32790-09-3

Basic information

• Product Name: 17,18-Didehydrovincamine
• Synonyms: (3α,14S,16α)-14,15-Dihydro-17,18-didehydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester;(3α,14S,16α)-17,18-Didehydro-14,15-dihydro-14β-hydroxyeburnamenine-14-carboxylic acid methyl ester;(3α,16α)-14,15-Dihydro-17,18-didehydro-14-hydroxyeburnamenine-14α-carboxylic acid methyl ester;14,15-Dehydrovincamine;17,18-Didehydrovincamine;Δ14-Vincamine
• CAS NO: 32790-09-3
• Molecular Formula: C₂₁H₂₄N₂O₃
• Molecular Weight: 352.42686
• Mol File: 32790-09-3.mol

Chemical Properties

• Melting Point: 224-225 °C
• Boiling Point: 508.7±50.0 °C(Predicted)
• Appearance: /
• Density: 1.35±0.1 g/cm3(Predicted)
• PKA: 12.20±0.40(Predicted)
• CAS DataBase Reference: 17,18-Didehydrovincamine(CAS DataBase Reference)
• NIST Chemistry Reference: 17,18-Didehydrovincamine(32790-09-3)
• EPA Substance Registry System: 17,18-Didehydrovincamine(32790-09-3)

Safety Data

• Hazardous Substances Data: 32790-09-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
17,18-Didehydrovincamine is used as a nootropic agent for combating the effects of aging. It is often used in conjunction with other nootropics, such as piracetam, to enhance cognitive function and memory.
Used in Neurological Applications:
17,18-Didehydrovincamine is used as a peripheral vasodilator to increase blood flow to the brain. This improved blood flow can help support brain health and function, making it a potential candidate for the treatment of various neurological disorders.
Used in Research and Development:
Due to its structural similarity to Vincamine, 17,18-Didehydrovincamine is also used in research and development to study its potential therapeutic effects and to develop new drugs with improved efficacy and safety profiles.

Upstream product

• 4429-63-4 tabersonine 
• 112817-47-7 (5aR,10aS,11R,12aR,12bS)-5a-Amino-12a-ethyl-11-hydroxy-4,5,5a,10,11,12,12a,12b-octahydro-3H-3a,10-diaza-indeno[1,7-ma]fluorene-11-carboxylic acid methyl ester 
• 112924-07-9 C₂₁H₂₅N₃O₃ 

Downstream Products

• 55872-13-4 criocerine 
• 1617-90-9 vincamin 

Relevant articles and documents

Synthesis of vinca alakaloids and realated compounds 98 [1]. Oxidation with dimethyldioxirane of compounds containing the aspidospermane and quebrachamine ring system. A simple synthesis of (7s,20S)-(+)-rhazidigenine and (2R,7S,20S)-(+)-rhazidine

The oxidation of (-)-tabersonine (1) with dimethyldioxirane (DMD) in neutral and acidic medium gave 16-hydroxytabersonine-N-oxide (3) and the didehydrovincamine isomers 4 and 5, respectively. (+)-14,15-Didehydro-quebrachamine (7) furnished the hydroxyindolenine 9, and the pentacyclic derivative 11. (+)- Quebrachamine (8) and DMD in neutral medium gave (7S,20S)-(+)-rhazidigenine (12) which was converted to (2R,7S,20S)-(+)-rhazidine (13b) with hydrochloric acid.

Oxidation of β-Anilinoacrylate Alkaloids Vincadifformine and Tabersonine by Fremy's Salt. A Mechanistic Insight into the Rearrangement of Aspidosperma to Hunteria Alkaloids

β-Anilinoacrylate Aspidosperma alkaloids vincadifformine (2a) and tabersonine (2b) react with Fremy's salt in aqueous acidic conditions via radical coupling at C-16.The resulting zwitterionic compounds 7a and 10 rearange to isoxazolidines 8 and then ultimately to azepinoindoles 9.The mechanism of these reactions is discussed, and the structures of 7a, 8b, and 9a were established by single-crystal X-ray analysis.Diazotization of amine 20b (X = NH2) affords fragmentation-cyclization products corresponding to eburnanes 18 and 21.This reaction mimics the skeletal rearrangement of Aspidosperma -> Hunteria alkaloids, and these findings support Wenkert's biogenetic proposal.

Synthesis of 18-hydroxyvincamines and epoxy-1,14-secovincamines; A new proof for the aspidospermane-eburnane rearrangement

Chemical transformations started from tabersonine were studied. A one-pot oxidative ring-transformation with permaleic acid in methanol yielded 17,18-dehydrovincamine. Hydroboration-oxidation of the latter compound led to alkaloid 17,18-dehydrovincamone. Hydroboration-oxidation of tabersonine resulted 14β-hydroxyvincadifformine and 15β-hydroxyvincadifformine. Allowing 14β- and 15β- hydroxyvincadifformines to react with permaleic acid/methanol provided 1,14-secovincamines, serving as new evidence for the mechanism of the aspidospermane-eburnane transformation. On the other hand 18β-hydroxyvincamine was obtained from 14β-hydroxyvincadifformine by reaction with 3-chloroperbenzoic acid and successive treatment with triphenylphosphine/aqueous acetic acid.

Dye-sensitized Photo-oxygenation of the Aspidosperma Alkaloids Vincadifformine and Tabersonine. A New, Convenient Approach to Vincamine

The dye-sensitized photo-oxygenation of (-)-vincadifformine (1) and (-)-tabersonine (3) is discribed.Reaction takes place through the intermediate formation of 16-hydroperoxyindolenines, which decompose to give 2,16-seco-products or which can be efficently trapped by reductants to give a new stereoselective synthesis of the 16-hydroxy-indoles (10) and (14).These compounds are the key precursors to the eburnane alcaloids vincamine (4) and Δ14-vincamine (6).Suitable experimental conditions give compounds (4) and (6) in good yields directly from their Aspidosperma precursor.

Ozonation in Alkaloid Chemistry: a Mild and Selective Conversion of Vincadifformine into Vincamine

Vincamine has been obtained in a 'one-pot' method by ozonation of vincadifformine.

AROMATIC SUBSTITUTION EFFECTS IN THE ASPIDOSPERMANE-EBURNANE REARRANGEMENT OF INDOLE ALKALOIDS

The influence of substitutions in aromatic part of indole alkaloids with aspidosperma skeleton on their rearrangement into products with eburnane-type structure is studied.Results are applied to vincamine derivatives.