64482-27-5Relevant academic research and scientific papers
Synthesis of Methoxy-, Methylenedioxy-, Hydroxy-, and Halo-Substituted Benzophenanthridinone Derivatives as DNA Topoisomerase IB (TOP1) and Tyrosyl-DNA Phosphodiesterase 1 (TDP1) Inhibitors and Their Biological Activity for Drug-Resistant Cancer
Hu, De-Xuan,Tang, Wen-Lin,Zhang, Yu,Yang, Hao,Wang, Wenjie,Agama, Keli,Pommier, Yves,An, Lin-Kun
, p. 7617 - 7629 (2021/06/25)
As a recently discovered DNA repair enzyme, tyrosyl-DNA phosphodiesterase 1 (TDP1) removes topoisomerase IB (TOP1)-mediated DNA protein cross-links. Inhibiting TDP1 can potentiate the cytotoxicity of TOP1 inhibitors and overcome cancer cell resistance to
Preparation of amino-substituted indenes and 1,4-dihydronaphthalenes using a one-pot multireaction approach: Total synthesis of oxybenzo[c]phenanthridine alkaloids
Calder, Ewen D. D.,McGonagle, Fiona I.,Harkiss, Alexander H.,McGonagle, Grant A.,Sutherland, Andrew
, p. 7633 - 7648 (2014/09/17)
Allylic trichloroacetimidates bearing a 2-vinyl or 2-allylaryl group have been designed as substrates for a one-pot, two-step multi-bond-forming process leading to the general preparation of aminoindenes and amino-substituted 1,4-dihydronaphthalenes. The synthetic utility of the privileged structures formed from this one-pot process was demonstrated with the total synthesis of four oxybenzo[c]phenanthridine alkaloids, oxychelerythrine, oxysanguinarine, oxynitidine, and oxyavicine. An intramolecular biaryl Heck coupling reaction, catalyzed using the Hermann-Beller palladacycle was used to effect the key step during the synthesis of the natural products.
Antibacterial activity of substituted 5-methylbenzo[c]phenanthridinium derivatives
Parhi, Ajit,Kelley, Cody,Kaul, Malvika,Pilch, Daniel S.,Lavoie, Edmond J.
, p. 7080 - 7083 (2013/01/15)
Antibiotic resistance has prompted efforts to discover antibiotics with novel mechanisms of action. FtsZ is an essential protein for bacterial cell division, and has been viewed as an attractive target for the development of new antibiotics. Sanguinarine is a benzophenanthridine alkaloid that prevents cytokinesis in bacteria by inhibiting FtsZ self-assembly. In this study, a series of 5-methylbenzo[c]phenanthridinium derivatives were synthesized and evaluated for antibacterial activity against Staphylococcus aureus and Enterococcus faecalis. The data indicate that the presence of a 1- or 12-phenyl substituent on 2,3,8,9-tetramethoxy-5-methylbenzo[c]phenanthridinium chloride significantly enhances antibacterial activity relative to the parent compound or sanguinarine.
Microwave-assisted domino hydroformylation/cyclization reactions: Scope and limitations
Airiau, Etienne,Chemin, Claire,Girard, Nicolas,Lonzi, Giacomo,Mann, Andre,Petricci, Elena,Salvadori, Jessica,Taddei, Maurizio
experimental part, p. 2901 - 2914 (2010/10/21)
Hydroformylation of alkenes can be carried out in short time and with low syngas pressure under microwave (MW) dielectric heating. Alkenes, carrying O-, N-, or C-nucleophilic fragments, can be designed for domino reactions, mainly cyclocondensations. Ally
Synthesis of isoindolobenzazepine alkaloids based on radical reactions or Pd(0)-catalyzed reactions
Onozaki, Yu,Kurono, Nobuhito,Senboku, Hisanori,Tokuda, Masao,Orito, Kazuhiko
experimental part, p. 5486 - 5495 (2009/12/06)
(Chemical Equation Presented) Methods for synthesis of a ring system characteristic of isoindolobenzazepine alkaloids were studied. Synthesis of lennoxamine and a formal synthesis of chelenine were accomplished in a short route via radical or Pd(0)-cataly
Structure-activity relationship studies of phenanthridine-based Bcl-X L inhibitors
Bernardo, Paul H.,Wan, Kah-Fei,Sivaraman, Thirunavukkarasu,Xu, Jin,Moore, Felicity K.,Hung, Alvin W.,Mok, Henry Y. K.,Yu, Victor C.,Chai, Christina L. L.
experimental part, p. 6699 - 6710 (2009/10/23)
Despite their structural similarities, the natural products chelerythrine (5) and sanguinarine (6) target different binding sites on the pro-survival Bcl-XL protein. This paper details the synthesis of phenanthridine-based analogues of the natu
Synthesis of 3-(arylmethylene)isoindolin-1-ones from ynamides by Heck-Suzuki-Miyaura domino reactions. Application to the synthesis of lennoxamine
Couty, Sylvain,Liegault, Beno?t,Meyer, Christophe,Cossy, Janine
, p. 3882 - 3895 (2007/10/03)
Substituted 3-(arylmethylene)isoindolin-1-ones can be efficiently synthesized from various ynamides and boronic acids by palladium-catalyzed Heck-Suzuki-Miyaura domino reactions. This methodology has been applied to the total synthesis of lennoxamine and a concise route to this isoindolobenzazepine alkaloid was achieved in eight steps from 2,3-dimethoxybenzoic acid via a key intermediate ynamide.
A short synthesis of lennoxamine via ynamides
Couty, Sylvain,Meyer, Christophe,Cossy, Janine
, p. 767 - 769 (2007/10/03)
Lennoxamine was synthesized in eight steps from 2,3-dimethoxybenzoic acid via an intermediate ynamide by using palladium-catalyzed Heck-Suzuki-Miyaura domino reactions.
Total synthesis of benzo[c]phenanthridine alkaloids, chelerythrine and 12-methoxydihydrochelerythrine, by a palladium-assisted internal biaryl coupling reaction
Harayama,Akiyama,Akamatsu,Kawano,Abe,Takeuchi
, p. 444 - 450 (2007/10/03)
A covenient and versatile synthesis of benzo[c]phenanthridine alkaloids, chelerythrine (1) and 12-methoxydihydrochelerythrine (5), was accomplished via an internal aryl-aryl coupling reaction of haloamides 8 and 9 by a palladium-assisted cyclization reaction.
Total synthesis of (±)-lennoxamine and (±)-aphanorphine by intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins
Fuchs, James R.,Funk, Raymond L.
, p. 3923 - 3925 (2007/10/03)
equation presented Intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins constitute the key steps in the total syntheses of lennoxamine and aphanorphine. The aldehyde moiety of one cyclization product was transformed to a double
