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Novel fluorinated thiazolidin-4-one derivatives: synthesis and anti-cancer potential against HepG2 and HCT116 cell lines 新型氟化噻唑烷-4-酮衍生物：合成及对 HepG2 和 HCT116 细胞系的抗癌潜力
IF 1.1 4区 化学
Australian Journal of Chemistry Pub Date : 2024-08-19 DOI: 10.1071/ch23123
Shreyash D. Kadam, Denni Mammen, Vishwanath Zunjar, Rahul R. Bagul
{"title":"Novel fluorinated thiazolidin-4-one derivatives: synthesis and anti-cancer potential against HepG2 and HCT116 cell lines","authors":"Shreyash D. Kadam, Denni Mammen, Vishwanath Zunjar, Rahul R. Bagul","doi":"10.1071/ch23123","DOIUrl":"https://doi.org/10.1071/ch23123","url":null,"abstract":"<p>A novel synthetic route has been designed to introduce fluorine functionality into a series of compounds containing thiazolidin-4-one rings. These compounds were synthesised from various aniline derivatives using a two-step approach: an addition reaction of ethyl isothiocyanate with different aromatic fluorinated anilines, followed by cyclisation to yield the final products. A total of 15 novel fluorinated thiazolidinone compounds were synthesised and characterised using <sup>1</sup>H NMR, <sup>19</sup>F NMR, Fourier transform–infrared, elemental analysis and liquid chromatography–mass spectrometry. Stereochemistry around the imine bond in the synthesised derivatives was determined using nuclear Overhauser effect spectroscopy. The <i>in vitro</i> anticancer potential of the compounds was tested against two human cancer cell lines, liver (HepG2) and colon (HCT116). The study revealed that the derivatives having fluorine functionality at both the <i>m-</i>positions in the aromatic ring showed promising anticancer potential, as compared to those at <i>o-</i> and <i>p-</i>positions.</p>","PeriodicalId":8575,"journal":{"name":"Australian Journal of Chemistry","volume":"62 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2024-08-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142223856","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Unlocking therapeutic potential: the role of adamantane in drug discovery 挖掘治疗潜力：金刚烷在药物研发中的作用
IF 1.1 4区 化学
Australian Journal of Chemistry Pub Date : 2024-08-02 DOI: 10.1071/ch24075
Chianna Dane, Grace A. Cumbers, Beau Allen, Andrew P. Montgomery, Jonathan J. Danon, Michael Kassiou
{"title":"Unlocking therapeutic potential: the role of adamantane in drug discovery","authors":"Chianna Dane, Grace A. Cumbers, Beau Allen, Andrew P. Montgomery, Jonathan J. Danon, Michael Kassiou","doi":"10.1071/ch24075","DOIUrl":"https://doi.org/10.1071/ch24075","url":null,"abstract":"<p>The unique structural and physicochemical properties of adamantane and its derivatives have attracted considerable attention in the field of medicinal chemistry. Substituting phenyl rings for adamantane or its derivatives has provided a promising strategy to introduce lipophilicity and escape the ‘flat land’ of modern drug discovery. Additionally, the unique three-dimensional structure of adamantane facilitates the precise positioning of substituents allowing for a more effective exploration of drug targets. Evidently, we have seen an increased use of adamantane in pharmaceutically relevant molecules. The following Account highlights our group’s research in five drug discovery programs over the past 15 years showcasing the use of adamantane and its analogues in these studies.</p>","PeriodicalId":8575,"journal":{"name":"Australian Journal of Chemistry","volume":"22 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141935737","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Significant promotion of NO separation selectivity from flue gas by the –NH 2 functional group on Fe–Ni bimetallic MOF at ambient conditions 在环境条件下，Fe-Ni 双金属 MOF 上的 -NH 2 官能团可显著提高烟气中 NO 的分离选择性
IF 1.1 4区 化学
Australian Journal of Chemistry Pub Date : 2024-07-19 DOI: 10.1071/ch24060
Hao Li, Han Zhang, Xinyu Yue, Jingshu Ban, Jie Hu, Fushun Tang
