10252-12-7

Usage

Uses

Used in Pharmaceutical Industry:
Rauwolscine is used as a potential treatment for erectile dysfunction due to its alpha-2 adrenergic receptor antagonist properties, which may help improve blood flow and erectile function.
Used in Dietary Supplements:
Rauwolscine is used as a dietary supplement for weight loss and athletic performance enhancement. Its alpha-2 adrenergic receptor antagonist activity may contribute to increased metabolism and energy expenditure, promoting weight loss and improved physical performance.
Used in Drug Development and Medicinal Research:
Rauwolscine's structure and pharmacological activities make it a subject of interest in drug development and medicinal research. Its potential applications in treating various conditions, such as erectile dysfunction, weight loss, and athletic performance enhancement, warrant further investigation and development of new therapeutic agents.

Upstream product

• 99545-58-1 (S)-12-Methoxymethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizine 
• 6067-48-7 1,2,3,4,6,7-Hexahydro-12H-indolo<2.3-a>chinolizinium-chlorid 
• 6026-86-4 methyl 4-formylbutanoate 
• 496910-16-8 1-allyl-1,2,3,4-tetrahydro-2-(2,2,2-trichloroethoxycarbonyl)-β-carboline 
• 16502-01-5 tetrahydrobetacarboline 
• 1444254-66-3 (-)-(1S,12bR)-1-hydroxy-2,3,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-4(1H)-one 
• 1444254-70-9 (1S,12bR)-4-oxo-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]-quinolizin-1-yl phenyl carbonate 
• 1444254-42-5 tert-butyl (S)-3-(2-(5-oxotetrahydrofuran-2-carboxamido)ethyl)-1H-indole-1-carboxylate 
• 167015-84-1 3-(2-aminoethyl)-indole-1-carboxylic acid tert-butyl ester 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 1444254-46-9 tert-butyl (S)-3-(2-(3-hydroxy-2,6-dioxopiperidin-1-yl)ethyl)-1H-indole-1-carboxylate 
• 1444254-50-5 tert-butyl (S)-3-(2-(3-acetoxy-2,6-dioxopiperidin-1-yl)ethyl)-1H-indole-1-carboxylate 
• 1444254-58-3 tert-butyl (1S,12bR)-1-acetoxy-4-oxo-1,3, 4 ,6,7,12bhexahydroindolo[2,3-a]quinolizine-12(2H)-carboxylate 
• 4942-85-2 1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-4-one 

Relevant academic research and scientific papers

Highly stereoselective synthesis of the indolo[2,3-a]quinolizine ring system and application to indole natural product synthesis

We report a novel, facile and highly stereoselective approach to the indolo[2,3-a]quinolizine ring system from a readily available, non-racemic chiral template. We demonstrate the potential for application of this methodology to natural product synthesis through conversion of the template to a simple indole alkaloid with high enantiomeric purity.

Antiproliferative activity of arborescidine alkaloids and derivatives

Current issues in cancer research involve searching for novel anticancer compounds that can be used to regulate the cell cycle and lead to more effective treatments of tumors. In this study, it was hypothesized that possessing a cyclic alkaloid similar to harmine, arborescidines can disrupt the proliferative state of cancer cells and block the activity of topoisomerases. The antiproliferative activity of arborescidines A-C and their derivatives was evaluated in vitro against four human tumor cell lines: gastric adenocarcinoma, lung cancer, bladder carcinoma and leukemia. Assuming the mechanism of action by topoisomerase II binding model, the compounds possessing the greatest activity had nonpolar side-chain into hydrophobic binding region on the DNA/topo II complex.

