Adamantane derivatives of sulfonamides: sublimation, solubility, solvation and transfer processes in biologically relevant solvents

2016 ◽  
Vol 18 (13) ◽  
pp. 9281-9294 ◽  
Author(s):  
G. L. Perlovich ◽  
T. V. Volkova ◽  
A. V. Sharapova ◽  
V. P. Kazachenko ◽  
N. N. Strakhova ◽  
...  
Keyword(s):  
Adamantane Derivatives ◽  
Biologically Relevant ◽  
Transfer Processes ◽  
Derivatives Of

Eight adamantane derivatives of sulfonamides were synthesized and characterized.

Synthesis and Antimicrobial Activity of Adamantyl Substituted Pyridoxine Derivatives

2019 ◽  
Vol 16 (12) ◽  
pp. 1360-1369 ◽  
Author(s):  
Rail Khaziev ◽  
Nikita Shtyrlin ◽  
Roman Pavelyev ◽  
Raushan Nigmatullin ◽  
Raylya Gabbasova ◽  
...  
Keyword(s):  
Influenza Virus ◽  
Lipid Membranes ◽  
Specific Activity ◽  
Tuberculosis H37rv ◽  
Microbial Pathogens ◽  
Adamantane Derivatives ◽  
Carbon Cage ◽  
H37rv Strain ◽  
Derivatives Of

Background: Adamantane derivatives possess multiple pharmacological activities such as antiviral, anticancer, antimycobacterial, antidiabetic, antiparkinsonian and others. The interest of medicinal chemists in adamantane compounds is due to their unique spatial structure, high lipophilicity, and carbon cage rigidity. As a result, these molecules can easily penetrate biological lipid membranes and often have unique target-specific activity profile. Another pharmacophore studied in this work is pyridoxine (vitamin B6). Pyridoxine plays highly important roles in living cells as a key cofactor of many enzymes. On the other hand, its molecular scaffold is a valuable structural platform which has led to the development of several launched drugs (Pyritinol, Pirisudanol, Cycletanine, Mangafodipir) and a wide number of preclinical and clinical drug candidates. Objective: The objective of this study is a synthesis of pyridoxine-adamantane and pyridoxinecyclooctane dipharmacophore molecules. The underlying idea was to assess the antibacterial and antiviral potential of such dipharmacophores, based on multiple examples of promising antiinfective agents which have in their structures adamantane and pyridoxine moieties. Another specific reason was to explore the ability of pyridoxine pharmacophore to suppress the potential of microbial pathogens to develop resistance to drug molecules. Methods: In this study, a series of pyridoxine-adamantane and pyridoxine-cyclooctane dipharmacophore molecules were synthesized based on reactions of three different cycloalkyl amines with the corresponding electrophilic derivatives of pyridoxine aldehydes, chlorides and acetates. All synthesized compounds have been tested for their in vitro activity against M. tuberculosis H37Rv strain and H3N2 (A/Aichi/2/68) influenza virus. Results: Series of pyridoxine-adamantane and pyridoxine-cyclooctane dipharmacophore molecules were synthesized based on reactions of three different cycloalkylamines with the corresponding electrophilic derivatives of pyridoxine aldehydes, chlorides and acetates. Reaction of cycloalkylamines with pyridoxine derivatives, in which meta-hydroxyl and ortho-hydroxymethyl groups are protected by acetyl groups, represents a useful alternative to reductive amination of aldehydes and nucleophilic substitution of alkyl halides. According to a tentative mechanism, it proceeds via paraand ortho-pyridinone methides which readily react with nucleophiles. None of the synthesized dipharmacophore compounds showed activity against M. tuberculosis H37Rv strain. At the same time, three compounds demonstrated some antiviral activity against H3N2 (A/Aichi/2/68) influenza virus (EC50 52-88 µg/mL) that was comparable to the activity of Amantadine, though lower than the activity of Rimantadine. The results of this work can be useful in the design of physiologically active derivatives of pyridoxine and adamantane. Conclusion: The results of this work can be useful in the design of physiologically active derivatives of pyridoxine and adamantane.

