An improved synthesis of an umbelliferyl 5-thioxylopyranoside, precursor of the antithrombotic drug Iliparcil

Collette, Yves; Ou, Khan; Pires, Joaquim; Baudry, Michel; Descotes, G.; Praly, Jean‐Pierre; Barberousse, Véronique

doi:10.1016/s0008-6215(99)00085-3

Cited by 12 publications

(13 citation statements)

References 18 publications

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“…1, 170.7, 170.0, 169.7 (8 C=O, acetyl), 161.5 (2 CONH), 152. 1,149.5,143.4 (6 C q ,Ar), 140.0 (CH Ar ), 128.7 (2 C q , Ar), 125.7 (2 CH Ar ), 119.8 (2 C q , Ar), 110.5 (2 CH Ar ), 104.1 (2 CH Ar ), 76.6 (2 C-5), 74.9 (2 C-3), 73.4 (2 C-1), 72.4 (2 C-2), 69.2 (2 C-4), 68.2 (2)(3)(4)(5)(6)57.1,56.8 (4 OCH 3 ),21.2,21.1,21.1,20.9 (8 CH 3 ,acetyl). …”

Section: N-carbonyl-(6-ethoxycarbonyl-2-pyridyl)-4-(2346-tetra-oacmentioning

confidence: 99%

“…13 C NMR (75.5 MHz,CDCl 3 ): d = 186.3,182.8 (2 C=O,benzoquinone),171.0,170.4,170.3,170.0 (4 C=O,acetyl),164.2 (CONH),150.8,146.9,138.7,138.3 (4 C q ,Ar), 130.6 (CH Ar ), 129.0 (2 CH Ar ), 124.7 (2 CH Ar ), 115.6 (CH Ar ), 76.7 (C-5), 73.8 (C-3), 73.3 (C-2), 72.1 (C-1), 68.7 (C-4), 62.5 (C-6), 21.2,21.0,21.0,20.9 (4 CH 3 ,acetyl 1 H NMR (300.13 MHz,CDCl 3 ): d = 8.89 (s,1 H,CONH),7.94 (d,J = 8.1 Hz,2 H,Ar),7.73 (d,J = 8.4 Hz,3 H,Ar),7.73 (s,1 H,Ar),7.44 (m,3 H,Ar) 0, 170.4, 170.4, 170.0 (4 C=O, acetyl), 165.9 (CONH), 146. 6,146.2,139.8,138.8,131.9 (5 C q ,Ar),130.7,129.5,129.5,128.9,128.3,128.3,128.0,128.0,127.7,…”

Section: -(B-d-glucopyranosyl)-14-dimethoxy-5-(4-nitrobenzamido)benmentioning

confidence: 99%

“…6,146.2,139.8,138.8,131.9 (5 C q ,Ar),130.7,129.5,129.5,128.9,128.3,128.3,128.0,128.0,127.7,127.7,114.7 (11 CH Ar ), 76.6 (C-5), 73.9 (C-3), 73.2 (C-2), 72.1 (C-1), 68.7 (C-4), 62.5 (C-6), 21.2,21.0,21.0,21.0 (4 CH 3 ,acetyl 0,170.4,170.3,170.0 (4 C=O,acetyl),166.3 (CONH),146.6,138.9,135.8,132.9 (4 C q ,Ar), 130.7 (CH Ar ), 130.6 (C q , Ar), 129.7, 129. 6,129.1,128.8,128.3,127.7,123.6,114.8 (8 CH Ar ), 76.7 (C-5), 74.0 (C-3), 73.2 (C-2), 72.1 (C-1), 68.7 (C-4), 62.5 (C-6), 21.2,21.0,21.0,20.9 (4 CH 3 ,acetyl Ar),130.7,129.4,129.0,128.5,128.1 (5 CH Ar ), 127.8 (C q , Ar), 127.5 (CH Ar ), 120.1 (CH alkene ), 119.2 (C q , Ar), 110.0 (CH Ar ), 77.2 ...…”

Section: -(B-d-glucopyranosyl)-14-dimethoxy-5-(4-nitrobenzamido)benmentioning

confidence: 99%

“…However, glycosyl arenes (also termed C-aryl glycosides) 2 are currently attracting increasing interest, as regard to their synthesis 3 and because of bioactivities 2,4 anticipated for such glycomimics, based on possible interactions with sugar-processing enzymes and on their resistance to both acid-, and enzyme-catalyzed hydrolysis. 5 Our interest in this field stems from earlier studies devoted to the synthesis of 5-thio-b-D-xylopyranosides 6 and C-5-thio-b-D-xylopyranosyl compounds 7 as orally active venous antithrombotics. C-5-Thio-b-D-xylopyranosyl derivatives of phenol, resorcinol, phloroglucinol were obtained by aromatic electrophilic substitution, or by O → C-glycoside rearrangement, showing the reactivity of electron-rich aryls, in agreement with studies aiming at preparing C-glycosyl flavonoids, 8,9 or D-glycosyl derivatives (furanose 10 or pyranose 11 type) of dimethylhydroquinone.…”

