Concise Synthesis of (±)-Rhinacanthin A, Dehydro α-Lapachone, and β-Lapachone, and Pyranonaphthoquinone Derivatives

Wang, Xue; Chen, Ye; Lee, Yong Rok

doi:10.5012/bkcs.2011.32.1.153

Cited by 8 publications

(2 citation statements)

References 31 publications

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“…The next step in the synthesis involved dehydration of stenocarpoquinone A( 6a), which was allowed to react with PPh 3 in CCl 4 /MeCN at reflux (Scheme 2). Reaction of 9a with mCPBA effectedthe epoxide, which was reduced with NaBH 3 CN in the presence of BF 3 ·Et 2 O [24] to yield rhinacanthin A( 12 a) [25] in 21 %y ield. Reagents and conditions:a)1-bromo-3-methyl-2-butene, Pd(PPh 3 ) 4 ,Et 3 N, dioxane, RT,4h; b) H 2 SO 4 ,CH 2 Cl 2 ,08C, 1h.…”

Section: Synthesis Of Furonaphthoquinones and Pyranonaphthoquinones Fmentioning

confidence: 99%

“…Catalytic hydrogenation of 9a furnished a-lapachone 11 a in 87 %yield. Reaction of 9a with mCPBA effectedthe epoxide, which was reduced with NaBH 3 CN in the presence of BF 3 ·Et 2 O [24] to yield rhinacanthin A( 12 a) [25] in 21 %y ield. These procedures allowed the syntheses of the methoxylated analogues (Scheme 2).…”

Section: Synthesis Of Furonaphthoquinones and Pyranonaphthoquinones Fmentioning

confidence: 99%

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Synthesis, Characterization, and Antileukemic Properties of Naphthoquinone Derivatives of Lawsone

et al. 2015

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Naphthoquinones are considered privileged structures for anticancer drug molecules. The Heck reaction of 2-hydroxy-1,4-naphthoquinone (lawsone) with 1-bromo-3-methyl-2-butene offered easy access to lapachol. Several naturally occurring linear and angular heterocyclic quinoids (α-lapachone, β-lapachone, dunnione, and related analogues) were prepared from lapachol. Furthermore, we demonstrated that the synthetic naphthoquinones inhibit cell proliferation in human leukemia HL-60 cells. In particular, angular-type derivatives were found to possess moderate cytotoxicity and to elevate the levels of intracellular glutathione disulfide (GSSG). Our work highlights the significant potential of naturally occurring angular-series naphthoquinones as antileukemic agents.

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Section: Synthesis Of Furonaphthoquinones and Pyranonaphthoquinones Fmentioning

confidence: 99%

Section: Synthesis Of Furonaphthoquinones and Pyranonaphthoquinones Fmentioning

confidence: 99%

Synthesis, Characterization, and Antileukemic Properties of Naphthoquinone Derivatives of Lawsone

et al. 2015

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ChemInform Abstract: Concise Synthesis of (.+‐.)‐Rhinacanthin A (VI), Dehydro α‐Lapachone (IV), and β‐Lapachone (VIII), and Pyranonaphthoquinone Derivatives (XII).

2011

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UV–VIS spectral and GC–MS characterization of Handroanthus serratifolius (Vahl.) Grose (a.k.a. Tabebuia serratifolia (Vahl.) Nichols/Lapacho) heartwood main extractives: a comparison of protocols aimed at a practical evaluation of Lapachol and Dehydro-α-Lapachone content

Segoloni

Maria

2018

Eur. J. Wood Prod.

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Concise Synthesis of (±)-Rhinacanthin A, Dehydro α-Lapachone, and β-Lapachone, and Pyranonaphthoquinone Derivatives

Cited by 8 publications

References 31 publications

Synthesis, Characterization, and Antileukemic Properties of Naphthoquinone Derivatives of Lawsone

Synthesis, Characterization, and Antileukemic Properties of Naphthoquinone Derivatives of Lawsone

ChemInform Abstract: Concise Synthesis of (.+‐.)‐Rhinacanthin A (VI), Dehydro α‐Lapachone (IV), and β‐Lapachone (VIII), and Pyranonaphthoquinone Derivatives (XII).

UV–VIS spectral and GC–MS characterization of Handroanthus serratifolius (Vahl.) Grose (a.k.a. Tabebuia serratifolia (Vahl.) Nichols/Lapacho) heartwood main extractives: a comparison of protocols aimed at a practical evaluation of Lapachol and Dehydro-α-Lapachone content

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