- Synthesis of carbazoloquinone derivatives and their antileukemic activity via modulating cellular reactive oxygen species
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Carbazoloquinone alkaloids are of great interest as privileged structures for anticancer drug molecules. The purpose of this study was to investigate the structure-activity relationships of carbazoloquinone derivatives as anticancer agents. A series of ca
- Suematsu, Natsumi,Ninomiya, Masayuki,Sugiyama, Hodaka,Udagawa, Taro,Tanaka,Koketsu, Mamoru
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supporting information
p. 2243 - 2247
(2019/07/03)
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- Palladium-Catalyzed Regioselective Synthesis of 1-Hydroxycarbazoles Under Aerobic Conditions
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A palladium-catalyzed aerobic C?H amidation of N-Ts-2-amino-3′-hydroxylbiaryls has been developed to afford a diverse range of 1-hydroxycarbazoles with high regioselectivity and efficiency. This protocol benefits from operational simplicity, robustness, a
- Youn, So Won,Kim, Young Ho,Jo, Yoon Hyung
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supporting information
p. 462 - 468
(2019/01/04)
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- Divergent Syntheses of Carbazole Alkaloids
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Starting from common intermediate methyl 1-hydroxy-9 H -carbazole-3-carboxylate, synthetic routes toward murrayaquinone A, olivacine, and N -methylcalothrixin B were developed.
- Ji, Feixiang,Huang, He,Li, Mengyang,Guo, Yanqin,Song, Chuanjun,Chang, Junbiao
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p. 3921 - 3926
(2018/09/29)
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- Exploiting Alkylquinone Tautomerization for the Total Synthesis of Calothrixin A and B
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The pentacyclic alkaloid calothrixin B (1) has been synthesized in 5 steps from murrayaquinone A (9). The key step involved the union of boryl aniline 31 with brominated murrayaquinone A (26). In this transformation, alkylquinone 26 undergoes tautomerization to a quinone methide, which is intercepted by boryl aniline 31 to forge a new C-N bond. An intramolecular Suzuki coupling, followed by dehydrogenative aromatization, completed the synthesis of calothrixin B. Subsequent N-oxidation of calothrixin B delivered calothrixin A. The successful synthesis of these alkaloids and the challenges that led to the development of the final synthesis plan are reported herein.
- Mori-Quiroz, Luis M.,Dekarske, Madeline M.,Prinkki, Austin B.,Clift, Michael D.
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p. 12257 - 12266
(2017/12/08)
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- Concise synthesis and antiproliferative activity evaluation of ellipticine quinone and its analogs
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We developed a concise protocol for the synthesis of ellipticine quinone from the appropriate 3-iodoindole-2-carbaldehydes in four steps. The key step is the construction of carbazole-1,4-quinone through tandem Ring-Closing Metathesis (RCM) and dehydrogen
- Nishiyama, Takashi,Hatae, Noriyuki,Mizutani, Masataka,Yoshimura, Teruki,Kitamura, Tsuyoshi,Miyano, Mana,Fujii, Mami,Satsuki, Nanase,Ishikura, Minoru,Hibino, Satoshi,Choshi, Tominari
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- Short synthesis of carbazole alkaloids: Ekeberginine, murrayaquinone A, and glycozoline
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Three differently substituted, naturally occurring, biologically active carbazole derivatives (viz. ekeberginine, murrayaquinone A, and glycozoline) were synthesized in good yield using short and simple routes. The prenyl group was selectively introduced at the C4 position using a Stille coupling reaction in the synthesis of ekeberginine. Murrayaquinone A was synthesized using Raney nickel–mediated desulfurization of dithiane as a key step. Synthesis of glycozoline was achieved in two steps from 3-methyl carbazole via an intermediate 3-bromo-6-methyl carbazole.
- Momin, Aadil A.,Urmode, Tukaram D.,Bhosale, Shrikar M.,Kusurkar, Radhika S.
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supporting information
p. 1292 - 1298
(2016/08/16)
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- Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells
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We report a convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O2 atmosphere as an important step. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types.
