95462-14-9

Usage

Uses

Used in Pharmaceutical Industry:
InterMedine N-Oxide is utilized as a potential anticancer agent for its ability to target and combat cancer cells. Its application in this field is driven by the need for novel and effective treatments against various types of cancer.
Used in Research and Development:
In the realm of scientific research and drug development, InterMedine N-Oxide serves as a valuable compound for studying its anticancer properties and potential mechanisms of action. This aids in the advancement of cancer treatment strategies and the discovery of new therapeutic agents.

Upstream product

• 95462-10-5 (4S,5R)-4-Isopropyl-2,2,5-trimethyl-[1,3]dioxolane-4-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester 
• 109305-72-8 1,2-O-isopropylidene-3-O-benzyl-5-deoxy-3-C-isopropyl-β-D-lyxofuranose 
• 109305-75-1 tetraol 
• 109305-71-7 1,2-O-isopropylidene-5-deoxy-3-C-isopropyl-β-D-lyxofuranose 
• 94773-28-1 trans-α-isopropylcrotonic acid 
• 23944-47-0 (+/-)-trachelanthic acid 
• 95462-08-1 4(S)-(1-methylethyl)-2,2,5(R)-trimethyl-1,3-dioxolane-4-carboxylic acid 
• 23944-48-1 (2S,3R)-2,3-dihydroxy-2-(1-methylethyl)butyric acid 
• 10285-06-0 intermedine 
• 109305-76-2 2-O-benzyl-(+)-trachelanthic acid 

Downstream Products

• 480-82-0 lycopsamine A 

Relevant academic research and scientific papers

Semi-automated separation of the epimeric dehydropyrrolizidine alkaloids lycopsamine and intermedine: Preparation of their N-oxides and NMR comparison with diastereoisomeric rinderine and echinatine

Introduction The diversity of structure and, particularly, stereochemical variation of the dehydropyrrolizidine alkaloids can present challenges for analysis and the isolation of pure compounds for the preparation of analytical standards and for toxicology studies. Objective To investigate methods for the separation of gram-scale quantities of the epimeric dehydropyrrolizidine alkaloids lycopsamine and intermedine and to compare their NMR spectroscopic data with those of their heliotridine-based analogues echinatine and rinderine. Methods Lycopsamine and intermedine were extracted, predominantly as their N-oxides and along with their acetylated derivatives, from commercial samples of comfrey (Symphytum officinale) root. Alkaloid enrichment involved liquid-liquid partitioning of the crude methanol extract between dilute aqueous acid and n-butanol, reduction of N-oxides and subsequent continuous liquid-liquid extraction of free base alkaloids into CHCl3. The alkaloid-rich fraction was further subjected to semi-automated flash chromatography using boronated soda glass beads or boronated quartz sand. Results Boronated soda glass beads (or quartz sand) chromatography adapted to a Biotage Isolera Flash Chromatography System enabled large-scale separation (at least up to 1-2 g quantities) of lycopsamine and intermedine. The structures were confirmed using one- and two-dimensional 1H- and 13C-NMR spectroscopy. Examination of the NMR data for lycopsamine, intermedine and their heliotridine-based analogues echinatine and rinderine allowed for some amendments of literature data and provided useful comparisons for determining relative configurations in monoester dehydropyrrolizidine alkaloids. A similar NMR comparison of lycopsamine and intermedine with their N-oxides showed the effects of N-oxidation on some key chemical shifts. A levorotatory shift in specific rotation from +3.29° to -1.5° was observed for lycopsamine when dissolved in ethanol or methanol respectively. Conclusion A semi-automated flash chromatographic process using boronated soda glass beads was standardised and confirmed as a useful, larger scale preparative approach for separating the epimers lycopsamine and intermedine. The useful NMR correlations to stereochemical arrangements within this specific class of dehydropyrrolizidine alkaloid cannot be confidently extrapolated to other similar dehydropyrrolizidine alkaloids.

THE TOTAL SYNTHESES OF (-)-INDICINE N-OXIDE AND INTERMEDINE N-OXIDE

The total syntheses of (-)-indicine N-oxide, the enantiomer of natural indicine N-oxide and intermedine N-oxide have been achieved.

Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents

(-)- and (+)-trachelanthic and (-)- and (+)-viridifloric acids were synthesized and their isopropylidene derivatives were regiospecifically coupled, at C-9, with (-)-retronecine (2) obtained by hydrolysis of monocrotaline (1), isolated from Crotalaria spectabilis. Hydrolysis, followed by oxidation, led to the N-oxides of indicine (7), intermedine (13), lycopsamine (15), and the new nonnatural product 16, respectively. Each of these analogues was screened in the P388 lymphocytic leukemia system at the same time as indicine N-oxide, and the results were compared. Other related analogues were prepared and similarly screened and the results compared with those from indicine N-oxide.