Synthesis of Hydroxypropyl-β-cyclodextrin Bonded Silica-gel and its Application to Resolution

In order to set up a simple and effective method for resolution of optical isomers, hydroxypropyl-β-cyclodextrin was bonded to silica-gel, which can be used for preparation of thin-layer chromatography plates. Resolution of clenbuterol and propranolol were investigated on these thin-layer chromatography plates using different combinations of solvent systems at ambient temperature. The best simultaneous resolution was achieved in solvent system of acetonitrilen-butanol （50：50, v/v）. Rst values of resolution of clenbuterol hydrochloride and propranolol hydrochloride are 3.6 and 4.3, respectively. The spots of different enantiomers are separated clearly. The results showed that hydroxypropyl-β-cyclodextrin bonded silica-gel could be successful in resolution of chiral adrenergic drugs. The study offers a direct, rapid and reliable method for separation of this kind of optically active compounds.

Synthesis of β-Cyclodextrin Bonded Metal Porphyrins

6-Deoxy- 6-iodo-β-cyclodextrin (1) reacted with 5-(p-aminophenyl)-10, 15,20-triphenyl porphyrin(2), 5-(p-aminophenyl)-10,15,20-triphenyl nickel(Ⅱ) porphyrin [NiⅡTPPNH2P](3),5-(p-aminophenyl)-10,15,20-triphenyl manganese(Ⅲ) porphyrin [MnⅢTPPNH2P] (4) and 5-(p-aminophenyl)-10,l5,20-triphenyl carbonyl ruthenium porphyrin [RuⅡ (CO)TPPNH2P] (5) to generate the compounds 6-9, respectively. Those new compound 5-9 have been identified by 1H NMR, IR, MS and UV-visible spectra and elemental analysis.

POLYMER-SUPPORTED β-CYCLODEXTRIN CATALYST FOR SELECTIVE SYNTHESISOF 4-H YDROXYBENZOIC ACID

4-hydroxybenzoic acid was synthesized by one pot method using polymer-bonded β-aminopropionic acid-2-β-cyclodextrin as a catalyst.by which the selectivity for 4-hydroxybenzoic acid is 87%. A possible carboxylation mechanism in the presence of the title catalyst is discussed. Also.the recovery and reusage of the catalyst is studied.

Synthesis and Characterization of β-Cyclodextrin Bonded Metal Porphyrins

Reactions of 5-(p-aminophenyl)-10, 15, 20-triphenyl porphyrin (1) withRu_3(CO)_(12) or M(OCOCH_3)_2 (M= Ni, Mn) afforded metalloporphyrins (4―6), respectively.6-Deoxy-6-io-do-β-cyclodextrin (2) and mono (6-O-trifluoromethanesulfonyl) pennethylatedβ-cyclodextrin (3) reacted with complexes 4―6 to give β-cyclodextrin bonded metal porphyrins(7―9) and permethylated β-cyclodextrin bonded me-tal porphyrins (10―12) respectively. These newcomplexes were identified by MS, IR, UV-visible and ~1H NMR spectra, and elemental analysis.

Synthesis and fluorescence properties of CdSe/CdS nanoparticles in aqueous media

On the basis of unique structural characteristics of α-cyclodextrin,α-cyclodextrin modified CdSe/CdS nanoparticles have been successfully synthesized in aqueous media.Techniques of AFM,TEM,EDS,FTIR,UV-vis absorbance and photoluminescence spectra were used to characterize the morphology,composition and optical characteristics of the synthesized nanoparticles.The results showed that the as-synthesized nanoparticles were elliptical and composed of several small particles.Their average length and diameter were about 20 nm and 15 nm.CdSe/CdS nanoparticles had single well-crystallized hexagonal structure.Packaged with a shell of CdS on the surface,α-CD/CdSe-CdS nanoparticles exhibited a red shift in the absorption spectrum,intensity growth in the emission spectrum and a substantial increase in Quantum yields.The size distribution could be adjusted by precursor ratios in the presence of α-cyclodextrins.

Facile preparation and characterization of novel oleanane-type triterpene functionalized β-cyclodextrin conjugates

Oleanolic acid(OA) and echinocystic acid(EA), two naturally occurring pentacyclic oleanane triterpenes,are gaining increasing attention due to their promising pharmacological activities. Conjugation with amphiphilic α(β)-cyclodextrin(CD) via "click chemistry" can improve their solubility and anti-HCV entry potency. In the present work,four water-soluble β-CD-pentacyclic triterpene conjugates were designed and synthesized, in which OA and EA was coupled to one of the primary hydroxyl groups of β-CD via ester and amide bonds. The structures of the conjugates were unambiguously determined by ~1H NMR, ^(13)C NMR and HRMS or MALDI-TOF-MS. All the conjugates showed lower hydrophobicity(AlogP) than their parent compounds and no significant cytotoxicity was found to HL-60, A549, Hela and Bel-7402 cells at concentrations up to 10 μmol/L. Further anti-HCV entry activity and mechanism studies are under way in our laboratory.