- Nishiyama, Takashi,Hatae, Noriyuki,Yoshimura, Teruki,Takaki, Sawa,Abe, Takumi,Ishikura, Minoru,Hibino, Satoshi,Choshi, Tominari
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p. 561 - 577
(2016/07/06)
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- Synthesis of Carbazolequinones by Formal [3 + 2] Cycloaddition of Arynes and 2-Aminoquinones
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A formal cycloaddition reaction for the synthesis of biologically and pharmaceutically important carbazolequinones via the annulation of aminoquinones with arynes has been developed. This practical and metal-free cascade reaction proceeds through successive C-C/C-N bond formations. Moreover, this novel method has been utilized for the concise synthesis of bioactive murrayaquinone A and koeniginequinone B and their analogues.
- Guo, Jian,Kiran, I. N. Chaithanya,Reddy, R. Santhosh,Gao, Jiangsheng,Tang, Meiqiong,Liu, Yuyin,He, Yun
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supporting information
p. 2499 - 2502
(2016/06/09)
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- Palladium mediated intramolecular multiple C-X/C-H cross coupling and C-H activation: Synthesis of carbazole alkaloids calothrixin B and murrayaquinone A
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Straightforward palladium mediated syntheses of calothrixin B and murrayaquinone A are described. Regioselective palladium mediated intramolecular multiple C-X/C-H cross coupling reaction on N-(4-((2-bromophenyl)amino)-2,5- dimethoxybenzyl)-N-(2-iodophenyl)acetamide followed by CAN oxidation afforded calothrixin B in excellent yield in two steps. A linear synthesis has also been developed for calothrixin B. Utilizing C-H functionalization as well as palladium mediated intramolecular C-X/C-H cross coupling reaction, murrayaquinone A synthesis was achieved. Overall, these synthetic methodologies provide an expedient entry to these biologically active alkaloids in a short reaction sequence. This journal is the Partner Organisations 2014.
- Kaliyaperumal, Srinivasan A.,Banerjee, Shyamapada,Syam Kumar
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p. 6105 - 6113
(2014/08/05)
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- Synthesis of murrayaquinone A and analogues via ring-closing C-H arylation
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A compact synthesis of Murrayaquinone A is reported, based on sequential Buchwald-Hartwig amination/annulative C-H activation followed by oxidation of the intermediate carbazole. The methodology can be readily extended to other analogues with electron-rich quinone rings.
- Bedford, Robin B.,Bowen, John G.,Weeks, Amanda L.
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p. 4389 - 4394
(2013/06/26)
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- An in-water, on-water domino process for synthesis
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An in-water, on-water domino process has been engineered as a green strategy for chemical synthesis. The process is driven by the different aqueous solubility of organic reactants and products, which are shuttled between the two phases of an emulsion. During this process, water serves as a reaction medium, a product partitioner and a reaction catalyst. The Royal Society of Chemistry 2012.
- Norcott, Philip,Spielman, Calan,McErlean, Christopher S. P.
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supporting information; experimental part
p. 605 - 609
(2012/04/23)
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- New and efficient routes for the synthesis of murrayaquinone A and murrayanine
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Three new routes were established for the synthesis of biologically active murrayaquinone A and a new method was developed for synthesis of murrayanine from the same starting material as 4-hydroxy carbazole. During the synthetic course a few novel observation were recorded, which include two one pot reaction sequences and C-N bond cleavage by sodium cyanoborohydride.
- Bhosale, Shrikar M.,Momin, Aadil A.,Kusurkar, Radhika S.
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p. 6420 - 6426
(2012/08/28)
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- New synthesis of carbazole-1,4-quinone using a tandem ring-closing metathesis and dehydrogenation reaction under oxygen atmosphere, and its application to the synthesis of murrayaquinone A
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A tandem ring-closing metathesis and dehydrogenation reaction under oxygen atmosphere was newly developed to the synthesis of carbazole-1,4-quinones. This new tandem reaction was applied to the synthesis of murrayaquinone A in four steps.
