Action of antitheines with different mnemic effects on cAMP-independent protein kinases of brain chromatin

Богданова, Н. А.; Куликова, О. Г.; Borodkin, Yu. S.

doi:10.1007/bf00842676

Cited by 3 publications

(3 citation statements)

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“…Heterocyclic compounds are important in both materials and in biological systems and often interact in the system in a manner dependent upon their hydrogen-bonding properties. Imidazole-4,5-dicarboxylic acid derivatives have been studied in terms of their physical properties as well as for their diverse biological activities, − including the use of imidazole-4,5-dicarboxamides (I45DCs) in the development of human immunodeficiency virus (HIV-1) protease inhibitors . Oligomeric I45DCs have been shown to form metal complexes and have also been included in polyamides …”

Section: Introductionmentioning

confidence: 99%

Intramolecular Hydrogen Bonding and Intermolecular Dimerization in the Crystal Structures of Imidazole-4,5-dicarboxylic Acid Derivatives

Baures

Rush

Wiznycia

et al. 2002

Crystal Growth & Design

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Diamide and amide-ester derivatives of imidazole-4,5-dicarboxylic acid form reliable hydrogen-bonding motifs in the solid state. The crystal structures of symmetrically substituted and dissymmetrically substituted diamides as well as amide-ester combinations were analyzed in order to identify the intermolecular hydrogen-bonding patterns. An intramolecular seven-membered hydrogen-bonded conformation forms in all derivatives where the possibility existed due to the functionality present. The motifs observed for the diamides include intermolecular NH···O and NH···N hydrogen-bonded dimers, with the exceptions to these motifs occurring in compounds having benzylamine substituents. The amines with a higher classification (i.e., 3° > 2° > 1°) in the dissymmetrically substituted diamides are the intramolecular hydrogen bond donors in the solid state, consistent with the capacity of the alkyl group to stabilize developing carbocation character resulting from bond polarization. The amide-ester derivatives also form an intramolecular hydrogen bond and an intermolecular motif based on NH···N and two different C2−H···O hydrogen bonds. A pyrrole amide-ester derivative forms an intramolecular NH···O hydrogen bond in the solid state and an intermolecular NH···O hydrogen-bonded chain. With the exception of the benzylamine-substituted diamides, the intermolecular hydrogen-bonded motifs appear reliable for these imidazole-4,5-dicarboxylic acid derivatives and will be useful in the design of analogues for specific applications.

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Section: Introductionmentioning

confidence: 99%

Intramolecular Hydrogen Bonding and Intermolecular Dimerization in the Crystal Structures of Imidazole-4,5-dicarboxylic Acid Derivatives

Baures

Rush

Wiznycia

et al. 2002

Crystal Growth & Design

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“…For the properties and biological activity of imidazole-4,5dicarboxylic acid and its derivatives, see: Baures (1999); Bogdanova et al (1992); Borodkin et al (1984); Reichardt et al (1992); Su et al (2001).…”

Section: Related Literaturementioning

confidence: 99%

“…E67, m408 (Su et al, 2001). Imidazole-4,5-dicarboxylic acid and derivatives have been studied in terms of their physical properties as well as for their diverse biological activities (Bogdanova et al, 1992;Borodkin et al, 1984;Reichardt et al, 1992), including the use of imidazole-4,5-dicarboxylic acid amides in the development of human immunodeficiency virus (HIV-1) protease inhibitors (Baures, 1999). Here we present the synthesis and structure of the title complex derived from 2-propyl-1H-imidazole-4,5-dicarboxylic acid.…”

