Synthesis of Functionalized Acenaphthenes and a New Class of Homooxacalixarenes

AlHujran, Tayel A.; Georghiou, Paris E.

doi:10.1021/ol301538s

Cited by 16 publications

(6 citation statements)

References 19 publications

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“…Calix[ n ]arenes are cyclic oligomers that have different sizes depending on the number of the repeated phenolic unit, ranging from 4 to 8 units [ 7 , 8 , 9 , 10 ]. This type of macrocyclic has a well-defined deep hydrophobic cavity surrounded by a hydrophobic upper rim and hydrophilic lower rim.…”

Section: Introductionmentioning

confidence: 99%

Studying the Complex Formation of Sulfonatocalix[4]naphthalene and Meloxicam towards Enhancing Its Solubility and Dissolution Performance

et al. 2021

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The interaction between meloxicam and sulfonatocalix[4]naphthalene was investigated to improve the meloxicam solubility and its dissolution performance. Solubility behavior was investigated in distilled water (DW) and at different pH conditions. Besides, solid systems were prepared in a 1:1 molar ratio using coevaporate, kneading, and simple physical mixture techniques. Further, they were characterized by PXRD, FT-IR, DCS, and TGA. In vitro dissolution rate for coevaporate, kneaded, and physical mixture powders were also investigated. Solubility study revealed that meloxicam solubility significantly increased about 23.99 folds at phosphate buffer of pH 7.4 in the presence of sulfonatocalix[4]naphthalene. The solubility phase diagram was classified as AL type, indicating the formation of 1:1 stoichiometric inclusion complex. PXRD, FT-IR, DCS, and TGA pointed out the formation of an inclusion complex between meloxicam and sulfonatocalix[4]naphthalene solid powders prepared using coevaporate technique. In addition, in vitro meloxicam dissolution studies revealed an improvement of the drug dissolution rate. Furthermore, a significantly higher drug release (p ≤ 0.05) and a complete dissolution was achieved during the first 10 min compared with the other solid powders and commercial meloxicam product. The coevaporate product has the highest increasing dissolution fold and RDR10 in the investigated media, with average values ranging from 5.4–65.28 folds and 7.3–90.7, respectively. In conclusion, sulfonatocalix[4]naphthalene is a promising host carrier for enhancing the solubility and dissolution performance of meloxicam with an anticipated enhanced bioavailability and fast action for acute and chronic pain disorders.

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Section: Introductionmentioning

confidence: 99%

Studying the Complex Formation of Sulfonatocalix[4]naphthalene and Meloxicam towards Enhancing Its Solubility and Dissolution Performance

et al. 2021

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“…(Guo et al, 2018; Luo et al, 2018; Ma et al, 2018) have been widely used in host-guest chemistry, self-assembly materials, and biomedical field (Song and Yang, 2015; Alsbaiee et al, 2016; Li et al, 2017; Jie et al, 2018; Chen et al, 2019; Yang et al, 2019). Naphthalene-based macrocyclic arenes, termed as calixnaphthalenes, have also been produced (Poh et al, 1989; Andreetti et al, 1993; Shorthill et al, 2004; AlHujran et al, 2012; Avetta et al, 2012). However, calixnaphthalenes have not become highly popular receptors because they do not have unique molecular recognition properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Host–Guest Properties of Acyclic Pillar[n]naphthalenes

et al. 2019

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Here we report a new class of synthetic receptors, acyclic pillar[n]naphthalene (n = 2–4, Dimer, Trimer, and Tetramer) oligomers, which are made up of 2,3-diethoxynaphthalene units linked by methylene bridges at the 1- and 4-positions. They can be synthesized through a one-step condensation of 2,3-diethoxynaphthalene monomer and paraformaldehyde in the presence of BF3•(Et)2O catalyst. The crystal structure of Tetramer has an interesting pseudo-cycle shaped structure in the solid state. Their complexation behaviors toward several organic ammonium cations (1+-15+) and electron–deficient neutral guests (16–17), were examined by means of 1H NMR spectroscopy. Tetramer shows good host-guest properties toward the ammonium guests, giving association constants (Ka) in the magnitude of 102-104 M−1, which are comparable with those for some macrocyclic hosts.

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“…21,22 However, majority of such naphthalene-based molecular cavitand suffered from difficult regioisomeric products with ill-defined and shallow cavities, and scarcely displayed satisfactory guest binding. 23,24 To overcome these difficulties, recently Jiang et al 25−28 reported flexible naphthalene based macrocycles viz., oxatub[n]arene (n = 4, 5, and 6) and synthesized by the one-pot reaction under high dilution condition in which the repeating 2,6-dihydroxynaphthalene units are connected by ether (CH 2 −O−CH 2 ) linkage at the 1,5-positions, which minimize the potential isomerism and avoid the self-occupation of the cavity and also helps in maintaining the depth of cavities. Additionally, the flexible naphthalene moieties lead to multiple conformers which bring forth effective guest binding.…”

Section: ■ Introductionmentioning

confidence: 99%

Molecular Recognition, Conformational Behavior, and Spectral Characteristics of Oxatub[4]arene Macrocycle

Lande

Gejji

2018

J. Phys. Chem. A

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In the present work, we analyze molecular recognition behavior of synthetic hydroxylated oxatub[4]arene (TA4) receptor toward the methyl viologen in different redox states. The supramolecular binding of methyl viologen guest toward TA4 macrocyclic scaffold has been studied employing the dispersion corrected ωB97X-D based density functional theory. The methyl viologen in dicationic and neutral forms revealed distinct features in electronic, H nuclear magnetic resonance, and infrared spectra. Quantum theory of atoms in molecules in conjunction with the noncovalent interaction reduced density gradient in real space have been used as tools to characterize the underlying host-guest binding.

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Synthesis of Functionalized Acenaphthenes and a New Class of Homooxacalixarenes

Cited by 16 publications

References 19 publications

Studying the Complex Formation of Sulfonatocalix[4]naphthalene and Meloxicam towards Enhancing Its Solubility and Dissolution Performance

Studying the Complex Formation of Sulfonatocalix[4]naphthalene and Meloxicam towards Enhancing Its Solubility and Dissolution Performance

Synthesis and Host–Guest Properties of Acyclic Pillar[n]naphthalenes

Molecular Recognition, Conformational Behavior, and Spectral Characteristics of Oxatub[4]arene Macrocycle

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