Dioncophylline A as a Growth-Retarding Agent against the Herbivorous Insect Spodoptera littoralis:  Structure−Activity Relationships

Abstract

Dioncophylline A (1) represents a novel insecticidal agent, as documented by its enhanced growth-retarding effect on larvae of the polyphagous pest insect Spodoptera littoralis. Within the scope of the work described here, the potential of this as yet most active naphthylisoquinoline alkaloid was further elucidated by the preparation and testing of selected analogues. Investigation of a broad series of structurally modified dioncophylline A analogues (2-20) revealed the free amine function to be essential for the growth inhibitory effect, whereas a modification of the OH function partially led to a distinct increase of activity. In particular, the 8-O-alkyl (especially 8-O-benzylated) derivatives (14 and 15 as well as 16-19) displayed pronounced effects. In the case of 8-O-(p-bromobenzyl)dioncophylline A (16), the activity of the natural parent compound dioncophylline A (1) (EC50 = 277 micrograms/g fresh wt of diet; concentration that inhibits larval growth by 50%) was even improved by a factor of > 15 (EC50 = 15.6 micrograms/g fresh wt).

Rhodium(III)-Catalyzed [4+2] Annulation via C-H Activation: Synthesis of Multi-Substituted Naphthalenone Sulfoxonium Ylides

“…Substituted naphthols have been characterized as crucial organic motifs and are embedded in various pharmaceuticals and natural products such as rifampicin [1,2,3], gossypol [4,5,6], dioncophylline A [7,8,9], propranolol [10,11,12,13], and naftopidil [14,15,16] (Figure 1). As a result, the development of efficient methods to synthesize multi-substituted naphthols is important [17,18,19,20].…”

Molluscicidal Activity (Biomphalaria glabrata) of Dioncophylline A: Structure-Activity Investigations#

“…2 bis), WUrzburg, Germany. Derivatives 2b-2e were synthesized using established highly selective reaction sequences, which have been published elsewhere (6). Molluscicidal activities against Biomphalana glabrata were determined as published earlier (7).…”

Biological evaluation of molecules of the azaBINOL class as antiviral agents: Inhibition of HIV-1 RNase H activity by 7-isopropoxy-8-(naphth-1-yl)quinoline

“…13,14 For example, the axially chiral dimeric naphthylisoquinolone alkaloids first isolated from Anicistrocladus korupensis in 1991 and later named the michellamines, exhibit selective anti-HIV activity. [15][16][17][18][19] Given these facts taken together with the existence of other antiviral biaryl natural products (e.g., dioncophylline 20 ) and recently identified synthetic antiviral drug leads with multiple aromatic ring systems (e.g., arbidol, 21 peptide triazoles, 22 rhodanine derivatives, 23 naphthylhydrazones, 24 and hydroxypyridones 25 ), we elected to test a library of heterocyclic biaryl compounds available to us and belonging to the so-called 'azaBINOL' chiral ligand family for inhibition of HIV-1 infection.…”