Beilstein Journal of Organic Chemistry最新文献

{"title":"Synthesis, structure, ionochromic and cytotoxic properties of new 2-(indolin-2-yl)-1,3-tropolones.","authors":"Yurii A Sayapin, Eugeny A Gusakov, Inna O Tupaeva, Alexander D Dubonosov, Igor V Dorogan, Valery V Tkachev, Anna S Goncharova, Gennady V Shilov, Natalia S Kuznetsova, Svetlana Y Filippova, Tatyana A Krasnikova, Yanis A Boumber, Alexey Y Maksimov, Sergey M Aldoshin, Vladimir I Minkin","doi":"10.3762/bjoc.21.26","DOIUrl":"10.3762/bjoc.21.26","url":null,"abstract":"<p><p>The acid-catalyzed reaction of benzo[<i>e</i>(<i>g</i>)] derivatives of 2,3,3-trimethylindolenines with <i>o</i>-chloranil leads to new 2-(benzo[<i>e</i>(<i>g</i>)]indolin-2-yl)-5,6,7-trichloro-1,3-tropolones and 2-(benzo[<i>e</i>(<i>g</i>)]indolin-2-yl)-4,5,6,7-tetrachloro-1,3-tropolones. Based on the results of PBE0/6-311+G(d,p) calculations, the structural and energetic characteristics of the tautomeric forms of the obtained 1,3-tropolones were determined. The structure of 2-(3,3-dimethyl-3<i>H</i>-benzo[<i>g</i>]indolin-2-yl)-5,6,7-trichloro-1,3-tropolone was determined by X-ray diffraction analysis. The compounds obtained are capable of switching emission at 420-440 nm and 476-530 nm upon successive exposure to CN^- and Hg²⁺ ions in an acetonitrile solution. 2-(1,1-Dimethyl-1<i>H</i>-benzo[<i>e</i>]indolin-2-yl)-5,6,7-trichloro-1,3-tropolone exhibited high in vitro cytotoxic activity against A431 skin cancer and H1299 lung cancer cell lines.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"358-368"},"PeriodicalIF":2.2,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11849549/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143490430","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, characterization, antimicrobial, cytotoxic and carbonic anhydrase inhibition activities of multifunctional pyrazolo-1,2-benzothiazine acetamides.","authors":"Ayesha Saeed, Shahana Ehsan, Muhammad Zia-Ur-Rehman, Erin M Marshall, Sandra Loesgen, Abdus Saleem, Simone Giovannuzzi, Claudiu T Supuran","doi":"10.3762/bjoc.21.25","DOIUrl":"10.3762/bjoc.21.25","url":null,"abstract":"<p><p>The advent of antibiotic resistance in microorganisms requires the discovery and synthesis of novel antibiotics. At the same time, human pathogens are contributing to chronic and persistent inflammation. Motivated by these two concerning issues, new antibiotic drug candidates are synthesized by incorporation of benzothiazine, pyrazole, and amide moieties in a new scaffold to create multifunctional derivatives of pyrazolo-1,2-benzothiazine. The presented compounds have been synthesized and analyzed using spectroscopic and spectrometric techniques including FTIR, HRMS, ¹H and ¹³C NMR spectroscopy. All compounds were tested against five human microbial strains including three different strains of <i>Staphylococcus aureus</i> (ATCC 25923, ATCC BAA-41, and ATCC BAA-44), <i>Escherichia coli</i> (ATCC 8739), and <i>Candida albicans</i> (ATCC 90027) to evaluate their antibiotic potential. The results showed that out of fourteen synthesized compounds, <b>7b</b> (MIC₉₀ = 16 μg/mL) and <b>7h</b> (MIC₉₀ = 8.0 μg/mL) exhibited potent antibiotic activity against different strains of <i>S. aureus</i> (susceptible, methicillin-resistant, and multidrug-resistant). Cytotoxic studies against the human colon cancer mammalian cell line HCT-116 (ATCC CCL-247) revealed that only compound <b>7l</b> inhibited cell viability, while the rest of the compounds including <b>7b</b> and <b>7h</b> showed no significant decrease in mammalian cell viability. Results of human carbonic anhydrase (hCA) inhibition assays discovered that monoalkylated derivatives have low to negligible inhibition potential but dialkylated ones have no inhibition potential at all for directed CAs (I, II, IX, and XII). From the low inhibiting compounds, <b>7b</b> showed the highest inhibition potential with a minimum <i>K</i> _i value of 72.9 μM. In light of the above findings, these newly prepared scaffolds are valuable additions to the class of pyrazolo-1,2-benzothiazine antibiotics with selective antistaphylococcal activity.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"348-357"},"PeriodicalIF":2.2,"publicationDate":"2025-02-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11833175/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143447931","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 new condensed naphthoquinone, pyran and pyrimidine furancarboxylates.","authors":"Kirill A Gomonov, Vasilii V Pelipko, Igor A Litvinov, Ilya A Pilipenko, Anna M Stepanova, Nikolai A Lapatin, Ruslan I Baichurin, Sergei V Makarenko","doi":"10.3762/bjoc.21.24","DOIUrl":"10.3762/bjoc.21.24","url":null,"abstract":"<p><p>New representatives of dioxodihydronaphtho[2,3-<i>b</i>]furan-, furo[3,2-<i>c</i>][1]benzopyran-, furo[2,3-<i>d</i>]pyrano[4,3-<i>b</i>]pyran-, furo[2',3':4,5]pyrano[3,2-<i>c</i>]chromene-, and furo[2,3-<i>d</i>]pyrimidine carboxylates were obtained from the reactions of alkyl 3-bromo-3-nitroacrylates with representatives of carbo- and heterocyclic CH-acids under simple conditions, without the use of organocatalysts. The structures of the synthesized compounds were proven by a set of physicochemical methods, including X-ray diffraction analysis.