105608-27-3

Basic information

• Product Name: Prostephanaberrine
• Synonyms: Prostephanaberrine
• CAS NO: 105608-27-3
• Molecular Formula: C19H21NO5
• Molecular Weight: 343.37374
• Mol File: 105608-27-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 530°Cat760mmHg
• Flash Point: 274.3°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 4.63E-12mmHg at 25°C
• Refractive Index: 1.664
• CAS DataBase Reference: Prostephanaberrine(CAS DataBase Reference)
• NIST Chemistry Reference: Prostephanaberrine(105608-27-3)
• EPA Substance Registry System: Prostephanaberrine(105608-27-3)

Safety Data

• Hazardous Substances Data: 105608-27-3(Hazardous Substances Data)

Usage

General Description

Prostephanaberrine is a natural alkaloid compound found in plants such as Stephania succifera and Stephania cepharantha. It belongs to the class of isoquinoline alkaloids and has been studied for its potential therapeutic properties. Research has shown that Prostephanaberrine exhibits significant anti-inflammatory, antiviral, and antifungal activities, making it a promising candidate for the development of new drug treatments. Additionally, it has been investigated for its potential anti-cancer properties and is being studied for its ability to inhibit the growth of certain cancer cells. Prostephanaberrine is also being explored for its potential as a neuroprotective agent, with studies suggesting its ability to protect against certain neurodegenerative diseases. Overall, the unique properties of Prostephanaberrine make it a valuable target for further research and drug development in various healthcare applications.

InChI:InChI=1/C19H21NO5/c1-20-6-5-18-4-3-14(23-2)17(22)19(18,20)9-13(21)11-7-15-16(8-12(11)18)25-10-24-15/h3,7-8,13,21H,4-6,9-10H2,1-2H3/t13-,18+,19+/m0/s1

Upstream product

• 1025023-05-5 (7β,8β,10β)-8,10-epoxy-7,8-dimethoxy-2,3-[methylenebis(oxy)]-17-methyl-6-oxohasubanan 

Downstream Products

• 105608-29-5 (-)-stephanaberrine 

Relevant articles and documents

Development of enantioselective synthetic routes to the hasubanan and acutumine alkaloids

We describe a general strategy to prepare the hasubanan and acutumine alkaloids, a large family of botanical natural products that display antitumor, antiviral, and memory-enhancing effects. The absolute stereochemistry of the targets is established by an enantioselective Diels-Alder reaction between 5-(trimethylsilyl)cyclopentadiene (36) and 5-(2-azidoethyl)-2,3- dimethoxybenzoquinone (24). The Diels-Alder adduct 38 is transformed to the tetracyclic imine 39 by a Staudinger reduction-aza-Wittig sequence. The latter serves as a universal precursor to the targets. Key carbon-carbon bond constructions include highly diastereoselective acetylide additions to the N-methyliminium ion derived from 39 and Friedel-Crafts and Hosomi-Sakurai cyclizations to construct the carbocyclic skeleton of the targets. Initially, this strategy was applied to the syntheses of (-)-acutumine (4), (-)-dechloroacutumine (5), and four hasubanan alkaloids (1, 2, 3, and 8). Herein, the synthetic route is adapted to the syntheses of six additional hasubanan alkaloids (12, 13, 14, 15, 18, and 19). The strategic advantage of 5-(trimethylsilyl)cyclopentadiene Diels-Alder adducts is demonstrated by site-selective functionalization of distal carbon-carbon π-bonds in the presence of an otherwise reactive norbornene substructure. Evaluation of the antiproliferative properties of the synthetic metabolites revealed that four hasubanan alkaloids are submicromolar inhibitors of the N87 cell line.