Synthesis of 3-Amino- and 3-Acylamino-1-cyclopropylquinolin-4(1H)-ones

1994 ◽  
Vol 59 (9) ◽  
pp. 2123-2126 ◽  
Author(s):  
Stanislav Rádl
Keyword(s):  
Carboxylic Group ◽  
Amino Derivatives

Antibacterial quinolones have attracted an increasing attention as a source of clinically useful drugs. During our research into antibacterial quinolones we were also interested in compounds having at the position 3 various groups that could mimic the carboxylic group present in these drugs. Having our own procedure for the preparation of 3-nitroquinolones, we decided to investigate the question of possible activity of 3-amino derivatives and 3-acylamino derivatives.

Synthesis, Docking Studies into CDK-2 and Anticancer Activity of New Derivatives Based Pyrimidine Scaffold and Their Derived Glycosides

2019 ◽  
Vol 19 (13) ◽  
pp. 1093-1110 ◽  
Author(s):  
Adel A.H. Abdel Rahman ◽  
Ibrahim F. Nassar ◽  
Amira K.F. Shaban ◽  
Dina S. EL-Kady ◽  
Hanem M. Awad ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Human Liver ◽  
Docking Studies ◽  
Cyclin Dependent Kinase ◽  
Binding Interaction ◽  
Enzyme Active Site ◽  
Human Liver Cancer ◽  
Amino Derivatives ◽  
Activity Behavior ◽  
Derivatives Of

Background & Objective:New diaryl-substituted pyrimidinedione compounds, their thioxo derivatives as well as their bicyclic thiazole compounds were synthesized and characterized.Methods:The glycosylamino derivatives of the synthesized disubstituted derivatives of the pyrimidine scaffold were also prepared via reaction of the N3-amino derivatives with a number of monosaccharides followed by acetylation.Results:The anticancer activity of the synthesized compounds was studied against human liver cancer (HepG2) and RPE-1cell lines. Compounds 2a, 2b, 3a and 12 showed potent activities with IC50 results comparable to that of doxorubicin.Conclusion:Docking investigations into Cyclin-dependent kinase 2 (CDK-2) enzyme, a potential target for cancer medication, were also reported showing the possible binding interaction into the enzyme active site to support their activity behavior.

Thermal cyclocondensations of 3-N(4- and 5-benzimidazolyl and benztriazolyl)amino derivatives of 2-propenoic acid

1987 ◽  
Vol 52 (12) ◽  
pp. 2918-2925 ◽  
Author(s):  
Viktor Milata ◽  
Dušan Ilavský
Keyword(s):  
Uv Spectra ◽  
Propenoic Acid ◽  
Amino Derivatives ◽  
Derivatives Of ◽  
C Nmr ◽  
Ir And Uv Spectra

The cyclization of 3-N(4- and 5-benzimidazolyl and benztriazolyl)amino-2-cyano- and 2-ethoxycarbonyl-2-propenoate esters Ia, b-IVa, b under the conditions of the Gould-Jacobs reaction leads to angularly ring-fused substituted imidazo or triazolo[4,5-f] (V, VI) and [4,5-h] (VII, VIII) quinolines, respectively. The esters Vb-VIIIb have been transformed into the corresponding chloroderivatives Vc-VIIIc. 3-N(5-Benzimidazolyl and 5-benztriazolyl)amino-2-cyano-2-propenenitriles are cyclized in the presence of aluminium(III) chloride to give the aminoquinolines Vd, VId. The structure of the products has been characterized by their 1H, 13C NMR, IR, and UV spectra.

The preparation of 3-amino-3-deoxy-1,2-O-isopropylidene-α-L-erythrofuranose, 3-amino-3-deoxy-1,2-O-isopropylidene-β-D-threofuranose and their derivatives

1980 ◽  
Vol 45 (12) ◽  
pp. 3378-3390 ◽  
Author(s):  
Jiří Jarý ◽  
Milena Masojídková ◽  
Ivan Kozák ◽  
Miroslav Marek ◽  
Jan Staněk
Keyword(s):  
Nucleophilic Substitution ◽  
Sodium Azide ◽  
Sodium Benzoate ◽  
Nmr Spectra ◽  
Subsequent Reduction ◽  
H Nmr ◽  
Amino Derivatives

The title amino derivatives VI and XIV were prepared by nucleophilic substitution of p-toluenesulfonyl derivatives II and XVII with sodium azide or hydrazine and subsequent reduction. Nucleophilic substitution of compounds II and XVII with sodium benzoate was also investigated. The 1H NMR spectra of the substances prepared are discussed.