mentioning

confidence: 99%

“…H NMR (300.13 MHz, CDCl 3 ): d = 8.58(s, 1 H, CONH), 8.33 (s, 1 H, Ar), 7.85 (d, J = 8.7 Hz, 2 H, Ar), 6.99 (d, J = 8.7 Hz, 2 H, Ar), 6.95 (s, 1 H, Ar), 5.39 (t, J 3,4 = 9.3 Hz, 1 H,, 5.30 (t, J 2,3 = 9.6 Hz, 1 H,, 5.24 (t, J 4,5 = 9.6 Hz, 1 H,, 5.01 (d, J 1,2 = 9 6. Hz, 1 H, H-1), 4.30 (dd, J 5,6 = 4.8 Hz, J 6,6¢ = 12.3 Hz, 1 H, H-6), 4.15 (dd, J 5,6¢ = 1.8 Hz, 1 H, H-6¢), 3.92 (s, 3 H, OCH 3 ), 3.90-3.83 (hidden, 1 H, H-5), 3.87 (s, 3 H, OCH 3 ), 3.86 (s, 3 H, OCH 3 ), 2.08, 2.07, 2.02, 1.81 (4 s, 12 H, OCOCH 3 ).…”

mentioning

confidence: 99%

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C-Glycosyl Amino-Substituted Hydro- and Benzoquinones: Synthesis and Preliminary Biological Evaluation

Zhang¹,

Chen²,

Praly³

2007

Synthesis

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Reaction of C-b-D-glycopyranosyl-1,4-dimethoxybenzenes with acetyl nitrate afforded 2-(b-D-glycopyranosyl)-1,4-dimethoxy-5-nitrobenzenes in high yields. These were converted smoothly (reduction to amines, N-acylation, oxidation, and reduction) into the corresponding C-glycosyl-hydro(benzo)quinone derivatives, with different amide-based substituents at C-5. Reduction of the nitro compounds to amines proceeded smoothly by catalytic hydrogen transfer with HCO 2 NH 4 .

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Section: N-carbonyl-(6-ethoxycarbonyl-2-pyridyl)-4-(2346-tetra-oacmentioning

confidence: 99%

Section: -(B-d-glucopyranosyl)-14-dimethoxy-5-(4-nitrobenzamido)benmentioning

confidence: 99%

Section: -(B-d-glucopyranosyl)-14-dimethoxy-5-(4-nitrobenzamido)benmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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C-Glycosyl Amino-Substituted Hydro- and Benzoquinones: Synthesis and Preliminary Biological Evaluation

Zhang¹,

Chen²,

Praly³

2007

Synthesis

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Naphthyl Thio‐ and Carba‐xylopyranosides for Exploration of the Active Site of β‐1,4‐Galactosyltransferase 7 (β4GalT7)

Thorsheim

Willén

Tykesson

et al. 2017

Chemistry A European J

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Xyloside analogues with substitution of the endocyclic oxygen atom by sulfur or carbon were investigated as substrates for β-1,4-galactosyltransferase 7 (β4GalT7), a key enzyme in the biosynthesis of glycosaminoglycan chains. The analogues with an endocyclic sulfur atom proved to be excellent substrates for β4GalT7, and were galactosylated approximately fifteen times more efficiently than the corresponding xyloside. The 5a-carba-β-xylopyranoside in the d-configuration proved to be a good substrate for β4GalT7, whereas the enantiomer in the l-configuration showed no activity. Further investigations by X-ray crystallography, NMR spectroscopy, and molecular modeling provided a rationale for the pronounced activity of the sulfur analogues. Favorable π-π interactions between the 2-naphthyl moiety and a tyrosine side chain of the enzyme were observed for the thio analogues, which open up for the design of efficient GAG primers and inhibitors.

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ChemInform Abstract: An Improved Synthesis of an Umbelliferyl 5‐Thioxylopyranoside, Precursor of the Antithrombotic Drug Iliparcil.

Collette

Pires

et al. 1999

ChemInform

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An improved synthesis of an umbelliferyl 5-thioxylopyranoside, precursor of the antithrombotic drug Iliparcil

Cited by 12 publications

References 18 publications

C-Glycosyl Amino-Substituted Hydro- and Benzoquinones: Synthesis and Preliminary Biological Evaluation

C-Glycosyl Amino-Substituted Hydro- and Benzoquinones: Synthesis and Preliminary Biological Evaluation

Naphthyl Thio‐ and Carba‐xylopyranosides for Exploration of the Active Site of β‐1,4‐Galactosyltransferase 7 (β4GalT7)

ChemInform Abstract: An Improved Synthesis of an Umbelliferyl 5‐Thioxylopyranoside, Precursor of the Antithrombotic Drug Iliparcil.

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