Synthesis and biological activity of aminoalkyl derivatives of 5-hydroxyindole

Grinev, A. N.; Panisheva, E. K.; Cherkasova, A. A.; Stolyarchuk, A. A.; Иванова, Н. И.; Lysaya, T. I.; Storozhuk, B. G.

doi:10.1007/bf00764691

Cited by 3 publications

(10 citation statements)

References 3 publications

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“…At the same time there are data indicating that the reaction of certain 2,3-disubstituted 5-hydroxyindoles with bisdimethylaminomethane leads to simultaneous aminomethylation at positions 4 and 6 [20].…”

Section: Synthesis Of Indole Derivatives Containing a Dimethylaminomementioning

confidence: 91%

“…Thus, the action of aqueous dimethylamine on 2-bromomethyl-1,3-dibenzoylindole leads to the initial formation of 3-benzoyl-2-dimethylaminomethylindole, the debenzoylation of which with p-toluenesulfonic acid in ethylene glycol gives unsubstituted 2-isogramine [15]. The corresponding 2-dialkylaminomethyl derivatives were obtained by the analogous reaction of substituted 2-bromomethylindoles with dimethylamine [16][17][18][19][20][21] and diethylamine [22,23]. By this procedure it is possible to obtain unsubstituted 2-isogramine (3) from 2-methyl-3-phenylthioindole (6) using the following sequence of transformations [16] …”

Section: Synthesis Of 2-dimethylaminomethylindolesmentioning

confidence: 98%

“…There are data on the short-term antihypertensive, antiarrhythmic, antifibrillation, and anticonvulsive activity of the bisdimethylaminomethyl derivative of indole -ethyl 5-hydroxy-4,6-bis(dimethylaminomethyl)-2-methylindole-3-carboxylate [20].…”

Section: Pharmacological Characteristics Of Isograminesmentioning

confidence: 99%

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Methods for the Synthesis of Isogramines and Their Chemical Properties. (Review)

Семенов

Yurovskaya

2005

Chem Heterocycl Compd

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Section: Synthesis Of Indole Derivatives Containing a Dimethylaminomementioning

confidence: 91%

Section: Synthesis Of 2-dimethylaminomethylindolesmentioning

confidence: 98%

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Methods for the Synthesis of Isogramines and Their Chemical Properties. (Review)

Семенов

Yurovskaya

2005

Chem Heterocycl Compd

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“…6-Bromo-2-((dimethylamino)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylic acid ethyl ester hydrochloride (4a). 1 Hydrochlorides of substituted ethyl esters of 2-aminomethyl-5-hydroxy-1H-indole-3-carboxylic acids (7a -i), general method. Pyridylboronic acid (197 mg, 1.6 mmol), Na 2 CO 3 (212 mg, 2 mmol) and water (5 ml) were added to a solution of 1 mmol of one of compounds 4a -g in 10 ml of ethanol.…”

Section: Experimental Chemical Sectionmentioning

confidence: 99%

“…Yields were 22 -56%. 1 1 This produced compound 11, which was converted to the hydrochloride by addition of an equivalent quantity of 3 M HCl solution in dioxane to 5 ml of a solution of compound 11 in acetone; the resulting precipitate was collected by filtration, washed with ether, and dried in vacuo. This was recrystallized from absolute ethanol.…”

Section: Experimental Chemical Sectionmentioning

confidence: 99%

Synthesis and Antiviral Activity of Substituted Ethyl-2-Aminomethyl-5-Hydroxy-1H-Indole-3-Carboxylic Acids and Their Derivatives

