Synthesis of Prenylated Xanthones: An Overview

Pinto, Maurício R.; Castanheiro, Raquel A. P.

doi:10.2174/138527209788921747

Cited by 26 publications

(13 citation statements)

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“…These substituents are strongly dependent on their biosynthetic origins and modification reactions [3]. Prenylxanthones, an important subgroup of naturally occurring xanthones, exhibit diverse biological and pharmaceutical activities, because of their specific substitution patterns [4]. In many conditions, activities are associated with prenylation of the xanthone skeleton [5].…”

Section: Introductionmentioning

confidence: 99%

New Prenylxanthones from the Deep-Sea Derived Fungus Emericella sp. SCSIO 05240

et al. 2014

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Four new prenylxanthones, emerixanthones A–D (1–4), together with six known analogues (5–10), were isolated from the culture of the deep-sea sediment derived fungus Emericella sp. SCSIO 05240, which was identified on the basis of morphology and ITS sequence analysis. The newstructures were determined by NMR (1H, 13C NMR, HSQC, HMBC, and 1H-1H COSY), MS, CD, and optical rotation analysis. The absolute configuration of prenylxanthone skeleton was also confirmed by the X-ray crystallographic analysis. Compounds 1 and 3 showed weak antibacterial activities, and 4 displayed mild antifungal activities against agricultural pathogens.

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Section: Introductionmentioning

confidence: 99%

New Prenylxanthones from the Deep-Sea Derived Fungus Emericella sp. SCSIO 05240

et al. 2014

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“…Interest in hemisynthesis has therefore waned, especially when the aim is to obtain more complex molecules. Many reviews on xanthone synthesis can be found in the specialized literature . Azevedo et al .…”

Section: Synthetic Routesmentioning

confidence: 99%

“…Many reviews on xanthone synthesis can be found in the specialized literature. [4,8,[140][141][142] Azevedo et al [143] reviewed the synthesis of xanthones based on five approaches: (i) one-step synthesis starting from two aryl building blocks, adequately functionalized, focusing on reactions via benzyne and catalyzed by palladium; (ii) synthesis via benzophenone; (iii) synthesis starting from diaryl ether, which generally leads to the two-step xanthone scaffold; (iv) synthesis starting from chromen-4-ones using Michael addition heteroannulations, and pericyclic and photochemical reactions, and (v) less common strategies, which can be a viable alternative to the classical methodologies (Scheme 1).…”

Section: Synthetic Routesmentioning

confidence: 99%

Xanthones and Cancer: from Natural Sources to Mechanisms of Action

Klein‐Júnior

Campos

Niero

et al. 2020

Chemistry & Biodiversity

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Xanthones are a class of heterocyclic natural products that have been widely studied for their pharmacological potential. In fact, they have been serving as scaffolds for the design of derivatives focusing on drug development. One of the main study targets of xanthones is their anticancer activity. Several compounds belonging to this class have already demonstrated cytotoxic and antitumor effects, making it a promising group for further exploration. This review therefore focuses on recently published studies, emphasizing their natural and synthetic sources and describing the main mechanisms of action responsible for the anticancer effect of promising xanthones.

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“…Xanthone scaffold is envisioned as a privileged structure in many biologically active molecules [53], and it is conventionally synthesized through the cyclodehydration of 2,2 ′ -dihydroxybenzophenones and electrophilic cycloacylation of 2-aryloxybenzoic acids [54]. To refine these synthetic routes, Lei and coworkers described a Pd-catalyzed double C-H activation/carbonylation of diaryl ethers to afford xanthones (Scheme 3.28) [55].…”

Section: Palladium-catalyzed C-h Activation/c-c Formation To Construcmentioning

confidence: 99%