期刊文献+
共找到19篇文章
< 1 >
每页显示 20 50 100
Advancing ophthalmic delivery of flurbiprofen via synergistic chiral resolution and ion-pairing strategies
1
作者 Zhining Ma Yuequan Wang +3 位作者 Huiyang He Tong Liu Qikun Jiang Xiaohong Hou 《Asian Journal of Pharmaceutical Sciences》 SCIE CAS 2024年第3期177-189,共13页
Flurbiprofen(FB),a nonsteroidal anti-inflammatory drug,is widely employed in treating ocular inflammation owing to its remarkable anti-inflammatory effects.However,the racemic nature of its commercially available form... Flurbiprofen(FB),a nonsteroidal anti-inflammatory drug,is widely employed in treating ocular inflammation owing to its remarkable anti-inflammatory effects.However,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 effects.Additionally,the limited corneal permeability of FB significantly restricts its bioavailability.In this study,we successfully separated the chiral isomers of FB to obtain the highly active(S)-FB.Subsequently,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 salt.Among the various formulations,S-FBTMA exhibited superior water solubility(about 1–12 mg/ml),lipid solubility(1<lgP_(ow)<3)and corneal permeability.In comparison to Ocufen^(R),S-FBTMA demonstrated significantly higher in vivo antiinflammatory activity and lower ocular irritability(such as conjunctival congestion and tingling).The findings from this research highlight the potential of chiral separation and ion-pair enhanced permeation techniques in providing pharmaceutical enterprises focused on drug development with a valuable avenue for improving therapeutic outcomes. 展开更多
关键词 FLURBIPROFEN ANTI-INFLAMMATORY Ophthalmic delivery chiral resolution ION-PAIRING
下载PDF
Chiral Resolution of β-dl-Phenylalanine Using Chiral Macrocyclic Nickel(Ⅱ) Complexes 被引量:2
2
作者 欧光川 李治章 +1 位作者 张敏 袁先友 《Chinese Journal of Structural Chemistry》 SCIE CAS CSCD 2014年第5期707-712,共6页
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)]... 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. 展开更多
关键词 chiral resolution macrocyclic nickel(Ⅱ) complexes β-dl-phenylalanine
下载PDF
Chiral resolution of furofuran lignans and their derivatives from the stems of Dendrobium'Sonia' 被引量:1
3
作者 QIU Kaimei QIU Hao +5 位作者 XIE Yanqiao ZHANG Siyu ZHANG Qian WANG Zhengtao HAN Zhuzhen YANG Li 《Chinese Journal of Natural Medicines》 SCIE CAS CSCD 2024年第10期937-944,共8页
Five new furofuran lignans and their derivatives,(-)-glaberide I 4-O-β-D-glucopyranoside(1a),(+)-glaberide I 4-O-β-D-glucopyranoside(1b),(+)-glaberide I 7'-ethoxy-4-O-β-D-glucopyranoside(2a),(-)-glaberide I 7&#... Five new furofuran lignans and their derivatives,(-)-glaberide I 4-O-β-D-glucopyranoside(1a),(+)-glaberide I 4-O-β-D-glucopyranoside(1b),(+)-glaberide I 7'-ethoxy-4-O-β-D-glucopyranoside(2a),(-)-glaberide I 7'-ethoxy-4-O-β-D-glucopyranoside(2b),and(-)-isoeucommin A(3b),along with fifteen known analogs were isolated from the stems of Dendrobium'Sonia'.These compounds were classified into ten pairs of enantiomers or diastereoisomers via chiral resolution,and their structures were determined based on extensive spectroscopic data.Their absolute configurations were determined by hydrolysis,comparison of experimental and calculated electronic circular dichroism(ECD)data,and single-crystal X-ray diffraction analysis.The isolates were evaluated for their ability to inhibit nitric oxide(NO)production in RAW264.7 cells.Among them,syringaresinol(5)exhibited prominent inhibition activity,with an IC50 value of 28.4±3.0μmol·L~(-1),and there was a slight difference between 5a,5b and the racemic mixture 5. 展开更多
关键词 Furofuran lignans chiral resolution ENANTIOMERS DIASTEREOISOMERS Dendrobium'Sonia' ANTI-INFLAMMATORY
原文传递
Direct Optical Resolution of Chiral Pesticides by High Performance Liquid Chromatography 被引量:1
4
作者 LI Xiaogang LIU Yiping +3 位作者 HU Changdi BAI Lianyang GAO Bida HUANG Kelong 《Chinese Journal of Chemical Engineering》 SCIE EI CAS CSCD 2011年第4期603-609,共7页
