Syntheses of some N-carboxymethyl derivatives of 4,9-dihydro-3-methyl-4-oxo-1H-(2H)-pyrazolo[3,4-b]quinoline with antiviral effects

1985 ◽  
Vol 50 (9) ◽  
pp. 2010-2014 ◽  
Author(s):  
Stanislav Rádl ◽  
Viktor Zikán ◽  
František Šmejkal
Keyword(s):  
Encephalomyocarditis Virus ◽  
Antiviral Effects ◽  
Derivatives Of

The paper describes the syntheses of 4,9-dihydro-9-carboxymethyl-1,3-dimethyl-4-oxo-1H-pyrazolo[3,4-b]quinoline (Ic), 4,9-dihydro-9-carboxymethyl-2,3-dimethyl-4-oxo-2H-pyrazolo[3,4-b]quinoline (IIc), 4,9-dihydro-1-carboxymethyl-3-methyl-4-oxo-1H-pyrazolo[3,4-b]quinoline (Id), 4,9-dihydro-1-carboxymethyl-3,9-dimethyl-4-oxo-1H-pyrazolo[3,4-b]quinoline (If) and 4,9-dihydro-2-carboxymethyl-3,9-dimethyl-4-oxo-2H-pyrazolo[3,4-b]quinoline (IIf). The compounds were tested in vivo in mice for their efficacy against the virus A2-Hongkong and the encephalomyocarditis virus.

Syntheses of some 4-dialkylaminoalkylamino derivatives of 2,3-dimethyl-2H- and 3,9-dimethyl-9H-pyrazolo[3,4-b]quinoline

1986 ◽  
Vol 51 (8) ◽  
pp. 1692-1697 ◽  
Author(s):  
Stanislav Rádl ◽  
Viktor Zikán
Keyword(s):  
Influenza Virus ◽  
Thionyl Chloride ◽  
Encephalomyocarditis Virus ◽  
Methoxy Derivative ◽  
Derivatives Of

Reactions of 4-chloro-2,3-dimethyl-2H-pyrazolo[3,4-b]quinoline and 4-chloro-6-methoxy-2,3-dimethyl-2H-pyrazolo[3,4-b]quinoline with 3-dimethylaminopropylamine and/or 2-dimethylaminoethylamine afforded 4-(3-dimethylaminopropylamino)-2,3-dimethyl-2H-pyrazolo[3,4-b]quinoline (IIa), its 6-methoxy derivative (IIc), 4-(2-diethylaminoethylamino)-2,3-dimethyl-2H-pyrazolo[3,4-b]quinoline (IIb) and its 6-methoxy derivative (IId). Reaction of 4,9-dihydro-3,9-dimethyl-4-oxo-1H-pyrazolo[3,4-b]quinoline with thionyl chloride gave an intermediate, whose reaction with 3-dimethylaminopropylamine afforded 4-(3-dimethylaminopropylamino)-3,9-dimethyl-9H-pyrazolo[3,4-b]quinoline (III). The compounds were tested in vivo in mice for efficacy against the A2-Hongkong influenza virus and the encephalomyocarditis virus.

Hydrolytic products of 4-aryl-2,3-dicyano-1-naphthol derivatives

1981 ◽  
Vol 46 (9) ◽  
pp. 2207-2216 ◽  
Author(s):  
Jiří Křepelka ◽  
Iva Vančurová ◽  
Jiří Holubek ◽  
Jiří Roubík
Keyword(s):  
Dicarboxylic Acids ◽  
Ring Closure ◽  
Partial Hydrolysis ◽  
H Nmr ◽  
Antiviral Effects ◽  
Hydrolysis Of ◽  
Derivatives Of ◽  
Naphthol Derivatives ◽  
Intramolecular Ring

Depending on the conditions of hydrolysis, vicinal aromatic dicyano derivatives Ia-Ic gave anhydrides IIa-IIe and imides of 4-aryl-1-alkoxynaphthalene-2,3-dicarboxylic acids, IIIa,b, along with products of partial hydrolysis, decarboxylation and demethylation, IVa-IVd, IVf-IVg, and derivatives of benzo(c)fluorene, Va-Vc. The derivatives Va-Vc were also obtained by acid hydrolysis of dicyano derivatives Id-Ig. Methanolysis of the anhydride IId gave a mixture of positional isomers, IVh, which was esterified to the diester IVe. Intramolecular ring closure of the isomers IVh afforded derivatives of benzo(c)fluorene, VIa-VIb. The structures of the selected compounds were corroborated by IR and 1H NMR spectra. The compounds Va-Vc exhibited antiviral effects and interferonogenic activities in vivo.

