Beilstein Journal of Organic Chemistry最新文献

{"title":"The surprising reaction of (chloro- and methanesulfonyloxy)(phenyl)methylphosphonates and -(phenyl)methylphosphine oxides with potassium diphenylphosphide followed by oxidation.","authors":"Zsuzsanna Szalai, Janka Bednárik, András Miskó, Angéla Takács, László Kőhidai, László Drahos, György Keglevich","doi":"10.3762/bjoc.22.93","DOIUrl":"10.3762/bjoc.22.93","url":null,"abstract":"<p><p>α-Hydroxyphosphonates and α-hydroxyphosphine oxides are important intermediates for additional biologically active species. While (hydroxy(phenyl)methyl)(diphenyl)phosphine oxide did not even undergo chlorination with thionyl chloride, the reaction of diethyl chloro(phenyl)methylphosphonate with potassium diphenylphosphide followed by oxidation with hydrogen peroxide resulted in the expected bis(>P(O)-functionalized) product only as a minor component. The similar reaction of the analogous (methanesulfonyloxy)(phenyl)methyl derivative afforded a mixture of a diethyl (diethoxyphosphonyl)(phenyl)methyl phosphate, a diethyl (diphenylphosphinyl)(phenyl)methyl phosphate, and a ((diphenylphosphinyl)(phenyl)methyl) diphenylphosphinate. The formation of the unexpected products was explained assuming rearrangements and reversible formation of the hydroxymethylene-bis(>P(O)-functionalized) intermediate. Contrary to the earlier experiences, the reaction of ((methanesulfonyloxy)(phenyl)methyl)(diaryl)phosphine oxides with potassium diphenylphosphide followed by oxidation took place in a clear-cut manner providing, with one exception, the corresponding α-phosphinylated α-hydroxyphosphine oxides that could also be synthesized by direct phosphinylation of the starting α-hydroxyphosphine oxide. Cell viability assays performed on U266 myeloma cells revealed concentration-dependent antiproliferative effects of the synthesized compounds on U266 myeloma cells, highlighting the key role of the phosphinoyloxy moiety in the cytotoxic activity, which may be enhanced further by 4-methyl groups in the P-phenyl rings.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1160-1167"},"PeriodicalIF":2.7,"publicationDate":"2026-08-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13501233/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148811949","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":"A cascade synthesis of 2-aminothiochromones from 2-fluorophenyl ketone and thiocarbonyldiimidazole.","authors":"Kai Zhang, Haofan Shao, Kangjun Liao, Ying Xu, Shimei Du, Yanfang Zhao, Gang Li, Wenzhen Xu, Haihong Huang, Peng Li","doi":"10.3762/bjoc.22.92","DOIUrl":"https://doi.org/10.3762/bjoc.22.92","url":null,"abstract":"<p><p>A highly efficient cascade synthesis of various substituted 2-aminothiochromones was developed. The commercially available thiocarbonyldiimidazole (TCDI) acted as a key precursor in the construction of a sulfur-containing scaffold from 2-fluorophenyl ketone. Subsequent conjugated addition-elimination resulted in the corresponding 2-aminothiochromones under mild conditions. This simple protocol tolerates a broad range of functional groups and provides concise access to various 2-aminothiochromones in good to excellent yields (up to 94%).</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1151-1159"},"PeriodicalIF":2.7,"publicationDate":"2026-08-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13478896/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148787678","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":"Construction of CF₂ moieties in FDA-approved drugs (2016-2025): industrial routes, mechanisms, and scale-up considerations.","authors":"Wenyan Yao, Huanhuan Zhang, Xiaolong Yang, Feng Liu","doi":"10.3762/bjoc.22.91","DOIUrl":"10.3762/bjoc.22.91","url":null,"abstract":"<p><p>The incorporation of CF₂ moieties into drug molecules offers unique advantages in improving metabolic stability and target affinity, making their efficient construction a major focus in pharmaceutical process chemistry. This review systematically examines the synthetic processes of 12 FDA-approved CF₂-containing drugs from 2016 to 2025, categorizing them according to the chemical environment of the CF₂ group (alkyl-CF₂, heteroaryl-CF₂, and ArO-CF₂). For each drug, the industrial routes for CF₂ construction and the reasons for eliminating alternative routes are analyzed. Methods for CF₂ formation are classified into two major strategies: fluorinating reagent-based approaches and building block-based approaches. Key process steps and scale-up data are summarized in Table 1. The article systematically discusses four types of reaction mechanisms - nucleophilic fluorination, electrophilic fluorination, radical pathways, and carbene insertion - and evaluates their applicability in industrial production. The analysis shows that for alkyl-CF₂ groups, the industry strongly favors preformed CF₂ building blocks or indirect fluorination strategies to avoid hazardous reagents and harsh conditions. Continuous flow technology using SF₄ has emerged as an important complement to traditional fluorination methods. For heteroaryl-CF₂ groups, metal-catalyzed direct introduction of the CF₂ unit still faces challenges for industrial application, whereas the difluorocarbene route for ArO-CF₂ has been validated. This review provides a reference for process development of new CF₂-containing drugs, from strategic design to scale-up evaluation.