Chirality最新文献_第10页

Total synthesis of (6R,12R)-6,12-dimethylpentadecan-2-one, the sex pheromone of Diabrotica balteata LeConte Diabrotica balteata LeConte 的性信息素 (6R,12R)-6,12-dimethylpentadecan-2-one 的全合成。

IF 2 4区化学

Chirality Pub Date : 2024-02-27 DOI: 10.1002/chir.23658

Jianwei Wu, Chuanwen Lin, Dan Liu, Qinghua Bian, Min Wang, Jiangchun Zhong

引用次数: 0

Chiral recognition and discrimination studies of tyrosine enantiomers on (−)-18-crown-6-tetracarboxylic acid as a chiral selector by nuclear magnetic resonance spectroscopy and docking simulations 通过核磁共振波谱和对接模拟，研究(-)-18-冠醚-6-四羧酸作为手性选择剂的酪氨酸对映体的手性识别和区分。

IF 2 4区化学

Chirality Pub Date : 2024-02-26 DOI: 10.1002/chir.23656

Gaeun Lee, Suraj Adhikari, Sunho Lee, Jeong Yeon Lee, Yun-Cheol Na, Wonjae Lee, Eunjung Bang

{"title":"Chiral recognition and discrimination studies of tyrosine enantiomers on (−)-18-crown-6-tetracarboxylic acid as a chiral selector by nuclear magnetic resonance spectroscopy and docking simulations","authors":"Gaeun Lee, Suraj Adhikari, Sunho Lee, Jeong Yeon Lee, Yun-Cheol Na, Wonjae Lee, Eunjung Bang","doi":"10.1002/chir.23656","DOIUrl":"10.1002/chir.23656","url":null,"abstract":"Considering the substantial significance of chiral biomolecules, such as amino acids, in our daily routines, we performed chiral recognition and discrimination of tyrosine (Tyr) enantiomers on (−)-(18-crown-6)-2,3,11,12-tetracarboxylic acid [(−)-18-C-6-TA] as crown-ether type chiral selector (CS) by nuclear magnetic resonance (NMR) spectroscopy and docking simulations. In this study, successful discrimination of the enantiomers of Tyr was achieved, as evidenced by the proton chemical shift differences (ΔΔδ) of Tyr enantiomers observed in the 1H NMR spectra with (−)-18-C-6-TA CS. We compared the results of these two techniques with the findings obtained from high performance liquid chromatography (HPLC) investigations. In both NMR and HPLC experimental and docking simulation studies, a stronger interaction between the L-Tyr enantiomer with (−)-18-C-6-TA CS than the D-Tyr was consistently observed. Also, the binding energy differences (ΔΔEL-D) found in simulation data that correspond to enantioselectivity aligned well with the NMR experimental result.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 3","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139971077","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

Mid-IR and CH stretching vibrational circular dichroism spectroscopy to distinguish various sources of chirality: The case of quinophaneoxazoline based ruthenium(II) complexes 用中红外光谱和 CH 伸展振动圆二色光谱区分手性的各种来源：以喹吩恶唑啉基钌（II）配合物为例。

IF 2 4区化学

Chirality Pub Date : 2024-02-26 DOI: 10.1002/chir.23649

Marco Fusè, Giuseppe Mazzeo, Sergio Abbate, Renzo Ruzziconi, Julien Bloino, Giovanna Longhi

引用次数: 0

Study on the anti-cancer activity of α-phenethylamine ferrocenecarboxylic acid co-crystals α-苯乙胺二茂铁羧酸共晶体的抗癌活性研究

