- Synthesis and biological evaluation of caulibugulones A-E
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The marine bryozoan metabolites caulibugulone A-E were prepared from a readily available isoquinoline dione. These natural products were found to be potent and selective inhibitors of the dual specificity phosphatase Cdc25B.
- Wipf, Peter,Joo, Beomjun,Nguyen, Theresa,Lazo, John S.
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- Total synthesis of the marine alkaloids Caulibugulones A and D
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Total synthesis of the marine cytotoxic alkaloids Caulibugulones A and D is accomplished in three steps with an overall yield of 60-62% from easily accessible starting materials. The key features include isoquinoline-5,8-diol core construction by ammonia mediated iminoannulation of 2-ethynyl-3,6-dihydroxybenzaldehyde, and subsequent in situ oxidation followed by oxidative amination.
- Prakash,Nagarajan, Rajagopal
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Read Online
- Ezrin inhibitors and methods of making and using
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The invention encompasses compound and pharmaceutical composition comprising the compound of the following Formula (I): or pharmaceutically acceptable salts or prodrugs thereof, that are useful for inhibiting ezrin protein in a cell or for inhibiting the growth of a cancer cell.
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Page/Page column 50
(2017/01/05)
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- Design, synthesis and biological evaluation of ezrin inhibitors targeting metastatic osteosarcoma
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Respiratory failure due to pulmonary metastasis is the major cause of death for patients with osteosarcoma. However, the molecular basis for metastasis of osteosarcoma is poorly understood. Recently, ezrin, a member of the ERM family of proteins, has been associated with osteosarcoma metastasis to the lungs. The small molecule NSC 668394 was identified to bind to ezrin, inhibit in vitro and in vivo cell migration, invasion, and metastatic colony survival. Reported herein are the design and synthesis of analogues of NSC 668394, and subsequent functional ezrin inhibition studies. The binding affinity was characterized by surface plasmon resonance technique. Cell migration and invasion activity was determined by electrical cell impedance methodology. Optimization of a series of heterocyclic-dione analogues led to the discovery of compounds 21k and 21m as potential novel antimetastatic agents.
- Paige, Mikell,Kosturko, George,Bulut, Güllay,Miessau, Matthew,Rahim, Said,Toretsky, Jeffrey A.,Brown, Milton L.,üren, Aykut
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p. 478 - 487
(2014/01/17)
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- Exploitation of a tuned oxidation with N -haloimides in the synthesis of caulibugulones A-D
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Marine alkaloids caulibugulones A-D were synthesized in six steps starting from the readily available 2,5-dimethoxybenzaldehyde. Pomeranz-Fritsch reaction of N-(2,5-dimethoxybenzyl)-N-(2,2-dimethoxyethyl)-2-nitrobenzenesulfonamide proceeded smoothly to gi
- Naciuk, Fabrício F.,Milan, Julio C.,Andre?o, Almir,Miranda, Paulo C.M.L.
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p. 5026 - 5030
(2013/07/11)
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- μ-oxo-bridged hypervalent iodine(III) compound as an extreme oxidant for aqueous oxidations
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We have found that in aqueous oxidations the -oxo-bridged hypervalent iodine trifluoroacetate reagent 1 {[(PhI(OCOCF]} is generally more reactive than the corresponding monomeric reagent, especially toward phenolic substrates. -Oxo-bridged 1 in aqueous media thus provided dearomatized quinones 3 in excellent yields in most cases compared to conventional phenyliodine(III) diacetate and bis(trifluoroacetate), as a result of the rapid oxidation of both phenols and naphthols 2. Furthermore, the oxidation reactions proceeded even in water using water-soluble -oxo oxidant 1, which has promise for -oxo-bridged reagent 1 to become the favored reagent over hydrophobic phenyliodine(III) diacetate and bis(trifluoroacetate). Georg Thieme Verlag Stuttgart New York.