- Nishiyama, Takashi,Choshi, Tominari,Kitano, Kohdai,Hibino, Satoshi
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scheme or table
p. 3876 - 3878
(2011/08/06)
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- Structure-activity delineation of quinones related to the biologically active Calothrixin B
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Quinones such as Calothrixins A and B display a range of biological properties. As part of our ongoing studies to elucidate the mechanism of action of the Calothrixins, several related quinones were synthesized and tested for biological activity. The resu
- Bernardo, Paul H.,Chai, Christina L.L.,Guen, Maurice Le,Smith, Geoffrey D.,Waring, Paul
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- Indoloquinones, part 8.1 palladium(II)-catalyzed total synthesis of murrayaquinone A, koeniginequinone A, and koeniginequinone B
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Regioselective addition of the appropriate arylamines to 2-methyl-1,4-benzoquinone followed by a palladium(II)-catalyzed oxidative cyclization opens up an efficient route to the naturally occurring 3-methylcarbazole-1,4-quinone alkaloids murrayaquinone A, koeniginequinone A, and koeniginequinone B.
- Knoelker, Hans-Joachim,Reddy, Kethiri R.
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p. 1049 - 1052
(2007/10/03)
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- Palladium-catalyzed synthesis of 1,2-dihydro-4(3H)-carbazolones. Formal total synthesis of murrayaquinone A
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Two sequential palladium-catalyzed reactions are the key steps in a novel synthetic route to 1,2-dihydro-4(3H)-carbazolones. The steps are an intermolecular Stille cross-coupling followed by a reductive N-heteroannulation. A formal total synthesis of murrayaquinone A, employing this sequence, is reported.
- Scott, Tricia L.,S?derberg, Bj?rn C. G.
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p. 6323 - 6332
(2007/10/03)
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- Photochemical oxidation of 3-methylcarbazole: Synthesis of murrayaquinone-A
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3-Methylcarbazole 1 undergoes photochemical oxidation in methanol to furnish murrayaquinone-A 2, the carbazoloquinone alkaloid isolated from Murraya euchrestifolia. The reaction has been succesfully extended to 3,6- dimethylcarbazole 3 to yield 3,6-dimethylcarbazole-1,4-quinone 5.
- Chowdhury,Jha, Shailendra,Kar, Bibek Ranjan,Saha
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p. 1106 - 1107
(2007/10/03)
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- Oxygen as oxidant in palladium-catalyzed inter- and intramolecular coupling reactions
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Facile palladium-catalyzed cyclizations of arylaminoquinones giving biologically important carbazoloquinones in high yields have been performed with oxygen as the single oxidant. By a slight modification of the catalyst, diphenylamine, diphenyl ether, and related compounds can be cyclized. The system could also be used in intermolecular couplings between naphthoquinones and benzene or naphthalene.
- Hagelin, Helena,Oslob, Johan D.,Akermark, Bjoern
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p. 2413 - 2416
(2007/10/03)
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- Bromoquinone-enaminone annulations: Syntheses of murrayaquinone-A and (±)-bismurrayaquinone-A
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A total synthesis of the carbazolequinone alkaloid, murrayaquinone-A was achieved by an initial annulation of the N-benzyl enamine 8 with 2-methyl-5-bromobenzoquinone 6. Shapiro deoxygenation-olefination followed by heating with DDQ resulted in the exclusive formation of N-benzylmurrayaquinone-A 16. Debenzylation proved very difficult but was finally achieved by heating briefly in trifluoroacetic acid with a catalytic quantity of trifluoromethanesulfonic acid. A single dimeric annulation side product was also formed in the annulation reaction. By using the same synthetic sequence as was employed in the synthesis of 1, the N,N-bis-p-methoxybenzyl dimer 13 was successfully converted to (±)-bismurrayaquinone-A 5.
