5-Thio-D-fructofuranose

Chmielewski, Marek; Whistler, Roy L.

doi:10.1021/jo00893a021

Cited by 21 publications

(13 citation statements)

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“…Replacement of the oxygen atom in the hemiacetal ring of normal sugars by a carbon or heteroatom leads to the formation of pseudo-sugars, several of which have been heavily investigated in the fields of synthetic, biological, and medical chemistry [3]. Novel nucleoside derivatives of pseudo-or hetero-sugars reported to date include aza-sugar (nitrogen instead of an oxygen atom; amino sugar) [4][5][6][7], thio-sugar (or thia-sugar; sulfur instead of an oxygen atom) [8,9], and carba-sugar (oxygen atom replaced by a methylene group) [10,11]. Further, the potential bioactivity of hetero-sugar nucleosides and glycosides (e.g., glycosidase and nojirimycin) has also been reported [12].…”

Section: Introductionmentioning

confidence: 99%

Development and pharmacologic characterization of deoxybromophospha sugar derivatives with antileukemic activity

et al. 2009

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Here, we synthesized two phospha sugar derivatives, 2,3,4-tribromo-3-methyl-1-phenylphospholane 1-oxide (TMPP) and 2,3-dibromo-3-methyl-1-phenylphospholane 1-oxide (DMPP) by reacting 3-methyl-1-phenyl-2-phospholene 1-oxide with bromine, and investigated their potential as antileukemic agents in cell lines. Both agents showed inhibitory effects on leukemia cell proliferation, with mean IC(50) values of 6.25 micromol/L for TMPP and 23.7 micromol/L for DMPP, indicating that inhibition appeared to be dependent on the number of bromine atoms in the structure. Further, TMPP at 10 micromol/L and DMPP at 20 micromol/L induced G2/M cell cycle block in leukemia cells, and TMPP at 20 micromol/L induced apoptosis in these cells. TMPP treatment effected a reduction in both cell cycle progression signals (FoxM1, KIS, Cdc25B, Cyclin D1, Cyclin A, and Aurora-B) and tumor cell survival (p27(Kip1) and p21(Cip1)), as well as induced the activation of caspase-3 and -9. Further, treatment with TMPP significantly reduced the viability of AML specimens derived from AML patients, but only slightly reduced the viability of normal ALDH(hi) progenitor cells. We also observed that FoxM1 mRNA was overexpressed in AML cells, and treatment with TMPP reduced FoxM1 mRNA expression in AML cells. Here, we report on the synthesis of TMPP and DMPP and demonstrate that these agents hinder proliferation of leukemia cells by FoxM1 suppression, which leads to G2/M cell cycle block and subsequent caspase-3-dependent apoptosis in acute leukemia cells. These agents may facilitate the development of new strategies in targeted antileukemic therapy.

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Section: Introductionmentioning

confidence: 99%

Development and pharmacologic characterization of deoxybromophospha sugar derivatives with antileukemic activity

et al. 2009

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“…spectrum of this product showed a strong resemblance to that of the starting material (5) with the exception that the signal for 4-H was at higher field. The 'H n.m.r.…”

Section: -Thiopyranoses Part 12' Sulphur Participation In Displacementioning

confidence: 74%

“…Chromatography on silica (9 g) and elution with benzene4iethyl ether (9: 1) gave first the dibenzoate ( (5).-The diol (1) (150 mg) was dissolved in dry dichloromethane (3.5 ml) containing triethylamine (0.5 ml) and the solution was stirred and cooled to -10 "C. A cold solution of methanesulphonyl chloride (0.2 ml) in dichloromethane (3.5 ml) was added slowly to the above stirred solution. After the mixture had been kept for 16 h at 0°C water (0.1 mi) was added to decompose any remaining benzoyl chloride and, after 10 min, the mixture was washed successively with dilute sulphuric acid and dilute aqueous potassium hydrogen carbonate and dried.…”

Section: Benzoylation Of Methyl 23-anhydro-5-thio-a-~-allo-mentioning

confidence: 99%

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5-Thiopyranoses. Part 12. Sulphur participation in displacement reactions of sulphonate esters of 5-thio-D-allose, 5-thio-D-altrose, and 5-thio-D-glucose derivatives

