Chirality最新文献_第2页

Chirooptical 2,2′-Dimethoxybiphenyl Crystals Generated From Suzuki–Miyaura Coupling Reaction Catalyzed by Pd-Loaded Chiral Silica 载pd手性二氧化硅催化Suzuki-Miyaura偶联反应制备的手光学2,2 ' -二甲氧基联苯晶体

IF 2.8 4区化学

Chirality Pub Date : 2025-02-11 DOI: 10.1002/chir.70026

Shunpei Yoshimori, Ren-Hua Jin

{"title":"Chirooptical 2,2′-Dimethoxybiphenyl Crystals Generated From Suzuki–Miyaura Coupling Reaction Catalyzed by Pd-Loaded Chiral Silica","authors":"Shunpei Yoshimori, Ren-Hua Jin","doi":"10.1002/chir.70026","DOIUrl":"https://doi.org/10.1002/chir.70026","url":null,"abstract":"In this work, we report a one-pot approach that combines crystal ripening with the Suzuki–Miyaura coupling reaction. We investigated the reaction between 2-methoxyphenyl bromide and 2-methoxyphenylboronic acid, catalyzed by a series of Pd-loaded chiral optical (D- or L-) and racemic (DL-) silica/polyethyleneimine (PEI) systems, which produced crystalline 2,2′-dimethoxybiphenyl (DMB). The silica used as a catalyst was prepared using our previously established method, in which chirality was imparted to the silica through catalytic templates composed of polyethyleneimine (PEI) and tartaric acid. Both enantiopure (D- or L-; 100% ee) and racemic (DL-; 0% ee) tartaric acid-mediated silica, after tartaric acid removal and palladium (Pd) loading, exhibited similar catalytic activities, leading to the quantitative precipitation of 2,2′-dimethoxybiphenyl in a water/ethanol (1:1 by volume) medium. Interestingly, the 2,2′-dimethoxybiphenyl crystals formed and ripened in the presence of Pd-loaded chiral D- and L-silica/PEI exhibited octahedral morphology and displayed remarkable chiroptical activity with a mirror-image relationship. This represents a novel example of using chiral Pd-loaded silica to synthesize axially chiral biphenyl in crystalline form.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 2","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.70026","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143389141","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

Voltammetric Sensor for Naproxen Enantiomers Based on a Paste Electrode Modified With a Chiral Nickel(II) Complex 基于手性镍（II）配合物修饰的膏状电极的萘普生对映体伏安传感器

IF 2.8 4区化学

Chirality Pub Date : 2025-02-10 DOI: 10.1002/chir.70025

Rufina A. Zilberg, Julia B. Teres, Ivan V. Vakulin, Elena O. Bulysheva, Genghiskhan R. Mukhametdinov, Maria A. Sycheva, Anastasia А. Volkova, Aleksei A. Titov, Victor I. Maleev, Vladimir A. Larionov

{"title":"Voltammetric Sensor for Naproxen Enantiomers Based on a Paste Electrode Modified With a Chiral Nickel(II) Complex","authors":"Rufina A. Zilberg, Julia B. Teres, Ivan V. Vakulin, Elena O. Bulysheva, Genghiskhan R. Mukhametdinov, Maria A. Sycheva, Anastasia А. Volkova, Aleksei A. Titov, Victor I. Maleev, Vladimir A. Larionov","doi":"10.1002/chir.70025","DOIUrl":"https://doi.org/10.1002/chir.70025","url":null,"abstract":"<div>\u0000 \u0000 An enantioselective voltammetric sensor (EVS) comprising a paste electrode made of graphitized thermal Carboblack C (CBPE) modified with a Ni(II) complex based on (S)-(2-aminomethyl)pyrrolidine and 3,5-di-tert-butylsalicylaldehyde was developed for the recognition and determination of naproxen (Nap) enantiomers. The proposed sensor was characterized by scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDS-SEM), Fourier-transform infrared spectroscopy (FT-IR), molecular dynamics and quantum chemical simulations, electrochemical impedance spectroscopy (EIS), and cyclic voltammetry (CV) methods. Using the differential pulse voltammetry (DPV), the CBPE@(S)-Ni sensor was found to have good selectivity for Nap enantiomers (ip1S/ip1R = 1.43, ip2S/ip2R = 1.27 for the first/second peaks, respectively). The sensor demonstrates the highest sensitivity to (S)-Nap (6.44 and 6.90 μA/mM for the first and second peaks). The linear concentration range is from 5.0 × 10−5 to 1 × 10−3 M and from 2.0 × 10−4 to 1 × 10−3 M for (S)- and (R)-Nap, respectively, where the detection limits for the first and second peaks are 5.31 × 10−7 M and 4.96 × 10−7 M for (S)-Nap and 7.40 × 10−7 and 6.79 × 10−7 for (R)-Nap. The suggested sensor was successfully tested for the determination of Nap enantiomers in mixtures, in biological fluids, and in medicinal drug forms. In all the cases, the relative standard deviation (RSD) does not exceed 4.7%; the recovery percentage is in the range of 99.2%–101.3%.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 2","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143380300","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

