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chiral resolution of β-dl-Phenylalanine Using chiral Macrocyclic Nickel(Ⅱ) Complexes

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Chinese Journal of Structural Chemistry 2014年第5期33卷 707-712页

作者：欧光川李治章张敏袁先友 Department of Biology and Chemistry Hunan University of Science and Engineering

The reactions of chiral four-coordinated nickel（Ⅱ） complex [Ni（RR-L）]（ClO4）2/[Ni（SS- L）]（ClO4）2 with β-dl-phenylalanine in acetonitrile/water gave a six-coordinated enantiomer of [Ni（RR-L）（β-d-HPhe）]（ClO4）2（1） and [Ni（SS-L）（β-l-HPhe）]（ClO4）2（2）, respectively（L = 5,5,7, 12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, HPhe = phenylalanine）. Single-crystal X-ray diffraction analyses revealed that the nickel（Ⅱ） atom displays a distorted octahedral coordination geometry by coordinating with four nitrogen atoms of L in a folded configuration, and two carboxylate oxygen atoms of β-d/l-HPhe in cis-position in both complexes. The monomers of [Ni（RR-L）（β-d-HPhe）]2＋ and [Ni（SS-L）（β-l-HPhe）]2＋ are connected through intermolecular hydrogen bonds to generate one-dimensional zigzag chains, respectively. The homochiral natures of 1 and 2 are confirmed by the results of CD spectroscopy.

关键词： chiral resolution macrocyclic nickel(Ⅱ) complexes β-dl-phenylalanine

A Concise,Practical chiral resolution Approach of Racemic (E)-4,4-Dimethyl-1-(4-nitrophenyl) pent-1-en-3-ol to Its both Enantiomers via Strategy of Diastereomeric Ester Formation and Crystallization Using both N-Boc-D- and N-Boc-L-phenylglycines as chiral Auxiliaries

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Chemical Research in Chinese Universities 2024年第6期40卷 1096-1105页

作者： JIANG Shanshan YUAN Jia QIN Yanlan LUO Ying JIN Zhengsheng ZHAO Guilong TI Huihui School of Chinese Materia Medica Guangdong Pharmaceutical UniversityGuangzhou 510006P.R.China Zhongshan Institute for Drug Discovery Shanghai Institute of Materia MedicaChinese Academy of SciencesZhongshan 528400P.R.China Shanghai Institute of Materia Medica Chinese Academy of SciencesShanghai 201203P.R.China School of Chemistry and Chemical Engineering Guangdong Pharmaceutical UniversityGuangzhou 510006P.R.China

chiral secondary alcohols are an important class of functionalities commonly seen in drugs and other bioactive *** an ongoing drug discovery program in our laboratories,a nitro-bearing racemic allylic secondary alcohol (±)-1 was discovered as a promising drug candidate,and in the following preclinical studies,a concise,reliable,practical synthetic approach to its both enantiomers with high optical purities was greatly *** the present study,we developed a chiral resolution approach of (±)-1 to its both enantiomers,i.e.,(+)-1 and (-)-1,via the strategy of diastereomeric ester formation and crystallization using both N-Boc-D- and N-Boc-L-phenylglycines as chiral *** absolute configurations of all the four key intermediates were unambiguously determined by single-crystal X-ray diffraction,providing a solid foundation for the stereochemistry of the present *** two enantiomers were obtained in high optical *** approach is characterized by scalability and practicality and is envisaged to enable the chiral resolution of other racemic secondary alcohols,especially those with labile groups,such as NO_(2);olefinic C=C bond.

关键词： chiral resolution Phenylglycine chiral auxiliary chiral secondary alcohol Diastereomeric ester formation

Advancing ophthalmic delivery of flurbiprofen via synergistic chiral resolution and ion-pairing strategies

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Asian Journal of Pharmaceutical Sciences 2024年第3期19卷 177-189页

作者： Zhining Ma Yuequan Wang Huiyang He Tong Liu Qikun Jiang Xiaohong Hou School of Pharmacy Shenyang Pharmaceutical UniversityShenyang 110016China Wuya College of Innovation Shenyang Pharmaceutical UniversityShenyang 110016China Liaoning Provincial Institute of Drug Inspection and Testing Shenyang 110036China School of Pharmaceutical Engineering Shenyang Pharmaceutical UniversityShenyang 110016China

