Die aliphatische Säureamidgruppierung als Partialstruktur in Virustatika 3. Mitt. Antivirale Wirkstoffe

Kreutzberger, A.; Schröders, Hans-Helmut

doi:10.1002/ardp.19743071007

Cited by 10 publications

(3 citation statements)

References 14 publications

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“…Some secondary and tertiary amines containing an adamantane fragment, such as compounds 2, 3 , and tromantadine 4 , demonstrated pronounced vaccinia virus inhibitory effects [ 15 ]. It was shown in [ 16 ] that diphenyl derivative amide 5 inhibits vaccinia virus reproduction in cell culture in the range from 72% to 100% at a concentration of 2 µg/mL. However, the activity of these compounds against other types of orthopoxviruses was not investigated.…”

Section: Introductionmentioning

confidence: 99%

Structure-Based Design, Synthesis, and Biological Evaluation of the Cage–Amide Derived Orthopox Virus Replication Inhibitors

Mozhaitsev

Суслов

Rastrepaeva

et al. 2022

Viruses

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Despite the fact that the variola virus is considered eradicated, the search for new small molecules with activity against orthopoxviruses remains an important task, especially in the context of recent outbreaks of monkeypox. As a result of this work, a number of amides of benzoic acids containing an adamantane fragment were obtained. Most of the compounds demonstrated activity against vaccinia virus, with a selectivity index SI = 18,214 for the leader compound 18a. The obtained derivatives also demonstrated activity against murine pox (250 ≤ SI ≤ 6071) and cowpox (125 ≤ SI ≤ 3036). A correlation was obtained between the IC50 meanings and the binding energy to the assumed biological target, the p37 viral protein with R2 = 0.60.

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Section: Introductionmentioning

confidence: 99%

Structure-Based Design, Synthesis, and Biological Evaluation of the Cage–Amide Derived Orthopox Virus Replication Inhibitors

Mozhaitsev

Суслов

Rastrepaeva

et al. 2022

Viruses

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“…3 1-Adamantanecarboxylic acid amide containing the (-)-10-amino-2-pinene fragment (structure C) 4 and N-(1-adamantyl)-2,2-diphenylacetamide D proved to be effective inhibitors of smallpox virus. 5 In addition, compounds containing the adamantyl fragment such as memantine E (Fig. 1) are also capable of inhibiting the N-methyl-D-aspartate receptor, which allows them to be considered as potential agents for the treatment of moderate and severe Alzheimer's disease.…”

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confidence: 99%

Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2H-tetrazoles

Mikolaichuk

Zarubaev

Мурылева

et al. 2021

Chem Heterocycl Comp

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The reaction of 5-aryl-NH-tetrazoles with adamantan-1-ol in concentrated sulfuric acid proceeds regioselectively with the formation of the corresponding 2-adamantyl-5-aryl-2H-tetrazoles. Nitration of these compounds leads to 2-(adamantan-1-yl)-5-(3-nitroaryl)-2Htetrazoles. The structures and composition of the obtained novel 2-adamantyl-5-aryltetrazoles were proven by IR spectroscopy, 1 H and 13 C NMR spectroscopy, high-resolution mass spectrometry, and also by X-ray structural analysis. According to the simultaneous thermal analysis data, the obtained compounds are thermally stable up to a temperature of about 150°C. In vitro studies have shown that some of the 2-adamantyl-5-aryltetrazoles exhibit moderate inhibitory activity against influenza A (H1N1) virus. The antiviral selectivity index (SI) of 2-[2-(adamantan-1-yl)-2H-tetrazol-5-yl]-6-bromo-4-nitroaniline is significantly higher (SI 11) than that of the reference drug rimantadine (SI 5).

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

et al. 1999

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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

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Die aliphatische Säureamidgruppierung als Partialstruktur in Virustatika 3. Mitt. Antivirale Wirkstoffe

Cited by 10 publications

References 14 publications

Structure-Based Design, Synthesis, and Biological Evaluation of the Cage–Amide Derived Orthopox Virus Replication Inhibitors

Structure-Based Design, Synthesis, and Biological Evaluation of the Cage–Amide Derived Orthopox Virus Replication Inhibitors

Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2H-tetrazoles

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

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