Synthesis and biological activity of adamantane derivatives. VI. Antiinflammatory action of pyridinecarboxylic acid adamantylamides

Danilenko, G. I.; Mokhort, N. A.; Trinus, F. P.

doi:10.1007/bf00758089

Cited by 4 publications

(3 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The starting compound Na + [ trans -Ru III Cl 4 (DMSO) 2 ] − was prepared from the parent [DMSOH] + [ trans -Ru III Cl 4 (DMSO) 2 ] − by substituting Na + for [DMSOH] + according to a previously reported procedure . Ruthenium(III) compounds 1 – 3 were obtained by reacting Na + [ trans -Ru III Cl 4 (DMSO) 2 ] − with the appropriate substituted pyridine or imidazole base, − as shown in Figure . The preparation of the pyridine- and imidazole-based ligands is described in section .…”

Section: Resultsmentioning

confidence: 99%

“…grade were used without further purification. Na + [ trans -RuCl 4 (DMSO) 2 ] − and Na + [ trans -RhCl 4 (DMSO) 2 ] − were prepared according to previously reported procedures. , Similarly, the ligands (esters and amides) containing pyridine or imidazole and adamantane or cyclohexane units (Figure ) were prepared as reported previously. − …”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Through-Space Paramagnetic NMR Effects in Host–Guest Complexes: Potential Ruthenium(III) Metallodrugs with Macrocyclic Carriers

et al. 2018

View full text Add to dashboard Cite

The potential of paramagnetic ruthenium(III) compounds for use as anticancer metallodrugs has been investigated extensively during the past several decades. However, the means by which these ruthenium compounds are transported and distributed in living bodies remain relatively unexplored. In this work, we prepared several novel ruthenium(III) compounds with the general structure Na[ trans-RuCl(DMSO)(L)] (DMSO = dimethyl sulfoxide), where L stands for pyridine or imidazole linked with adamantane, a hydrophobic chemophore. The supramolecular interactions of these compounds with macrocyclic carriers of the cyclodextrin (CD) and cucurbit[ n]uril (CB) families were investigated by NMR spectroscopy, X-ray diffraction analysis, isothermal titration calorimetry, and relativistic DFT methods. The long-range hyperfine NMR effects of the paramagnetic guest on the host macrocycle are related to the distance between them and their relative orientation in the host-guest complex. The CD and CB macrocyclic carriers being studied in this account can be attached to a vector that attracts the drug-carrier system to a specific biological target and our investigation thus introduces a new possibility in the field of targeted delivery of anticancer metallodrugs based on ruthenium(III) compounds.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Through-Space Paramagnetic NMR Effects in Host–Guest Complexes: Potential Ruthenium(III) Metallodrugs with Macrocyclic Carriers

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Amines and amides of the adamantane series exhibit a broad spectrum of pharmacological activity, including analgesic [1], antiinflammatory [2], anticonvulsive [3], and antivirat [4,5]. Adamantane and its derivatives are capable of changing the hexagonal packing of methylene groups in the alkyl chains of phospholipids, thus affecting the functional properties of membrane proteins.…”

Section: Synthesis and Membranotropic Activity Of N-adamantanoylaminomentioning

confidence: 99%

Synthesis and membranotropic activity of N-adamantanoylamino and N-adamantylacetylamino acids

et al. 1999

View full text Add to dashboard Cite

Amines and amides of the adamantane series exhibit a broad spectrum of pharmacological activity, including analgesic [1], antiinflammatory [2], anticonvulsive [3], and antivirat [4, 5]. Adamantane and its derivatives are capable of changing the hexagonal packing of methylene groups in the alkyl chains of phospholipids, thus affecting the functional properties of membrane proteins. Data obtained on models of erythrocytic membranes and liposomes showed that remantadine may incorporate into the lipid membranes, modifying their structure and imparting to them a more "liquid-phase" character [6]. In the context of an investigation of the membrane activity of adamantane derivatives and the role of this factor in the antiviral and cytotoxic properties of these compounds, of special interest are amides containing, on the one hand, the adamantyl radical and, on the other hand, an amino acid residue.The purpose of this work was to synthesize some new adamantane-containing amino acids (IIIa, IIIb, and IV) and to study their effects upon the state of hemoglobin and membranes in human blood erythrocytes.The adamantane-containing amino acids IIIa, IIIb, and IV were synthesized by interaction of l-adamantanecarboxylic (I) and (1-adamantyl)acetic (11) acids with glycine, D,L-alanine, and L-valine.Ilia. IIIb;, 1V Ad = l-adamantyl; n = 0 (I, Ilia, Illb), 1 (II, IV); R = H (Ilia), iso-Pr (lllb), Me (IV). EXPERIMENTAL CHEMICAL PARTThe IR absorption spectra were measured on an IKS-29 spectrophotometer (LOMO, Russia) using samples pelletized i Samara State University, Samara, Russia. 2 State Technical University, Samara, Russia. 132 with KBr. The I H NMR spectra were recorded on a Bruker HX-90 spectrometer using CD3OD as the solvent and HMDS as the internal standard. The TLC analyses were conducted on Silufol UV-254 plates. The data of elemental analyses agree with the results of analytical calculations. (Ilia). To a solution of 2.25 g (30 mmole) of glycine in 7.5 ml of water were successively added 7.5 ml (30 mmole) of a 4 N aqueous NaOH solution, 7 ml of 1,4-dioxane, and eventually, by portions with stirring, a solution of 6 g (30 mmole) of adamantanoyl chloride in 20 ml of absolute 1,4-dioxane. As the reaction proceeded, 4 N aqueous NaOH solution was added to maintain the initial level of pH 9-11. The chloroanhydride solution was added in five portions over a time period of approximately 45 rain. The stirring was continued for 30 min at 20~ Then the reaction mixture was doubly diluted with water and acidified to pH 2-3 with HCI. The white clotted precipitate was filtrated, washed with water until neutral pH, dried, and recrystallized from acetone to obtain 6.4 g (90.0 %) of compound Illa; m.p.,[191][192] Aides Ilia and IV were obtained by similar procedures. N-Adamantanoylglyeine

show abstract

Rimantadine derivatives with antiviral activity against flaviviruses and rimantadine-resistant strain of influenza A virus

Zefirov,

Khvatov,

Nurieva

et al. 2024

Russ Chem Bull

View full text Add to dashboard Cite

Synthesis and biological activity of adamantane derivatives. VI. Antiinflammatory action of pyridinecarboxylic acid adamantylamides

Cited by 4 publications

References 1 publication

Through-Space Paramagnetic NMR Effects in Host–Guest Complexes: Potential Ruthenium(III) Metallodrugs with Macrocyclic Carriers

Through-Space Paramagnetic NMR Effects in Host–Guest Complexes: Potential Ruthenium(III) Metallodrugs with Macrocyclic Carriers

Synthesis and membranotropic activity of N-adamantanoylamino and N-adamantylacetylamino acids

Rimantadine derivatives with antiviral activity against flaviviruses and rimantadine-resistant strain of influenza A virus

Contact Info

Product

Resources

About