,"abstract":"<p><p>Antimicrobial therapy is becoming increasingly ineffective over infections due to the gradual microbial resistance to conventional treatments. This aspect highlights the urgent need for the development of new antimicrobial agents. In this context, the amino acid-derived surfactants have proven to be a promising alternative to eradicate numerous microorganisms and their biofilms. The antimicrobial action of these agents can be explained by their amphiphilic structure, a configuration that allows interactions with structural components, such as the microorganism membranes and extracellular matrices of biofilms, promoting destructive effects on the cellular integrity and microbial vital processes. In addition, these surfactants can be easily synthesized using green chemistry principles, are biodegradable and more biocompatible than commercial quaternary ammonium surfactants. This paper aimed to elucidate the relevance of amino acid-derived surfactants with antimicrobial properties, presenting their structural compositions and connecting to the novel evidences on their mechanism of action. An integrative review was conducted, drawing upon findings from scientific articles published in the last 20 years (between 2005 and 2025), exclusively in English, retrieved from the PubMed database. This research employs a qualitative approach, adopting a basic research design with descriptive objectives, using a bibliographic method to explore the topic. The results indicate that the search for new amino acid-derived surfactants with antimicrobial activity has gradually grown over the last years. These molecules have shown promising characteristics, singular structures leading to innovative mechanisms of action, capable of overcoming the defenses of resistant microorganisms. In conclusion, the ability of these compounds to inhibit the growth of bacteria, yeasts, and fungi has been demonstrated, offering an effective approach to prevent and combat the spread of infections, especially in the context of microbial resistance.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1067-1085"},"PeriodicalIF":2.7,"publicationDate":"2026-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13382959/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148598580","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis of functionalized, 13-alkyl-substituted coralyne derivatives and investigation of their interactions with duplex and abasic site-containing DNA.","authors":"Laurin Beckmann, Jason Lennard Kunze, Hannah Karola Strunk, Maurice Michel, Heiko Ihmels","doi":"10.3762/bjoc.22.84","DOIUrl":"10.3762/bjoc.22.84","url":null,"abstract":"<p><p>With the goal to develop coralyne-based ligands for abasic site-containing DNA (AP-DNA), different synthetic routes towards the functionalization of coralyne were tested. In particular, the alkylation of the benzylic position in papaverine and subsequent cyclization by treatment with acetic anhydride in sulfuric acid led to the synthesis of a coralyne derivative with an alkoxyamine-functionalized linker attached at position C13. Firstly, it was demonstrated with a resembling model compound that the alkylation of the coralyne scaffold does not influence the DNA-binding properties. Furthermore, it was shown that the alkoxyamine function can be readily released from a Boc-protected precursor and that the corresponding coralyne-alkoxyamine conjugate can operate as a ligand for AP-DNA and as inhibitor of enzymatic repair of abasic sites.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1057-1066"},"PeriodicalIF":2.7,"publicationDate":"2026-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13382958/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148598553","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"One-pot four-component sequential synthesis of <i>S</i>-alkyl dithiocarbamates using lipase as a biocatalyst.","authors":"Mansour Shahedi, Pargol Tahmasebi Pour, Zohreh Habibi","doi":"10.3762/bjoc.22.83","DOIUrl":"10.3762/bjoc.22.83","url":null,"abstract":"<p><p>Dithiocarbamates are widely recognized for their versatile applications in both agriculture as effective pesticides and medicine, where they serve as antifungal and anticancer agents. As a result, their synthesis has garnered significant attention in recent years. In this study, we present an efficient one-pot four-component approach for the synthesis of these scaffolds, utilizing aldehydes, ethyl acetoacetate, carbon disulfide (CS₂), and amines. Initially, α,β-unsaturated carbonyl compounds, serving as Michael acceptors, were generated from aldehydes and ethyl acetoacetate through a decarboxylative Knoevenagel reaction under mild conditions, using lipase as a biocatalyst. These intermediates then sequentially undergo a nucleophilic addition reaction with dithiocarbamate anions, which are generated in situ by reacting CS₂ with amines. This sequence successfully yields 15 derivatives of <i>S</i>-alkylated dithiocarbamates with high to excellent yields ranging from 69% to 96%.