1805-85-2

Usage

Uses

Used in Pharmaceutical Industry:
Hasubanonine is used as a potential therapeutic agent for various health conditions due to its diverse pharmacological properties. Its anti-inflammatory activity makes it a candidate for treating inflammatory diseases, while its anticancer properties suggest its potential use in cancer treatment, particularly for solid malignancies.
Used in Antimicrobial Applications:
Hasubanonine is used as an antimicrobial agent to combat various microbial infections. Its broad-spectrum activity against bacteria, fungi, and viruses highlights its potential in developing new antimicrobial drugs to address the growing issue of antibiotic resistance.
Used in Nervous System Research:
Hasubanonine is used as a research tool to study its effects on the nervous system, particularly its modulation of dopamine receptors. This research could lead to the development of new medications for neurological and psychiatric disorders, such as Parkinson's disease and schizophrenia, where dopamine dysregulation plays a significant role.

InChI:InChI=1/C21H27NO5/c1-22-11-10-20-12-14(23)17(25-3)19(27-5)21(20,22)9-8-13-6-7-15(24-2)18(26-4)16(13)20/h6-7H,8-12H2,1-5H3/t20-,21+/m0/s1

Upstream product

• 186581-53-3 diazomethane 
• 1337926-86-9 C₂₉H₃₆BrNO₅Si 
• 1337926-96-1 C₂₁H₂₂BrNO₅ 
• 1337926-87-0 C₂₁H₂₄BrNO₅ 
• 1337926-97-2 C₂₁H₂₄BrNO₅ 
• 1337926-98-3 C₂₁H₂₅NO₅ 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 90772-55-7 1-bromo-2-ethynyl-4,5-dimethoxybenzene 

Downstream Products

• 54784-24-6 Acetic acid 1,2,5,6-tetramethoxy-phenanthren-3-yl ester 
• 54784-25-7 1,2,3,5,6-pentamethoxyphenanthrene 

Relevant academic research and scientific papers

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.

Efficient entry to the hasubanan alkaloids: First enantioselective total syntheses of (-)-hasubanonine, (-)-runanine, (-)-delavayine, and (+)-periglaucine B

Maximized divergence: The hasubanan alkaloids given in the scheme have been synthesized in eight or nine steps from the aryl azide 1. The utility of 5-trimethylsilylcyclopentadiene as an easily removed, stabilizing stereocontrol element has been demonstrated.