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1122-1150"},"PeriodicalIF":2.7,"publicationDate":"2026-08-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13454886/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148705329","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":"Discovery of sugarnitriles A and B, and structural reassignment of SF-2140, from a sugarcane endophytic actinomycete <i>Amycolatopsis</i> sp. JS-O27.","authors":"Qiuyun Li, Ying Liu, Baoyue Wei, Yu Sun, Di Mao, Yanmin Zou, Shan Lu","doi":"10.3762/bjoc.22.90","DOIUrl":"10.3762/bjoc.22.90","url":null,"abstract":"<p><p>Three rare cyano-substituted indole <i>N</i>-glycosides, SF-2140 (<b>1</b>) and its two previously undescribed derivatives, sugarnitriles A (<b>2</b>) and B (<b>3</b>), were isolated from a sugarcane endophytic actinomycete <i>Amycolatopsis</i> sp. JS-O27. The planar structures of <b>1</b>-<b>3</b> were established by HRESIMS data and detailed 1D/2D NMR spectroscopic analysis, and the conformations of the sugar moieties were deduced by the analysis of ³ <i>J</i> _H-H coupling constants and NOESY data, and comparison of their electronic circular dichroism (ECD) spectra. Compounds <b>1</b> and <b>3</b> exhibited moderate to weak antibacterial activity against <i>Escherichia coli</i> at 100 μg/mL.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1114-1121"},"PeriodicalIF":2.7,"publicationDate":"2026-07-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13430523/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148668213","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":"Rhodopyran, a carboxylated hexahydrocyclopenta[<i>b</i>]pyran from <i>Rhodococcus</i>.","authors":"Enjuro Harunari, Sara Fushimi, Yasuhiro Igarashi","doi":"10.3762/bjoc.22.89","DOIUrl":"10.3762/bjoc.22.89","url":null,"abstract":"<p><p>A new bicyclic metabolite, rhodopyran (<b>1</b>), was isolated from the culture broth of <i>Rhodococcus</i> sp. strain RD066637. The planar structure was elucidated by 1D/2D NMR analyses and HRMS spectrometry, and the relative configuration was assigned from vicinal coupling constants and NOESY correlations, while the absolute configuration remains undetermined. Rhodopyran represents a structurally unusual carboxylated hexahydrocyclopenta[<i>b</i>]pyran and expands the known metabolite diversity of <i>Rhodococcus</i>, highlighting <i>Rhodococcus</i> as a source of uncommon natural-product scaffolds.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1107-1113"},"PeriodicalIF":2.7,"publicationDate":"2026-07-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13430524/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148668147","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":"Controlled supramolecular assemblies of luminescent tridentate cyclometalated alkynylgold(III) amphiphiles in aqueous media.","authors":"Kelvin Sze-Yim Cai, Brian Boyan Liu, Franco King-Chi Leung","doi":"10.3762/bjoc.22.88","DOIUrl":"10.3762/bjoc.22.88","url":null,"abstract":"<p><p>Gold(III) complexes and amphiphiles have been extensively investigated over a decade. Supramolecular assemblies of gold(III) amphiphiles in aqueous media exhibit high sensitivities to external stimulations for soft functional materials. Herein, we introduce a new molecular design of a tridentate cyclometalated gold(III) amphiphile (<b>GA</b>) with flexible molecular structure modifications. Counterion exchange with sodium tosylate induces notable luminescent enhancement and enables control over supramolecular assembly processes. This approach drives a supramolecular assembly transformation of <b>GA</b> from disordered nanosheets to well-ordered nanoribbons upon the additions of multiple equivalents of counterion, enabling a tunable pathway for controlled supramolecular transformation.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1097-1106"},"PeriodicalIF":2.7,"publicationDate":"2026-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13402995/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148598583","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 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}