{"title":"Significant promotion of NO separation selectivity from flue gas by the –NH 2 functional group on Fe–Ni bimetallic MOF at ambient conditions","authors":"Hao Li, Han Zhang, Xinyu Yue, Jingshu Ban, Jie Hu, Fushun Tang","doi":"10.1071/ch24060","DOIUrl":"https://doi.org/10.1071/ch24060","url":null,"abstract":"<p>In this paper, the bimetallic metal–organic frameworks (MOFs) of FeNi-BDC and FeNi-BDC-NH<sub>2</sub> (BDC, 1,4-benzenedicarboxylate) with similar Fe/Ni molar ratio, crystal structure, porosity and thermal stability were synthesized by a solvothermal method. The results of adsorption experiments at ambient conditions showed that the adsorptive uptake of NO, CO<sub>2</sub>, O<sub>2</sub> and N<sub>2</sub> on FeNi-BDC were all very small under different adsorption partial pressures, with FeNi-BDC displaying a weak adsorption property because of its lack of unsaturated adsorption sites. On the contrary, at 100 kPa, the adsorption of NO by FeNi-BDC-NH<sub>2</sub> was considerably higher than that by FeNi-BDC, indicating that the incorporation of NH<sub>2</sub> on the ligand could effectively enhance the adsorption of NO. The adsorption capacity of FeNi-BDC-NH<sub>2</sub> for NO reached 142.17 cm<sup>3</sup> g<sup>−1</sup>, which was considerably higher than its capacity for CO<sub>2</sub>, O<sub>2</sub> and N<sub>2</sub> under the same conditions. Ideal Adsorption Solution Theory simulations calculated the adsorption selectivity for NO/CO<sub>2</sub> and NO/O<sub>2</sub> under a mixed atmosphere to reach 1325 and 13,346 respectively, demonstrating high adsorption selectivity. Through <i>in situ</i> infrared experiments and calculations of the enthalpy of adsorption, it was demonstrated that FeNi-BDC-NH<sub>2</sub> adsorbed NO because NO can combine with NH<sub>2</sub> in the material to form a NONOate structure. A preliminarily exploration of the mechanism of NO adsorption and the influence of NH<sub>2</sub> functional groups on the adsorption and separation of NO revealed that the selectivity of adsorption was closely related to the variability of the enthalpy of adsorption. This also provided a new strategy for the adsorption and separation of NO in the flue gas environment.</p>","PeriodicalId":8575,"journal":{"name":"Australian Journal of Chemistry","volume":"24 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2024-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141746325","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis, characterization and base hydrolysis of cobalt(III) complexes coordinated by substituted phenylthioether ligands 取代苯硫醚配体配位的钴(III)配合物的合成、表征和碱水解
IF 1.1 4区 化学
Australian Journal of Chemistry Pub Date : 2024-07-17 DOI: 10.1071/ch24012
Lee Roecker, Alicia Cohn, Thomas Cox, Rachel Ceaglske, Olivia Rick, Ella Miller Knagge, Sean Parkin
{"title":"Synthesis, characterization and base hydrolysis of cobalt(III) complexes coordinated by substituted phenylthioether ligands","authors":"Lee Roecker, Alicia Cohn, Thomas Cox, Rachel Ceaglske, Olivia Rick, Ella Miller Knagge, Sean Parkin","doi":"10.1071/ch24012","DOIUrl":"https://doi.org/10.1071/ch24012","url":null,"abstract":"<p>A synthetic route to the preparation of cobalt(III) complexes coordinated by bidentate phenylthioether ligands is described. Complexes of the type ((2-(X-phenylthio)ethylamine)-<i>N</i>,<i>S</i>)bis(ethylenediamine)cobalt(III) perchlorate, [(en)<sub>2</sub>Co(<i>S</i>(X-phenyl)CH<sub>2</sub>CH<sub>2</sub><i>N</i>H<sub>2</sub>)](ClO<sub>4</sub>)<sub>3</sub>, where X = 4-methoxy (<b>2a</b>), 4-methyl (<b>2b</b>), 3-methyl (<b>2c</b>), nothing (<b>2d</b>), 3-methoxy (<b>2e</b>), 4-bromo (<b>2f</b>) and 3-bromo (<b>2g</b>) were prepared. The synthetic route involves reaction of <i>trans</i>-dichloridobis(ethylenediamine)cobalt(III) chloride with NH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>SC<sub>6</sub>H<sub>4</sub>X to produce <i>cis</i>-[(en)<sub>2</sub>CoCl(<i>N</i>H<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>SC<sub>6</sub>H<sub>4</sub>X)]Cl<sub>2</sub> (<b>1a</b>–<b>g</b>). Formation of the Co–S bond, completing the ring closure, is then accomplished by removing the coordinated chlorido by addition of AgClO<sub>4</sub> in sulfolane. Complexes were characterized by <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy, UV-Vis spectroscopy and elemental analysis. In addition, the solid-state structure (X-ray) of the monohydrate of <b>2d</b> confirms the coordination mode of the ligand. Preliminary kinetic investigations in basic solution show that the Co–S bond is broken resulting in the formation of [(en)<sub>2</sub>Co(OH)(<i>N</i>H<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>SC<sub>6</sub>H<sub>4</sub>X)]<sup>2+</sup>. At 15.0°C, a Hammett Plot is linear (<i>r</i><sup>2</sup> = 0.981) with <i>ρ</i> = 2.24 ± 0.13.