Reaction of chlorodithiophosphoric acid pyridiniumbetaine with adamantane derivatives containing amino group

Polyhedron ◽  
2009 ◽  
Vol 28 (18) ◽  
pp. 3985-3992 ◽  
Author(s):  
Marie Sotolářová ◽  
Jan Houška ◽  
Marek Nečas ◽  
Josef Havel ◽  
Jiří Příhoda
Keyword(s):  
Adamantane Derivatives ◽  
Amino Group

Reactions of Triformylmethane with Adamantane Derivatives Containing Primary Amino Group

1992 ◽  
Vol 57 (9) ◽  
pp. 1947-1950 ◽  
Author(s):  
Jiří Burkhard ◽  
Zdeněk Arnold
Keyword(s):  
Adamantane Derivatives ◽  
Amino Group ◽  
Primary Amino ◽  
New Compounds

Six new compounds were obtained by condensation of triformylmethane with some aminoadamantane derivatives. The study also includes 7-amino-1,3,5-triazaadamantane.

Synthesis and properties of some gelatin derivatives with substituents at the amino group

1965 ◽  
Vol 15 (10) ◽  
pp. 479-488
Author(s):  
R. C. Clark ◽  
W. G. Cobbett ◽  
J. A. Gibbs ◽  
R. T. Jones ◽  
A. A. Leach ◽  
...  
Keyword(s):  
Amino Group

Aminocoumarins: A Privileged Precursor for the Synthesis of Fused Heterocycles

2019 ◽  
Vol 23 (9) ◽  
pp. 1045-1075 ◽  
Author(s):  
Saigal ◽  
Sumbulunnisan Shareef ◽  
Habibur Rahman ◽  
Md. Musawwer Khan
Keyword(s):  
Chemical Reactivity ◽  
Structural Systems ◽  
Natural Occurrence ◽  
Amino Group ◽  
Active Compounds ◽  
The Past ◽  
Fused Heterocycles

Aminocoumarins are one of the important core structural systems, present in several biologically and medicinally active compounds. Owing to its natural occurrence, potential pharmacological applications and remarkable versatility as a privileged precursor, several proficient synthetic protocols have been reported in the literature over the past years. The presence of an amino group and enamine carbon enhances its chemical reactivity and thus such functionality is repeatedly used for the construction of various fused and simple heterocycles. This review highlights the preparation of different aminocoumarins and their applications for the construction of a variety of five, six and eight membered fused heterocycles.

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.

Substituent Effects on the Basicity of ortho-, meta- and para-substituted N1,N1-Dimethyl-N2-phenylformamidines in Ethanol and in Water

1992 ◽  
Vol 57 (1) ◽  
pp. 113-118
Author(s):  
Ewa Daniela Raczyńska
Keyword(s):  
Quantitative Analysis ◽  
Aqueous Ethanol ◽  
Substituent Effects ◽  
Amino Group

The relative δpKa values of ortho-, meta-, and para-substituted N1,N1-dimethyl-N2-phenylformamidines obtained in 95.6% aqueous ethanol have been compared with those in water. The comparison shows only some differences in the ortho substituent effects. The meta and para substituent effects in ethanol are not very different from those in water. Quantitative analysis of the experimental δpKa values based on the Taft equation has led to separation of the total electromeric effects into the inductive and mesomeric effects. As compared to the amino group in anilines, the formamidine group is more sensitive to the transmission of the inductive than the mesomeric effects.

Induced Smectic Phases II. Influence of the Amino Substituent on the Induction of Smectic Phases

1981 ◽  
Vol 36 (10) ◽  
pp. 1086-1091 ◽  
Author(s):  
F. Schneider ◽  
N. K. Sharma
Keyword(s):  
Liquid Crystal ◽  
Electron Donor ◽  
Amino Group ◽  
Donor Property ◽  
Smectic Phases ◽  
Ct Complexes ◽  
Induced Smectic Phases

The diagrams of state have been studied for some liquid crystal mixtures which show the induction of smectic phases. Each of the systems studied contains one component with an amino group which influences the polarity and the electron donor property of the molecules. The discussion of the diagrams of state, of the thickness of the smectic layers and of the colours of the mixtures, which indicate the formation of CT complexes, shows that existing models can not explain the induction of smectic phases.

scholarly journals The site of attachment of retinal in bacteriorhodopsin. The epsilon-amino group in Lys-41 is not required for proton translocation.

1982 ◽  
Vol 257 (15) ◽  
pp. 8596-8599 ◽  
Author(s):  
K S Huang ◽  
M J Liao ◽  
C M Gupta ◽  
N Royal ◽  
K Biemann ◽  
...  
Keyword(s):  
Proton Translocation ◽  
Amino Group

scholarly journals Catalytic Antioxidant Activity of Bis-Aniline-Derived Diselenides as GPx Mimics

Molecules ◽  
2021 ◽  
Vol 26 (15) ◽  
pp. 4446
Author(s):  
Giancarlo V. Botteselle ◽  
Welman C. Elias ◽  
Luana Bettanin ◽  
Rômulo F. S. Canto ◽  
Drielly N. O. Salin ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Hydrogen Bond ◽  
Electronic Properties ◽  
Partial Charge ◽  
Amino Group ◽  
Diphenyl Diselenide ◽  
Charge Delocalization ◽  
Ipso Substitution ◽  
Efficient Route ◽  
Catalytic Performances

Herein, we describe a simple and efficient route to access aniline-derived diselenides and evaluate their antioxidant/GPx-mimetic properties. The diselenides were obtained in good yields via ipso-substitution/reduction from the readily available 2-nitroaromatic halides (Cl, Br, I). These diselenides present GPx-mimetic properties, showing better antioxidant activity than the standard GPx-mimetic compounds, ebselen and diphenyl diselenide. DFT analysis demonstrated that the electronic properties of the substituents determine the charge delocalization and the partial charge on selenium, which correlate with the catalytic performances. The amino group concurs in the stabilization of the selenolate intermediate through a hydrogen bond with the selenium.

Sign in / Sign up

Export Citation Format

Share Document