2744-45-8

Usage

Type of compound

Naturally occurring alkaloid

Plant sources

Tobacco smoke, coffee, and some common foods

Structure

Tricylic compound with a pyridoindole structure

Structural relation

Related to harmine and harmaline

Potential use

Psychotropic agent

Pharmacological effects

Monoamine oxidase inhibitor

Neurological effects

Investigated for effects on neuronal function and modulation of neurotransmitter systems in the brain

Research fields

Pharmacology and neurobiology

Upstream product

• 4238-66-8 11-demethylellipticine 
• 878003-42-0 Se-phenyl 3-((1,2-dimethyl-1,2,5,6-tetrahydro-3-pyridyl)methyl)-1H-2-indolecarboselenoate 
• 878003-43-1 1,2-dimethyl-1,2,3,4,4a,6,11,11a-octahydro-pyrido[4,3-b]carbazol-5-one 
• 64-17-5 ethanol 
• 98494-80-5 1,2,5-trimethyl-6H-pyrido[4,3-b]carbazolium; iodide 
• 67-56-1 methanol 
• 484-49-1 Guatambuinine 
• 74-88-4 methyl iodide 
• 40899-89-6 1-(1-benzenesulfonyl indole-2-yl)-1-(4-pyridyl)-ethanol 
• 40899-71-6 1-benzenesulfonylindole 
• 120-72-9 indole 
• 79820-57-8 indole-2-yl-1-(4-pyridyl)-ethanol 
• 79820-58-9 indole-2-yl-1-(4-pyridylmethiodide)-ethanol 

Downstream Products

• 484-49-1 Guatambuinine 

Relevant academic research and scientific papers

Synthesis and cytotoxicity of pyrido[4,3-b]carbazole alkaloids against HCT-116 and HL-60 cells

Ellipticine, olivacine, and their five reduced natural variants were synthesized via a palladium-catalyzed tandem cyclization/cross-coupling reaction as the key step. In addition, a previously unknown conformer of janetine was obtained through conformational inversion of the D ring in janetine. Because there are few synthetic approaches for reduced natural variants, little is known about the biological activities of these compounds. Six synthetic natural alkaloids and five of their derivatives were evaluated for their antiproliferative activity against HCT-116 and HL-60 cells. The activities of variants with the D-reduced ring or without the C(11)-Me group were lower than those of ellipticine. The conformer of guatambuine showed higher activities than guatambuine.

Regioselective 6-endo cyclizations of 2-indolylacyl radicals: Total synthesis of the pyrido[4,3-b]carbazole alkaloid guatambuine

A regioselective 6-endo reductive cyclization of 2-indolylacyl radicals constitutes the key step of a straightforward synthetic entry to the olivacine skeleton, illustrated by a total synthesis of the tetrahydropyridine alkaloid guatambuine.

STUDIES IN THE DIHYDROPYRIDINE SERIES. V. SYNTHESIS OF PYRIDOCARBAZOLE ALKALOIDS: OLIVACINE AND GUATAMBUINE.

The tricarbonylchromium(0) complex 8 effectively stabilized the very reactive dihydropyridine system during one carbon insertion.Release of the complex allowed cyclization to the pyridocarbazole product 13 which was elaborated to olivacine 1 and guatambuine 2.