- Dohi, Toshifumi,Nakae, Tomofumi,Takenaga, Naoko,Uchiyama, Teruyoshi,Fukushima, Kei-Ichiro,Fujioka, Hiromichi,Kita, Yasuyuki
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experimental part
p. 1183 - 1189
(2012/05/19)
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- Synthesis and biological evaluation of new cytotoxic azanaphthoquinone pyrrolo-annelated derivatives
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A series of azanaphthoquinone pyrrolo-annelated derivatives attached to basic side chains have been synthesized. The antiproliferative activities of all compounds were evaluated on at least four different cell lines. The effects on cell cycle and intercalation were investigated.
- Shanab, Karem,Schirmer, Eva,Knafl, Heike,Wulz, Eva,Holzer, Wolfgang,Spreitzer, Helmut,Schmidt, Peter,Aicher, Babette,Mueller, Gilbert,Guenther, Eckhard
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body text
p. 3950 - 3952
(2010/09/03)
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- Antiviral agents. I. Synthesis and antiviral evaluation of trimeric naphthoquinone analogues of conocurvone
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Conocurvone, a novel natural product isolated from the endemic Australian shrub Conosperum sp. (Proteaceae), exhibits anti-HIV activity but is a highly lipophilic compound, which suggests that there may be problems with its aqueous solubility and bioavailability. A general and convenient synthesis of trimeric naphthoquinones using the condensation of 2-hydroxynaphthoquinones and 2,3-dihaloquinones is described. The application of this method to the synthesis of a series of simpler and less lipophilic trimeric naphthoquinone simple analogues of conocurvone is also reported together with their anti-HIV activity. CSIRO 2008.
- Crosby, Ian T.,Rose, Mark L.,Collis, Maree P.,De Bruyn, Paula J.,Keep, Philip L. C.,Robertson, Alan D.
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p. 768 - 784
(2008/12/22)
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- Synthesis and biological evaluation of novel cytotoxic azanaphthoquinone annelated pyrrolo oximes
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Two series of azanaphthoquinone annelated pyrrolo oximes have been synthesized. The antiproliferative activities of 10 compounds were evaluated on at least four different cell lines. One series of pyrrolo derivatives showed high cytotoxic activity. The effects on cell cycle and caspase activity were investigated. Compounds 9a and 9b showed an accumulation of cells in G2/M phase. Substantial and dose-dependent caspase activity was found after treatment of cells with 9a and 9b. This indicates an apoptosis inducing property of these compounds.
- Shanab, Karem,Pongprom, Nipawan,Wulz, Eva,Holzer, Wolfgang,Spreitzer, Helmut,Schmidt, Peter,Aicher, Babette,Mueller, Gilbert,Guenther, Eckhard
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p. 6091 - 6095
(2008/09/16)
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- 7-(Substituted-phenyl)amino-5,8-isoquinolinediones: Synthesis and cytotoxic activities on cancer cell lines
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6-Chloro-7-(substituted-phenyl)amino-5,8-isoquinolinediones (3a-3u) and 7-(substituted-phenyl)amino-5,8-isoquinolinediones (4a-4d) were synthesized by nucleophilic substitution of 6,7-dichloro-5,8-isoquinolinedione (8) and 5,8-isoquinolinedione (9) with appropriate arylamines. The quinones 3a-3u and 4a-4d were evaluated for in vitro cytotoxic activities against five solid tumor cell lines such as A549, SK-OV-3, SK-MEL-2, XF498 and HCT-15. Among them, 3c, 3d, 3f and 3h exhibited potent activities against the cell lines HCT-15 and SK-MEL-2.
