A New Approach to Imidazo[1,5-a]indole Derivatives

2000 ◽  
Vol 65 (7) ◽  
pp. 1163-1172 ◽  
Author(s):  
Peter Kutschy ◽  
Mojmír Suchý ◽  
Milan Dzurilla ◽  
Mitsuo Takasugi ◽  
Vladimír Kováčik
Keyword(s):  
Antifungal Activity ◽  
Methyl Iodide ◽  
Potassium Carbonate ◽  
Lithium Hydride ◽  
Indole Derivatives ◽  
New Approach ◽  
Methyl Derivatives ◽  
Nucleophilic Reagents ◽  
Sodium Methanethiolate ◽  
Derivatives Of

Reaction of indole-2-carbonyl isothiocyanate (1) with sodium methanethiolate afforded 1-thioxo-1H-imidazo[1,5-a]indol-3(2H)-one (3). Its methylation with methyl iodide in the presence of lithium hydride in dimethylformamide, or potassium carbonate in acetone resulted in the formation of corresponding S- and N-methyl derivatives 4 and 5. N-(Indole-2-carbonyl)thiocarbamates and N-(indole-2-carbonyl)thioureas prepared by treatment of isothiocyanate 1 with corresponding nucleophilic reagents were S-methylated with methyl iodide in acetone in the presence of potassium carbonate. The obtained N-(indole- 2-carbonyl) substituted thiocarbonimidates 15, 16 and isothioureas 17-20 afforded by treatment with lithium hydride in dimethylformamide the derivatives of imidazo[1,5-a]- indol-3-one 23-28 in 49-87% yields. Antifungal activity of the prepared compounds has been examined, using the fungus Bipolaris leersiae. 1-Methylsulfanyl-3H-imidazo-[1,5-a]- indol-3-one (4) exhibited the highest antifungal activity.

Imidazo(1,2-a)indole and s-triazolo(2,3-a)indole derivatives by intramolecular cyclization of 1-(o-acetylphenytyl)azoles

1968 ◽  
Vol 46 (15) ◽  
pp. 2629-2631 ◽  
Author(s):  
Misbahul Ain Khan ◽  
J. B. Polya ◽  
Brian M. Lynch
Keyword(s):  
Magnetic Resonance ◽  
Intramolecular Cyclization ◽  
Proton Magnetic Resonance ◽  
Indole Derivatives ◽  
Ring Systems ◽  
Methyl Derivatives ◽  
Derivatives Of ◽  
Magnetic Resonance Spectra

9-Hydroxy-9-methyl derivatives of the ring systems named in the title are formed along with the expected 1-(o-acetylphenyl)azoles in the Ullmann condensations of o-bromoacetophenone with imidazole and with 1,2,4-triazole. The structures of these compounds follow from their characteristic proton magnetic resonance spectra.

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.

Physical Properties of TCNQ Salts with N-Methyl Derivatives of Pyridine

1982 ◽  
Vol 85 (1) ◽  
pp. 257-263 ◽  
Author(s):  
A. Graja ◽  
M. Przybylski ◽  
B. Butka ◽  
R. Swietlik
Keyword(s):  
Physical Properties ◽  
Methyl Derivatives ◽  
Derivatives Of

Methyl derivatives of furan

1974 ◽  
Vol 39 (11) ◽  
pp. 3109-3116 ◽  
Author(s):  
J. Šrogl ◽  
M. Janda ◽  
I. Stibor ◽  
V. Skála ◽  
P. Trška ◽  
...  
Keyword(s):  
Methyl Derivatives ◽  
Derivatives Of

O'-Methyl derivatives of arabinosylcytosine

1972 ◽  
Vol 46 (4) ◽  
pp. 1734-1741 ◽  
Author(s):  
E. Darżynkiewicz ◽  
J.T. Kuśmierek ◽  
D. Shugar
Keyword(s):  
Methyl Derivatives ◽  
Derivatives Of
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