Enantiomer separation is one of the most important prerequisites for the investigation of environmental enantioselective behavior for chiral pesticides.The enantiomeric separation of three chiral pesticides,indoxacarb... Enantiomer separation is one of the most important prerequisites for the investigation of environmental enantioselective behavior for chiral pesticides.The 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 condition.The 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 examined.The thermodynamical mechanism of enantioseparation and chiral recognition mechanism were discussed.Better 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,respectively.The resolution factor(Rs) decreased as the flow rate increased from 0.4 to 1.1 ml·min-1.The retention factor(k') and selectivity factor for the enantiomers of analytes decreased as temperature increased.The 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 enthalpy.Hydrogen 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. 展开更多
关键词 chiral resolution high-performance liquid chromatography INDOXACARB LAMBDA-CYHALOTHRIN simeconazole thermodynamical mechanism
下载PDF
Lipase immobilized on HOOC-MCF:A highly enantioselective catalyst for transesterification resolution of (R,S)-1-phenylethanol 被引量:4
5
作者 Ping Xue Xiang Hui Yan Zheng Wang 《Chinese Chemical Letters》 SCIE CAS CSCD 2007年第8期929-932,共4页
Pseudomonas cepacia lipase (PSL) immobilized on the carboxyl-functionalized meso-cellular foams (HOOC-MCF) was used for the transesterification resolution of (R,S)-l-phenylethanol in organic solvent. The results... Pseudomonas cepacia lipase (PSL) immobilized on the carboxyl-functionalized meso-cellular foams (HOOC-MCF) was used for the transesterification resolution of (R,S)-l-phenylethanol in organic solvent. The results showed that the ee value of (S)-1- phenylethanol and (R)-1-phenylethyl acetate reached 99% with 50% conversion of 1-phenylethanol using toluene as solvent. Furthermore, it was found that PSL/HOOC-MCF exhibited high enantioselectivity in organic solvent with log P ≤ 2 such as toluene and hexane. 展开更多
关键词 Immobilized lipase ENANTIOSELECTIVITY chiral resolution 1-Phenylethanol
下载PDF
Chiral basket-handle porphyrin-Co complexes for the catalyzed asymmetric cycloaddition of CO_2 to epoxides 被引量:1
6
作者 Xiying Fu Xinyao Jing +4 位作者 Lili Jin Lilong Zhang Xiaofeng Zhang Bin Hu Huanwang Jing 《Chinese Journal of Catalysis》 SCIE EI CAS CSCD 北大核心 2018年第5期997-1003,共7页
The catalytic synthesis of cyclic carbonates via the cycloaddition of CO2 to epoxides is a standard methodology for CO2 fixation.For this purpose,chiral basket-handle porphyrin-Co complexes were devised,prepared,and f... The catalytic synthesis of cyclic carbonates via the cycloaddition of CO2 to epoxides is a standard methodology for CO2 fixation.For this purpose,chiral basket-handle porphyrin-Co complexes were devised,prepared,and fully characterized by nuclear magnetic resonance,mass spectrometry,Fourier transform infrared spectroscopy,ultraviolet-visible spectroscopy,and specific rotation.The proposed metalloporphyrin catalysts were synthesized with either 1,1'-bi-2-naphthol or L-phenylalanine,which have different chirality,and then applied to the coupling of propylene oxide and CO2 for generating chiral cyclic carbonates with good enantioselectivity under extremely mild conditions in the presence of tetrabutyl ammonium chloride as a co-catalyst.The good enantioselectivity in the cycloaddition reaction is attributed to a synergistic interplay between the chiral porphyrin catalysts and the substrate.The mechanism and enantioselectivity of the asymmetric cycloaddition reaction is discussed. 展开更多
关键词 Carbon dioxide fixation chiral resolution CYCLOADDITION EPOXIDE chiral porphyrin-cobalt complex
下载PDF
Chiral Isothiourea-Catalyzed Acylative Dynamic Kinetic Resolution of 3-Hydroxyphthalides for Enantioselective Synthesis of Phthalidyl Esters
7
作者 Zeyang Hao Wei Lin +2 位作者 Zi-Qi Yuan Wei Zhang Xin Li 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2024年第19期2341-2345,共5页
