Total synthesis of aldehyde-containing Garcinia natural products isomorellin and gaudichaudione A

Liu, Zongliang; Wang, Xiaojian; Li, Nian‐Guang; Sun, Haopeng; Qin, You

doi:10.1016/j.tet.2011.05.029

Cited by 12 publications

(9 citation statements)

References 18 publications

(18 reference statements)

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“…According to our earlier report, [19] we obtained xanthone derivative 9 from 2,3,4-trihydroxybenzoic acid and phloroglucinol through 6 steps with a 22.7 % combined yield. Further removal of the acetyl group in 9 with K 2 CO 3 led to 10, which was then selectively reduced to precursor 11 using the Lindlar catalyst.…”

Section: Resultsmentioning

confidence: 97%

Synthesis and Bioevaluation of Novel Oxa-Caged Garcinia Xanthones as Anti-Tumour Agents

Miao

Yang

et al. 2015

Aust. J. Chem.

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Gambogic acid (GA), a special category of Garcinia xanthones, has attracted great attention owing to its striking bioactivities and unique structure. To further explore its structure-activity relationship, we prepared seven novel oxa-caged Garcinia xanthones that were for the first time varied at the C-2 position of B ring and at the C-21/22 or C-23 position of the prenyl group in the caged scaffold. Some compounds exhibited strong anti-proliferation activities in different cancer cell lines. Particularly, compound 8 showed more potent cytotoxic activity and better selectivity towards the A549 cell line than GA. Oxa-caged xanthones 8 was identified as an A549 cell apoptosis inducer through observations of morphological changes and Annexin-V/PI double-staining assay. Additionally, the structure-activity relationships of these new analogues were discussed.

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Section: Resultsmentioning

confidence: 97%

Synthesis and Bioevaluation of Novel Oxa-Caged Garcinia Xanthones as Anti-Tumour Agents

Miao

Yang

et al. 2015

Aust. J. Chem.

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“…The substrates (11a-f) were conveniently prepared by the method reported by our group previously 12,17 . As shown in Table 2, different substrates were successfully converted into caged Garcinia natural products and analogues (12a-f, 13d-f) under MWI in a very short time (3 min) with good overall yields (85-94%).…”

Section: Resultsmentioning

confidence: 99%

“…The scope of the microwave-assisted Claisen/D-A reaction was extended to different xanthone-based and chromone-based substrates (Scheme 1, Table 2) using the optimum reaction conditions at 110 °C for 3 min in 80% aqueous methanol (entry 15, Table 1). The substrates (11a-f) were conveniently prepared by the method reported by our group previously 12,17 . As shown in Table 2, different substrates were successfully converted into caged Garcinia natural products and analogues (12a-f, 13d-f) under MWI in a very short time (3 min) with good overall yields (85-94%).…”

Section: Resultsmentioning

confidence: 99%

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Microwave-Assisted Claisen Rearrangement/Diels–Alder Cascade reaction for the Synthesis of Caged Garcinia Natural Products and Analogues

Zhang

et al. 2011

Journal of Chemical Research

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A microwave-assisted Claisen rearrangement/Diels-Alder cascade reaction was used to synthesise caged Garcinia natural products and analogues containing the unique 4-oxa-tricyclo[4.3.1.0 3,7 ]decan-2-one scaffold from xanthonebased and chromone-based substrates. Forbesione and cluvenone as well as two new and six known caged analogues were obtained. Compared with the traditional thermal method, the reaction time was reduced dramatically and the yield was greatly improved under microwave irradiation. In addition, the regioselectivity observed in the cascade reaction has also been rationalised. Garcinia have long been used in folk medicines for their healing, antibacterial, and cytotoxic activities.

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“…The synthesis of the C6,C18-dihydroxylated caged xanthones 12 and 13 is shown in Scheme 1. Condensation of phloroglucinol (5) with 2,3,4-trihydroxybenzoic acid (6) under ZnCl 2 /POCl 3 conditions [55] produced a tetrahydroxylated xanthone that was subsequently protected with diphenyldichloromethane to form compound 7 (42% yield over two steps) [56]. Selective protection of the more reactive C18-phenol with MOMCl/DIPEA followed by deprotection of the diphenyl ketal (H 2 , Pd/C) gave rise to xanthone 8 (100% yield over two steps).…”

Section: Synthesis Of A-ring Modified Caged Xanthonesmentioning

confidence: 99%

Synthesis, structure-activity relationship and in vitro pharmacodynamics of A-ring modified caged xanthones in a preclinical model of inflammatory breast cancer

Chantarasriwong

Milcarek

Habarth-Morales

et al. 2019

European Journal of Medicinal Chemistry

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Inflammatory breast cancer (IBC) is a highly metastatic, lethal form of breast cancer that lacks targeted therapeutic strategies. Inspired by the promising cytotoxicity of gambogic acid and related caged xanthones in spheroids MARY-X , an in vitro preclinical IBC model, we constructed a library of synthetic analogs and performed structure-activity relationship studies. The studies revealed that functionalizing the Aring of the caged xanthone framework can significantly affect potency. Specifically, introduction of hydroxyl or fluorine groups at discrete positions of the A-ring leads to enhanced cytotoxicity at submicromolar concentrations. These compounds induce complete dissolution of spheroids MARY-X with subsequent apoptosis of both the peripherally-and centrally-located cells, proliferative and quiescentprone (e.g. hypoxic), respectively. These results highlight the structural flexibility and pharmacological potential of the caged xanthone motif for the design of IBC-targeting therapeutics.

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Total synthesis of aldehyde-containing Garcinia natural products isomorellin and gaudichaudione A

Cited by 12 publications

References 18 publications

Synthesis and Bioevaluation of Novel Oxa-Caged Garcinia Xanthones as Anti-Tumour Agents

Synthesis and Bioevaluation of Novel Oxa-Caged Garcinia Xanthones as Anti-Tumour Agents

Microwave-Assisted Claisen Rearrangement/Diels–Alder Cascade reaction for the Synthesis of Caged Garcinia Natural Products and Analogues

Synthesis, structure-activity relationship and in vitro pharmacodynamics of A-ring modified caged xanthones in a preclinical model of inflammatory breast cancer

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