Flurbiprofen(FB),a nonsteroidal anti-inflammatory drug,is widely employed in treating ocular inflammation owing to its remarkable anti-inflammatory ***,the racemic nature of its commercially available formulation(Ocufen^(R))limits the full potential of its therapeutic activity,as the(S)-enantiomer is responsible for the desired antiinflammatory ***,the limited corneal permeability of FB significantly restricts its *** this study,we successfully separated the chiral isomers of FB to obtain the highly active(S)-***,utilizing ion-pairing technology,we coupled(S)-FB with various counter-ions,such as sodium,diethylamine,trimethamine(TMA),and l-arginine,to enhance its ocular bioavailability.A comprehensive evaluation encompassed balanced solubility,octanol-water partition coefficient,corneal permeability,ocular pharmacokinetics,tissue distribution,and in vivo ocular anti-inflammatory activity of each chiral isomer *** the various formulations,S-FBTMA exhibited superior water solubility(about 1–12 mg/ml),lipid solubility(1chiral separation and ion-pair enhanced permeation techniques in providing pharmaceutical enterprises focused on drug development with a valuable avenue for improving therapeutic outcomes.

关键词： Flurbiprofen Anti-inflammatory Ophthalmic delivery chiral resolution Ion-pairing

A SIMPLE METHOD FOR chiral resolution OF 1,1'-BI-2-NAPHTHOL

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Journal of Zhejiang University-Science A(Applied Physics & Engineering) 2001年第3期 36-38页

作者：李晓桃蒋珖珖陈卫祥徐铸德

An improved method for preparing enantiomerically pure 1,1’\|bi\|2\|naphthols is described. 1,1’\|bi\|2\|naphthol boric anhydride was generated from the reaction of racemic 1,1’\|bi\|2\|naphthol and boric anhydride. Its two diastereoisomers could be efficiently separated in THF using (L)\|proline as the resolving agent. Treatment in three successive steps yielded 79% and 74% enantiomerically pure (S)\| and (R)\|1,1’\|bi\|2\|naphthol respectively.

关键词： bi\|2\|naphthol chiral resolution

chiral resolution of Ofloxacin Using carboxylated Multi-walled Carbon Nanotubes Mediated Thinlayer Chromatography

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Chiral Resolution of Ofloxacin Using carboxylated Multi-wall...

chiral Recognition and resolution Based on Helical Polymers

2014中国功能材料科技与产业高层论坛

作者： Dushu Huang Yunhui Long YongHong Jing Wang Min Zhong Jie Wu College of Science HongheUniversity School of Chemistry and Chemical Engineering Hunan Institute of Science and Technology

To resolute chiral ofloxacin,we demonstrated a new method of using carboxylatedmulti-walled carbon nanotubes（MWCNTs）impregnated thin-lay chromatography（TLC）.The relativeRF value of carboxylated MWCNTs impregnated TLC was 31.3.A general discussion that focuses on the possibility offunctionalizedMWCNTs in the field of chromatographic chiral resolution is presented.

关键词： Carboxylated Multi-walled Carbon Nanotubes chiral resolution Ofloxacin Thin-layer Chromatography

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Chinese Journal of Polymer Science 2021年第12期39卷 1521-1527页

作者： Hui Zou Qi-Liang Wu Li Zhou Xiao-Hua Hou Na Liu Zong-Quan Wu Department of Polymer Science and Engineering School of Chemistry and Chemical EngineeringHefei University of Technology and Anhui Key Laboratory of Advanced Catalytic Materials and Reaction EngineeringHefei 230009China

Helical polymers have attracted a great deal of attention and been extensively investigated due to their various *** of the most importa nt applicati ons of helical polymers is chiral recog nition and resolutio n ofe nan tiomersforthe reas on that a pair of e nan tiomers is comm only with differe nt physiological and toxicological behaviors in biological *** polymers usually prese nt un expected high chiral recogniti on ability to a variety of racemic compo *** more,the chiral recog nition and resolution abilities of the system are depe ndent on the highly ordered helical structures of the helical *** mini review mainly focuses on the recent progress in chiral recognition and resolution based on helical *** synthetic methodology for helical polymers is firstly discussed *** recent advances of chiral recog nition and resoluti on systems based on helical polymers,especially polyacetylenes and polyisocya nides,are *** hope this mini review will in spire more in terest in developing helical polymers and en courage further advances in chiral-related disciplines.

