Glucopyranosides derived from 2-hydroxy-1,4-naphthoquinones

Cote, Philip N.; Goodman, Leon

doi:10.1016/s0008-6215(00)85047-8

Cited by 10 publications

(7 citation statements)

References 8 publications

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“…NSC708044 (2-butenoic acid, 4,4-dicyano-4-[(phenylmethylene)amino]-,methyl ester, (Z,E)-(9CI)) has an effect on chemoresistance, mediated by glutathione transport system . NSC654206 (Naphthsaritone) and its related compounds was used in the treatment and control of insulin resistance and hyperglycemia (Cote and Goodman, 1973). NSC138333 (Cyclohexanone, 2,6-bis (4-(1,3-dihydro-2H-pyrrolo[3,4-b] quinolin-2-ylcarbonyl)-2oxotetrahydro-3-furanyl)methyl acetate), one of pyrroloquinoline derivative, is a potent inhibitor for PI3-kinase related kinases (Peng et al, 2002).…”

Section: Network Analysis Of the Relationship Between Compound Responmentioning

confidence: 99%

Gene Expression Signatures for Compound Response in Cancers

He¹,

Yoon²

2011

Genomics & Informatics

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Section: Network Analysis Of the Relationship Between Compound Responmentioning

confidence: 99%

Gene Expression Signatures for Compound Response in Cancers

He¹,

Yoon²

2011

Genomics & Informatics

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“…It was reported previously that deacetylation of acetylated naphthoquinone O-glucosides with sodium methoxide in methanol is accompanied by nucleophilic replacement of the glycoside residue by methoxide ion with rupture of the O-glycoside bond [19,20]. As shown later in [9,21], the hydroxy group neighboring to the glycoside moiety is deprotonated in basic medium, thus hampering replacement of the latter, and 2,3-dihydroxynaphthazarin and 2,3-dihydroxy-1,4-naphthoquinone O-monoglycosides are stable under these conditions.…”

Section: Iii-xv Xvia Xvib Xviiia Xviiib XIX Xxmentioning

confidence: 99%

Synthesis and properties of water-soluble 5,8-dihydroxy-1,4-naphthoquinone thioglucosides structurally related to echinochrome

Полоник

2009

Russ J Org Chem

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Acetylated hydroxynaphthazarin di-and trithioglucosides structurally related to echinochrome were synthesized. Their deacetylation by the action of sodium methoxide in methanol and the effect of hydroxy groups on this process were studied. Water-soluble echinochrome thioglucosides were synthesized for the first time.Naphthoquinones are widespread in nature, and they exhibit diverse physiological activity [1, 2]. Among these compounds, polyhydroxynaphthoquinones of the naphthazarin (5,8-dihydroxy-1,4-naphthoquinone) series occupy a particular place. Due to specificity of their structure, they are capable of effectively trapping free radicals and binding Fe 2+ ions responsible for the formation of active oxygen species [3,4]; excess concentration of the latter in an organism promotes development of various pathological states [5].Echinochrome (I, 6-ethyl-2,3,5,7,8-pentahydroxy-1,4-naphthoquinone) is a pigment isolated from the sea urchin shell (Echinodea); it was used as active substance of the drug Gistokhrom for the treatment of eye injuries and burns, as well as of myocardial infarction [6]. The results of recent experiments in animals showed that Gistokhrom is also effective in the treatment of hemorrhagic stroke [7,8]. Unfortunately, echinochrome is poorly soluble in water. In order to improve the solubility and bioavailability, echinochrome was converted into the corresponding tris-Oglucoside [9]. However, the latter turned out to be unstable: it decomposed shortly after isolation.S-Glycosides are known to be more stable toward acids and bases than their O-glycoside analogs [10]. It was shown previously that chlorine atoms in the naphthazarin core are readily replaced by acetylglucoside residues under conditions of base catalysis [11]. It was also found that nucleophilic addition of chlorine atoms is accompanied by Michael 1,4-addition of thiols to the quinoid ring [12].The present article describes the synthesis of acetylated naphthazarin S-glucosides that are structurally related to echinochrome and deacetylation of the acetylglucosides by the action of sodium methoxide, which afforded stable water-soluble thioglucosides of the echinochrome series; the effect of hydroxy groups in the naphthazarin core on the deacetylation process was also studied.

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“…As early as in 1973 Cote and Goodman first reported the synthesis and isolation of four 1,4-naphthoquinone Oglycosides [1]. No biological activity for these compounds was published.…”

Section: Introductionmentioning

confidence: 99%

“…Juglone derivatives possessing acetylated sugar moiety (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) are significantly more active than that possessing sugar moiety with free hydroxyl groups (15, 16).…”

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confidence: 99%

Antileukemic Properties and Structure-Activity Relationships of O- and SGlycosylated Derivatives of Juglone and Related 1,4-Naphthoquinones

Fedorov¹

2011

TOGLYJ

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Glycosylated derivatives of physiologically active natural compound juglone and related 1,4-naphthoquinones are known as antifungal, immunomodulatory, and antitumor substances. However, their antileukemic properties and structure-activity relationships have been studied insufficiently. Antileukemic effects and structure-activity relationships (SAR) of the 50 1,4-naphthoquinone derivatives were examined using HL-60 human promyelocytic leukemia cells and MTS method of the study of cell viability. As was shown, the substances inhibited viability of HL-60 cells at the wide range of concentrations. SAR study revealed the structure peculiarities which lead to increase or decrease of the antileukemic activity of the compounds studied. In conclusion, O-or S-glycosylated derivatives of juglone and related 1,4-naphthoquinones have potential for development of the new antileukemic agents and should be further investigated.

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Glucopyranosides derived from 2-hydroxy-1,4-naphthoquinones

Cited by 10 publications

References 8 publications

Gene Expression Signatures for Compound Response in Cancers

Gene Expression Signatures for Compound Response in Cancers

Synthesis and properties of water-soluble 5,8-dihydroxy-1,4-naphthoquinone thioglucosides structurally related to echinochrome

Antileukemic Properties and Structure-Activity Relationships of O- and SGlycosylated Derivatives of Juglone and Related 1,4-Naphthoquinones

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