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The synthesis and molecular recognition study of β-cyclodextrin derivatives modified by spiro[2H-benzopyran-2,2′-indoline]

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Abstract

In this study, we adopted the condensation reaction between the aldehyde group in spiro[2H-benzopyran-2,2′-indoline] and the ethylene diamine in β-cyclodextrins to synthesize 1,3,3-trimethyl-6′-mono-(6-deoxy-ethylenediimine-β-cyclodextrin)-spiro[2H-benzopyran-2,2′-indoline] (β-CD-SPBI). The structure of the target compound was characterized by elemental analysis, NMR and IR spectroscopy. The UV–Vis and fluorescence spectroscopy were investigated in different solvents. The preliminary study of its molecular recognition was also conducted. The results indicated that β-CD-SPBI existed as two structural isomers, both of which showed significant fluorescent characteristics and β-CD-SPBI could showed the capacity of dual molecular recognition of a drug, ribavirin.

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Abbreviations

β-CD:

β-Cyclodextrin

β-CD-SPBI:

1,3,3-Trimethyl-6′-mono-(6-deoxy-ethylenediimine-β-cyclodextrin)-spiro[2H-benzopyran-2,2′-indoline]

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Acknowledgment

This research is financially supported by Shaanxi Province Natural Science Foundation of China under the grant number of 2007B16.

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  1. School of Chemistry and Chemical Engineering, Xianyang Normal University, 712000, Xianyang, China

    Yi Huang & Jin C. Guo

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  1. Yi Huang
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  2. Jin C. Guo
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Correspondence to Yi Huang.

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Huang, Y., Guo, J.C. The synthesis and molecular recognition study of β-cyclodextrin derivatives modified by spiro[2H-benzopyran-2,2′-indoline]. J Incl Phenom Macrocycl Chem 68, 109–116 (2010). https://doi.org/10.1007/s10847-010-9743-2

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  • DOI: https://doi.org/10.1007/s10847-010-9743-2

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