5-Benzyloxyindole

Synthesis and biological evaluation of novel oxophenylarcyriaflavins as potential anticancer agents.[Pubmed:18528573]

Org Biomol Chem. 2008 Jun 21;6(12):2108-17.

We report the synthesis and biological evaluation of new oxophenylarcyriaflavins designed as potential anticancer agents. An efficient synthesis involving palladium-catalyzed Suzuki and Stille reactions is presented, without any indolic protective group. The central ring closure of the scaffold was performed through an electrophilic reaction on the position C-2 of the indole ring. The use of indole and 5-Benzyloxyindole, along with substituted phenyl rings, generated three different scaffolds, which were successively exploited to modulate the structure. The cytotoxicity of the newly designed compounds on four cancer cell lines and activities against three kinases (CDK1, CDK5 and GSK3) were evaluated. Several compounds showed a marked cytotoxicity with IC(50) values in the sub-micromolar range, and induced important cell cycle perturbations, with a G2/M arrest. Some compounds revealed DNA binding properties and were found to inhibit topoisomerase-mediated DNA relaxation of supercoiled DNA, but these properties are not mandatory for a cytotoxic action. A novel lead compound () has been identified and warrants further investigations.

Lasting chemiluminescence of 3-indoleglyoxylyl chloride and its enhancement.[Pubmed:12558035]

Anal Sci. 2003 Jan;19(1):123-7.

The chemiluminescence (CL) intensities of various indole derivatives substituted with a glyoxylyl group at the 3-position and a hydroxyl group at the 5-position of the indole ring were compared upon the addition of H2O2 in alkaline media. The CL intensities of 3-indoleglyoxylyl chloride, 3-indoleglyoxylic acid, 5-hydroxyindole and 5-Benzyloxyindole in CH3CN were 5.9-, 48-, 5.9- and 3.3-fold stronger than that of 3-methylindole. A lasting CL of 3-indoleglyoxylyl chloride was found. Under appropriate conditions, the CL emission reached a maximum within 10 min after the addition of H2O2 in the presence of NaOH, and the intensity was retained for 25 min. One of the final products via the CL reaction of 3-indoleglyoxylyl chloride was indole-3-carboxylic acid. 3-Indoleglyoxylyl chloride emitted light by decompositions via both dioxetane and dioxetanedione. An enhancement effect of beta-cyclodextrin and bovine serum albumin on the CL of 3-indoleglyoxylyl chloride was also found.

Actions of some analogues of 5-hydroxytryptamine on the isolated rat uterus and the rat fundus strip preparations.[Pubmed:13662587]

Br J Pharmacol Chemother. 1959 Jun;14(2):265-72.

The search for substances which antagonize 5-hydroxytryptamine, and for those which act like it, has been extended to cover 5-substituted indoles which are analogues of 5-hydroxytryptamine, rather than analogues of tryptamine like the compounds previously studied by us. The isolated rat uterus and rat fundus strip preparations have been used to determine activity. The relationships between structure and activity of the compounds studied were not the same on the two preparations nor were they the same from one homologous series to another. These differences may be partly explained by the presence of amine oxidase in the rat fundus, as Vane (1959) has suggested, and by supposing that it is absent from the rat uterus. None of the compounds had marked antagonist activity. The most active antagonist on the rat uterus was 3-(2-aminopropyl)-5-Benzyloxyindole, but this was less potent than 5-benzyloxygramine. On the rat fundus strip, however, the only antagonist, 5-benzyloxy-3-(2-dimethylaminoethyl)indole, was more active than 5-benzyloxygramine. On both preparations the most active stimulant was 3-(2-aminopropyl)-5-Benzyloxyindole, which was about half as potent as 5-hydroxytryptamine. The next most active were 3-(2-aminopropyl)-5-methoxyindole and bufotenine.