Beilstein Journal of Organic Chemistry最新文献_第2页

One-pot four-component sequential synthesis of S-alkyl dithiocarbamates using lipase as a biocatalyst. 以脂肪酶为生物催化剂，一锅法四组分顺序合成s -烷基二硫代氨基甲酸酯。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-07-10 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.83

Mansour Shahedi, Pargol Tahmasebi Pour, Zohreh Habibi

引用次数: 0

Synthesis of novel 1,2,4-oxadiazole-isoxazoline hybrids and their in silico potential with adenosine receptors. 新型1,2,4-恶二唑-异恶唑啉杂合体的合成及其与腺苷受体的硅电位。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-07-06 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.82

Pshtiwan S Mohammed, Mohammed K S Dalo, Onur C Yazıcı, Muhammet Yildirim, Akın Sağırlı

{"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":"A concise and efficient synthetic route to novel 1,2,4-oxadiazole-isoxazoline hybrids 7 has been developed via regioselective 1,3-dipolar cycloaddition of in situ-generated nitrile oxides with 3-(p-substituted-aryl)-5-vinyl-1,2,4-oxadiazoles 6. The target compounds 7a-ay 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 7a-ay 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.","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}

引用次数: 0

Semisynthesis, characterisation, and antibacterial evaluation of a novel lecanoric acid-derived amide library. 一种新型皂荚酸衍生酰胺文库的半合成、表征和抗菌评价。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-07-01 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.81

Ethan D Abbott, Sasha Hayes, Jonathan M White, Bernd H A Rehm, Rohan A Davis

{"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":"The known lichen depside, lecanoric acid (1), 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 Parmotrema tinctorum resulted in the purification of ≈1 g of the desired scaffold 1, along with other known lichen metabolites that included divaricatic acid (2), orcinol (3), orsellinic acid (4), and methyl orsellinate (5). Parallel solution-phase synthesis using amidation chemistry on the abundant scaffold 1 afforded a series of novel amide derivatives 6-13 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 1-13 were evaluated for antibacterial activity against the human pathogen Pseudomonas aeruginosa using a biofilm inhibition assay. Of the new semisynthetics, amide analogue 12 showed the greatest planktonic cell growth inhibition (13% at 50 µM), whilst amide analogue 11 was the most active at inhibiting the formation of biofilm (21% at 50 µM).","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}

引用次数: 0

Synthesis and optical resolution of 4,5-diaminohomoadamantane: a promising scaffold for chiral ligands and bioactive compounds. 4,5-二氨基金刚烷的合成及光学分辨：一种有前途的手性配体和生物活性化合物支架。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-07-01 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.80

Polina Anatolyevna Man'kova, Vadim Andreevich Shiryaev, Olga S Podlipnova, Marat M Khisyamov, Dmitry Sergeevich Nikerov, Alexander Nikolaevich Reznikov, Yuri Nikolaevich Klimochkin

{"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":"Vicinal diamines based on a rigid polycyclic framework such as homoadamantane remain underexplored. We anticipated that the unique steric and lipophilic properties of chiral trans-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 cis- and trans-isomers by reduction of the corresponding vicinal azidoxime with LiAlH4. In contrast, the trans-isomer was selectively obtained via ring-opening of an N-Tf-protected aziridine. The racemic trans-4,5-diaminohomoadamantane was resolved with dibenzoyl-ʟ-tartaric acid. The absolute (4R,5R)-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 (4R,5R)-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 N,N-ligands is promising.","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}

引用次数: 0

Z-Selective semihydrogenation of alkynes via Ni/Lewis acid synergistic catalyzed system using DMF as hydrogen source and solvent. 以DMF为氢源和溶剂，Ni/Lewis酸协同催化体系中炔的z选择性半加氢。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-30 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.79

Lei Kang, Haifeng Gao, Luo Yang

引用次数: 0

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-a]isoquinoline. Rh（III）催化螯合辅助2-芳基咪唑啉与环重氮-1,3-二羰基化合物的C-H活化/环化：制备2,3-二氢咪唑[2,1-a]异喹啉四环衍生物的新方法。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-30 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.78

Ivan Lyutin, Grigory Kantin, Olga Bakulina, Dmitry Dar'in

引用次数: 0

The role of spacer length and flexibility in peptide self-assembly. 间隔段长度和灵活性在肽自组装中的作用。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-25 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.77

Julian Link, Albin Lahu, Manfred Wagner, Tanja Weil, David Y W Ng

引用次数: 0

Novel macrocycles: from synthesis to supramolecular function. 新型大环：从合成到超分子功能。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-24 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.76

Veronica Iuliano, Carmen Talotta, Margherita De Rosa, Paolo Della Sala, Konrad Tiefenbacher, Pablo Ballester, Carmine Gaeta

引用次数: 0

Electrochemical reduction of unsaturated carbon-carbon bonds via 3d transition-metal catalysis. 通过三维过渡金属催化的电化学还原不饱和碳-碳键。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-17 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.75

Geon Kang, Minki Jeon, Pooja Kumari Jat, Cheoljae Kim, Isaac Choi

引用次数: 0

Synthesis of sterically shielded piperidine nitroxides via acid-catalyzed heterocyclization of β-aminoketone derivatives with ketones. 酸催化β-氨基酮衍生物与酮的杂环化合成立体屏蔽哌啶类氮氧化物。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-17 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.74

Mark M Gulman, Yurii I Glazachev, Sergey A Dobrynin

{"title":"Synthesis of sterically shielded piperidine nitroxides via acid-catalyzed heterocyclization of β-aminoketone derivatives with ketones.","authors":"Mark M Gulman, Yurii I Glazachev, Sergey A Dobrynin","doi":"10.3762/bjoc.22.74","DOIUrl":"10.3762/bjoc.22.74","url":null,"abstract":"The capabilities of modern methods for the synthesis of sterically shielded piperidine nitroxides with acyclic substituents are largely limited to symmetrical tetraethyl structures and do not allow the introduction of functional groups into position 2. We propose an alternative approach that allows for the variation of substituents adjacent to the nitroxyl group, which significantly expands the potential of sterically hindered nitroxides for promising applications in materials science and structural biology. The new heterocyclization strategy implies the construction of a 2,2,6-trisubstituted piperidine scaffold from β-aminoketone acetals and dialkyl ketones under acid catalysis. The resulting amines were oxidized to the corresponding ketonitrones and subsequent reaction with moderately basic organometallic reagents, such as 2-alkynyl- and 2-allylmagnesium halides, enables the facile introduction of diverse substituents, including those with functional groups. If necessary, the multiple carbon-carbon bonds in the side chain can be subjected to hydrogenation to give saturated alkyl or functionalized alkyl groups. The study of reduction kinetics for alkyl and allyl-substituted piperidine nitroxides in ascorbate/glutathione media (30% EtOH, pH 7.5) yielded second-order rate constants of ≈10-2 M-1·s-1, which is close to that earlier reported for 2,2,6,6-tetraethylpiperidine (TEEPONE).","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"948-954"},"PeriodicalIF":2.7,"publicationDate":"2026-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13284749/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148306585","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}

引用次数: 0