Synthesis of 1,2, and 9-methyl derivatives of 4,9-dihydro-6-methoxy-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline and 4,9-dihydro-6-hydroxy-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline and their antiviral activity

1987 ◽  
Vol 52 (3) ◽  
pp. 788-792 ◽  
Author(s):  
Stanislav Rádl ◽  
Viktor Zikán
Keyword(s):  
Influenza Virus ◽  
Antiviral Activity ◽  
Hydrobromic Acid ◽  
Encephalomyocarditis Virus ◽  
Methyl Derivative ◽  
Pyridine Hydrochloride ◽  
Methyl Derivatives ◽  
Derivatives Of

The paper describes syntheses of 4,9-dihydro-6-methoxy-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline (Ia), its 1-methyl derivative (Ic), 1,9-dimethyl derivative (Ie), 2-methyl derivative (IIa), and 2,9-dimethyl derivative (IIc). Demethylation of these compounds with hydrobromic acid afforded 4,9-dihydro-6-hydroxy-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline (Ib), its 1-methyl derivative (Id), 1,9-dimethyl derivative (If), 2-methyl derivative (IIb), and 2,9-dimethyl derivative (IId) respectively. 4,9-Dihydro-6-hydroxy-3,9-dimethyl-4-oxo-1H-pyrazolo[3,4-b]quinoline (Ig) was prepared by demethylation of Ie and/or IIc with pyridine hydrochloride. The compounds prepared were tested for antiviral activity in vivo in mice against influenza virus A2-Hongkong and encephalomyocarditis virus.

Syntheses of 1, 2, and 9-methyl derivatives of 4,9-dihydro-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline and their antiviral activity

1985 ◽  
Vol 50 (5) ◽  
pp. 1057-1063 ◽  
Author(s):  
Stanislav Rádl ◽  
Viktor Zikán ◽  
František Šmejkal
Keyword(s):  
Influenza Virus ◽  
Antiviral Activity ◽  
Methyl Iodide ◽  
Room Temperature ◽  
Encephalomyocarditis Virus ◽  
Methyl Derivative ◽  
Sodium Salts ◽  
Methyl Derivatives ◽  
Derivatives Of

The paper describes syntheses of 4,9-dihydro-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline (Ia), its 1-methyl derivative (Ib), 2-methyl derivative (IIa), 9-methyl derivative (Ic), 1,9-dimethyl derivative (Id) and 2,9-dimethyl derivative (IIb). Sodium salts of compounds Ia, Ib, Ic and IIa were methylated with methyl iodide in dimethylformamide at room temperature, compounds Id and IIb were demethylated with pyridine hydrochloride. The compounds prepared were tested for antiviral activity in vivo in mice against influenza virus A2-Hongkong and the Encephalomyocarditis virus.

scholarly journals Baculovirus Stimulates Antiviral Effects in Mammalian Cells

1999 ◽  
Vol 73 (12) ◽  
pp. 9944-9951 ◽  
Author(s):  
Ann M. Gronowski ◽  
David M. Hilbert ◽  
Kathleen C. F. Sheehan ◽  
Gianni Garotta ◽  
Robert D. Schreiber
Keyword(s):  
Mammalian Cells ◽  
Autographa Californica ◽  
Encephalomyocarditis Virus ◽  
Alternative Mechanism ◽  
Human Cell Lines ◽  
Uv Treatment ◽  
Antiviral Effects ◽  
Rnase Treatment ◽  
Novel Model

ABSTRACT Herein, we report that Autographa californicanucleopolyhedrovirus, a member of the Baculoviridae family, is capable of stimulating antiviral activity in mammalian cells. Baculoviruses are not pathogenic to mammalian cells. Nevertheless, live baculovirus is shown here to induce interferons (IFN) from murine and human cell lines and induces in vivo protection of mice from encephalomyocarditis virus infection. Monoclonal antibodies specific for the baculovirus envelope gp67 neutralize baculovirus-dependent IFN production. Moreover, UV treatment of baculovirus eliminates both infectivity and IFN-inducing activity. In contrast, the IFN-inducing activity of the baculovirus was unaffected by DNase or RNase treatment. These data demonstrate that IFN production can be induced in mammalian cells by baculovirus even though the cells fail to serve as a natural host for an active viral infection. Baculoviruses, therefore, provide a novel model in which to study at least one alternative mechanism for IFN induction in mammalian cells.