Principles for Stereoselective Separation of Chiral Drug Compounds Enantiomers and Diastereomers in Pharmaceuticals and Biopharmaceuticals Using Liquid Chromatography 用液相色谱法立体选择分离药品和生物制药中手性药物化合物对映体和非对映体的原理

IF 2.8 4区化学

Chirality Pub Date : 2025-02-03 DOI: 10.1002/chir.70017

Niroja Vadagam, Sharath Babu Haridasyam, Narasimha S. Lakka, Chandrasekar Kuppan, Poornima Ravinathan, Sanjeeva R. Chinnakadoori

{"title":"Principles for Stereoselective Separation of Chiral Drug Compounds Enantiomers and Diastereomers in Pharmaceuticals and Biopharmaceuticals Using Liquid Chromatography","authors":"Niroja Vadagam, Sharath Babu Haridasyam, Narasimha S. Lakka, Chandrasekar Kuppan, Poornima Ravinathan, Sanjeeva R. Chinnakadoori","doi":"10.1002/chir.70017","DOIUrl":"https://doi.org/10.1002/chir.70017","url":null,"abstract":"<div>\u0000 \u0000 In the fields of pharmaceuticals and biopharmaceuticals, chiral liquid chromatography techniques including high-performance liquid chromatography and ultra-performance liquid chromatography are frequently used to isolate, identify, separate, and quantify chiral isomers, including enantiomers and diastereomers (stereoisomers), due to the significant differences in biological activity and therapeutic effects of stereoisomers. The authors have provided a comprehensive overview of the fundamental principles necessary for using liquid chromatography to separate and accurately estimate chiral compounds that exhibit stereoisomerism (both enantiomers and diastereomers). The development strategies outlined include the selection of chromatographic conditions, optimization of sample preparation, evaluation of degradation pathways, establishment of system suitability criteria, and execution of method validation studies. Additionally, this article supports the development of robust and stability-indicating methods by applying one factor at a time and design of experiments concepts for chiral drugs and their chiral impurities in pharmaceuticals and biopharmaceuticals. The method validation attributes essential to evaluate the characteristics of the developed method were discussed in this write-up. The validation parameters include specificity, linearity, detection limit, quantitation limit, accuracy, precision, solution stability.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 2","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143111351","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

A Review on Carbazole and Its Derivatives as Anticancer Agents From 2013 to 2024 2013 - 2024年咔唑及其衍生物抗癌研究进展

IF 2.8 4区化学

Chirality Pub Date : 2025-01-30 DOI: 10.1002/chir.70021

Priyanka Sanjay Waghmare, Anuruddha Rajaram Chabukswar, Kunal Ganesh Raut, Pooja Tanaji Giri

{"title":"A Review on Carbazole and Its Derivatives as Anticancer Agents From 2013 to 2024","authors":"Priyanka Sanjay Waghmare, Anuruddha Rajaram Chabukswar, Kunal Ganesh Raut, Pooja Tanaji Giri","doi":"10.1002/chir.70021","DOIUrl":"10.1002/chir.70021","url":null,"abstract":"<div>\u0000 \u0000 Carbazole, a natural alkaloid, has been recognized as an effective anticancer agent for over 40 years. However, only a limited number of carbazole-based compounds have received FDA approval for cancer treatment. Current cancer therapies are often associated with significant side effects, causing physical, emotional, and financial burdens for patients. Additionally, despite advancements, cancer prevention and treatment remain challenging due to suboptimal clinical outcomes. The development of new drugs is crucial for achieving safer and more effective cancer therapies. This review focuses on various carbazole derivatives and hybrid composites, highlighting their interactions with distinct receptors and their mechanisms of anticancer action, along with a general structure–activity relationship (SAR). It also emphasizes carbazole-based compounds employed in chemoprevention, which aim to delay or prevent malignant progression. By covering carbazole derivatives and their anticancer potential from 2013 to the present, along with their current clinical status, this study offers valuable insights and updates for researchers in the field.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 2","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143064012","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

150 Years of the Tetrahedral Carbon: A Toast to Chirality 四面体碳的150年：为手性干杯。

IF 2.8 4区化学

Chirality Pub Date : 2025-01-26 DOI: 10.1002/chir.70022

Pedro Cintas

引用次数: 0

On the Influence of Additives and Modifiers on the Chiral HPLC Separation of the Enantiomers of Nicotine 添加剂和改性剂对烟碱对映体手性HPLC分离的影响。