Synthesis of isomeric 1,1'-phenylene-bis(6-azauracil-5-carbonitriles)

1990 ◽  
Vol 55 (12) ◽  
pp. 2967-2976 ◽  
Author(s):  
Jan Slouka
Keyword(s):  
General Formula ◽  
Mutual Distance ◽  
Planar Molecules ◽  
Amino Derivatives

The described synthesis of all three isomeric 1,1'-phenylene-bis(6-azauracil-5-carbonitriles) IVa-IVc starts from the respective 1-nitrophenyl-6-azauracil-5-carbonitriles Ia-Ic which were reduced to the corresponding amino derivatives IIa-IIc, diazotized, and coupled with ethyl cyanoacetylcarbamate to give the isomeric hydrazones IIIa-IIIc which were finally cyclized to the title compounds containing two 6-azauracil rings. A general formula is presented for calculation of mutual distance of arbitrary atoms in any planar molecules.

119Sn, 13C and 1H NMR Spectra of Tris(1-butyl)stannyl D-Glucuronate

1997 ◽  
Vol 62 (8) ◽  
pp. 1169-1176 ◽  
Author(s):  
Antonín Lyčka ◽  
Jaroslav Holeček ◽  
David Micák
Keyword(s):  
Chemical Shift ◽  
Carbonyl Group ◽  
1H Nmr ◽  
Equatorial Plane ◽  
Title Compound ◽  
Nmr Spectra ◽  
Hydroxyl Groups ◽  
Carboxylic Group ◽  
H Nmr ◽  
Oxygen Atoms

The 119Sn, 13C and 1H NMR spectra of tris(1-butyl)stannyl D-glucuronate have been measured in hexadeuteriodimethyl sulfoxide, tetradeuteriomethanol and deuteriochloroform. The chemical shift values have been assigned unambiguously with the help of H,H-COSY, TOCSY, H,C-COSY and 1H-13C HMQC-RELAY. From the analysis of parameters of 119Sn, 13C and 1H NMR spectra of the title compound and their comparison with the corresponding spectra of tris(1-butyl)stannyl acetate and other carboxylates it follows that in solutions of non-coordinating solvents (deuteriochloroform) the title compound is present in the form of more or less isolated individual molecules with pseudotetrahedral environment around the central tin atom and with monodentately bound carboxylic group. The interaction of tin atom with oxygen atoms of carbonyl group and hydroxyl groups of the saccharide residue - if they are present at all - are very weak. In solutions in coordinating solvents (hexadeuteriodimethyl sulfoxide or tetradeuteriomethanol), the title compound forms complexes with one molecule of the solvent. Particles of these complexes have a shape of trigonal bipyramid with the 1-butyl substituents in equatorial plane and the oxygen atoms of monodentate carboxylic group and coordinating solvent in axial positions.

Kinetics and Mechanism of Decomposition of 1,3-Bis(4-methylphenyl)triazene Catalyzed with Substituted Benzoic Acids in 25% Aqueous Methanol-General or Specific Catalysis?

1994 ◽  
Vol 59 (9) ◽  
pp. 2029-2041
Author(s):  
Oldřich Pytela ◽  
Taťjana Nevěčná
Keyword(s):  
Benzoic Acids ◽  
Hammett Equation ◽  
Aqueous Methanol ◽  
Mechanism Of Decomposition ◽  
Kinetics Of Decomposition ◽  
Independent Variable ◽  
Amino Derivatives ◽  
Substituted Benzoic Acids ◽  
The Individual ◽  
Kinetics Of