Acyl-Enzymes as Thrombolytic Agents in Dog Models of Venous Thrombosis and Pulmonary Embolism

1984 ◽  
Vol 51 (02) ◽  
pp. 248-253 ◽  
Author(s):  
R J Dupe ◽  
P D English ◽  
R A G Smith ◽  
J Green
Keyword(s):  
Pulmonary Embolism ◽  
Side Effects ◽  
Venous Thrombosis ◽  
Active Site ◽  
Acute Pulmonary Embolism ◽  
Quantitative Model ◽  
Beagle Dog ◽  
Thrombosis Model ◽  
Derivatives Of

SummaryA quantitative model of venous thrombosis in the beagle dog is described. The model was adapted to permit ageing of isolated experimental clots in vivo. A model of acute pulmonary embolism in this species is also described. In the venous thrombosis model, infusion of streptokinase (SK) or SK-activated human plasmin gave significant lysis but bolus doses of SK. plasmin complex were ineffective. Active site anisoylated derivatives of SK. plasminogen complex, SK-activated plasmin and activator-free plasmin were all active when given as bolus doses in both models. At lytic doses, the acyl-enzymes caused fewer side-effects attributable to plasminaemia than the corresponding unmodified enzymes.

Synthesis and In Vivo Antimalarial Activity of Novel Derivatives of 6- Mercaptopurine

2013 ◽  
Vol 10 (8) ◽  
pp. 741-747 ◽  
Author(s):  
Roberta Soares ◽  
Roberta Corrales ◽  
Fernanda Lopes ◽  
Marcio Alves ◽  
Adilson Silva ◽  
...  
Keyword(s):  
Antimalarial Activity ◽  
Derivatives Of

Derivatives of Deoxypodophyllotoxin Induce Apoptosis Through Bcl-2/Bax Proteins Expression

2020 ◽  
Vol 20 ◽  
Author(s):  
Ya-Nan Li ◽  
Ni Ning ◽  
Lei Song ◽  
Yun Geng ◽  
Jun-Ting Fan ◽  
...  
Keyword(s):  
Annexin V ◽  
Mtt Method ◽  
Anthriscus Sylvestris ◽  
Anti Tumor Activity ◽  
Derivatives Of ◽  
Toxicity In Vitro ◽  
Ht 29 ◽  
Mcf 7

Background: Deoxypodophyllotoxin, isolated from theTraditional Chinese Medicine Anthriscus sylvestris, is well-known because of its significant antitumor activity with strong toxicity in vitro and in vivo. Objective: In this article, we synthesized a series of deoxypodophyllotoxin derivatives, and evaluated their antitumor effectiveness.Methods:The anti tumor activity of deoxypodophyllotoxin derivatives was investigated by the MTT method. Apoptosis percentage was measured by flow cytometer analysis using Annexin-V-FITC. Results: The derivatives revealed obvious cytotoxicity in the MTT assay by decreasing the number of late cancer cells. The decrease of Bcl-2/Bax could be observed in MCF-7, HepG2, HT-29 andMG-63 using Annexin V-FITC. The ratio of Bcl-2/Bax in the administration group was decreased, which was determined by the ELISA kit. Conclusion: The derivatives of deoxypodophyllotoxin could induce apoptosis in tumor cell lines by influencing Bcl-2/Bax.

Some 1-substitution derivatives of 4-aryl-2,3-dihalogeno-1-naphthols

1984 ◽  
Vol 49 (1) ◽  
pp. 110-121 ◽  
Author(s):  
Jiří Křepelka ◽  
Drahuše Vlčková ◽  
Milan Mělka
Keyword(s):  
Thionyl Chloride ◽  
Oxirane Ring ◽  
Secondary Amines ◽  
Two Phase ◽  
Lytic Effect ◽  
Primary And Secondary Amines ◽  
Phase Medium ◽  
Chloro Derivatives ◽  
Derivatives Of

Alkylation of derivatives of 4-aryl-1-naphthols (I-V) by 2,3-epoxypropyl chloride in methanolic sodium hydroxide gave epoxy derivatives VI, VIII, IX, XI and XII, apart from products of cleavage of the oxirane ring, VII and X. Analogous alkylation of compounds I, IV and V by 2-(N,N-diethylamino)ethyl chloride hydrochloride in a two-phase medium afforded basic ethers XIII to XV. The cleavage of the oxirane ring in compound VI by the action of primary and secondary amines, piperidine and substituted piperazines led to compounds XVI-XXIV. Reaction of thionyl chloride with compounds XXI, XXII and XXIV gave chloro derivatives XXV-XXVII.Exposure of compound XXII to 4-methylbenzenesulfonyl chloride produced compound XXVIII, retaining the secondary alcoholic group. In an antineoplastic screening in vivo none of the compounds prepared had an appreciable activity. Compound XVII, being an analogue of propranolol, was used in the test of isoproterenolic tachycardia, and showed a beta-lytic effect comparable with that of propranol.

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