- Murphy, William S.,Bertrand, Martial
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p. 4115 - 4119
(2007/10/03)
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- New syntheses of murrayafoline-A and murrayaquinone-A via Fischer indolization of 2-sulfonyloxyphenylhydrazone (Fischer indolization and its related compounds. Part 29)
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Two carbazole alkaloids, murrayafoline-A (4a) and murrayaquinone-A (4b), were synthesized from 1, 2, 3, 4-tetrahydro-8-methanesulfonyloxy-6- methylcarbazole (8) prepared in the application of Fischer indolization of 2- sulfonyloxyphenylhydrazone.
- Murakami, Yasuoki,Yokoo, Hiroshi,Watanabe, Toshiko
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p. 127 - 132
(2007/10/03)
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- Bismurrayaquinone A: Synthesis, Chromatographic Enantiomer Resolution, and Stereoanalysis by Computational and Experimental CD Investigations
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The first total synthesis of a naturally occurring dimeric carbazole alkaloid, bismurrayaquinone A (4), is described, by oxidation of dimeric O-demethylmurrayafoline A, a still hypothetic natural product recently synthesized.By chromatography on a chiral phase, the two atropoenantiomers were separated.The absolute configurations of these two rotational isomers were elucidated by comparison of their calculated spectra with those measured experimentally.
- Bringmann, Gerhard,Ledermann, Alfons,Stahl, Martin,Gulden, Klaus-Peter
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p. 9353 - 9360
(2007/10/02)
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- Catalytic oxidative aromatic cyclizations with palladium
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Using tert-butyl hydroperoxide as oxidant, facile palladium-catalyzed cyclizations of arylaminoquinones have been performed.
- Akermark, Bjoern,Oslob, Johan D.,Heuschert, Ulrich
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p. 1325 - 1326
(2007/10/02)
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- A novel synthesis of quinazolinequinone and carbazolequinone through anionic cycloaddition: Its application to a synthesis of murrayaquinone A
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A novel synthesis of the quinazolinequinone (5) and the carbazolequinone (9) is described. Anionic cycloaddition of the heterocyclic esters (1 and 6) with phenyl β-trimethylsilylvinyl sulfone (2c) afforded the cycloadducts (3 and 7), which were converted
- Wada,Hirai,Hanaoka
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p. 416 - 418
(2007/10/02)
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- Synthesis of murrayaquinone-A
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Murrayaquinone-A, one of the carbazolequinone alkaloids isolated from Murraya euchrestifolia Hayata (Rutaceae), was prepared starting from 1,2,3,4- tetrahydrocarbazol-4(9H)-one in good overall yield.
- Matsuo,Ishida
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p. 1325 - 1327
(2007/10/02)
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- Transition metal-diene complexes in organic synthesis - 16.1 Iron-mediated total synthesis of 1-oxygenated carbazole alkaloids
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Using a methodology of consecutive iron-induced C - C and C - N bond formation we describe the total synthesis of murrayafoline A, murrayaquinone A, koenoline, murrayanine, mukoeic acid, and mukonine.
- Knoelker, Hans-Joachim,Bauermeister, Michael
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p. 11221 - 11236
(2007/10/02)
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- A NEW ROUTE TO 1-OXYGENATED CARBAZOLES. SYNTHESIS OF THE CARBAZOLE ALKALOIDS MURRAYAFOLINE-A AND MURRAYAQUINONE-A
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1-Oxygenated carbazoles are prepared in 4 steps from indole-2-carboxylates by condensation with γ-butyrolactones to give the lactones (12), followed by hydrolysis with concomitant decarboxylation to the alcohols (13), and oxidation to the aldehydes (14).The aldehydes (14) cyclise to 1-methoxycarbazoles on treatment with boron trifluoride-methanol or with methanolic hydrogen chloride.The methoxycarbazoles (15a) and (4) were converted into the corresponding carbazolequinones (18) and (7) by demethylation, and oxidation.The carbazole alkaloids murrayafoline-A (4) and murrayaquinone-A (7) were prepared.
- Martin, Tracey,Moody, Christopher J.
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p. 235 - 240
(2007/10/02)
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