1,4-Bis(2-indol-3-ylethyl)piperidines

Abstract

Access to a new class of indole derivatives was gained when Gray and Archer published their work on the pyridylethylation of indoles.1 The usefulness of this general reaction was enhanced by the finding that catalytic hydrogenation of indolylethylpyridines led to selective saturation of the pyridine ring.2 3 Alkylation of the resultant uidolylethylpiperidines gave products which displayed marked depressant effects on the central nervous system of mice and dogs. Certain

Medicinal Chemistry and Animal Pharmacology of Indoramin

“…An interest in the antihypertensive activity of some so called 'Bis-indoles' (Archibald, Baum & Childress, 1970) was a prelude to the development of indoramin. These compounds were unrelated to any known antihypertensive agent and their detailed mode of action remained unknown, but a-blockade was believed to play an important part in their hypotensive effects.…”

A new strategy for hit generation: Novel in cellulo active inhibitors of CYP121A1 from Mycobacterium tuberculosis via a combined X-ray crystallographic and phenotypic screening approach (XP screen)

“…Compounds 4 – 9 were prepared by heating the appropriately substituted indole with either 2-vinylpyridine (for 4 – 6 ) or 4-vinylpyridine (for 7 – 9 ) in acetic acid as described previously [ [12] , [13] , [14] , [15] ]. Similar reactions [ 13 ] between 2-chloro-4-vinylpyrimidine [ 16 ] in a mixture of acetic acid and 1,4-dioxane afforded 11 – 13 .…”

“…Compounds 4 , [ 12 ], 6 , [ 14 ] 7 , [ 12 ] 8 , [ 13 ] 9 , [ 15 ] 10 , [ 13 ] 11 , [ 13 ] 41 , [ 19 ] 43 , [ 15 ] 45 , [ 9 ] 66 , [ 23 ] 67 , [ 24 ] 68 [ 24 ] and 69 [ 24 ] were prepared as described previously.…”

Chemical conversion of the psychotomimetic amine 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane to 5-hydroxy-2,6-dimethylindole

“…1.4-Bis(3-indoleglyoxyloyl)piperazine (1). Piperazine (2.6 g, 30 mmol) in dry 1,2-DME (100 ml) was stirred while 3-indoleglyoxyloyl chloride (4.3 g, 20 mmol) in 1,2-DME (25 ml) was added dropwise.…”

“…Theoretical Method. The same postulate as in part 1 is made; i.e., the rate of biological response is expressed in the simple form d(biological response) _ At AC x p3i (Brownian) x p*2 (binding) (1) where C is the drug concentration, p(Brownian) is the probability of successful penetration of a drug molecule in the Brownian-like motion (see Figure 1) through biomembranes to reach a receptor, p(binding) is the probability of a successful binding between a drug molecule and a receptor, and al and a2 are constants.…”