Synthesis and Anion Recognition of Macrocycle Containing Isophthalamide Unit

Wei, Xiao-kang; Gu, Jing-Chi; Liu, Xingli; Huang, Chao; Zhu, Bin

doi:10.6023/cjoc201805012

Cited by 2 publications

(1 citation statement)

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“…由芳香单体形成的腙类大环分子, 由于共轭大环的强堆积作用, 其溶解性一般很低, 需要引入多个长的亲水侧链或正离子才能制备, 分离和纯化相应大环 [14] . 本文研究结果显示, 通过开环葫芦脲的水相增溶作用, 可以实现普通条件下不能进行的一些反应, 为一些低溶解性的特殊结构分子特别是大环分子的合成提供了一个新的思路 [15] .…”

Section: 结论unclassified

Water-Solubilization of Acyclic Cucurbiturils for Arenes and Aromatic Aldehydes and the Promotion for the Generation of Two Hydrazine-Based Macrocycles

Liu¹,

Lin²,

Wang³

et al. 2020

Chin. J. Org. Chem.

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The promotion of two sulfate or carboxylate-bearing acyclic cucurbiturils for the water-solubility of arenes and aromatic aldehydes is described. 1 H NMR experiments reveals that sulfate-bearing acyclic cucurbituril (acCB-1) signficantly improves the water-solubility of a number of arenes and aldehydes. For 4,4'-dimethylbiphenyl and biphenyl-4,4'dicarbaldehyde, the solubility can be improved to 8.9 and 11.2 mmol/L, respectively. 19 F NMR experiments demonstrate that carboxylate-bearing acyclic cucurbituril can increase the water-solubilities of pentafluorotoluene and hexafluorobenzene to 5.6 and 3.0 mmol/L, respectively. It is also found that the water-solubilization of acCB-1 for aromatic aldehydes can promote their reaction with acylhydrazines to form hydrozone derivatives. By making use of this promotion, two hydrazone-based macrocycles can be formed from the coupling reactions of two aromatic dialdehdes and one diacylhydrazine in water.

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Section: 结论unclassified

Water-Solubilization of Acyclic Cucurbiturils for Arenes and Aromatic Aldehydes and the Promotion for the Generation of Two Hydrazine-Based Macrocycles

Liu¹,

Lin²,

Wang³

et al. 2020

Chin. J. Org. Chem.

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Enantiomers Identification of Penicillamine by Chiral Mono-Schiff Base Macrocycles

Tian¹,

Lin²,

Han³

et al. 2023

Acta Chimica Sinica

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A large number of chiral drug molecules have a chiral structure containing both D-and L-enantiomers, leading to the mirror image arrangements of the two forms eliciting quite different physiological responses. Penicillamine (Pen) is a common chiral drug that is obtained from penicillin, and researchers have been making continuous efforts to achieve rigorous analysis and discrimination of the two enantiomers. Based on chiral Schiff base macrocycles containing NH functionalities have the advantages of mild synthesis conditions and convergence of structural arrangement. Here we report two enantiomers of the mono-Schiff base macrocycle containing chiral NH moiety in the cyclic structure (CR and CS), and the binding affinity and enantioselectivity of the cyclic enantiomers toward small molecules penicillamine (D-Pen and L-Pen). The crystal structures of the mono-Schiff base cyclic enantiomers were determined by X-ray diffraction analysis, and the results show that the two cyclic enantiomers exhibit twisted non-planar conformation, in which the chiral NH proton points to the inside of the ring cavity. The interactions between different enantiomers of the chiral macrocycle and penicillamine were investigated by ultraviolet visible (UV-Vis) and hydrogen nuclear magnetic resonance ( 1 H NMR) titration, and the results show that the chiral macrocycle binds with the enantiomers of penicillamine with a bonding ratio of 1∶1, binding constants around 10 7 L•mol −1 , and the complexes of [C-Pen＋H] ＋ can be easily formed and detected by electrospray ionization-mass spectrometry (ESI-MS). The interactions between different enantiomers of the chiral macrocycle and penicillamine are attributed to the intermolecular hydrogen bonding of enantiomers by the asymmetrical chiral NH moiety in the mono-Schiff base macrocycle. Comparison of bonding constants based on the chiral macrocycle binds with the enantiomers of penicillamine, the results show that the chiral CR exhibits higher enantioselectivity for L-Pen, while CS exhibits the higher enantioselectivity for D-Pen, with a binding constant ratio around 2, respectively. Further, investigation of circular dichroism (CD) spectroscopic titration indicate that the penicillamine with the same chirality as the host macrocycle binds stronger with the host than its enantiomer with the host.

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Synthesis and Anion Recognition of Macrocycle Containing Isophthalamide Unit

Cited by 2 publications

References 0 publications

Water-Solubilization of Acyclic Cucurbiturils for Arenes and Aromatic Aldehydes and the Promotion for the Generation of Two Hydrazine-Based Macrocycles

Water-Solubilization of Acyclic Cucurbiturils for Arenes and Aromatic Aldehydes and the Promotion for the Generation of Two Hydrazine-Based Macrocycles

Enantiomers Identification of Penicillamine by Chiral Mono-Schiff Base Macrocycles

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