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

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 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.

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

scholarly journals Synthesis and antimicrobial activity of new adamantane derivatives I.

2000 ◽  
Vol 47 (1) ◽  
pp. 87-94 ◽  
Author(s):  
A Orzeszko ◽  
R Gralewska ◽  
B J Starościak ◽  
Z Kazimierczuk
Keyword(s):  
Staphylococcus Aureus ◽  
Antimicrobial Activity ◽  
Minimal Inhibitory Concentration ◽  
Enterococcus Faecium ◽  
Inhibitory Concentration ◽  
Adamantane Derivatives ◽  
Bacillus Sp ◽  
Trimellitic Anhydride ◽  
Derivatives Of

A series of fourteen derivatives of adamantane was synthesised. The new compound 4-(adamant-1-ylmethoxycarbonyl)phthalanhydride obtained from 1-adamantane-methanol and trimellitic anhydride chloride appeared very useful for preparation of a number of N-substituted phthalimides. Antimicrobial activity of the newly obtained derivatives such as, for example, 4-(adamant-1-ylmethoxycarbonyl)-N-(5-carboxypentamethylene)p hthalimide or 4-(adamant-1-ylmethoxycarbonyl)-N-(L-alanyl)phthalimide was tested against Staphylococcus aureus, Bacillus sp., Micrococcus flavus and Enterococcus faecium. The minimal inhibitory concentration (MIC) for these compounds against S. aureus were 0.022 and 0.05 microg/ml, respectively.

Adamantane derivatives of thiazolyl-N-substituted amide, as possible non-steroidal anti-inflammatory agents

2009 ◽  
Vol 44 (3) ◽  
pp. 1198-1204 ◽  
Author(s):  
Omar Kouatly ◽  
Athina Geronikaki ◽  
Charalambos Kamoutsis ◽  
Dimitra Hadjipavlou-Litina ◽  
Phaedra Eleftheriou
Keyword(s):  
Adamantane Derivatives ◽  
Anti Inflammatory ◽  
Derivatives Of

ChemInform Abstract: ADAMANTANE DERIVATIVES. V. SYNTHESIS AND RADIOPROTECTANT PROPERTIES OF N-ADAMANTYL DERIVATIVES OF AMINOTHIOLS

1984 ◽  
Vol 15 (18) ◽  
Author(s):  
V. V. ZNAMENSKII ◽  
V. YU. KOVTUN ◽  
A. V. TEREKHOV ◽  
B. A. TITOV ◽  
V. M. PLAKHOTNIK ◽  
...  
Keyword(s):  
Adamantane Derivatives ◽  
Derivatives Of

Anticataleptic activity of adamantane derivatives. I. Derivatives of 1-aminoadamantane and 3,3?-diamino-1,1?-diadamantyl

1980 ◽  
Vol 14 (3) ◽  
pp. 185-188 ◽  
Author(s):  
Yu. I. Vikhlyaev ◽  
O. V. Ul'yanova ◽  
T. A. Voronina ◽  
N. V. Klimova ◽  
L. N. Lavrova ◽  
...  
Keyword(s):  
Adamantane Derivatives ◽  
Anticataleptic Activity ◽  
Derivatives Of
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