Enantioselective synthesis of some tetrahydroisoquinoline and tetrahydro-β-carboline alkaloids

Four alkaloids: (R)-(+)-cryspine A 5, (R)-(+)-octahydroindolo[2,3-a]quinolizidine 8, (R)-(+)-harmicine 19 and (R)-(+)-desbromoarborescidine 22 were prepared via the asymmetric transfer hydrogenation reaction of a prochiral enamine (iminium salt). The enan

Synthetic studies in the alkaloid field-VII1 1 VI: M. Lounasmaa and M. Puhakka, Acta. Chem. Scand. B32, 77 (1978). Stereochemistry of 1,2,3,4,6,7,12,12b-octahydroindolo [2,3-a]quinolizine derivatives prepared by alkaline decarboalkoxylative cyclization or acid-induced cyclization of appropriate tetrahydropyridines

The C(12b)-C(1)-C(2) stereochemical relationship in several racemic 1,2,3,4,6,7,12,12b-octahydroindolo [2,3-a]quinolizine derivatives has been determined by 13C NMR spectral analysis. The proper shift assignment was confirmed by recording the spectra of selectively deuterated derivatives. The C(12b)-C(1)-C(2) stereochemical relationship in indolo[2,3-a]quinolizines obtained either by alkaline decarboalkoxylative cyclization or by acid-induced cyclization of partially hydrogenated 1-[2-(3-indolyl)ethyl]-3-methoxycarbonylpyridine derivatives is discussed. The ambiguity existing in the preparation of dl-18,19-dihydroantirhine 2 by analogous decarboalkoxylative cyclization is considered.

Enantioselective total synthesis of desbromoarborescidines A-C and the formal synthesis of (S)-deplancheine

Starting from Boc-protected tryptamine and (S)-tetrahydro-5-oxo-2- furancarboxylic acid, facile enantioselective total synthesis of desbromoarborescidines A-C and the formal synthesis of (S)-deplancheine have been accomplished via a common intermediate (S

A highly enantioselective access to tetrahydroisoquinoline and β-carboline alkaloids with simple noyori-type catalysts in aqueous media

Silver enhancement: A very convenient modified protocol for the enantioselective transfer hydrogenation of dihydroisoquinoline skeletons under aqueous conditions is reported. Unmodified Noyori ligands can be used and the activity of the catalyst is greatly enhanced with silver additives (see scheme). The protocol was used in a very short synthesis of the alkaloids (S)-harmicine and (S)-crispine.

A highly stereoselective synthesis of the indolo[2,3-a]quinolizine ring system and application to natural product synthesis

We present a facile and highly stereoselective approach to the indolo[2,3-a]quinolizine ring system from a readily available, non-racemic chiral template. We demonstrate the potential for application of this methodology to natural product synthesis throug

Syntheses of 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]-quinolizine and harmicine using a chiral 1-allyl-1,2,3,4-tetrahydro-β-carboline as the starting material

Total syntheses of (S)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a] quinolizine and (S)-harmicine were carried out using chiral 1-allyl-1,2,3,4-tetrahydro-β-carboline as the starting material.

Microwave assisted McFadyen-Stevens and Huang-Minlon reactions

Microwave irradiation has been employed in McFadyen-Stevens reaction to convert p-toluenesulfonyl hydrazides 1 to the aldehydes 2. Also, microwave has been applied in Huang-Minlon reduction of carbonyl compounds 3 to the corresponding hydrocarbons 4.

Stereoselective Additions of Chiral α-Sulfinyl Ketimine Anions to Ene Esters. Asymmetric Syntheses of Indoloquinolizidine and Yohimban Alkaloids

The in-situ 1,4-addition/ring-closure reactions of chiral α-sulfinyl ketimine anions with acyclic and cyclic ene esters offer a simple, convenient route for the construction of chiral cyclic alkaloids having a nitrogen-atom ring juncture.Asymmetric induction in the conjugate-addition reaction of the carbanions derived from α-sulfinyl ketimines possessing chiral sulfur with various cyclic and acyclic ene esters, subsequent ring-closure reaction, and reduction of the resulting β-sulfinyl enamides were utilized in the syntheses of (-)-1,2,3,4,6,7,12,12b-octahydroindoloquinolizine , (-)-alloyohimban , (+)-3-epi-alloyohimban , and (-)-yohimban .