IF 2 4区化学

Chirality Pub Date : 2024-02-25 DOI: 10.1002/chir.23653

Liao Youyin, Ma Yuexing, Chen Jiahao, Qian Kun, Yang Jie, Pan Rongbin, Xu Yiyong

{"title":"Study on the anti-cancer activity of α-phenethylamine ferrocenecarboxylic acid co-crystals","authors":"Liao Youyin, Ma Yuexing, Chen Jiahao, Qian Kun, Yang Jie, Pan Rongbin, Xu Yiyong","doi":"10.1002/chir.23653","DOIUrl":"10.1002/chir.23653","url":null,"abstract":"Ferrocene derivatives show a wide range of pharmacological activities in the medical field, especially in the anti-tumor field, and can be used as candidate drugs or lead compounds for the treatment of tumors and other diseases. And α-phenethylamine is an important intermediate for the preparation of fine chemical products. (R)-(+)-1-Phenethylamine ferrocenecarboxylic acid/(S)-(−)-1-phenethylamine ferrocenecarboxylic acid were prepared, named compounds 1 and 2, respectively. Single crystal X-ray diffraction showed that compounds 1 and 2 crystallized in the orthorhombic system space group P212121, and the crystal structures of compounds 1 and 2 exhibited mirror symmetry. The inhibitory effect of two compounds on SW480, MDA-MB-231, and H1299 cells was tested by MTT colorimetry. The IC50 values of the compounds against cancer cells were also calculated. The anti-cancer effect was more pronounced for compounds in the S-configuration. Compound 2 made the wild-type cancer cells undergo apoptosis, thus preventing cancer; it also had the function of helping the cell gene repair defects.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 3","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139968779","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

Correction to “Effect of chirality in the supramolecular polymerization of N-annulated perylenediimides: Cancelling pathway complexity” 对 "手性在 N-annulated perylenediimides 超分子聚合中的影响：消除途径的复杂性"

IF 2 4区化学

Chirality Pub Date : 2024-02-21 DOI: 10.1002/chir.23650

引用次数: 0

Correction to “Switching the on-surface orientation of oxygen-functionalized helicene” 对 "改变氧官能化螺旋烯的表面取向 "的更正

IF 2 4区化学

Chirality Pub Date : 2024-02-21 DOI: 10.1002/chir.23651

引用次数: 0

Enantioselective separation and determination of ibuprofen: Stereoselective pharmacokinetics, pharmacodynamics and analytical methods 对映体选择性分离和测定布洛芬：立体选择性药代动力学、药效学和分析方法。

IF 2 4区化学

Chirality Pub Date : 2024-02-14 DOI: 10.1002/chir.23647

Vinod Kumar Vashistha, Tarun Kumar, Suman Yadav, Dipak Kumar Das

引用次数: 0

Preparation of a bis-triazolyl bridged β-cyclodextrin stationary phase and its application for enantioseparation of chiral compounds by HPLC 双三唑桥接β-环糊精固定相的制备及其在高效液相色谱法手性化合物对映体分离中的应用

IF 2 4区化学

Chirality Pub Date : 2024-02-14 DOI: 10.1002/chir.23644

Qingli Zeng, Zhiqin Huang, Dan Li, Laisheng Li

{"title":"Preparation of a bis-triazolyl bridged β-cyclodextrin stationary phase and its application for enantioseparation of chiral compounds by HPLC","authors":"Qingli Zeng, Zhiqin Huang, Dan Li, Laisheng Li","doi":"10.1002/chir.23644","DOIUrl":"10.1002/chir.23644","url":null,"abstract":"A novel bis-triazolyl bridged β-cyclodextrin was first synthesized by the Click reaction between azido-β-cyclodextrin and 1,6-heptadiyne. Then it was bonded onto silica gel to obtain a bis-triazolyl bridged β-cyclodextrin-based chiral stationary phase (BCDP). After structure characterization, the HPLC performance of BCDP was systematically evaluated by using different types of compounds as probes. The results showed that BCDP could well separate 18 kinds of achiral aromatic compounds (homologues, positional isomers, etc.) and 35 kinds of chiral drugs or pesticides, such as triazoles (Rs = 1.33–3.15), flavanones (Rs = 1.49–2.62), dansyl amino acids (Rs = 0.96–1.99), and β-blocker drugs (Rs = 0.68–2.78). BCDP could separate a wider range of compounds (53 kinds); especially, some chiral substance pairs that were difficult to be resolved on the ordinary cyclodextrin CSPs, including triazoles containing two chiral carbons (triadimenol, bitertanol, metconazole, and triticonazole), strongly ionized amino acids (acidic Asp, alkalic Arg, and polar Thr) and β-blockers with bulky groups (carvedilol, propranolol, and pindolol). Obviously, the unique synergistic inclusion effect of bridged cyclodextrin with double cavities and the bis-triazole bridging group could provide multiple action sites, such as hydrogen bonding, π-π stacking and acid–base action sites, thus improving its chiral chromatographic performance.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 2","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139729119","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 and absolute configuration of cyclic synthetic cathinones derived from α-tetralone 从α-四氢萘酮衍生的环状合成卡西酮的合成和绝对构型。

