DMSO-mediated transformation of 3-amino-2-hydroxynaphthazarins to natural 2,3-dihydroxynaphthazarins and related compounds

Polonik, N. S.; Полоник, С. Г.

doi:10.1016/j.tetlet.2016.06.056

Cited by 6 publications

(2 citation statements)

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“…Naphthazarin (Fluka) (1) was recrystallized from ethanol, while 2-hydroxynaphthazarin (naphthopurpurin) (2), 2-hydroxy-3-methylnaphthazarin (3) and 2-hydroxy-3-ethylnaphthazarin (4) were prepared according with Anufriev's paper [54]; 2,3-Dihydroxynaphthazarin (5), 2,3-dihydroxy-6-methynaphthazarin (6), 6-ethyl-2,3-dihydroxynaphthazarin (7) and spinochrome D (8) were obtained according the the method described in our previous papers [55,56]; 2,3,6-Trihydroxy-7-ethylnaphthazarin (echinochrome A) (9) was isolated from sea urchins Scaphechinus mirabilis; 3,4,6-Tri-O-acetyl-α-d-glucopyranose 1,2-(tert-butoxy orthoacetate) 11 was prepared according to a method described in [57]; 2-Hydroxy-6,7-dimethylnaphthazarin (22) and 6,7-dichloro-2-hydroxynaphthazarin (23) were prepared according to a method described in [14]; 2-Hydroxy-7-methoxynaphthazarin (24) and 2-hydroxy-6,7-dimethoxynaphthazarin (25) were prepared as described in our previous work [58]. Tetra-O-acetyl-1-thio-β-d-glucopyranose (27), tetra-O-acetyl-1-thio-β-d-galactopyranose (53), tetra-O-acetyl-1-thio-β-d-mannopyranose (54), tri-O-acetyl-1-thio-β-d-xylopyranose (55) were prepared as described in [59].…”

Section: General Chemistry (Reagents Solvents and Equipment)mentioning

confidence: 99%

Synthesis, Cytotoxic Activity Evaluation and Quantitative Structure-ActivityAnalysis of Substituted 5,8-Dihydroxy-1,4-naphthoquinones and Their O- and S-Glycoside Derivatives Tested against Neuro-2a Cancer Cells

et al. 2020

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Based on 6,7-substituted 2,5,8-trihydroxy-1,4-naphtoquinones (1,4-NQs) derived from sea urchins, five new acetyl-O-glucosides of NQs were prepared. A new method of conjugation of per-O-acetylated 1-mercaptosaccharides with 2-hydroxy-1,4-NQs through a methylene spacer was developed. Methylation of 2-hydroxy group of quinone core of acetylthiomethylglycosides by diazomethane and deacetylation of sugar moiety led to 28 new thiomethylglycosidesof 2-hydroxy- and 2-methoxy-1,4-NQs. The cytotoxic activity of starting 1,4-NQs (13 compounds) and their O- and S-glycoside derivatives (37 compounds) was determined by the MTT method against Neuro-2a mouse neuroblastoma cells. Cytotoxic compounds with EC50 = 2.7–87.0 μM and nontoxic compounds with EC50 > 100 μM were found. Acetylated O- and S-glycosides 1,4-NQs were the most potent, with EC50 = 2.7–16.4 μM. Methylation of the 2-OH group innaphthoquinone core led to a sharp increase in the cytotoxic activity of acetylated thioglycosidesof NQs, which was partially retained for their deacetylated derivatives. Thiomethylglycosides of 2-hydroxy-1,4-NQs with OH and MeO groups in quinone core at positions 6 and 7, resprectively formed a nontoxic set of compounds with EC50 > 100 μM. A quantitative structure-activity relationship (QSAR) model of cytotoxic activity of 22 1,4-NQ derivatives was constructed and tested. Descriptors related to the cytotoxic activity of new 1,4-NQ derivatives were determined. The QSAR model is good at predicting the activity of 1,4-NQ derivatives which are unused for QSAR models and nontoxic derivatives.

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Section: General Chemistry (Reagents Solvents and Equipment)mentioning

confidence: 99%

Synthesis, Cytotoxic Activity Evaluation and Quantitative Structure-ActivityAnalysis of Substituted 5,8-Dihydroxy-1,4-naphthoquinones and Their O- and S-Glycoside Derivatives Tested against Neuro-2a Cancer Cells

et al. 2020

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“…Treatment of 16 with sodium hydroxide resulted in new quinone 17 in 86% yield. Synthetic spinazarins (3-5) [20] as well as isolated from sea urchins spinochrome E (6) were readily converted into di-and tetramethoxy derivatives 18-21 by careful treatment with diazomethane solution [12a]. The prolonged processing of tetramethoxyquinone 21 by excess of diazomethane within 4 h at room temperature led to pentamethoxyquinone 22.…”

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confidence: 99%

Synthesis and Comparative Evaluation of Polymethoxy Substituted 1,4-Naphthoquinones and their Acetyl-O-glucosides as Cytotoxic Agents

Sabutskii

Semenova

Yurchenko

et al. 2017

Natural Product Communications

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Twenty five hydroxy-, chloro-and methoxy derivatives of natural and synthetic naphthazarins and their acetylated O-glycosides were synthesized. Targeted compounds were screened as cytotoxic agents on mouse Ehrlich ascites carcinoma cells using MTT test. Chloro-and methoxy-substituted naphthoquinones as well as naphthoquinone O-acetylglucosides were the most potent with IC 50 in low micromolar concentration range. Glucosidation of hydroxynaphthoquinones was shown to enhance cytotoxicity, whereas methoxylation yielded both more active and less active derivatives depending on the number and position of methoxy groups. Evaluation using a phenotypic sea urchin embryo assay suggested that naphthazarins exerted their cytotoxic effects through tubulin-unrelated mechanism.

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ChemInform Abstract: DMSO‐Mediated Transformation of 3‐Amino‐2‐hydroxynaphthazarins to Natural 2,3‐Dihydroxynaphthazarins and Related Compounds

Polonik

Полоник

2016

ChemInform

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DMSO-mediated transformation of 3-amino-2-hydroxynaphthazarins to natural 2,3-dihydroxynaphthazarins and related compounds

Cited by 6 publications

References 34 publications

Synthesis, Cytotoxic Activity Evaluation and Quantitative Structure-ActivityAnalysis of Substituted 5,8-Dihydroxy-1,4-naphthoquinones and Their O- and S-Glycoside Derivatives Tested against Neuro-2a Cancer Cells

Synthesis, Cytotoxic Activity Evaluation and Quantitative Structure-ActivityAnalysis of Substituted 5,8-Dihydroxy-1,4-naphthoquinones and Their O- and S-Glycoside Derivatives Tested against Neuro-2a Cancer Cells

Synthesis and Comparative Evaluation of Polymethoxy Substituted 1,4-Naphthoquinones and their Acetyl-O-glucosides as Cytotoxic Agents

ChemInform Abstract: DMSO‐Mediated Transformation of 3‐Amino‐2‐hydroxynaphthazarins to Natural 2,3‐Dihydroxynaphthazarins and Related Compounds

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