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"340-347"},"PeriodicalIF":2.2,"publicationDate":"2025-02-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11833173/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143447840","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":"Antibiofilm and cytotoxic metabolites from the entomopathogenic fungus <i>Samsoniella aurantia</i>.","authors":"Rita Toshe, Syeda J Khalid, Blondelle Matio Kemkuignou, Esteban Charria-Girón, Paul Eckhardt, Birthe Sandargo, Kunlapat Nuchthien, J Jennifer Luangsa-Ard, Till Opatz, Hedda Schrey, Sherif S Ebada, Marc Stadler","doi":"10.3762/bjoc.21.23","DOIUrl":"10.3762/bjoc.21.23","url":null,"abstract":"<p><p>During the course of our studies on the secondary metabolism of rare, hitherto untapped Thai insect-associated fungi, the ethyl acetate (EtOAc) extract derived from solid-state cultivation of <i>Samsoniella aurantia</i> on rice afforded one previously undescribed tetramic acid derivative, farinosone D (<b>1</b>), along with the known 2-pyridones, farinosones A (<b>2</b>) and B (<b>3</b>), and the known cyclodepsipeptides beauvericins A-C (<b>4</b>-<b>6</b>). All isolated compounds were assessed for their antimicrobial and cytotoxic activities while farinosones D (<b>1</b>) and A (<b>2</b>) were selected for biofilm inhibitory activity assay. Farinosone B (<b>3</b>) and beauvericins A-C (<b>4</b>-<b>6</b>) showed significant cytotoxic activities with IC₅₀ values in the low micromolar to nanomolar range against several mammalian cell lines. On the other hand, farinosone A (<b>2</b>), which lacked potent cytotoxic effects, revealed potent antibiofilm activity, inhibiting approximately 70% of <i>Staphylococcus aureus</i> biofilms at concentrations as low as 3.9 µg/mL.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"327-339"},"PeriodicalIF":2.2,"publicationDate":"2025-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11833177/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143447838","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":"Red light excitation: illuminating photocatalysis in a new spectrum.","authors":"Lucas Fortier, Corentin Lefebvre, Norbert Hoffmann","doi":"10.3762/bjoc.21.22","DOIUrl":"10.3762/bjoc.21.22","url":null,"abstract":"<p><p>Red-light-activated photocatalysis has become a powerful approach for achieving sustainable chemical transformations, combining high efficiency with energy-saving, mild conditions. By harnessing the deeper penetration and selectivity of red and near-infrared light, this method minimizes the side reactions typical of higher-energy sources, making it particularly suited for large-scale applications. Recent advances highlight the unique advantages of both metal-based and metal-free catalysts under red-light irradiation, broadening the range of possible reactions, from selective oxidations to complex polymerizations. In biological contexts, red-light photocatalysis enables innovative applications in phototherapy and controlled drug release, exploiting its tissue penetration and low cytotoxicity. Together, these developments underscore the versatility and impact of red-light photocatalysis, positioning it as a cornerstone of green organic chemistry with significant potential in synthetic and biomedical fields.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"296-326"},"PeriodicalIF":2.2,"publicationDate":"2025-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11809576/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143389909","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":"Oxidation of [3]naphthylenes to cations and dications converts local paratropicity into global diatropicity.","authors":"Abel Cárdenas, Zexin Jin, Yong Ni, Jishan Wu, Yan Xia, Francisco Javier Ramírez, Juan Casado","doi":"10.3762/bjoc.21.20","DOIUrl":"10.3762/bjoc.21.20","url":null,"abstract":"<p><p>Oxidized states of polycyclic aromatic hydrocarbons are of importance as they represent charged conductive species in organic semiconductor substrates. In this work, we investigated the properties of radical cations and dications of linear and angular [3]naphthylenes, consisting of fused aromatic naphthalenoid and antiaromatic cyclobutadienoid moieties and containing different degrees of paratropicity. Electronic absorption and vibrational Raman spectroscopies were used to describe the more relevant bonding changes. Stretching force constants were evaluated to monitor the aromatic-antiaromatic alternation pattern upon oxidation. They showed us that the dication of linear [3]naphthylene became an overall global π-electron delocalized molecule. This result was supported by nucleus independent chemical shift (NICS) calculations and anisotropy of the current induced density (ACID) plots, as they evidenced the presence of a perimetral diatropic global ring current upon oxidation.