et al. 2015

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Novel substituted 5-hydroxy-2-aminomethyl-1H-indole-3-carboxylic acids and their derivatives were synthesized. The antiviral properties of these compounds were investigated in relation to bovine viral diarrhea virus (BVDV), hepatitis C virus (HCV), and influenza A/Aichi/2/69 (H3N2) virus. Of the compounds synthesized here, only the 5-hydroxy-2-(dimethylaminomethyl)-1-methyl-6-pyridin-3-yl-and 5-hydroxy-2-(dimethylaminomethyl)-1-methyl-6-fluoro-1H-indole-3-carboxylic acid ethyl ester hydrochlorides had significant activity against these viruses, these agents not only suppressing the replication of influenza A/Aichi/2/69 (H3N2) virus in cell cultures at micromolar concentrations, but also demonstrating high efficacy, greater than that of Arbidol, in a model of influenza pneumonia in mice infected with influenza A/Aichi/2/69 (H3N2) virus, when given at a dose of 25 mg/kg/day.Keywords: 2-aminomethyl-5-hydroxy-1H-indole-3-carboxylic acids, antiviral activity, antiinfluenza activity, influenza A/Aichi/2/69 (H3N2), BVDV, HCV.Substituted 2-and 4-aminomethyl-5-hydroxyl-1H-indole-3-carboxylic acids are known to have some degree of antiviral activity [1 -3]. In particular, 1-benzyl-2-dimethylaminomethyl-3-carbethoxy-5-acetoxy-6-bromoindole hydrochloride demonstrated antiinfluenza activity in studies using a mouse model of influenza pneumonia [3]. We have previously described the synthesis and antiviral activity of a series of 2-aminomethyl-5-hydroxy-1H-indole-3-carboxylic acids and have shown them to have limited activity against influenza A/New Caledonia/20/99 (H1N1) virus, bovine viral diarrhea virus (BVDV), and HCV [4].We describe here the synthesis and antiviral activities of novel derivatives of 2-aminomethyl-5-hydroxy-1H-indole-3-carboxylic acids (compounds 4 -7, 11, 16 -20, 24). Substituted ethyl esters of 2-aminomethyl-5-hydroxy-1H-indole-3-carboxylic acids 4 -7 were prepared (scheme 1) from 1-substituted ethyl esters of 5-hydroxy-2-methyl-1H-indole-3-carboxylic acids 1a -e, which, by analogy [5] with 1,2-dimethylindole (compound 1a), were sequentially converted to 5-acetyloxy-(compounds 2a -e) and 5-acetyloxy-6-bromoindoles (compounds 3a -e). Interaction of these latter compounds with dimethylamine, pyrrolidine, and morpholine gave the corresponding 2-aminomethyl-6-bromoindoles (4a -g). 6-Bromoindoles 4b,c were hydrogenated with hydrogen on 10% Pd/C to form indoles unsubstituted at position 6 (compounds 5a, b); reaction of 6-bromoindole 4a with copper (I) cyanide in N-methylpyrrolidone (NMP) produced the corresponding 6-cyanoindole compound 6, while use of

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Development of 2‐Alkyl‐5‐((phenylsulfonyl)oxy)‐1H‐indole‐3‐carboxylate Derivatives as Potential Anti‐Biofilm Agents

Chen

Xiong

et al. 2023

ChemistrySelect

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A series of novel 2-alkyl-5-((phenylsulfonyl)oxy)-1H-indole-3carboxylate derivatives were synthesized and evaluated for their cytotoxicity, antibacterial and anti-biofilm activities. Some of these compounds were able to inhibit biofilm formation of the tested strains with biofilm inhibitory concentration in the range of 12.5-50 μM. The results indicated N-methylpiperazine moiety was the key factor affecting the compound's activity. Compounds 5 l and 5 m with F substituent at the phenyl ring at 5-position of indole ring, presented the most potent biofilm inhibitory activity (more than 90 % inhibition percentage) against E. faecalis 16C51 at biofilm inhibitory concentration (12.5 μM). Furthermore, compounds 5 f and 5 h with Br/CH 3 substituent at the phenyl ring at 1-position of indole ring, showed the greatest biofilm inhibitory activity (more than 85 % inhibition percentage) against MRSA YUSA145 at biofilm inhibitory concentration (12.5 μM).

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Synthesis and biological activity of aminoalkyl derivatives of 5-hydroxyindole

Cited by 3 publications

References 3 publications

Methods for the Synthesis of Isogramines and Their Chemical Properties. (Review)

Methods for the Synthesis of Isogramines and Their Chemical Properties. (Review)

Synthesis and Antiviral Activity of Substituted Ethyl-2-Aminomethyl-5-Hydroxy-1H-Indole-3-Carboxylic Acids and Their Derivatives

Development of 2‐Alkyl‐5‐((phenylsulfonyl)oxy)‐1H‐indole‐3‐carboxylate Derivatives as Potential Anti‐Biofilm Agents

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