- 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
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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
- Hu, De-Xuan,Tang, Wen-Lin,Zhang, Yu,Yang, Hao,Wang, Wenjie,Agama, Keli,Pommier, Yves,An, Lin-Kun
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p. 7617 - 7629
(2021/06/25)
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- Preparation of amino-substituted indenes and 1,4-dihydronaphthalenes using a one-pot multireaction approach: Total synthesis of oxybenzo[c]phenanthridine alkaloids
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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.
- Calder, Ewen D. D.,McGonagle, Fiona I.,Harkiss, Alexander H.,McGonagle, Grant A.,Sutherland, Andrew
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p. 7633 - 7648
(2014/09/17)
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- Antibacterial activity of substituted 5-methylbenzo[c]phenanthridinium derivatives
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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.
- Parhi, Ajit,Kelley, Cody,Kaul, Malvika,Pilch, Daniel S.,Lavoie, Edmond J.
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p. 7080 - 7083
(2013/01/15)
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- Microwave-assisted domino hydroformylation/cyclization reactions: Scope and limitations
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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
- Airiau, Etienne,Chemin, Claire,Girard, Nicolas,Lonzi, Giacomo,Mann, Andre,Petricci, Elena,Salvadori, Jessica,Taddei, Maurizio
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experimental part
p. 2901 - 2914
(2010/10/21)
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- Synthesis of isoindolobenzazepine alkaloids based on radical reactions or Pd(0)-catalyzed reactions
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(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
- Onozaki, Yu,Kurono, Nobuhito,Senboku, Hisanori,Tokuda, Masao,Orito, Kazuhiko
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experimental part
p. 5486 - 5495
(2009/12/06)
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- Structure-activity relationship studies of phenanthridine-based Bcl-X L inhibitors
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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
- 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.
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experimental part
p. 6699 - 6710
(2009/10/23)
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- A short synthesis of lennoxamine via ynamides
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Lennoxamine was synthesized in eight steps from 2,3-dimethoxybenzoic acid via an intermediate ynamide by using palladium-catalyzed Heck-Suzuki-Miyaura domino reactions.
- Couty, Sylvain,Meyer, Christophe,Cossy, Janine
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p. 767 - 769
(2007/10/03)
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- Synthesis of 3-(arylmethylene)isoindolin-1-ones from ynamides by Heck-Suzuki-Miyaura domino reactions. Application to the synthesis of lennoxamine
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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.
- Couty, Sylvain,Liegault, Beno?t,Meyer, Christophe,Cossy, Janine
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p. 3882 - 3895
(2007/10/03)
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- Total synthesis of benzo[c]phenanthridine alkaloids, chelerythrine and 12-methoxydihydrochelerythrine, by a palladium-assisted internal biaryl coupling reaction
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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.
- Harayama,Akiyama,Akamatsu,Kawano,Abe,Takeuchi
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p. 444 - 450
(2007/10/03)
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- Total synthesis of (±)-lennoxamine and (±)-aphanorphine by intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins
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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
- Fuchs, James R.,Funk, Raymond L.
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p. 3923 - 3925
(2007/10/03)
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- Synthesis of an indole analog of magallanesine via the [1,2]-Meisenheimer rearrangement
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Ring expansion of azetopyridoindole 11 via the [1,2]-Meisenheimer rearrangement of the corresponding N-oxide 12 gave azocinoindole 14, which was converted into the N-benzoylenaminone 18 in 5 steps. Intramolecular cyclization of 18 was accomplished by a mo
- Yoneda, Ryuji,Kimura, Tetsuya,Kinomoto, Junko,Harusawa, Shinya,Kurihara, Takushi
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p. 1909 - 1913
(2007/10/03)
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- An efficient synthesis of magallanesine using [1,2]-Meisenheimer rearrangement and Heck cyclization
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A straightforward total synthesis of magallanesine 1 was accomplished from readily available isoquinolineacetate 14. This synthesis is emphasized by the following two points; i. the [1,2]-Meisenheimer rearrangement of the azetidine N-oxide 22 for the prep
- Yoneda, Ryuji,Sakamoto, Yasuhiko,Oketo, Yoshifumi,Harusawa, Shinya,Kurihara, Takushi
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p. 14563 - 14576
(2007/10/03)
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- Sulfur-directed 5-exo selective aryl radical cyclization onto enamide: A simple route to chilenine
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Bu3SnH-mediated aryl radical cyclization of the N-(o-bromoaroyl)enamine 5 took place in a 5-exo-trig manner exclusively to give isoindolone 7, which was transformed into the key intermediate 11 for the synthesis of isoindolobenzazepine alkaloid chilenine (2).
- Ishibashi, Hiroyuki
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p. 6733 - 6734
(2007/10/02)
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- Synthesis of (+/-)-8-Oxotetrahydropalmatine and (+/-)-Gusanlung B
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The 8-oxotetrahydroprotoberberine alkaloids (+/-)-8-oxotetrahydropalmatine and (+/-)-gusanlung B have been synthesized by radical-initiated 1,6-cyclization of the corresponding 2-arylcarbonyl-1-methylenetetrahydroisoquinolines.
- Nimgirawath, Surachai,Ponghusabun, Ong-ard
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p. 951 - 956
(2007/10/02)
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- A Total Synthesis of Magallanesine via -Meisenheimer Rearrangement
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A straightforward synthesis of magallanesine 1 from azetoisoquinoline 4 has been accomplished via -Meisenheimer rearrangement and an intramolecular Heck cyclization as the key reactions.
- Yoneda, Ryuji,Sakamoto, Yasuhiko,Oketo, Yoshifumi,Minami, Kayoko,Harusawa, Shinya,Kurihara, Takushi
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p. 3749 - 3752
(2007/10/02)
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