</p>","PeriodicalId":8575,"journal":{"name":"Australian Journal of Chemistry","volume":"25 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141743372","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Structural diversity in nudibranch chemistry: elucidation of norditerpenes with a dendrillane scaffold from the Australian nudibranch Goniobranchus coi 裸鳃藻化学结构的多样性：从澳大利亚裸鳃藻 Goniobranchus coi 中阐明具有树枝烷支架的北萜烯类化合物
IF 1.1 4区 化学
Australian Journal of Chemistry Pub Date : 2024-07-09 DOI: 10.1071/ch24073
Louise C. Forster, Gregory K. Pierens, James J. De Voss, Mary J. Garson
{"title":"Structural diversity in nudibranch chemistry: elucidation of norditerpenes with a dendrillane scaffold from the Australian nudibranch Goniobranchus coi","authors":"Louise C. Forster, Gregory K. Pierens, James J. De Voss, Mary J. Garson","doi":"10.1071/ch24073","DOIUrl":"https://doi.org/10.1071/ch24073","url":null,"abstract":"<p>In addition to three known compounds (<b>1</b>–<b>3</b>), two new rearranged spongian diterpenes (<b>4</b> and <b>5</b>) with perhydroazulene and dioxabicyclooctane ring systems were isolated from the mantle and viscera of the Australian nudibranch <i>G<i>oniobranchus</i> coi</i>. The relative configuration of the major spiroepoxide <b>4</b> was explored by comparison with those of <i>m</i>-chloroperbenzoic acid oxidation products derived from dendrillolide A (<b>1</b>). Aldehydes <b>6</b> and <b>7</b> were identified as the ring-opened artefacts of the spiroepoxides <b>5</b> and <b>4</b> respectively, and yielded ketone <b>3</b> on storage. The relative configurations of lactols <b>8</b> and <b>9</b>, isolated as an inseparable mixture of diastereomers, were deduced by molecular modelling and computational studies. Acetylation of the lactol mixture provided dendrillolide A (<b>1</b>), further confirming the structural assignments of <b>8</b> and <b>9</b>. Dissection of animal tissue established that the norditerpenoid metabolites were present in both mantle and viscera tissues.</p>","PeriodicalId":8575,"journal":{"name":"Australian Journal of Chemistry","volume":"16 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2024-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141608272","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Chiral 1-D coordination polymer chains featuring 1,1′-binaphthyl 以 1,1′-联萘为特征的手性一维配位聚合物链
IF 1.1 4区 化学
Australian Journal of Chemistry Pub Date : 2024-06-14 DOI: 10.1071/ch24031
Hui Min Tay, Shannon Thoonen, Carol Hua
{"title":"Chiral 1-D coordination polymer chains featuring 1,1′-binaphthyl","authors":"Hui Min Tay, Shannon Thoonen, Carol Hua","doi":"10.1071/ch24031","DOIUrl":"https://doi.org/10.1071/ch24031","url":null,"abstract":"<p>Four 1-D chain coordination polymers containing bent 1,1′-binaphthyl ligands were synthesised with Ni<sup>II</sup>, Cu<sup>II</sup> and Ag<sup>I</sup>. The use of (<i>R</i>)-4,4′-(2,2′-diethoxy-[1,1′-binaphthalene]-6,6′)dipyridine as a ligand yielded isostructural 1-D looping chains with Ni<sup>II</sup> and Cu<sup>II</sup>, whereas the use of Ag<sup>I</sup> yielded both linear and helical 1-D chains. Changing the dipyridyl coordination groups to dicarboxylates in (<i>S</i>)-6,6′-dicarboxyl-2,2′-diethoxy-1,1′-binaphthalene yielded a 1-D looping chain with a Cu<sup>II</sup> paddlewheel motif. The Ag<sup>I</sup> 1-D chain features two crystallographically distinct 1-D chain morphologies with a triple helix and linear strips. The packing arrangement of the 1-D chains differs because of the intermolecular interactions present, with the steric bulk of the ethoxy substituent on the 1,1′-binaphthyl enabling the formation of large void spaces.</p>","PeriodicalId":8575,"journal":{"name":"Australian Journal of Chemistry","volume":"342 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2024-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141504658","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Coatings based on dopamine-modified hyaluronic acid and Pluronic F127 for tracheal intubation 用于气管插管的基于多巴胺改性透明质酸和 Pluronic F127 的涂层