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1048-1056"},"PeriodicalIF":2.7,"publicationDate":"2026-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13358900/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148435056","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis of novel 1,2,4-oxadiazole-isoxazoline hybrids and their in silico potential with adenosine receptors.","authors":"Pshtiwan S Mohammed, Mohammed K S Dalo, Onur C Yazıcı, Muhammet Yildirim, Akın Sağırlı","doi":"10.3762/bjoc.22.82","DOIUrl":"10.3762/bjoc.22.82","url":null,"abstract":"<p><p>A concise and efficient synthetic route to novel 1,2,4-oxadiazole-isoxazoline hybrids <b>7</b> has been developed via regioselective 1,3-dipolar cycloaddition of in situ-generated nitrile oxides with 3-(<i>p</i>-substituted-aryl)-5-vinyl-1,2,4-oxadiazoles <b>6</b>. The target compounds <b>7a-ay</b> were obtained in moderate to excellent yields (16-97%) and fully characterized by IR, NMR, and HRMS analyses. The reactions exhibited high regioselectivity, exclusively affording 5-isoxazoline derivatives, while substituent effects played a decisive role in modulating reaction efficiency. In silico studies revealed that all hybrids <b>7a-ay</b> display strong binding affinities toward the adenosine A₁ receptor (-10.0 to -8.3 kcal/mol), surpassing the co-crystallized ligand and engaging in key stabilizing interactions within the binding pocket. Furthermore, ADMET predictions indicated favorable drug-likeness, high gastrointestinal absorption, and suitable physicochemical properties. Overall, these findings identify 1,2,4-oxadiazole-isoxazoline hybrids as promising and tunable scaffolds for the development of adenosine A₁ receptor-targeted agents; however, further structural optimization and comprehensive biological evaluation are required to fully validate their therapeutic potential.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1033-1047"},"PeriodicalIF":2.7,"publicationDate":"2026-07-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13358917/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148435038","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Semisynthesis, characterisation, and antibacterial evaluation of a novel lecanoric acid-derived amide library.","authors":"Ethan D Abbott, Sasha Hayes, Jonathan M White, Bernd H A Rehm, Rohan A Davis","doi":"10.3762/bjoc.22.81","DOIUrl":"10.3762/bjoc.22.81","url":null,"abstract":"<p><p>The known lichen depside, lecanoric acid (<b>1</b>), was identified as a scaffold of interest for the generation of a unique semisynthetic biodiscovery screening library. Large-scale extraction and isolation on the Australian-sourced lichen <i>Parmotrema tinctorum</i> resulted in the purification of ≈1 g of the desired scaffold <b>1</b>, along with other known lichen metabolites that included divaricatic acid (<b>2</b>), orcinol (<b>3</b>), orsellinic acid (<b>4</b>), and methyl orsellinate (<b>5</b>). Parallel solution-phase synthesis using amidation chemistry on the abundant scaffold <b>1</b> afforded a series of novel amide derivatives <b>6</b>-<b>13</b> in high purity (>95%) and low to moderate yields (12-53%). All new semisynthetic compounds were fully characterised following 1D/2D NMR, MS and UV data analysis. Crystalline lecanoric acid was obtained during the chemical investigations of the lichen extract, enabling the first X-ray crystallographic analysis to be undertaken on this depside. Compounds <b>1</b>-<b>13</b> were evaluated for antibacterial activity against the human pathogen <i>Pseudomonas aeruginosa</i> using a biofilm inhibition assay. Of the new semisynthetics, amide analogue <b>12</b> showed the greatest planktonic cell growth inhibition (13% at 50 µM), whilst amide analogue <b>11</b> was the most active at inhibiting the formation of biofilm (21% at 50 µM).