IF 2 4区化学

Chirality Pub Date : 2024-02-14 DOI: 10.1002/chir.23646

Martin Paškan, Kristýna Dobšíková, Martin Kuchař, Vladimír Setnička, Michal Kohout

{"title":"Synthesis and absolute configuration of cyclic synthetic cathinones derived from α-tetralone","authors":"Martin Paškan, Kristýna Dobšíková, Martin Kuchař, Vladimír Setnička, Michal Kohout","doi":"10.1002/chir.23646","DOIUrl":"10.1002/chir.23646","url":null,"abstract":"The emergence of new synthetic cathinones continues to be a matter of public health concern. In fact, already known products (drugs) are being rapidly replaced by new structurally related alternatives, whereby modifications in the basic cathinone structure are used by manufacturers to circumvent the legislation. On the other hand, some derivatives of synthetic cathinones represent important pharmaceuticals with antidepressant properties. In the search for pharmaceutically relevant analogs, the main goal of the present study was to design and characterize novel cyclic α-tetralone-based derivatives of synthetic cathinones. We synthesized a series of derivatives and verified their chemical structure. Subsequently, chiral separation has been accomplished by high-performance liquid chromatography (HPLC) equipped with a circular dichroism (CD) detector, which directly provided CD spectra of the enantiomers of the analyzed substances at 252 nm. Using density functional theory calculations, we have obtained stable conformers of selected enantiomers in solution and their relative abundances, which we used to simulate their spectra. The experimental and calculated data have been used to assign the absolute configuration of six as-yet unknown synthetic cathinones.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 2","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.23646","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139729120","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

Chiral acidic molecularly imprinted polymer for enantio-separation of norepinephrine racemate 用于去甲肾上腺素外消旋体对映体分离的手性酸性分子印迹聚合物

IF 2 4区化学

Chirality Pub Date : 2024-02-07 DOI: 10.1002/chir.23645

May Abdullah Abomuti

{"title":"Chiral acidic molecularly imprinted polymer for enantio-separation of norepinephrine racemate","authors":"May Abdullah Abomuti","doi":"10.1002/chir.23645","DOIUrl":"https://doi.org/10.1002/chir.23645","url":null,"abstract":"We are looking into how well a copolymeric material made of poly (maleic acid–co-4-vinylpyridine) cross-linked with divinylbenzene can separate L-norepinephrine (L-NEP) from (±)-NEP. The initial step in this direction was the synthesis and subsequent analysis of L-NEP-maleimide chiral derivative. A 4-vinylpyridine/divinylbenzene combination was copolymerized with the resultant chiral maleimide. After heating the polymer materials in a high-alkaline environment to breakdown the connecting imide bonds, they were acidified in an HCl solution to eliminate the incorporated L-NEP species. Fourier transform infrared spectroscopy (FTIR) and a scanning electron microscope were used to examine the imprinted L-NEP-imprinted materials. The manufactured L-NEP-imprinted materials exhibited selectivity characteristics that were over 11 times greater for L-NEP than D-norepinephrine. The highest capacity observed in Langmuir adsorption studies was 170 mg/g at a pH of 7. After optical separation using a column technique, it was determined that the enantiomeric excess levels of D-norepinephrine and L-NEP in the first feeding and subsequent recovery solutions were 95% and 81%, respectively.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 2","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139700647","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