Synthesis and pharmacological activity of metabolites of the 5-HT4 receptor antagonist SB-207266

Synthesis and pharmacological properties of novel hydrophilic 5-HT4 receptor antagonists

“…The following known intermediates and reference compounds were synthesized according to literature procedures: 1-benzyl-4-aminomethylpiperidine, 22 23 Spectral data of all described compounds were consistent with the proposed structures.…”

Monoindole Alkaloids from a Marine Sponge Spongosorites sp.

“…The EIMS fragments at m/z 132 and 160 corroborated the proposed structure ( Figure 1). Therefore, compound 6 was defined as (6-hydroxy-1H-indol-3-yl) carboxylic acid methyl ester, which was known as an intermediate in the organic synthesis of a 5-HT 4 receptor antagonist [20], but has not been reported from a natural source. Compound 7 was also isolated as a yellow, amorphous powder.…”

Improved procedure for the preparation of 7-methoxy-2-methyl-1-(2-morpholinoethyl)-1H-indole-3-carboxylic acid, key intermediate in the synthesis of novel 3-amidoindole and indolopyridone cannabinoid ligands

“…Alternatively, the indole-3-carboxylate could be prepared by acylation of 7-methoxy-2-methyl-1H-indole 4 with trichloroacetyl chloride followed by alcoholysis. 3,5 An example of this preferred approach is the preparation of methyl indole-3-carboxylate 5b, which was obtained in 92% yield. 3 The introduction of the N-morpholinoethyl side chain onto the indole-3-carboxylate 5 was accomplished by treating 5 with 4-(2-chloroethyl)morpholine hydrochloride 6 in the presence of a large excess of base.…”