Comprehensive Summary Phthalides serve as core structures pervasive in a wide array of natural products and drug molecules,which display a diverse array of biological activities.We report herein a highly efficient dyn... Comprehensive Summary Phthalides serve as core structures pervasive in a wide array of natural products and drug molecules,which display a diverse array of biological activities.We report herein a highly efficient dynamic kinetic resolution of 3-hydroxyphthalides by chiral isothioureas(ITUs)catalyzed asymmetric acylation,facilitating the effective synthesis of a variety of chiral phthalidyl esters with good yields and enantioselectivities.Notably,this reaction features mild reaction conditions,expansive substrate scope as well as good functional group compatibility.In addition,the practicality of this method is underscored by the large-scale synthesis,reduced catalyst loading experiment and the synthesis of the chiral phthalidyl ester prodrug. 展开更多
关键词 Asymmetric catalysis Phthalidyl ester Dynamic kinetic resolution chiral isothiourea ACYLATION Methodology and reactions Syntheticmethods
原文传递
Attempt to Resolute Chiral Clusters by Optically Active Hydrazide
8
作者 Yu Hua ZHANG Wei Qiang ZHANG +4 位作者 Yu Gang CHEN Zhi CHEN Xin Yi ZHU Huan Wang JING Yuan Qi YIN 《Chinese Chemical Letters》 SCIE CAS CSCD 2001年第1期69-70,共2页
A new kind of hydrazone (I) diastereoisomers was prepared with enantiomeric hydazide (II) and chiral cluster (III), which was characterized by HMBC. Unfortunately, the mixture could not be separated into pure diastere... A new kind of hydrazone (I) diastereoisomers was prepared with enantiomeric hydazide (II) and chiral cluster (III), which was characterized by HMBC. Unfortunately, the mixture could not be separated into pure diastereoisomer. This could be a direction to separate the racemic chiral clusters. 展开更多
关键词 chiral clusters optically active hydrazone chiral resolution DIASTEREOISOMER HMBC.
下载PDF
Study on extraction kinetics ofα-cyclopentylmandelic acid enantiomers with hydroxyethyl-β-cyclodextrin as chiral selector
9
作者 Panliang Zhang Pan Jiang +4 位作者 Weifeng Xu Yu Liu Biquan Xiong Yunren Qiu Kewen Tang 《Chinese Journal of Chemical Engineering》 SCIE EI CAS CSCD 2018年第1期67-72,共6页
In this work,the kinetic study on reactive extraction ofα-cyclopentylmandelic acid(α-CPMA)enantiomers was performed in a Lewis cell using hydroxyethyl-β-cyclodextrin(HE-β-CD)as chiral selector.The enantioselective... In this work,the kinetic study on reactive extraction ofα-cyclopentylmandelic acid(α-CPMA)enantiomers was performed in a Lewis cell using hydroxyethyl-β-cyclodextrin(HE-β-CD)as chiral selector.The enantioselective complexation equilibrium between HE-β-CD andα-CPMA enantiomers was studied by phase solubility method.The important process parameters affecting the initial extraction rate were separately studied and the reaction rate equations were deduced.The optimal conditions for kinetic study were as follows:stirring speed of 75 r·min^(-1),interfacial area of 12.56 cm^2,pH of 2.5,initial HE-β-CD concentration of 0.05 mol·L^(-1),initialα-CPMA concentration of 5 mmol·L^(-1),and temperature of 278 K.The reaction has been found to be first order inα-CPMA and second order in HE-β-CD with the forward rate constants of 2.056×10^(-3)m^6·mol^(-2)·s^(-1)and 1.459×10^(-3)m^6·mol^(-2)·s^(-1)for(S)-α-CPMA and(R)-α-CPMA,respectively.The complexation equilibrium constants were evaluated as 61 L·mol^(-1) and 117 L·mol^(-1)for(S)-α-CPMA and(R)-α-CPMA,and the intrinsic enantioselectivity is estimated as 1.92. 展开更多
关键词 Kinetics Liquid-liquid extraction chiral resolution α-Cyclopentylmandelic acid
下载PDF
Chiral Recognition and Resolution Based on Helical Polymers 被引量:2
10
作者 Hui Zou Qi-Liang Wu +3 位作者 Li Zhou Xiao-Hua Hou Na Liu Zong-Quan Wu 《Chinese Journal of Polymer Science》 SCIE CAS CSCD 2021年第12期1521-1527,共7页