关键词： Helical polymer chiral recog nition chiral resolution Polyacetylenes Polyisocyanides

Thermodynamic resolution of Pharmaceutical Precursor Modafinil Acid on the Basis of chiral-at-Metal Strategy

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Chinese Journal of Chemistry 2021年第6期39卷 1483-1490页

作者： Man-Li Cao Jun-Ling Zhu Zhong-Lan Zhi Bao-Hui Ye Su-Yang Yao Xiu-Lian Zhang Department of Chemistry Guangdong University of EducationGuangzhouGuangdong 510303China MOE Key Laboratory of Bioinorgonic and Synthetic Chemistry School of ChemistrySun Yat-sen UniversityGuangzhouGuangdong 510275China

chiral-at-metal strategy was developed to resolve the essential sulfoxide pharmaceutical intermediates R-modafinil acid and its ana-logues with high yields and ee *** efficient resolution process was achieved based on the diastereoselective discrimination caused by hydrogen bond and intramolecular π-π interaction between chiral-at-metal center and the coordinated chiral sulfoxide ***,the chiral Ir(lll)receptor can be reused with complete retention of their configurations and without the loss of reaction activity and *** work provides a new access to synthesize R-modafinil acid as well as its analogues and develops the application of chiral-at-metal strategy in chiral resolution.

关键词： chiral resolution chiral-at-metal complexes Modafinil acid chiral pharmaceutical Ir(III)complexes

Direct Optical resolution of chiral Pesticides by High Performance Liquid Chromatography

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Chinese Journal of Chemical Engineering 2011年第4期19卷 603-609页

作者： LI Xiaogang LIU Yiping HU Changdi BAI Lianyang GAO Bida HUANG Kelong College of Bio-safety Science & Technology Hunan Agricultural University Changsha 410128 China Hunan Institute for the Control ofAgrochemicals Changsha 410005 China Hunan Institute of Humanities Science and Technology Loudi 417000 China Institute of Functionalized Materials & Chemistry Central South University Changsha 410083 China

Enantiomer separation is one of the most important prerequisites for the investigation of environmental enantioselective behavior for chiral *** enantiomeric separation of three chiral pesticides,indoxacarb,lambda-cyhalothrin,and simeconazole,were studied on cellulose tris-(3,5-dimethylphenyl-carbamate)-coated chiral stationary phase(CDMPC-CSP) using high-performance liquid chromatography under normal phase *** effects of chromatographic conditions,such as the mobile phase composition including the concentration and type of alcohol modifiers in hexane,flow rate and column temperature,on enantiomer separation were *** thermodynamical mechanism of enantioseparation and chiral recognition mechanism were *** separation were achieved using 20% n-propanol for indoxacarb,2% iso-butanol for lambda-cyhalothrin,and 20% iso-propanol for simeconazole as modifiers in hexane at 25℃ with the selectivity factor(a) of 1.69,1.82 and 1.70,*** resolution factor(Rs) decreased as the flow rate increased from 0.4 to 1.1 ml·*** retention factor(k') and selectivity factor for the enantiomers of analytes decreased as temperature *** lna-1/T plots for racemic chiral pesticides were linear in the range of 15-35℃ in hexane/iso-propanol and the chiral separation was controlled by *** bonding,π-π and dipole-dipole interactions between enantiomers and CDMPC-CSP play an important role in chiral identification,and the fitting of the asymmetric portion of solutes in a chiral cavity or channel of the CSP is also important.

关键词： chiral resolution high-performance liquid chromatography indoxacarb lambda-cyhalothrin simeconazole thermodynamical mechanism

chiral Dynamic Thermodynamic resolution of Sulfoxide Enantiomers by chiral Iridium(Ⅲ) Complexes

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Chiral Dynamic Thermodynamic Resolution of Sulfoxide Enantio...