First Synthesis of a Series of New Natural Glucosides

Qu, Mengnan; Zhou, Ling; Cao, Xiao‐Ping

doi:10.1002/cjoc.200690304

Cited by 5 publications

(4 citation statements)

References 17 publications

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“…These compounds were synthesized according to previously published methods. [15][16][17][18][19][20][21][22][23] Briefly, HC was obtained by removing a methylene group of safrole. Chavibetol was synthesized via successive iodination and subsequent allylation by Stille coupling, followed by the deacetylation of methoxyphenyl acetate.…”

Section: Resultsmentioning

confidence: 99%

Structure–Activity Relationships and Docking Studies of Hydroxychavicol and Its Analogs as Xanthine Oxidase Inhibitors

et al. 2018

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SummaryHydroxychavicol (HC), which is obtained from the leaves of Piper betle Linn.(Piperaceae), inhibits xanthine oxidase (XO) with an IC 50 value of 16.7 μM, making it more potent than the clinically used allopurinol (IC 50 = 30.7 μM). Herein, a structure-activity relationship analysis of the polar part analogs of HC was conducted and an inhibitor was discovered with a potency 13 times that of HC. Kinetic studies have revealed that HC and its active analog inhibit XO in an uncompetitive manner. The binding structure prediction of these inhibitor molecules to the XO complex with xanthine suggested that both compounds (HC and its analog) could simultaneously form hydrogen bonds with xanthine and XO.

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Section: Resultsmentioning

confidence: 99%

Structure–Activity Relationships and Docking Studies of Hydroxychavicol and Its Analogs as Xanthine Oxidase Inhibitors

et al. 2018

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“…The synthesis of MA02 started with the preparation of tosylate 10 and α-bromoketone 12 for coupling reactions (Scheme ). Benzyl (Bn)-protection of the known trans - m -propenyl guaiacol ( 6 ) followed by asymmetric dihydroxylation of 7 provided diol 8 . Selective DDQ-oxidation of the benzylic hydroxyl group of 9 followed by tosylation successfully afforded 10 .…”

Section: Resultsmentioning

confidence: 99%

“…To a cooled (0 °C) solution of the known trans - m -propenyl guaiacol ( 6 ; 867 mg, 5.28 mmol) in dry DMF (13 mL, 0.4 M) were added NaH (60% dispersion in mineral oil, 304 mg, 7.92 mmol) and BnBr (0.63 mL, 5.28 mmol). The reaction mixture was allowed to warm to 25 °C.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Biological Evaluation of Manassantin Analogues for Hypoxia-Inducible Factor 1α Inhibition

Kwon

Lee

Weitzel³

et al. 2015

J. Med. Chem.

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To cope with hypoxia, tumor cells have developed a number of adaptive mechanisms mediated by hypoxia-inducible factor 1 (HIF-1) to promote angiogenesis and cell survival. Due to significant roles of HIF-1 in the initiation, progression, metastasis, and resistance to treatment of most solid tumors, a considerable amount of effort has been made to identify HIF-1 inhibitors for treatment of cancer. Isolated from Saururus cernuus, manassantins A (1) and B (2) are potent inhibitors of HIF-1 activity. To define the structural requirements of manassantins for HIF-1 inhibition, we prepared and evaluated a series of manassantin analogues. Our SAR studies examined key regions of manassantin’s structure in order to understand the impact of these regions on biological activity and to define modifications that can lead to improved performance and drug-like properties. Our efforts identified several manassantin analogues with reduced structural complexity as potential lead compounds for further development. Analogues MA04, MA07, and MA11 down-regulated hypoxia-induced expression of the HIF-1α protein and reduced the levels of HIF-1 target genes, including cyclin-dependent kinase 6 (Cdk6) and vascular endothelial growth factor (VEGF). These findings provide an important framework to design potent and selective HIF-1α inhibitors, which is necessary to aid translation of manassantin-derived natural products to the clinic as novel therapeutics for cancers.

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“…Bisabol-1-one (169) and curcudiol (170) were found only in G. chinensis [21]. Besides, two new isomeric rare acyclic C 13 -norisoprenoids, 171 and 172, were also obtained from the herb of S. chinensis [18].…”

mentioning

confidence: 99%

ChemInform Abstract: Secondary Metabolites from the Plants of the Family Saururaceae and Their Biological Properties

Zhuang

Huang

et al. 2015

ChemInform

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First Synthesis of a Series of New Natural Glucosides

Cited by 5 publications

References 17 publications

Structure–Activity Relationships and Docking Studies of Hydroxychavicol and Its Analogs as Xanthine Oxidase Inhibitors

Structure–Activity Relationships and Docking Studies of Hydroxychavicol and Its Analogs as Xanthine Oxidase Inhibitors

Synthesis and Biological Evaluation of Manassantin Analogues for Hypoxia-Inducible Factor 1α Inhibition

ChemInform Abstract: Secondary Metabolites from the Plants of the Family Saururaceae and Their Biological Properties

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