IF 1.1 4区 化学
Australian Journal of Chemistry Pub Date : 2024-04-19 DOI: 10.1071/ch23218
Chenggang Wu, Xiyi Yang, Xiaofeng Tang, Shuping Zhang
{"title":"Coatings based on dopamine-modified hyaluronic acid and Pluronic F127 for tracheal intubation","authors":"Chenggang Wu, Xiyi Yang, Xiaofeng Tang, Shuping Zhang","doi":"10.1071/ch23218","DOIUrl":"https://doi.org/10.1071/ch23218","url":null,"abstract":"<p>Endotracheal intubation holds significant importance in trauma point care and emergency medicine. However, laryngeal injury and subsequent chronic complications can result from the friction between the mucosa and the tube during intubation. Here we present a lubricant coating based on hyaluronic acid. Inspired by mussels, hyaluronic acid was first conjugated with dopamine to obtain HD, and then a triblock copolymer Pluronic F127 (F127) was complexed with HD to form a micelle layer. Dopamine can assist coating deposition on the tube under weak alkaline conditions, while improving the coating stability. The micelle layer formed by F127 and HD provides excellent water retention and lubrication performance. The friction coefficient of the HD-F127 coating was 56% lower than that of the control, as determined by a friction performance test.</p>","PeriodicalId":8575,"journal":{"name":"Australian Journal of Chemistry","volume":"101 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2024-04-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140801365","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Surface-enhanced Raman spectroscopy (SERS) substrate based on gold nanostars–silver nanostars for imidacloprid detection 基于金纳米柱-银纳米柱的表面增强拉曼光谱（SERS）基底用于吡虫啉检测
IF 1.1 4区 化学
Australian Journal of Chemistry Pub Date : 2024-04-04 DOI: 10.1071/ch23189
Norhayati Abu Bakar, Joseph George Shapter
{"title":"Surface-enhanced Raman spectroscopy (SERS) substrate based on gold nanostars–silver nanostars for imidacloprid detection","authors":"Norhayati Abu Bakar, Joseph George Shapter","doi":"10.1071/ch23189","DOIUrl":"https://doi.org/10.1071/ch23189","url":null,"abstract":"<p>Surface-enhanced Raman spectroscopy (SERS) is a powerful molecular spectroscopy technique that combines Raman spectroscopy with nanostructured metallic surfaces to amplify the Raman signals of target molecules by more than 10<sup>3</sup>. The high sensitivity of SERS poses a significant opportunity for pesticide detection in complex matrices at ultralow concentrations. In this study, we improved the SERS sensitivity for imidacloprid (IMD) by employing silver nanostars (AgNs) coated with gold nanostars (AuNs) as the SERS-active substrate. The SERS response towards IMD detection increased based on the combination of AuNs and AgNs on the substrate surface. The intensity of the SERS signal of IMD using the AuNs/AgNs substrate increased compared to using individual metal nanoparticle substrates. The excellent reproducibility of SERS intensity using the AuNs/AgNs substrate was achieved with a low relative standard derivative (RSD) of 4.87% for 20 different spots on the same sample and 5.19% for 20 different samples. This detection system can be used for multiple tests, which is crucial for the advancement of handheld sensors designed for field use, where minimal or no high-level technical support is accessible.</p>","PeriodicalId":8575,"journal":{"name":"Australian Journal of Chemistry","volume":"298 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2024-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140591736","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Research on the sustainable effect of ZnS and MoS 2 decorated biochar nanocomposites for removing quinolones from antibiotic-polluted aqueous solutions ZnS 和 MoS 2 装饰生物炭纳米复合材料去除抗生素污染水溶液中喹诺酮类药物的可持续效果研究