The kinetics of decomposition of 1,3-bis(4-methylphenyl)triazene catalyzed with 13 substituted benzoic acids of various concentrations have been measured in 25 vol.% aqueous methanol at 25.0 °C. The rate constants observed (297 data) have be used as values of independent variable in a series of models of the catalyzed decomposition. For the catalytic particles were considered the undissociated acid, its conjugated base, and the proton in both the specific and general catalyses. Some models presumed formation of reactive or nonreactive complexes of the individual reactants. The substituent effect is described by the Hammett equation. The statistically best model in which the observed rate constant is a superposition of a term describing the dependence on proton concentration and a term describing the dependence on the product of concentrations of proton and conjugated base is valid with the presumption of complete proton transfer from the catalyst acid to substrate, which has been proved. The behaviour of 4-dimethylamino, 4-amino, and 3-amino derivatives is anomalous (lower catalytic activity as compared with benzoic acid). This supports the presumed participation of conjugated base in the title process.

scholarly journals Semi-Synthesis of Small Molecules of Aminocarbazoles: Tumor Growth Inhibition and Potential Impact on p53

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1637
Author(s):  
Solida Long ◽  
Joana B. Loureiro ◽  
Carla Carvalho ◽  
Luís Gales ◽  
Lucília Saraiva ◽  
...  
Keyword(s):  
Growth Inhibition ◽  
Small Molecules ◽  
Tumor Cells ◽  
Mutant P53 ◽  
Wild Type ◽  
Naturally Occurring ◽  
Growth Inhibitory ◽  
Growth Inhibitory Activity ◽  
Amino Derivatives ◽  
Carbazole Alkaloids

The tumor suppressor p53 is inactivated by mutation in approximately 50% of human cancers. Small molecules that bind and stabilize those mutants may represent effective anticancer drugs. Herein, we report the tumor cell growth inhibitory activity of carbazole alkaloids and amino derivatives, as well as their potential activation of p53. Twelve aminocarbazole alkaloids were semi-synthesized from heptaphylline (1), 7-methoxy heptaphylline (2), and 7-methoxymukonal (3), isolated from Clausena harmandiana, using a reductive amination protocol. Naturally-occurring carbazoles 1–3 and their amino derivatives were evaluated for their potential effect on wild-type and mutant p53 activity using a yeast screening assay and on human tumor cell lines. Naturally-occurring carbazoles 1–3 showed the most potent growth inhibitory effects on wild-type p53-expressing cells, being heptaphylline (1) the most promising in all the investigated cell lines. However, compound 1 also showed growth inhibition against non-tumor cells. Conversely, semi-synthetic aminocarbazole 1d showed an interesting growth inhibitory activity in tumor cells expressing both wild-type and mutant p53, exhibiting low growth inhibition on non-tumor cells. The yeast assay showed a potential reactivation of mutant p53 by heptaphylline derivatives, including compound 1d. The results obtained indicate that carbazole alkaloids may represent a promising starting point to search for new mutp53-reactivating agents with promising applications in cancer therapy.

Correlation between thermodynamic parameters (GLC) and structure of esters

1981 ◽  
Vol 59 (15) ◽  
pp. 2243-2246 ◽  
Author(s):  
F. Saura Calixto ◽  
P. M. Deyá
Keyword(s):  
Molecular Structure ◽  
Stationary Phase ◽  
Thermodynamic Parameters ◽  
Homologous Series ◽  
Phase Gazeuse ◽  
Carboxylic Group ◽  
Phase Stationnaire ◽  
De Formula ◽  
Branching Chains ◽  
Polar Stationary Phase

The ΔHs and [Formula: see text] values of some one hundred esters belonging to twenty different homologous series are determined experimentally in the polar stationary phase (Carbowax 1540) by gas–liquid chromatography.Correlations between thermodynamic values and the molecular structure of esters are studied. The influence of the number of carbon atoms in the acid and alcohol chains and the position of the carboxylic group and branching chains on the ΔHs and [Formula: see text] values is considered.Faisant appel à la chromatographie en phase gazeuse impliquant du Carbowax 1540 comme phase stationnaire on a déterminé expérimentalement les valeurs de ΔHs et de [Formula: see text] d'une centaine d'esters appartenant à 20 séries homologues différentes.

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