</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1023-1032"},"PeriodicalIF":2.7,"publicationDate":"2026-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13338597/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148403186","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis and optical resolution of 4,5-diaminohomoadamantane: a promising scaffold for chiral ligands and bioactive compounds.","authors":"Polina Anatolyevna Man'kova, Vadim Andreevich Shiryaev, Olga S Podlipnova, Marat M Khisyamov, Dmitry Sergeevich Nikerov, Alexander Nikolaevich Reznikov, Yuri Nikolaevich Klimochkin","doi":"10.3762/bjoc.22.80","DOIUrl":"10.3762/bjoc.22.80","url":null,"abstract":"<p><p>Vicinal diamines based on a rigid polycyclic framework such as homoadamantane remain underexplored. We anticipated that the unique steric and lipophilic properties of chiral <i>trans</i>-4,5-diaminohomoadamantane could provide the necessary stereoinduction in metal-catalyzed asymmetric reactions. In addition, such structures may serve as a novel scaffold for bioactive compounds. Herein, we report a synthetic approach to this previously inaccessible chiral scaffold. 4,5-Diaminohomoadamantane was prepared as a mixture of <i>cis</i>- and <i>trans</i>-isomers by reduction of the corresponding vicinal azidoxime with LiAlH₄. In contrast, the <i>trans</i>-isomer was selectively obtained via ring-opening of an <i>N</i>-Tf-protected aziridine. The racemic <i>trans</i>-4,5-diaminohomoadamantane was resolved with dibenzoyl-ʟ-tartaric acid. The absolute (4<i>R</i>,5<i>R</i>)-configuration was proposed on the basis of TDDFT calculations of the specific optical rotation using the CAM-B3LYP functional and the 6-311G++(2d,2p) basis set with solvation by CH₂Cl₂ in the SMD model on the base of conformational analysis. Catalytic systems based on (4<i>R</i>,5<i>R</i>)-4,5-diaminohomoadamantane derivatives exhibited low to moderate asymmetric induction in Henry and Michael reactions. These results suggest that further molecular design of homoadamantane-based chiral <i>N</i>,<i>N</i>-ligands is promising.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1013-1022"},"PeriodicalIF":2.7,"publicationDate":"2026-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13338599/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148403244","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"<i>Z</i>-Selective semihydrogenation of alkynes via Ni/Lewis acid synergistic catalyzed system using DMF as hydrogen source and solvent.","authors":"Lei Kang, Haifeng Gao, Luo Yang","doi":"10.3762/bjoc.22.79","DOIUrl":"10.3762/bjoc.22.79","url":null,"abstract":"<p><p>A Ni/Lewis acid dual-catalytic system has been developed for the <i>Z</i>-selective semihydrogenation of alkynes. Utilizing DMF as both the hydrogen donor and reaction medium, this method affords <i>Z</i>-alkenes in high yield with excellent stereoselectivity under mild conditions. The protocol employs cost-effective and readily available catalysts, and demonstrates broad applicability across a wide range of substrates.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1004-1012"},"PeriodicalIF":2.7,"publicationDate":"2026-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13338598/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148403223","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Rh(III)-catalyzed chelation-assisted C-H activation/annulation of 2-arylimidazolines with cyclic diazo-1,3-dicarbonyl compounds: a novel approach to tetracyclic annulated derivatives of 2,3-dihydroimidazo[2,1-<i>a</i>]isoquinoline.","authors":"Ivan Lyutin, Grigory Kantin, Olga Bakulina, Dmitry Dar'in","doi":"10.3762/bjoc.22.78","DOIUrl":"10.3762/bjoc.22.78","url":null,"abstract":"<p><p>2-Arylimidazolines were annulated with cyclic diazo-1,3-dicarbonyl compounds under Rh(III)-catalysis for the first time. The developed general and efficient approach based on CH-activation allowed the efficient preparation of five novel types of tetraheterocyclic systems derived from 2,3-dihydroimidazo[2,1-<i>a</i>]isoquinolines fused with an additional five-, six- or seven-membered carbocycle or <i>N</i>-/<i>O</i>-heterocycle.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"997-1003"},"PeriodicalIF":2.7,"publicationDate":"2026-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13338596/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148403210","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}