ChemInform Abstract: Pharmacological Activities of Benzophenanthridine and Phenanthrene Alkaloids

Siméon, S.; Rı́os, José-Luis; Villar, Amaya del

doi:10.1002/chin.199012356

Cited by 27 publications

(43 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…A large number of naturally occurring alkaloids that contain a benzo[c]phenanthridine ring system and have a known spectrum of activity are mentioned in the literature. [1,2] Aside from fagaronine (1), the most important representative of this group of natural products, other alkaloids with extensive pharmacological potential are nitidine (2), chelerythrine (3), and sanguinarine (4; Scheme 1). [3][4][5] The synthesis of these natural products is of great interest, because they can be isolated from plant materials only in very small amounts.…”

mentioning

confidence: 99%

A Two‐Step Synthesis of Cytostatically Active Benzo[c]phenanthridine Derivatives

et al. 2005

View full text Add to dashboard Cite

mentioning

confidence: 99%

A Two‐Step Synthesis of Cytostatically Active Benzo[c]phenanthridine Derivatives

et al. 2005

View full text Add to dashboard Cite

“…for fagaronine (for a review, see Simeon et al 1989). The present authors' have previously developed a very short synthetic route to benzo[c]phenanthridine derivatives with an exocyclic primary amine group in the ortho-position to the endocyclic nitrogen Kock et al 2005).…”

Section: Introductionmentioning

confidence: 98%

Metabolism of cytostatically active 6-aminobenzo[c]phenanthridines by human and porcine hepatic microsomes and recombinant cytochrome P450 enzymes

2006

View full text Add to dashboard Cite

A new and convenient two-step synthesis of 11-substituted 6-amino-11,12-dihydrobenzo[c]phenanthridines and 6-aminobenzo[c]phenanthridines (BPs and BP-Ds) was developed recently in the authors' laboratory. These compounds revealed a high antitumoral activity in in vitro and in vivo test systems. In particular, 11-phenyl-substituted derivatives with two or three methoxy groups showed good activity. It was not clear if the dihydro-derivatives (BPs) were transformed enzymatically into the phenanthridines (BP-Ds), thus acting as prodrugs. The in vitro metabolism of several of these cytostatically active 6-aminobenzo[c]phenanthridines was investigated using human and porcine liver microsomes and a range of expressed human cytochrome P450 enzymes. High-performance liquid chromatography and liquid chromatography-mass spectrometry analysis were used for the quantification and structural identification of the observed metabolites. Aromatic hydroxylation was observed to be the major metabolic pathway in addition to a number of other metabolites. The formation of N-hydroxy- and 6-oxo-derivatives was detected only in very small amounts. BP derivatives are not prodrugs of BP-Ds and no significant differences between human and porcine microsomes were observed, confirming the pig as a good model for metabolism studies of these compounds.

show abstract

“…[1] Chemical properties, metabolic stability,l ipophilicity and solubility can be changed by incorporation of aC F 3 group,o ften found in av ariety of pharmaceutical compounds. [5] They also have potential pharmaceutical applications [6] ands ignificanto ptoelectronic properties in materials cience. [5] They also have potential pharmaceutical applications [6] ands ignificanto ptoelectronic properties in materials cience.…”

mentioning

confidence: 99%

Visible‐Light‐Induced Trifluoromethylation of Isonitrile‐Substituted Methylenecyclopropanes: Facile Access to 6‐(Trifluoromethyl)‐7,8‐Dihydrobenzo[k]phenanthridine Derivatives

Yuan

Liu

et al. 2016

Chemistry A European J

View full text Add to dashboard Cite

A new visible-light-induced trifluoromethylation of isonitrile-substituted methylenecyclopropanes is developed. A range of substituted 6-(trifluoromethyl)-7,8-dihydrobenzo[k]phenanthridine derivatives are readily furnished by this newly developed tandem reaction with moderate to good yields. This reaction allows the direct formation of two six-membered rings and three new C-C bonds, including the C-CF3 bond, under visible light irradiation.

show abstract

ChemInform Abstract: Pharmacological Activities of Benzophenanthridine and Phenanthrene Alkaloids

Cited by 27 publications

References 0 publications

A Two‐Step Synthesis of Cytostatically Active Benzo[c]phenanthridine Derivatives

A Two‐Step Synthesis of Cytostatically Active Benzo[c]phenanthridine Derivatives

Metabolism of cytostatically active 6-aminobenzo[c]phenanthridines by human and porcine hepatic microsomes and recombinant cytochrome P450 enzymes

Visible‐Light‐Induced Trifluoromethylation of Isonitrile‐Substituted Methylenecyclopropanes: Facile Access to 6‐(Trifluoromethyl)‐7,8‐Dihydrobenzo[k]phenanthridine Derivatives

Contact Info

Product

Resources

About