Helical polymers have attracted a great deal of attention and been extensively investigated due to their various applications.One of the most importa nt applicati ons of helical polymers is chiral recog nition and res... Helical polymers have attracted a great deal of attention and been extensively investigated due to their various applications.One 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 systems.Helical polymers usually prese nt un expected high chiral recogniti on ability to a variety of racemic compo unds.Whatzs more,the chiral recog nition and resolution abilities of the system are depe ndent on the highly ordered helical structures of the helical polymers.This mini review mainly focuses on the recent progress in chiral recognition and resolution based on helical polymers.The synthetic methodology for helical polymers is firstly discussed briefly.Then recent advances of chiral recog nition and resoluti on systems based on helical polymers,especially polyacetylenes and polyisocya nides,are described.We hope this mini review will in spire more in terest in developing helical polymers and en courage further advances in chiral-related disciplines. 展开更多
关键词 Helical polymer chiral recog nition chiral resolution POLYACETYLENES POLYISOCYANIDES
原文传递
Thermodynamic Resolution of Pharmaceutical Precursor Modafinil Acid on the Basis of Chiral-at-Metal Strategy
11
作者 Man-Li Cao Jun-Ling Zhu +3 位作者 Zhong-Lan Zhi Bao-Hui Ye Su-Yang Yao Xiu-Lian Zhang 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2021年第6期1483-1490,共8页
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 values.The efficient resolution process was achieved b... 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 values.The 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 ligands.Moreover,the chiral Ir(lll)receptor can be reused with complete retention of their configurations and without the loss of reaction activity and enantioselectivity.This 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. 展开更多
关键词 chiral resolution chiral-at-metal complexes Modafinil acid chiral pharmaceutical Ir(III)complexes
原文传递
Boron-Stereogenic Compounds:Synthetic Developments and Opportunities
12
作者 Yonghong Guo Bing Zu +1 位作者 Cadmus Du Chen Chuan He 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2024年第19期2401-2411,共11页
Comprehensive Summary The 21st century has witnessed a continuous evolution in the development of boron-stereogenic chemistry.Since the 1990s,various innovations for the synthesis of tetracoordinate boron-stereogenic ... Comprehensive Summary The 21st century has witnessed a continuous evolution in the development of boron-stereogenic chemistry.Since the 1990s,various innovations for the synthesis of tetracoordinate boron-stereogenic compounds,which exhibited great potential applications,have been demonstrated by synthetic chemists.This paper reviews the significant progress and recent advances towards the assembly of enantioenriched boron-stereogenic compounds,and hopes to shed light on new perspectives and inspire further research in this emerging field. 展开更多
关键词 chiral organoboron Boron-stereogenic compounds chiral resolution Asymmetric synthesis Asymmetric catalysis chirality Heterocycles CHELATES
原文传递
Sarcocinerenoids A—J,Eight Rare Capnosane-Type and Two New Cage-Type Cembranoids with Promoting Angiogenesis Activity from the South China Sea Soft Coral Sarcophyton cinereum
13
作者 Yue Mi Yanan Yang +2 位作者 Xuli Tang Xiao Han Guoqiang Li 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2024年第8期815-822,共8页
Backgroundand Originality Content,Cembranoids are a structurally diverse class of diterpenoids commonly occurring in marine and terrestrial organisms.(+)-Cembrene was the first reported cembranoid diterpenoid discover... Backgroundand Originality Content,Cembranoids are a structurally diverse class of diterpenoids commonly occurring in marine and terrestrial organisms.(+)-Cembrene was the first reported cembranoid diterpenoid discovered in 1962,l and more than 1400 cembranoid diterpenoids have been identified in the last six decades,[2]Cembranoids are characterized by a 14-membered carbocyclic ring,an isopropyl group and three methyl groups,which form their core carbon skeleton.Enzymatic processes such as oxidation,oxidative rearrangements and transannular cyclizations occur in organisms,leading to the formation of distinctive specialized metabolites such as epoxide,lactone,ester,furan,pyrane and other ringbased cembranoids.[2-3] 展开更多
关键词 Soft coral Sarcophyton cinereum Capnosane-type cembranoids Absolute configurations Activities Natural products NMR spectroscopy Liquid chromatography X-raydiffraction chiral resolution