IF 1.1 4区 化学
Australian Journal of Chemistry Pub Date : 2024-04-03 DOI: 10.1071/ch23170
Ying-Jie Gan, Yue-hui Wang, Ya-ru Dang, Wen-jie Hao, Zheng-rong Hu, Zhi-wei Zhang, Yu-min Luo, Yan-bo Wu, Ai-jun Song, Zhong-bao Zhao
{"title":"Research on the sustainable effect of ZnS and MoS 2 decorated biochar nanocomposites for removing quinolones from antibiotic-polluted aqueous solutions","authors":"Ying-Jie Gan, Yue-hui Wang, Ya-ru Dang, Wen-jie Hao, Zheng-rong Hu, Zhi-wei Zhang, Yu-min Luo, Yan-bo Wu, Ai-jun Song, Zhong-bao Zhao","doi":"10.1071/ch23170","DOIUrl":"https://doi.org/10.1071/ch23170","url":null,"abstract":"<p>Antibiotic concentrations in wastewater generated by industries such as sewage treatment plants, medical pharmaceuticals and aquaculture has exceeded acceptable levels. It is particularly urgent to seek a method that can efficiently remove antibiotics. The removal potential of three quinolone antibiotics, pefloxacin (PF), levofloxacin (LF) and norfloxacin (NF), in simulated contaminated water was studied using a biochar-based nanomaterial prepared by a hydrothermal method. The data were fitted with adsorption kinetics, isotherms and thermodynamics. The results showed that ZnS–MoS<sub>2</sub> activated biochar (ZMMBC) acheived maximum adsorption amounts of 199.42, 125.00 and 142.58 mg g<sup>–1</sup> for PF, LF and NF, suggesting that ZMMBC has excellent adsorption performance. The adsorption mechanisms of PF, LF and NF molecules on ZMMBC include complexation, pore filling, π–π interactions, electrostatic interactions and hydrogen bond interactions.</p>","PeriodicalId":8575,"journal":{"name":"Australian Journal of Chemistry","volume":"52 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2024-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140591637","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Revisiting Staudinger and Ruzicka’s altered pyrethrolone: the cyclopentadienone dimers derived from pyrethrin I, cinerin I and jasmolin I 重温施陶丁格和鲁齐卡的改变的除虫菊酯：从除虫菊酯 I、辛内酯 I 和茉莉酮 I 衍生的环戊二烯酮二聚体
IF 1.1 4区 化学
Australian Journal of Chemistry Pub Date : 2024-03-08 DOI: 10.1071/ch23197
Oliver E. Hutt, Jamie A. Freemont, Stella Kyi, Stuart W. Littler, Ross P. McGeary, Peter J. Duggan, John Tsanaktsidis, Helen F. Cole, Maurice G. Kerr, Elizabeth H. Krenske, John H. Ryan
{"title":"Revisiting Staudinger and Ruzicka’s altered pyrethrolone: the cyclopentadienone dimers derived from pyrethrin I, cinerin I and jasmolin I","authors":"Oliver E. Hutt, Jamie A. Freemont, Stella Kyi, Stuart W. Littler, Ross P. McGeary, Peter J. Duggan, John Tsanaktsidis, Helen F. Cole, Maurice G. Kerr, Elizabeth H. Krenske, John H. Ryan","doi":"10.1071/ch23197","DOIUrl":"https://doi.org/10.1071/ch23197","url":null,"abstract":"<p>The reactions of pyrethrin I, cinerin I and jasmolin I with sodium hydroxide in ethanol afforded an approximately 1:1 ratio of two respective cyclopentadienone dimers, isolated in good yield. A combination of one-dimensional and two-dimensional NMR spectroscopic studies allowed determination of the structure and stereochemistry of the dimers. The dimers are formed by cycloaddition reactions of the less substituted alkene of the cyclopentadienone, and by regioisomeric <i>endo</i> transition states. Density functional theory calculations were in accord with the experimental findings showing the products formed by ambimodal transition states. One such transition state led to two initial products with the less stable product undergoing facile conversion to the other more stable, experimentally observed product. These studies clarify the structures of the altered pyrethrolone reported by Staudinger and Ruzicka in 1924.</p>","PeriodicalId":8575,"journal":{"name":"Australian Journal of Chemistry","volume":"41 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2024-03-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140107859","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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