Synthesis of β‐Lapachone, a Potential Anticancer Agent from the Lapacho Tree

Katoh, Takeru; Monma, Hiromitsu; Wakasugi, Jun; Narita, Kôichi; Katoh, Tadashi

doi:10.1002/ejoc.201403064

Cited by 9 publications

(2 citation statements)

References 64 publications

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“…Although the conversion of 20 into lapachones 15 and 22 is a classical strategy to achieve those 1,2‐dicarbonyl compounds, it is important to comment that lapachol ( 20 ) is quite expensive. Therefore, there are some alternatives described in literature to obtaining this quinoidal structure [15c,e] . Phenanthrenequinone has been synthesized via several different approaches, more often via oxidation of phenanthrene ( 23 ) or from similar compounds.…”

Section: Synthesismentioning

confidence: 99%

Imidazoles and Oxazoles from Lapachones and Phenanthrene‐9,10‐dione: A Journey through their Synthesis, Biological Studies, and Optical Applications

Dias

Paz

Nunes

et al. 2021

The Chemical Record

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Diverse structural frameworks are found in natural compounds and are well known for their chemical and biological properties; such compounds include the imidazoles and oxazoles. Researchers worldwide are continually working on the development of methods for synthesizing new molecules bearing these basic moiety and evaluating their properties and applications. To expand the knowledge related to azoles, this review summarizes important examples of imidazole and oxazole derivatives from 1,2-dicarbonyl compounds, such as lapachones and phenanthrene-9,10-diones, not only regarding their synthesis and biological applications but also their photophysical properties and uses. The data concerning the latter are particularly scarce in the literature, which leads to underestimation of the potential applications that can be envisaged for these compounds.

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Section: Synthesismentioning

confidence: 99%

Imidazoles and Oxazoles from Lapachones and Phenanthrene‐9,10‐dione: A Journey through their Synthesis, Biological Studies, and Optical Applications

Dias

Paz

Nunes

et al. 2021

The Chemical Record

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“…25) and tested for oncology indications. Several other variations were recently reported, made from p-benzoquinones through a cascade process (Katoh et al, 2014). Paradoxically, lapachol promotes hepatic nodular hyperplasia and cystic expansion in the kidneys of rats (Sandoval et al, 1996), even though it is considered to be a powerful anticancer drug.…”

Section: Pharmacological Activitymentioning

confidence: 99%

Quinoid systems in chemistry and pharmacology

et al. 2015

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In this paper, we present a brief review of quinoid systems, focusing on their chemical synthesis over the last decade. We address not only major methods of synthesizing quinoids, but also their involvement in biological processes. We highlight their medical relevance and versatility, including antitumor, antiretroviral, or antihypertensive agents, properties determined by their various patterns of substitution. Graphical AbstractKeywords Quinone Á Synthesis Á Cytotoxicity Á Natural products Á Pharmacology Á Redox Abbreviations 3a-HSD 3a-Hydroxysteroid dehydrogenase AIDS Acquired Immune Deficiency Syndrome AlnA Alnumycin A AlnB Alnumycin B BAQ Benzanthracene quinone (7,12-benzo[a] anthraquinone) BPQ Benzo[a]pyrene-7,8-dione CAN Ceric ammonium nitrate CC 50 50 % Cytotoxic concentration CDC25 Cell division cycle phosphatases Cyt Ferricytochrome d-A 2 0 -Deoxyadenosine DBU 1,8-Diazabicyclo[5.4.0]undec-7-ene DDQ 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone d-G, d-Guo 2'-Deoxyguanosine DMF N,N-dimethylformamide DMP Dess-Martin periodinane DMSO

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Total Synthesis of Marine Sesquiterpene Quinones (+)‐Cyclospongiaquinone‐1 and (–)‐Dehydrocyclospongiaquinone‐1 with a Tetracyclic Benzo[a]xanthene Skeleton

2017

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Two marine sesquiterpene quinones, (+)‐cyclospongiaquinone‐1 and (–)‐dehydrocyclospongiaquinone‐1, were efficiently synthesized in 10 and 12 steps and overall yields of 33 and 24 %, respectively, from commercially available (+)‐sclareolide. The synthetic strategy involves the following crucial steps: (i) assembly of the carbon skeleton by coupling the decalin segment to the aromatic moiety; (ii) one‐step construction of the dihydropyran ring by acid‐induced acetonide deprotection/ether cyclization of an olefinic decalin intermediate that contains the aromatic moiety; (iii) formation of the p‐benzoquinone moiety by oxidation of a p‐methoxyphenolic derivative to produce (+)‐cyclospongiaquinone‐1; and (iv) oxidative dehydrogenation at the C‐12–C‐12a bond of a tetracyclic intermediate to obtain (–)‐dehydrocyclospongiaquinone‐1.

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Synthesis of β‐Lapachone, a Potential Anticancer Agent from the Lapacho Tree

Cited by 9 publications

References 64 publications

Imidazoles and Oxazoles from Lapachones and Phenanthrene‐9,10‐dione: A Journey through their Synthesis, Biological Studies, and Optical Applications

Imidazoles and Oxazoles from Lapachones and Phenanthrene‐9,10‐dione: A Journey through their Synthesis, Biological Studies, and Optical Applications

Quinoid systems in chemistry and pharmacology

Total Synthesis of Marine Sesquiterpene Quinones (+)‐Cyclospongiaquinone‐1 and (–)‐Dehydrocyclospongiaquinone‐1 with a Tetracyclic Benzo[a]xanthene Skeleton

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