ChemInform Abstract: Synthesis and Antiviral Activity of 2‐Alkylaminomethyl Derivatives of 5‐Hydroxyindole.

Abstract

Starting with the bromomethyl compound (I), the aminomethyl derivatives (III), (IV), and (VI) are prepared as shown in the reaction scheme.

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

“…However, formation of the corresponding 4-isogramine (which has been proposed as an antiinflammatory agent) was also noticed for the 3-substituted 5-hydroxyindole 3-acetyl-5-hydroxy-2-(sulfanylmethyl)indole, in spite of the presence of the acetyl group at position 3 [42]. Regioselective dimethylaminomethylation at position 4, including cases where position 6 was free, has also been observed for a series of 1,2,3-trisubstituted 5-hydroxyindoles [43][44][45].…”

“…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] …”

“…Thus, for example, there data on the antiviral activity of 1,3,5-trisubstituted 2-diethylaminomethylindoles [22,23]. Activity against the influenza virus was exhibited by the hydrochloride of 5-acetoxy-1-benzyl-6-bromo-2-dimethylaminomethyl-3-ethoxycarbonylindole [19].…”

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

“…5 a-5 m were synthesized by a simple threestep process in Scheme 2. First, a nucleophilic substitution reaction of 2 a-2 i with substituted benzenesulfonyl chloride in acetone were taken place in the presence of potassium carbonate to obtain products 3 a-3 m. [20,21] The methyl group at 2-position of the indole ring was more prone to free radical reaction. When 3 a-3 m and NBS were mixed in CCl 4 with AIBN and refluxed for 6 h, compounds 4 a-4 m were formed.…”