原文传递
Triple Aza[6]helicenes with Circularly Polarized Luminescence:N-Alkylation as a Tool to Tune the Chiroptical Properties
14
作者 Xia Yufei Jiang Li +2 位作者 Yang Qiao Yu Xiu Chen Fengkun 《有机化学》 SCIE CAS CSCD 北大核心 2024年第9期2841-2846,共6页
Recently,multiple helicenes have attracted enormous attention due to their exceptionally distorted conjugated architectures,appealing optical properties and unique spatial stacking patterns.The electronic and optical ... Recently,multiple helicenes have attracted enormous attention due to their exceptionally distorted conjugated architectures,appealing optical properties and unique spatial stacking patterns.The electronic and optical properties of multiple helicenes could be modulated by heteroatom doping.Herein,the first triple aza[6]helicene was reported by an intramolecular oxidation reaction,which exhibited highly distorted propeller-like geometry revealed by single crystal X-ray diffraction analysis.In comparison to the reported triple oxa[6]helicene,the triple aza[6]helicene demonstrated increased quantum yield(5.5%),and chiroptical properties with a|gabs|value of 0.012 and a|glum|value of 3.0×10^(-3).Furthermore,the stability and chiroptical properties of the triple aza[6]helicene could be enhanced by N-alkylation. 展开更多
关键词 HELICENE multiple heterohelicene chiral resolution circularly polarized luminescence ALKYLATION
原文传递
Chiral Coordination Metallacycles/Metallacages for Enantioselec-tive Recognition and Separation 被引量:4
15
作者 Liyan Zhang Huiping Liu +1 位作者 Guozan Yuan Ying-Feng Han 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2021年第8期2273-2286,共14页
In recent years,chiral discrete supramolecular coordination complexes have attracted increasing interest as simple enzyme mimetics owing to their aesthetic architectures and potential applications in chiral science.Th... In recent years,chiral discrete supramolecular coordination complexes have attracted increasing interest as simple enzyme mimetics owing to their aesthetic architectures and potential applications in chiral science.This review summarizes the recent advances on chiral coordination metallacy-cles/metallacages with inherent cavities for enanti on selective recog nition and separation,including their design principles and synthesis,the in troduc-tion of chirality and functionality,structural adaptability,and host-guest bonding in enantioselective process.Finally,the perspectives on the remain-ing challenges and future opportunities are presented. 展开更多
关键词 chiralITY METALLACYCLES Metallacages Molecular recognition chiral resolution
原文传递
Extraction of Phenylalanine Phase Systems Containing Enantiomers by Aqueous Two Combinatorial Chiral Selector 被引量:1
16
作者 陈晓青 刘莉 +1 位作者 焦飞鹏 王珍 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2012年第4期965-969,共5页
In order to obtain a better enantioselectivity of phenylalanine enantiomers and establish the optimal chiral ex- traction conditions, the distribution behavior was investigated in aqueous two-phase systems which were ... In order to obtain a better enantioselectivity of phenylalanine enantiomers and establish the optimal chiral ex- traction conditions, the distribution behavior was investigated in aqueous two-phase systems which were composed of polyethylene glycol and ammonium sulfate containing combinatorial chiral selector: β-cyclodextrin and HP-β-cyclodextrin. The influence of the molar concentration ratio of combinatorial chiral selectors, the total molar concentration of combinatorial chiral selectors, pH value, buffer type and its concentration were thoroughly studied, respectively. The results show that the enantioselectivity reaches 1.53 under the optimal chiral extraction conditions This extraction is a potential economical and effective way for chiral resolution. 展开更多
关键词 aqueous two phase extraction combinatorial chiral selectors chiral resolution ENANTIOSELECTIVITY phenylalanine enantiomers
原文传递
Aphamines A-C,dimeric acyclic diterpene enantiomers from Aphanamixis polystachya
17