- Ryu, Chung-Kyu,Lee, In-Kyung,Jung, Sung-Hee,Kang, Hye-Young,Lee, Chong-Ock
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- Investigation on the photoreactions of nitrate and nitrite ions with selected azaarenes in water
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The photoreactions of selected azaarenes with nitrate and nitrite ions were investigated under irradiation at λ = 313 nm. The excitation of both anions leads to several photochemical reactions forming mainly hydroxyl radicals and nitrogen oxides. The purification capability of natural waters i.e. the oxidation of inorganic and organic substances results from the formation of hydroxyl radicals. Nitrated isomers of azaarenes were found among the main products of the investigated photoreactions. The nitrogen oxides were responsible for the production of nitrated derivatives which possess a high toxic potential. Their formation was explained by the parallel occurance of two mechanism, a molecular and a radical one. The molecular mechanism became more important with increasing ionisation potentials of the azaarenes. The spectrum of oxidized products corresponded to the one got in the photoreactions of azaarenes with hydrogen peroxide. The formation of several oxidation and nitration products of the pyridine ring with its low electron density was explained by the reaction of excited states of azaarenes. The photoreactions with nitrite ions only led to the formation of oxidized and nitrated products. Nitroso products were not formed. The reactivity of nitrogen monoxide is too low for its reaction with the azaarenes.
- Beitz, Toralf,Bechmann, Wolfgang,Mitzner, Rolf
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p. 351 - 361
(2007/10/03)
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- Synthesis of 5,6-,5,8- and 7,8-isoquinolinediones from the corresponding isoquinolinols and di-methoxyisoquinolines
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5,8-Isoquinolinediones (12, 18, 25), 7,8-isoquinolinediones (14, 19) and 5,6-isoquinolinediones (26) were synthesized by oxidative demethylation of the corresponding dimethoxyisoquinolines with cerium(IV) ammonium nitrate or silver-(II) oxide. 8-Dialkylam
- Kitahara,Nakai,Nakahara,Akazawa,Shimizu,Kubo
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p. 2256 - 2263
(2007/10/02)
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- Oxidation of phenols to quinones by bis(trifluoroacetoxy)iodobenzene
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Bis (trifluoroacetoxy) iodobenzene oxidizes phenols into quinones in good yield.
- Barret,Daudon
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p. 4871 - 4872
(2007/10/02)
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- Cycloaddition Routes to Azaanthraquinone Derivatives. 1. Use of Azadienophiles
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The mono- and diazanaphthoquinones underwent facile cycloaddition with cyclic and alicyclic dienes, and in the majority of these cycloadditions the initial 1:1-cycloadducts or their tautomers and intermediate products formed in the oxidation procedure leading to the final azaanthraquinones were isolated.Quinoline-5,8-dione and 1-methoxy-1,3-cyclohexadiene gave the 8-methoxy isomer in an essentially regiospecific cycloaddition; isoquinoline-5,8-dione, however, gave both the 5- and 8-methoxy isomers in a 2.8:1 ratio.These structural assignments were verified by alternative syntheses of the possible isomers using heteroatom-directed lithiation procedures.
- Potts, Kevin T.,Bhattacharjee, Debkumar,Walsh, Eileen B.
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p. 2011 - 2021
(2007/10/02)
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- A SIMPLE EFFICIENT SYNTHESIS OF 5,8-ISOQUINOLINEDIONE
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5,8-Isoquinolinedione was synthesized from 5-hydroxyisoquinoline by nitrosation at C-8, reduction of the nitroso group and oxidation of the resultant 5-hydroxy-8-aminoisoquinoline.
- Anderson, Wayne K.,Connarty, Bernard P.,El-Hajj, Toni
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p. 1557 - 1560
(2007/10/02)
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- Nucleophilic Alkenes. IX Addition of 1,1-Dimethoxyethene to Azanaphthoquinones: Synthesis of Bostrycoidin and 8-O-Methylbostrycoidin
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Reaction of 1,1-dimethoxyethene with azanaphthoquinones leads to pairs of isomeric dimethoxyazaanthraquinones by means of 1:2-addition.A photochemical procedure has been developed for substituting these dimethoxy products by a further methoxy, amino or a hydroxy group peri to carbonyl.In this way the antibiotic bostrycoidin (1) and its 8-O-methyl derivative (2), the only natural 2-azaanthraquinone, have been synthesized for the first time.
- Cameron, Donald W.,Deutscher, Kenneth R.,Feutrill, Geoffrey I.
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p. 1439 - 1450
(2007/10/02)
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