Design and synthesis of an α-mannosyl terpenoid as selective inhibitor of P-selectin

Ikeda, Tsuyoshi; Kajimoto, Tetsuya; Kondo, Hirosato; Wong, Chi Huey

doi:10.1016/s0960-894x(97)10022-1

Cited by 20 publications

(13 citation statements)

References 9 publications

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“…TCA activated sugar donors were prepared from D-galactose , D-mannose (Ikeda et al, 1997), D-xylose (Schmidt and Junq, 2000), L-rhamnose , D-glucose and D-fucose (Ross et al, 2001) following previously reported procedures. As a typical example (Scheme 1), D-fucose was first benzoylated using benzoyl chloride (BzCl) with 4-dimethylaminopyridine (DMAP) as the catalyst to afford the derivative 2 (94%).…”

Section: Synthesis Of A-bisabolol Glycosidesmentioning

confidence: 99%

“…This compound was prepared from a-bisabolol (55 ll, 0.23 mmol, 1) and 2,3,4,6-tetra-O-benzoyl-a-D-mannopyranosyl trichloroacetimidate (Ikeda et al, 1997) Table 4; HR-ESI-MS m/z 823.3447 [M+Na] 1H, J = 6.4 Hz, H-10), 5.12 (s, 1H, H 0 -1), 5.34 (br s, 1H, H-2); 13 C NMR (CDCl 3 ) see Table 5; HR-ESI-MS m/z 407.2392 [M+Na] …”

Section: General Procedures For the Synthesis Of Benzoylated A-bisabolmentioning

confidence: 99%

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Synthesis and cytotoxicity evaluation of natural α-bisabolol β-d-fucopyranoside and analogues

et al. 2009

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Section: Synthesis Of A-bisabolol Glycosidesmentioning

confidence: 99%

Section: General Procedures For the Synthesis Of Benzoylated A-bisabolmentioning

confidence: 99%

Synthesis and cytotoxicity evaluation of natural α-bisabolol β-d-fucopyranoside and analogues

et al. 2009

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“…Based on this analogy, various functional mannose-derived sLe X mimetics were prepared. [18] To test whether the activity of mimetic 13 could be retained or even improved in a similar fashion, the mannose analogue of compound 13 , C-mannoside 16 , was prepared accordingly from mannosylacetylene 14 (Scheme 4). …”

Section: Resultsmentioning

confidence: 99%

Chemoenzymatic Synthesis of Functional Sialyl Lewis^X Mimetics with a Heteroaromatic Core

Schlemmer

Wiebe

Ferenc

et al. 2014

Chemistry An Asian Journal

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Functional mimetics of the sialyl LewisX tetrasaccharide were prepared by the enzymatic sialylation of a 1,3-diglycosylated indole and a glycosyl azide, which was subsequently transformed into a 1,4-diglycosylated 1,2,3-triazole, by using the trans-sialidase of Trypanosoma cruzi. These compounds inhibited the binding of E-, L-, and P-selectin-coated nanoparticles to polyacrylamide-bound sialyl-LewisX-containing neighboring sulfated tyrosine residues (sTyr/sLeX-PAA) at low or sub-millimolar concentrations. Except for E-selectin, the mimetics showed higher activities than the natural tetrasaccharide.

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“…Moreover, the observation of competitive and noncompetitive inhibitions by molecules not related to natural substrates, such as L-azasugars and various alkaloids, against glycosyltransferase and glycosidases [80,81,173,174] suggest that the binding to even small part of the enzyme, regardless of competitive or non-competitive binding, can achieve effective inhibition. Such functional mimicary is potentially very important because an effective inhibitor of glycosidase or glycosyltransferase may not be necessary a carbohydrate-like derivative or even not a carbohydrate at all.…”

Section: Scheme (31)mentioning

confidence: 99%

C-Glycosides and Aza-C-Glycosides as Potential Glycosidase and Glycosyltransferase Inhibitors

Zou¹

2005

CTMC

146

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Glycosylation as one of most important post-translational modification of gene products is often critical to specific cellular biological functions. Since elevated glycoprocessing enzyme activities have been implicated in the development of various diseases including cancer metastasis, glycosidases and glycosyltransferases are considered as therapeutic targets. Azasugars, the first generation of enzyme inhibitors, have been extensively investigated and two azasugar-based drugs (Miglitol and Miglustat) have been approved. Aza-C-glycosides, molecules with an azasugar core and various C-aglycons attached at the pseudo anomeric center, have the potential to become the second-generation inhibitors with improved specificity and membrane permeability. In this review, C-glycosides, aza-C-glycosides, and aza-C-disaccharides are introduced as glycoprocessing enzyme inhibitors. The synthetic approaches toward those molecules are described based on the key reactions, which include reductive amination, nucleophilic ring opening of epoxides, nucleophilic addition to imines (C=N), and hetero-Michael additions. Aza-C-glycoside-based libraries are also described for the discovery of promising second-generation inhibitors.

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Design and synthesis of an α-mannosyl terpenoid as selective inhibitor of P-selectin

Cited by 20 publications

References 9 publications

Synthesis and cytotoxicity evaluation of natural α-bisabolol β-d-fucopyranoside and analogues

Synthesis and cytotoxicity evaluation of natural α-bisabolol β-d-fucopyranoside and analogues

Chemoenzymatic Synthesis of Functional Sialyl Lewis^X Mimetics with a Heteroaromatic Core

C-Glycosides and Aza-C-Glycosides as Potential Glycosidase and Glycosyltransferase Inhibitors

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Design and synthesis of an α-mannosyl terpenoid as selective inhibitor of P-selectin

Cited by 20 publications

References 9 publications

Synthesis and cytotoxicity evaluation of natural α-bisabolol β-d-fucopyranoside and analogues

Synthesis and cytotoxicity evaluation of natural α-bisabolol β-d-fucopyranoside and analogues

Chemoenzymatic Synthesis of Functional Sialyl LewisX Mimetics with a Heteroaromatic Core

C-Glycosides and Aza-C-Glycosides as Potential Glycosidase and Glycosyltransferase Inhibitors

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Chemoenzymatic Synthesis of Functional Sialyl Lewis^X Mimetics with a Heteroaromatic Core