Adamantane derivatives of sulfonamide molecular crystals: structure, sublimation thermodynamic characteristics, molecular packing, and hydrogen bond networks

CrystEngComm ◽  
2015 ◽  
Vol 17 (4) ◽  
pp. 753-763 ◽  
Author(s):  
German L. Perlovich ◽  
Alex M. Ryzhakov ◽  
Valery V. Tkachev ◽  
Alexey N. Proshin
Keyword(s):  
Hydrogen Bond ◽  
Crystal Structures ◽  
Molecular Crystals ◽  
Thermodynamic Characteristics ◽  
Molecular Packing ◽  
Adamantane Derivatives ◽  
X Ray Diffraction ◽  
X Ray ◽  
Hydrogen Bond Networks ◽  
Derivatives Of

The crystal structures of six adamantane derivatives of sulfonamides have been determined by X-ray diffraction and their sublimation and fusion processes have been studied.

Crystal Structure and Physicochemical Characteristics of Two Novel Adamantane Derivatives of Sulfonamides

2021 ◽  
Vol 66 (3) ◽  
pp. 424-428
Author(s):  
O. V. Kovalchukova ◽  
V. P. Kazachenko ◽  
V. V. Tkachev ◽  
A. N. Utenyshev ◽  
N. N. Strakhova ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Physicochemical Characteristics ◽  
Adamantane Derivatives ◽  
Derivatives Of

Synthesis of some adamantane derivatives of 2-aminobenzothiazoles

1971 ◽  
Vol 14 (12) ◽  
pp. 1222-1223 ◽  
Author(s):  
E. Costakis ◽  
P. Canonne
Keyword(s):  
Adamantane Derivatives ◽  
Derivatives Of

Ion-molecule reactions in Trihalo- and Tetrahalo-methanes

1970 ◽  
Vol 23 (5) ◽  
pp. 893 ◽  
Author(s):  
NA McAskill
Keyword(s):  
Gas Phase ◽  
Cross Sections ◽  
High Pressures ◽  
Rate Coefficients ◽  
Ion Transfer ◽  
Ion Energy ◽  
Transfer Processes ◽  
Ion Molecule Reactions ◽  
Ionic Systems ◽  
Derivatives Of

The ion-molecule reactions of eight highly halogenated derivatives of methane were studied in the gas phase using a mass spectrometer operated at high pressures. The compounds studied were CHCl3, CHCl2F, CHClF2, CHF3, CCl4, CCl2F2, CClF3, and CF4. These ionic systems were found to be less reactive than those of methane or the methyl and methylene halides. The main reactions observed were described as being halide ion transfer processes. The energy dependence of the cross sections and the rate coefficients of the reactant ions were determined.� Many rate coefficients for reactions between ions and polar molecules were found to be independent of the ion energy. Brief studies of the negative spectra at high pressures were also made.

scholarly journals Nitric oxide rapidly scavenges tyrosine and tryptophan radicals

1995 ◽  
Vol 310 (3) ◽  
pp. 745-749 ◽  
Author(s):  
J P Eiserich ◽  
J Butler ◽  
A van der Vliet ◽  
C E Cross ◽  
B Halliwell
Keyword(s):  
Nitric Oxide ◽  
Biologically Relevant ◽  
Tyrosine Residues ◽  
Transfer Processes ◽  
Diffusion Controlled ◽  
Electron Transfer Processes ◽  
Protein Radicals ◽  
First Time

By utilizing a pulse-radiolytic technique, we demonstrate for the first time that the rate constant for the reaction of nitric oxide (.NO) with biologically relevant tyrosine and tryptophan radicals (Tyr. and Trp. respectively) in amino acids, peptides and proteins is of the order of (1-2) x 10(9) M-1.s-1. We also show that .NO effectively interferes with electron-transfer processes between tryptophan and tyrosine residues in proteins subjected to pulse radiolysis. The near diffusion-controlled rates of these reactions, coupled with the increasingly recognized role of protein radicals in enzyme catalysis and oxidative damage, suggest that Tyr. and Trp. are likely and important targets for .NO generated in vivo.

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