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"277-285"},"PeriodicalIF":2.2,"publicationDate":"2025-02-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11809581/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143389905","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":"Three-component reactions of conjugated dienes, CH acids and formaldehyde under diffusion mixing conditions.","authors":"Dmitry E Shybanov, Maxim E Kukushkin, Eugene V Babaev, Nikolai V Zyk, Elena K Beloglazkina","doi":"10.3762/bjoc.21.18","DOIUrl":"10.3762/bjoc.21.18","url":null,"abstract":"<p><p>A diffusion mixing technique with a volatile reagent was successfully used to generate crotonic condensation adducts of active methylene compounds and formaldehyde at room temperature in the absence of strong acids and bases. The formed adducts were highly reactive intermediates capable of reacting with dienes in a three-component reaction, leading to the formation of Diels-Alder main reaction products.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"262-269"},"PeriodicalIF":2.2,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11809574/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143389932","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 characterizations of highly luminescent 5-isopropoxybenzo[<i>rst</i>]pentaphene.","authors":"Islam S Marae, Jingyun Tan, Rengo Yoshioka, Zakaria Ziadi, Eugene Khaskin, Serhii Vasylevskyi, Ryota Kabe, Xiushang Xu, Akimitsu Narita","doi":"10.3762/bjoc.21.19","DOIUrl":"10.3762/bjoc.21.19","url":null,"abstract":"<p><p>A benzo[<i>rst</i>]pentaphene (BPP) substituted by an isopropoxy group (BPP-OiPr) was synthesized in a facile manner. Its photophysical properties were investigated by UV-vis absorption and fluorescence spectroscopy in compassion to pristine BPP and its oxidation product, benzo[<i>rst</i>]pentaphene-5,8-dione (BPP-dione). BPP-OiPr exhibited a significantly enhanced photoluminescence quantum yield (PLQY), reaching 73% in comparison to pristine BPP (13%). BPP-dione, when compared to the parent BPP, also displayed improved absorption and emission from the first excited singlet (S₁) state with a PLQY of 62% and an intramolecular charge-transfer character. The rod-like nano- to microcrystals as well as longer wires of these BPPs were also revealed by scanning electron microscopy. The intriguing optical properties of BPP and its derivatives may lead to their application as fluorophores.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"270-276"},"PeriodicalIF":2.2,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11809583/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143389915","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 disulfides and 3-sulfenylchromones from sodium sulfinates catalyzed by TBAI.","authors":"Zhenlei Zhang, Ying Wang, Xingxing Pan, Manqi Zhang, Wei Zhao, Meng Li, Hao Zhang","doi":"10.3762/bjoc.21.17","DOIUrl":"10.3762/bjoc.21.17","url":null,"abstract":"<p><p>A new synthetic method for disulfides and 3-sulfenylchromones is reported. This innovative approach is based on the tetrabutylammonium iodide (TBAI)/H₂SO₄ reduction system using sodium sulfinate as key component, thus eliminating the need for thiols and redox reagents commonly used in traditional methods. Various disulfides and 3-sulfenylchromones were obtained in moderate to excellent yields through this methodology. Mechanistic studies indicate that thiosulfonates play an important role in the reaction process.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"253-261"},"PeriodicalIF":2.2,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11809575/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143389922","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":"Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory.","authors":"Misato Suganuma, Daichi Kitagawa, Shota Hamatani, Seiya Kobatake","doi":"10.3762/bjoc.21.16","DOIUrl":"10.3762/bjoc.21.16","url":null,"abstract":"<p><p>Aza-diarylethene has been developed as a new family of photochromic compounds. This study explores the photochromic properties and thermal back reactivities of various aza-diarylethene regioisomers (<b>N1</b>-<b>N4</b> and <b>I1</b>-<b>I4</b>) in <i>n</i>-hexane. These molecules exhibit fast thermally reversible photochromic reactions driven by 6π aza-electrocyclization. Kinetic analysis of the thermal back reaction revealed activation parameters, highlighting how the substitution position of the aryl group affects the thermal stability. Additionally, density functional theory calculations identified M06 and MPW1PW91 as the most accurate functionals for predicting the thermal back reactivity, closely matching the experimental data. These findings offer valuable insights for the design of advanced photochromic materials with tailored thermal and photophysical characteristics.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"242-252"},"PeriodicalIF":2.2,"publicationDate":"2025-01-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11789678/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143121747","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}