Structure–activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 2: Role of the alditol side chain stereochemistry

Tsutsui, Nozomi; Tanabe, Genzoh; Gotoh, Genki; Morita, Nao; Nomura, Naohisa; Kita, Ayako; Sugiura, Reiko; Muraoka, Osamu

doi:10.1016/j.bmc.2013.12.052

Cited by 9 publications

(4 citation statements)

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“…Acremomannolipin A was isolated from Acremonium strictum and is a potential calcium signal modulator . Very recently, Muraoka and co-workers accomplished the first total synthesis of acremomannolipin A adopting Crich’s glycosylation and evaluated the effect of configuration of glycosidic bond and alditols on its bioactivities . Herein, we describe our synthesis of acremomannolipin A and its analogue using 6 α as a glycosyl donor (Scheme ).…”

mentioning

confidence: 64%

“…To demonstrate the versatility of our synthesis and facilitate investigation into structure–activity relationships, we intended to install different acyl groups onto the mannosyl unit of acremomannolipin A. Such compounds have not been documented in the literature . Thus, selective benzoylation of the primary 6′-OH in 15 , and hexanoylation of 4′-OH in 18 gave 19 in 81% yield in two steps.…”

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confidence: 98%

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Construction of β-Mannosidic Bonds via Gold(I)-Catalyzed Glycosylations with Mannopyranosyl ortho-Hexynylbenzoates and Its Application in Synthesis of Acremomannolipin A

et al. 2015

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A mild and convenient protocol for direct synthesis of β-mannosides has been developed. Glycosylation of 4,6-O-benzylidene-protected mannosyl ortho-hexynylbenzoates with various alcohol acceptors catalyzed by gold(I) complex proceeded smoothly at 0 °C to room temperature and afforded the corresponding β-mannoside in high yield and satisfactory stereoselectivity. This reaction was applied to the total synthesis of acremomannolipin A and its analogue.

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confidence: 64%

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confidence: 98%

Construction of β-Mannosidic Bonds via Gold(I)-Catalyzed Glycosylations with Mannopyranosyl ortho-Hexynylbenzoates and Its Application in Synthesis of Acremomannolipin A

et al. 2015

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“…Next, 3,4,5-trichloro-furan-2(5H)-one reacted with propargylamine in 1,4-dioxane to obtain 8 in 45% yield [22]. Finally, N-propargyl-3,4-dichloro-5-hydroxy-2H-pyrrol-2-one 8 reacted with triisopropylsilyl chloride in the presence of imidazole and trimethylamine to obtain product 9 in 71% yield [42,43].…”

Section: Synthesismentioning

confidence: 99%

“…Cells survival fractions (SF) followed by 72 h MTT viability assay are presented in Supplementary File S1. chloro-5-hydroxy-2H-pyrrol-2-one 8 reacted with triisopropylsilyl chloride in the presence of imidazole and trimethylamine to obtain product 9 in 71% yield [42,43].…”

Section: Anticancer Screening 221 Cytotoxicity and Anticancer Activitiesmentioning

confidence: 99%

Glycoconjugates of Mucochloric Acid—Synthesis and Biological Activity

et al. 2023

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The pharmacological effects of the presence of a sugar moiety, 1,2,3-triazole ring and silyl groups in the structure of biologically active compounds have been extensively studied in drug design and medicinal chemistry. These components can be useful tools to tailoring the bioavailability of target molecules. Herein we present the study on the impact of the sugar substituent structure and triisopropylsilyl group presence on the anticancer activity of mucochloric acid (MCA) derivatives containing the furan-2(5H)-one or 2H-pyrrol-2-one core. The obtained results clearly indicated that tested compounds caused a significant decrease in cell viability of HCT116 and MCF-7 cell lines. MCF-7 cells indicate serious resistance toward investigated compounds in comparison with HCT116 cell line, it suggests that estrogen-dependent breast cancer cells are significantly less sensitive to the tested derivatives. Depending on the structure of the sugar, the type and site of connection with the furanone or 2H-pyrrol-2-one derivative and the presence of the silyl group, the selectivity of the compound towards cancer cells can be controlled. The obtained results may have an impact on the design of new furanone-based anticancer compounds.

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Recent Advances on SGLT 2 Inhibitors: Synthetic Approaches, Therapeutic Benefits, and Adverse Events

Matos

Calado

Washburn

et al. 2021

Successful Drug Discovery

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Structure–activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 2: Role of the alditol side chain stereochemistry

Cited by 9 publications

References 10 publications

Construction of β-Mannosidic Bonds via Gold(I)-Catalyzed Glycosylations with Mannopyranosyl ortho-Hexynylbenzoates and Its Application in Synthesis of Acremomannolipin A

Construction of β-Mannosidic Bonds via Gold(I)-Catalyzed Glycosylations with Mannopyranosyl ortho-Hexynylbenzoates and Its Application in Synthesis of Acremomannolipin A

Glycoconjugates of Mucochloric Acid—Synthesis and Biological Activity

Recent Advances on SGLT 2 Inhibitors: Synthetic Approaches, Therapeutic Benefits, and Adverse Events

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