Synthesis and selective lead(II) binding of achiral and enantiomerically pure chiral acridono-18-crown-6 ether type ligands

Szalay, Luca; Farkas, Viktor; Vass, Elemér; Hollósi, Miklós; Móczár, Ildikó; Huszthy, Péter

doi:10.1016/j.tetasy.2004.03.024

Cited by 25 publications

(23 citation statements)

References 19 publications

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“…6) were also prepared. The latter compounds bind selectively lead (II) cations as demonstrated by CD measurements [19]. The acridono-18-crown-6 ethers seem to have several advantageous features compared to their pyridono analogues.…”

Section: Proton-ionizable Crown Ethersmentioning

confidence: 95%

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Synthesis and molecular recognition studies of crown ethers

Huszthy¹,

Tóth²

2007

Per. Pol. Chem. Eng.

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This short review summarizes the synthesis and molecular recognition studies of crown ether type macrocycles accomplished at the Institute for Organic Chemistry of Budapest University of Technology and Economics in the last few years. The research work reported here belongs to the areas of protonionizable crown ethers and chiral macrocycles.Proton-ionizable crown ethers at higher pH s than their pK a values are mostly ionized to ligand anions which increase the cation-ligand complex stability with enhancement of selectivity and avoid the need for a counter anion to accompany the cation transport or solvent extraction. The latter factor is not only advantageous from energetical point of view, but is also important when counter anions are not required to be transported.Enantiopure chiral macrocycles have also drawn the attention of many researchers, because owing to their enantioselective complexation they are excellent candidates for effective sensors and selectors of the enantiomers of biologically important chiral compounds such as protonated primary organic amines, amino acids and the derivatives of the latters. Keywords molecular recognition · enantiomeric recognition · protonionizable crown ethers · chiral crown ethers · chiral stationary phases Acknowledgement This work was supported by the Hungarian Scientific Research Fund (OTKA K62654) and by the Ministry of Education of Hungary (Postdoctoral Fellowship PAL 11/2003). Péter HuszthyDepartment of Organic Chemistry, BME, H-1111, Budapest, Szent Gellért tér 4., Hungary e-mail: huszthy@mail.bme.hu Tünde TóthDepartment of Organic Chemistry, BME, H-1111, Budapest, Szent Gellért tér 4., Hungary 1 Introduction Molecular recognition is a generally occurring phenomenon in nature. Examples include the storage and retrieval of genetic information by the DNA double helix, the selective binding of a subtrate by the active site of an enzyme, the antibodyantigen interactions, selective transport of metal ions by natural ionophores through different biomembranes and incorporation of the single enantiomeric forms of amino acids and sugars in metabolic pathways. The latter two examples refer to enantiomeric recognition. Enantiomeric recognition, as a special case of molecular recognition involves the discrimination between enantiomers of the guest by a chiral host. It was believed a few decades ago that molecular recognition was the result of unique properties of complex biomolecules. However, recent successes in imitating such phenomena using relatively simple synthetic compounds have demonstrated that biological behaviour can be engineered into small molecules. Crown ether type macrocycles for example offer unusual opportunities for the study of molecular recognition. These kinds of studies are not only important, because we can get deeper insight and understandig of molecular recognition in the living organisms, but also, because as a result of these studies we can develop new molecular sensors and selectors for practical applications.Probably the greatest impetus...

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Section: Proton-ionizable Crown Ethersmentioning

confidence: 95%

“…Circular dicroism (CD) spectroscopic measurements indicated that the fairly acidic proton-ionizable acridono-crown ether 21 forms a complex with α-(1-naphthyl)ethylamine (1-NEA) [19].…”

Section: Proton-ionizable Crown Ethersmentioning

confidence: 99%

Synthesis and molecular recognition studies of crown ethers

Huszthy¹,

Tóth²

2007

Per. Pol. Chem. Eng.

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“…Quite a number of podands and macrocycles, as well as other derivatives, revealed applications as intercalating agents [65][66][67][68][69][70][71][72]. Macrocycles embedding these aromatic units also showed applications as sensors and chiral discriminators [73][74][75][76].…”

Section: Macrocycles With Phenothiazine Unitsmentioning

confidence: 99%

Macrocycles embedding phenothiazine or similar nitrogen and/or sulphur containing heterocycles

Rednic

Hădade

Bogdan

et al. 2014

J Incl Phenom Macrocycl Chem

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Macrocycles emerged as an important class of useful compounds with multiple applications ranging from selective complexation of different anions, cations or neutral molecules to the development of new sensors, materials with improved properties and biologically active compounds. In this review we focus our discussion on the synthesis and structural analysis of macrocycles containing dibenzoheterocycles with sulphur and/or nitrogen atoms in the central six-membered ring (i.e. 10H-phenothiazine, 9,10-dihydroacridine or acridane, acridone, thianthrene, phenoxathiine, acridine, phenazine). We further highlight selected application of these compounds as host molecules, DNA intercalating agents or enzyme inhibitors.

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“…Synthesis and molecular recognition studies of many crown ethers based on tricyclic heterocycles are reported in the literature, for example those of xanthone 10 -, dibenzofuran [11][12][13][14] -, phenanthroline [15][16][17][18][19][20][21][22] -, phenazine [23][24][25][26][27] -, or acridone-and acridine 23,[28][29][30][31][32][33][34][35][36][37] -based macrocycles. In the continuation of our research of crown ethers based on tricyclic ring systems, [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] our attention turned toward phenothiazine. The properties of the nitrogen of phenothiazine can not only be modified by substitution in the aromatic rings, but also by changing the oxidation state of the sulfur atom making it a promising building element of new macrocycles.…”

Section: Introductionmentioning

confidence: 99%