IF 2.8 4区化学

Chirality Pub Date : 2025-01-26 DOI: 10.1002/chir.70020

Mehdi Ashraf-Khorassini, William M. Coleman III, Weston J. Umstead

{"title":"On the Influence of Additives and Modifiers on the Chiral HPLC Separation of the Enantiomers of Nicotine","authors":"Mehdi Ashraf-Khorassini, William M. Coleman III, Weston J. Umstead","doi":"10.1002/chir.70020","DOIUrl":"10.1002/chir.70020","url":null,"abstract":"The influence of additives and modifiers on the chiral HPLC separation of the nicotine enantiomers using UV/Vis detection is discussed. Selected alcohols as modifiers and selected amines as additives were found to have a significant effect on the resolution and retention times of nicotine enantiomers even to the point of eliminating component elution. Systematic variations in the concentration of ethanol, methanol, and isopropanol, as modifiers, along with variations in the concentration of diethylamine, triethylamine, tributylamine, ethylenediamine, isopropylamine, as additives, revealed that the average resolution (R) of the nicotine enantiomers ranged from 2.9 to 7.57, using a mobile phase flow rate of 0.80 mL/min. The average retention times of the nicotine enantiomer pairs ranged from 7.64 and 8.34 min to 13.47 and 14.97 min, with the S(−) enantiomer eluting first. As expected, faster flow rates of 1.0 mL/min reduced retention times by approximately 1–2 min, with a slight decrease in the R values. The %RSD values for both resolution and retention times consistently remained below 2%. The detection limits for the enantiomers were approximately 5 μg/mL. The optimized method successfully detected one part in 100 for the minor R(+) enantiomer in the presence of the dominate S(−) enantiomer and adhered to all established QuEChERS method protocols.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 2","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11771616/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143045724","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

Enantiodifferentiation of Thiohydantoin Derivatives by NMR in the Presence of Chiral Solvating Agent: (1R,2S)-Ephedrine and Chiral Symmetrical and Unsymmetrical Thioureas 手性溶剂化剂(1R,2S)-麻黄碱、手性对称和不对称硫脲存在下硫代海因衍生物的NMR对映分化

IF 2.8 4区化学

Chirality Pub Date : 2025-01-23 DOI: 10.1002/chir.70013

Sevgi Sarigul Ozbek, Senel Teke Tuncel, Sule Erol Gunal, Ilknur Dogan

{"title":"Enantiodifferentiation of Thiohydantoin Derivatives by NMR in the Presence of Chiral Solvating Agent: (1R,2S)-Ephedrine and Chiral Symmetrical and Unsymmetrical Thioureas","authors":"Sevgi Sarigul Ozbek, Senel Teke Tuncel, Sule Erol Gunal, Ilknur Dogan","doi":"10.1002/chir.70013","DOIUrl":"10.1002/chir.70013","url":null,"abstract":"<div>\u0000 \u0000 2-Thiohydantoin derivatives, including different substitutions at N-1 and C-5 (5-methyl-, 5-isopropyl-, 1-acetyl-5-methyl-, and 1-acetyl-5-isopropyl-) (1–4, respectively), were synthesized by the known literature methods. In these synthetic pathways, it was reported that enantiomerically pure 2-thiohydantions were obtained in the absence of any solvent via the reaction of L-amino acids with thiourea (1&2) and via the reaction of L-amino acids with NH4SCN and acetic anhydride (3&4). However, in this study, in contrary to the previous literature studies, racemic mixtures of 2-thiohydantoins were obtained although the same synthetic methods were used. The racemic nature of 2-thiohydantoin derivatives (1–4) was proved by using 1H NMR analysis in the presence of (1R,2S)-(−)-ephedrine as a chiral auxiliary. In addition, the enantiomers of 3&4 were also resolved on chiral stationary phases by HPLC analyses. Furthermore, newly synthesized unsymmetrical chiral thioureas (S-1&S-2) and previously synthesized symmetrical ones (SS-3&SS-4) were used as chiral solvating agent (CSA) for the enantiodiscrimination of the thiohydantoins (5&6), previously reported. Optimal CSA/substrate ratios were determined for the best enantiodiscrimination.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 2","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143021639","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

Optimizing Enantiomeric Resolution of Chiral Triazoles in Supercritical Fluid Chromatography 超临界流体色谱法优化手性三唑对映体的分离。

IF 2.8 4区化学

Chirality Pub Date : 2025-01-23 DOI: 10.1002/chir.70016

Codruţa Frîncul, Alina Ghinet, Dalila Belei, Bezhan Chankvetadze, Sergiu Shova, Emmanuelle Lipka, Anca-Elena Dascălu

引用次数: 0

Controlling Sign and Magnitude of Circularly Polarized Luminescence of Axially Chiral Schiff-Base Boron Difluoride Complexes Bearing Polyethylene Glycol Chains 含聚乙二醇链的轴向手性席夫碱二氟化硼配合物圆偏振发光的控制符号和大小。

IF 2.8 4区化学

Chirality Pub Date : 2025-01-14 DOI: 10.1002/chir.70014

Masahiro Ikeshita, Miku Ichinose, Daiya Suzuki, Jungo Ono, Yoshitane Imai, Takashi Tsuno

引用次数: 0

Proceedings From 19th International Conference on Chiroptical Spectroscopy, Hiroshima, Japan 第十九届国际光谱学会议论文集，日本广岛。