Reductive transformations of 10-deoxydaunomycinone

Brand, David J.; Fisher, Jed F.

doi:10.1021/jo00295a052

Cited by 12 publications

(13 citation statements)

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“…Epidaunorubicin hydrochloride (EPIDAUN.HCl) was purchased from Sindan (Bucharest, Romania). DAUNol and IDAol were synthesized by a stereoselective enzymatic reduction of DAUN and IDA, respectively, according to a paper of Brand and Fisher [30] with minor modifications. HPLC-grade dichloromethane (stabilized with ethanol), pentane, diethylether and ethyl acetate were obtained from Biosolve (Valkenswaard, The Netherlands).…”

Section: Chemicals and Reagentsmentioning

confidence: 99%

Development and validation of a liquid chromatographic method for the simultaneous determination of four anthracyclines and their respective 13-S-dihydro metabolites in plasma and saliva

Maudens

Stove

Cocquyt

et al. 2009

Journal of Chromatography B

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Section: Chemicals and Reagentsmentioning

confidence: 99%

Development and validation of a liquid chromatographic method for the simultaneous determination of four anthracyclines and their respective 13-S-dihydro metabolites in plasma and saliva

Maudens

Stove

Cocquyt

et al. 2009

Journal of Chromatography B

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“…A citotoxicidade das quinonas leva à especulação de que existe uma propriedade química intrínseca na unidade quinonoídica, associada com outros fatores estruturais, que são responsáveis pela intensidade das atividades antitumorais 20 . Uma possibilidade plausível é a capacidade das quinonas se reduzirem pelas flavoenzimas celulares 21 .…”

Section: Introductionunclassified

Um panorama atual da química e da farmacologia de naftoquinonas, com ênfase na beta-lapachona e derivados

2003

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Recebido em 15/5/02; aceito em 18/11/02 AN OVERVIEW OF THE CHEMISTRY AND PHARMACOLOGY OF NAPHTHOQUINONES WITH EMPHASIS ON β-LAPACHONE AND DERIVATIVES. Naphthoquinones have been extensively studied due to their activity as topoisomerase inhibitors. These enzymes are critical to DNA replication in cells. In addition, naphthoquinones have been shown to induce what are known as "reactive oxygen species" that can cause damage to cells. β-Lapachone is a very important pyranaphthoquinone obtained from the heartwood of the lapacho tree, Tabebuia avellanedae Lorentz ex. Griseb. (Bignoniaceae), and other Tabebuia trees native to Central and South America and chemically from lapachol. β-Lapachone has a diversity of useful biological activities against various cancer cell lines such as human ovarian and prostate tumors and, at lower doses is a radiosensitizer of several human cancer cell lines. It gives rise to a variety of effects in vitro including the inhibition or activation of topoisomerase I an II in a distinct manner from that of other topoisomerase inhibitors. This review intend to discuss some details of the mechanisms of quinone-induced cell damage and death, and we also summarize results of the literature indicating that b-Lapachone may take part in quinone-elicited apoptosis despite the fact that its mechanism of action in vivo and its targets are still unknown.Keywords: beta-Lapachone; naphthoquinone; pyranaphthoquinone; apoptosis. INTRODUÇÃOAs quinonas representam uma ampla e variada família de metabólitos de distribuição natural 1,2 . Nos últimos anos intensificouse o interesse nestas substâncias, não só devido à sua importância nos processos bioquímicos vitais, como também ao destaque cada vez maior que apresentam em variados estudos farmacológicos. Na natureza, estão envolvidas em etapas importantes do ciclo de vida de seres vivos, principalmente nos níveis da cadeia respiratória e da fotossíntese, como por exemplo as ubiquinonas (1a) e as plastoquinonas (1b) 3 . As naftoquinonas, por exemplo as vitaminas do tipo K (2), de irrestrita necessidade aos seres vivos 4 , possuem ação controladora da coagulação sanguínea.De um modo geral, as quinonas naturais mais representativas são de vital importância para vegetais superiores, artrópodes, fungos, liquens, bactérias, algas e vírus. A distribuição dessas substân-cias nos variados organismos implica, possivelmente, em funções biológicas múltiplas, agindo de forma conspícua em seus diversos ciclos bioquímicos.Em estudos farmacológicos as quinonas mostram variadas biodinamicidades, destacando-se, dentre muitas, as propriedades microbicidas, tripanossomicidas, viruscidas, antitumorais e inibidoras de sistemas celulares reparadores, processos nos quais atuam de diferentes formas. Como exemplo, destaca-se o estresse oxidativo que provocam, ao induzirem a formação deletéria endógena de espécies bioativas derivadas do oxigênio ( 1 O 2 , . OH, O 2 .-e H 2 O 2 ) 5 , como ocorre no Trypanosoma cruzi, agente causador da doença de Chagas. Outra atividade marcante destas subst...

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“…8 While the present investigation was in progress, the same 5,7-deoxy chromophore was obtained as its 13-ol (7), by reduction of (5) with sodium borohydride, together with its 7,12-bisdeoxy analogue (8). 9 However, at the outset of this work there was no reported way in which such chromophoric modification of the parent anthracyclines (1) and (2) could be effected without prior reductive cleavage of the 7-glycoside, an ortho-hydroxybenzyl system. Thus mild catalytic hydrogenation of daunorubicin (1) mainly led to the 7-deoxy product (5).…”

Section: Introductionmentioning

confidence: 84%

5-Deoxy, 12-Deoxy, 5,12-Bisdeoxy, and 4,5,12-Trisdeoxy Anthracyclines: Synthesis of New Analogues of Daunorubicin and Doxorubicin by Controlled Deoxygenation of the C-Ring.

Cameron¹,

Feutrill²,

Griffiths³

2000

Aust. J. Chem.

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Hydrogenation of the anthracyclines daunorubicin (1) and doxorubicin (2) gave selective deoxygenation at position 5. Hydride reduction of (1) and (2) gave complementary regiocontrol, leading to 12-deoxygenation or 5,12- bisdeoxygenation. This chemistry allows retention of the 7-glycoside and the side-chain carbonyl groups. It has led to new anthracycline families possessing all of the stereochemical and most of the spatial characteristics of the parent compounds (1) and (2). These are typified by 5-deoxy (12), (15); 12-deoxy (22), (23); 5,12-bisdeoxy (34), (35); and 4,5,12-trisdeoxy systems (36). All possess high anticancer activity.

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Reductive transformations of 10-deoxydaunomycinone

Cited by 12 publications

References 0 publications

Development and validation of a liquid chromatographic method for the simultaneous determination of four anthracyclines and their respective 13-S-dihydro metabolites in plasma and saliva

Development and validation of a liquid chromatographic method for the simultaneous determination of four anthracyclines and their respective 13-S-dihydro metabolites in plasma and saliva

Um panorama atual da química e da farmacologia de naftoquinonas, com ênfase na beta-lapachona e derivados

5-Deoxy, 12-Deoxy, 5,12-Bisdeoxy, and 4,5,12-Trisdeoxy Anthracyclines: Synthesis of New Analogues of Daunorubicin and Doxorubicin by Controlled Deoxygenation of the C-Ring.

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