Section: Sup-1mentioning

confidence: 99%

Poly[[μ₂-aqua-μ₃-(4-carboxy-2-propyl-1H-imidazole-5-carboxylato-κ⁴N³,O⁴:O⁴:O⁵)-sodium] hemihydrate]

et al. 2011

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Key indicators: single-crystal X-ray study; T = 296 K; mean (C-C) = 0.003 Å; R factor = 0.034; wR factor = 0.106; data-to-parameter ratio = 13.1.In the title compound, {[Na(C 8 H 9 N 2 O 4 )(H 2 O)]Á0.5H 2 O} n , the Na + ion is coordinated by two bridging water molecules, one N atom and three O atoms from three 4-carboxy-2-propyl-1H-imidazole-5-carboxylate (H 2 pimdc) ligands. Adjacent Na + ions are linked alternately by two water O atoms and two carboxy O atoms into a chain along [001]. These chains are connected through the coordination of the carboxylate O atoms to the Na + ions, forming a three-dimensional structure. An intramolecular O-HÁ Á ÁO hydrogen bond and intermolecular N-HÁ Á ÁO and O-HÁ Á ÁO hydrogen bonds are present in the crystal structure. Related literature ExperimentalCrystal data [Na(C 8 Data collectionBruker APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.528, T max = 0.562 5971 measured reflections 1986 independent reflections 1669 reflections with I > 2 (I) R int = 0.020

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Small molecule inhibition of hepatitis C virus E2 binding to CD81

et al. 2003

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The hepatitis C virus (HCV) is a causal agent of chronic liver infection, cirrhosis, and hepatocellular carcinoma infecting more than 170 million people. CD81 is a receptor for HCV envelope glycoprotein E2. Although the binding of HCV-E2 with CD81 is well documented the role of this interaction in the viral life cycle remains unclear. Host specificity and mutagenesis studies suggest that the helix D region of CD81 mediates binding to HCV-E2. Structural analysis of CD81 has enabled the synthesis of small molecules designed to mimic the space and hydrophobic features of the solvent-exposed face on helix D. Utilizing a novel bis-imidazole scaffold a series of over 100 compounds has been synthesized. Seven related, imidazole-based compounds were identified that inhibit binding of HCV-E2 to CD81. The inhibitory compounds have no short-term effect on cellular expression of CD81 or other tetraspanins, do not disrupt CD81 associations with other cell surface proteins, and bind reversibly to HCV-E2. These results provide an important proof of concept that CD81-based mimics can disrupt binding of HCV-E2 to CD81.

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Action of antitheines with different mnemic effects on cAMP-independent protein kinases of brain chromatin

Cited by 3 publications

References 2 publications

Intramolecular Hydrogen Bonding and Intermolecular Dimerization in the Crystal Structures of Imidazole-4,5-dicarboxylic Acid Derivatives

Intramolecular Hydrogen Bonding and Intermolecular Dimerization in the Crystal Structures of Imidazole-4,5-dicarboxylic Acid Derivatives

Poly[[μ₂-aqua-μ₃-(4-carboxy-2-propyl-1H-imidazole-5-carboxylato-κ⁴N³,O⁴:O⁴:O⁵)-sodium] hemihydrate]

Small molecule inhibition of hepatitis C virus E2 binding to CD81

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Action of antitheines with different mnemic effects on cAMP-independent protein kinases of brain chromatin

Cited by 3 publications

References 2 publications

Intramolecular Hydrogen Bonding and Intermolecular Dimerization in the Crystal Structures of Imidazole-4,5-dicarboxylic Acid Derivatives

Intramolecular Hydrogen Bonding and Intermolecular Dimerization in the Crystal Structures of Imidazole-4,5-dicarboxylic Acid Derivatives

Poly[[μ2-aqua-μ3-(4-carboxy-2-propyl-1H-imidazole-5-carboxylato-κ4N3,O4:O4:O5)-sodium] hemihydrate]

Small molecule inhibition of hepatitis C virus E2 binding to CD81

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Poly[[μ₂-aqua-μ₃-(4-carboxy-2-propyl-1H-imidazole-5-carboxylato-κ⁴N³,O⁴:O⁴:O⁵)-sodium] hemihydrate]