作者 Panpan Zhang Shang Xue +4 位作者 Pengfei Tang Zhirong Cui Zefan Wang Jun Luo Lingyi Kong 《Chinese Chemical Letters》 SCIE CAS CSCD 2021年第4期1480-1484,共5页
Aphamines A-C(1-3),three pairs of acyclic diterpene dimer enantiomers with an unprecedent ploymerization pattern,were discovered from Aphanamixis polystachya by NMR-guided isolation and chiral resolution.The elucidati... Aphamines A-C(1-3),three pairs of acyclic diterpene dimer enantiomers with an unprecedent ploymerization pattern,were discovered from Aphanamixis polystachya by NMR-guided isolation and chiral resolution.The elucidation of their novel carbon skeletons was achieved based on spectroscopic analysis,exciton chirality,and calculated electronic circular dichroism(ECD).Plausible Claisen rearrangement,5-exo-trig cyclization,and reduction reactions may play important roles in the polymeric biosynthesis pathway.Compounds 1 and 3 showed inhibitory effects on nitric oxide(NO)production(IC_(50):6.71-15.36 μmol/L) and reduced the expression of iNOS in LPS-induced RAW 264.7 macrophages. 展开更多
关键词 Aphanamixis polystachya Acyclic diterpene dimer NMR-guided isolation chiral resolution Anti-inflammatory activity
原文传递
Applications of the crystallization process in the pharmaceutical industry
18
作者 Sohrab ROHANI 《Frontiers of Chemical Science and Engineering》 SCIE EI CSCD 2010年第1期2-9,共8页
The applications of the crystallization technique in the pharmaceutical industry as a purification and separation process for the isolation and synthesis of pure active pharmaceutical ingredients(API),co-crystals,cont... The applications of the crystallization technique in the pharmaceutical industry as a purification and separation process for the isolation and synthesis of pure active pharmaceutical ingredients(API),co-crystals,controlled release pulmonary drug delivery,and separation of chiral isomers are briefly discussed using a few case studies.The effect of process variables and solvent on the polymorphism and morphology of stavudine is discussed.The implementation of external control in the form of feedback and real-time optimal control using cooling and antisolvent crystallization of paracetamol in water-isopropyl alcohol is introduced.Two methods to prepare micronsized drug particles,namely,micro-crystallization and polymer-coated API-loaded magnetic nanoparticles for pulmonary drug delivery,are discussed.The significance of co-crystals in drug administration is highlighted using the theophylline-nicotinamide co-crystal system.Resolution of chloromandelic acid derivatives,a racemic compound,is achieved using direct crystallization and diastereomeric salts crystallization.The crystal structures of diastereomeric salts of chloromandelic acid and phenylethylamine are determined.The structure comparison between the less soluble and more soluble salts shows that weak interactions such as CH/πinteractions and van der Waals forces contribute to chiral recognition when the hydrogen bonding patterns are similar. 展开更多
关键词 CRYSTALLIZATION control of crystal properties POLYMORPHISM CO-CRYSTALS pulmonary drug delivery resolution of chiral isomers
原文传递
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
19
作者 JIANG Shanshan YUAN Jia +4 位作者 QIN Yanlan LUO Ying JIN Zhengsheng ZHAO Guilong TI Huihui 《Chemical Research in Chinese Universities》 SCIE CAS 2024年第6期1096-1105,共10页
Chiral secondary alcohols are an important class of functionalities commonly seen in drugs and other bioactive compounds.In an ongoing drug discovery program in our laboratories,a nitro-bearing racemic allylic seconda... Chiral secondary alcohols are an important class of functionalities commonly seen in drugs and other bioactive compounds.In 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 needed.In 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 auxiliaries.The 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 study.The two enantiomers were obtained in high optical purities.This 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. 展开更多
关键词 chiral resolution Phenylglycine chiral auxiliary chiral secondary alcohol Diastereomeric ester formation
原文传递
上一页 1 下一页 到第
使用帮助 返回顶部