Crystal structure and vibrational spectra of 2-chloromethyl-5-hydroxy-4H-pyran-4-one and 5-hydroxy-2-methyl-4H-pyran-4-one as potential ligands for Fe(III) complexes

Hryniewicz, Katarzyna; Stadnicka, Katarzyna; Pattek‐Janczyk, A.

doi:10.1016/j.molstruc.2008.09.021

Cited by 13 publications

(10 citation statements)

References 23 publications

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“…It seems that the experimental data are not significantly influenced by thermal motions (see footnote under Table 2). The crystal packing of the chlorokojic acid, in reference to the paper of Hryniewicz et al, 18 Those weak intermolecular interactions appear to play an important role in the formation of the crystal. Their full description will be given later.…”

Section: Resultsmentioning

confidence: 96%

“…16,17 The crystal structure of chlorokojic acid at low-temperature (100 K) and vibrational spectra were previously reported. 18 It was shown that chlorine atoms may form a pseudohexagonal arrangement with folded layers at 1/4, y, z and 3/4, y, z. It was also pointed out that, in the crystal structure, a few hydrogen bonds are present: three intermolecular ones O8−H8···O7 (−x + 1, −y + 1, z + 1/2), C3−H3···O7 (−x + 1, −y + 1, z − 1/2), and C6−H6···Cl1 (x, y, z + 1), and one intramolecular O8− H8···O7.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Experimental and Theoretical Charge Density Study of the Chemical Bonding in Chlorokojic Acid Crystal Structure

Krawczuk

Stadnicka

2012

J. Phys. Chem. A

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The experimental charge density in the chlorokojic acid crystal structure was investigated on the basis of high-resolution X-ray diffraction data collected at 80(2) K. The nature of chemical bonding and halogen interactions has been studied by means of deformation densities and by topological analysis using the Bader's quantum theory of atoms in molecules (QTAIM). A comparison between the experimental and theoretical results, from calculations concerning gas phase and periodic DFT/B3LYP, was performed. For the intermolecular hydrogen bonds of O-H···O, C-H···O, and C-H···Cl types, full characteristics of bond critical points (BCP's) were provided indicating closed-shell interactions. The topological analysis of charge density distribution revealed the presence of intermolecular C-Cl···O halogen bridge and halogen-halogen interactions of C-Cl···Cl-C type forming supramolecular Cl(3) synthons, crucial for three-dimensional structure formation of chlorokojic acid. The pronounced anisotropy of electrostatic potential at the Cl atom clarifies both electrophilic and nucleophilic properties of the substituent.

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Section: Resultsmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

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Experimental and Theoretical Charge Density Study of the Chemical Bonding in Chlorokojic Acid Crystal Structure

Krawczuk

Stadnicka

2012

J. Phys. Chem. A

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“…One of these two bonds is located between the keto and hydroxyl group and the other hydrogen bond can be formed weakly between the hydroxymethyl moiety and the intra-ring oxygen [20]. The details of crystal structure analyses data of chlorokojic acid and allomaltol were investigated and their molecular geometry was compared to the geometry of their close analog kojic acid [21,22]. In our previous studies, the structures of some Mannich bases of allomaltol derivatives were also determinated by X-ray analysis.…”

Section: Resultsmentioning

confidence: 99%

Anticonvulsant and Neurotoxicity Evaluation of Some Novel Kojic Acids and Allomaltol Derivatives

Aytemir

Calis

2010

Archiv der Pharmazie

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A series of new 3-hydroxy-6-hydroxymethyl/methyl-2-substituted 4H-pyran-4-ones were synthesized and prepared by the reaction of kojic acid or allomaltol with piperidine derivatives and formaline as potential anticonvulsant compounds. The structure of the synthesized compounds was confirmed using the elemental analysis results and the spectroscopic techniques such as IR, 1H-NMR, and ESI-MS. Anticonvulsant activities were examined by maximal electroshock (MES) and subcutaneous Metrazol (scMet)-induced seizure tests. Neurotoxicity was determined by the rotorod toxicity test. All these tests were performed in accordance with the procedures of the Antiepileptic Drug Development (ADD) program. According to the activity studies and at all doses, 3-hydroxy-2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-6-methyl-4H-pyran-4-one (compound 1), 2-{[4-(4-chlorophenyl)-3,6-dihydropyridin-1(2H)-yl]methyl}-3-hydroxy-6-methyl-4H-pyran-4-one (compound 6), 2-[(4-acetyl-4-phenylpiperidin-1-yl)methyl]-3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one (compound 11), and 2-{[4-(4-chlorophenyl)-3,6-dihydropyridin-1(2H)-yl] methyl}-3-hydroxy-6-hydroxymethyl-4H-pyran-4-one (compound 12) were found to have anticonvulsant activity against MES-induced seizures at 4 h. Also, 2-{[4-(4-bromophenyl)-4-hydroxypiperidin-1-yl]methyl}-3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one (compound 8) was determined to be the most active compound against scMet-induced seizures at all doses at 0.5 and 4 h. In the rotorod neurotoxicity screening, all compounds showed no toxicity at all doses.

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“…Also, it forms stable complexes of metal kojates via reaction of kojic acid with metal acetate salts such as tin, beryllium, zinc, copper, nickel, cobalt, iron, manganese, chromium, gold, palladium, indium, gallium, vanadium, and aluminium ( Fig. 2) (Barret, 2001;Cecconi, 2002;Emami, 2007;Finnegan, 1987;Hryniewicz, 2009;Masoud, 1989;Moggia, 2006;Naik, 1979;Sudhir, 2005;Yang, 2008;Zaremba, 2007;Zborowski, 2005). They were used as new drugs in the therapy of some diseases such as diabetes, anemia, fungal infections and neoplasia (Brtko, 2004;Song, 2002;Wolf, 1950).…”

Section: Kojic Acidmentioning

confidence: 99%

Kojic Acid Derivatives

Aytemir¹,

Karakaya²

2012

Medicinal Chemistry and Drug Design

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Medicinal Chemistry and Drug Design 2 browning in fruits and vegetables. In the food industry, tyrosinase is important in controlling the quality and economics of fruits and vegetables. Hence, tyrosinase inhibitors from natural sources have great potential in the food industry, as they are considered to be safe and largely free from adverse effects. Also in insects, tyrosinase is involved in melanogenesis wound healing, parasite encapsulation and sclerotisation (Seo, 2003). Therefore, tyrosinase inhibitors used as insecticides and insect control agents. Moreover, the tyrosinase is responsible from melanization in animals and is the key enzyme for the regulation of melanogenesis in mammals. Melanogenesis is the process by which melanin is produced and subsequently distributed by melanocytes within the skin and hair follicles. This process results in the synthesis of melanin pigments, which play a protective role against skin photocarcinogenesis (

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Crystal structure and vibrational spectra of 2-chloromethyl-5-hydroxy-4H-pyran-4-one and 5-hydroxy-2-methyl-4H-pyran-4-one as potential ligands for Fe(III) complexes

Cited by 13 publications

References 23 publications

Experimental and Theoretical Charge Density Study of the Chemical Bonding in Chlorokojic Acid Crystal Structure

Experimental and Theoretical Charge Density Study of the Chemical Bonding in Chlorokojic Acid Crystal Structure

Anticonvulsant and Neurotoxicity Evaluation of Some Novel Kojic Acids and Allomaltol Derivatives

Kojic Acid Derivatives

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