Al‐Masoudi¹,

Hughes²

1987

J. Chem. Soc., Perkin Trans. 1

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Bothsulphonate groups in methyl 2,3-anhydro-4,6-di-O-methylsulphonyl-5-thio-~-~allopyranoside (5) readily undergo displacement reactions. The 4-sulphonate is the more reactive and is displaced with retention of configuration. Participation by the ring sulphur atom and formation of intermediate episulphonium ions is proposed in each displacement. There is evidence to suggest that ring expansion to give methyl 2,3-anhydro-4,5-di-O-methyl-6-thio-P-~taloseptanoside (1 9) may occur in the reaction of (5) with methanol. Methyl 4,6-O-isopropylidene-2 -0met h ylsu phony I -5-t h io-3 -0 -p -to1 ylsu I p hony Itc-D -g I ucopyranoside (20) is u nreactive u nti I the acetal group is removed, when ring contraction to give 2,5-dideoxy-2,5-epithio-3-O-ptoly lsu I p hony I -Dman nose d imet hyl aceta I (23) occurs. Methyl 3,4 -0isopropy I idene -2,6d i -0methylsulphonyl-5-thio-a-o-altropyranoside (30) was too reactive to be isolated but appeared to react with methanol and chloride ions to give, via ring contraction, the 6-substituted 2,5-dideoxy-2,5-epithio-3,4-0-isopropylidene-~-allose dimethyl acetal derivatives (32) and (36), and, via ring contraction and ring expansion, 2,6-dideoxy-2,6 -epithio-3,4-0isopropylidene-5-0-methyl-Ltalose dimethyl acetal (35).In an earlier paper2 in this series it was shown that methyl 5-thiopentopyranoside 2or 4-sulphonate esters readily underwent nucleophilic displacement reactions either with retention of configuration or with ring contraction. It was suggested that these reactions proceeded uia intermediate episulphonium ions formed by neighbouring group participation from the ring sulphur atom (Schemes 1 and 2). Sulphonate esters at C-3 did not show any unusual reactivity; apparently the cyclic sulphonium ions that would be formed by sulphur participation are too strained. We have now extended these studies to sulphonate esters of some methyl 5-thiohexopyranosides. A sulphonate at C-6 is also a p-ester with respect to the ring sulphur and displacement reactions might be expected to proceed as shown in Scheme 3 to give either pyranoside or septanoside products. I c 8 M e Nui OMe Scheme 1. Ms = MeS(O),n n+ I Nu c D O M e + Nut-( b ) ( a ) OMe Scheme 2.I Nuc OMe O o M e + Scheme 3.The diol (1) was readily available from mild hydrolysis of methyl 2,3-anhydro-4,6-O-isopropylidene-5-thio-a-~-allo-pyran0side.j Methylsulphonylation of the diol (1) gave a crystalline disulphonate (9, which decomposed within hours when kept at room temperature. This disulphonate not only offered the opportunity of examining the behaviour of a 6sulphonate but also of comparing such a sulphonate with a 4-sulphonate in the same molecule. The behaviour of compound (5) with a variety of nucleophiles was examined.When compound (5) was left overnight in cold methanol containing sodium benzoate a good yield of a crystalline monobenzoate monomethanesulphonate (A) was obtained. When this product was heated with methanolic sodium benzoate it afforded the same crystalline dibenzoate (3) as could be obtained by direct benzoylation...

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“…By using reactions similar to those described above, 5-(alkylphosphinyl)-5-deoxy-3-0-methyl-(and benzyl)-D-xylopyranoses were also prepared (55 5 …”

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confidence: 99%

Methods for Introducing Atoms Other than Oxygen into Sugar Rings

Whistler

Anisuzzaman

1977

ACS Symposium Series

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5-Thio-D-fructofuranose

Abstract: temperatures m/e 645, 647 disappears and the base peak shifts to m/e 277 (PI13PCH3"1"), an ion not present in the original 18-mA spectrum. Fragments of m/e 262 (PhsP"*") and m/e 289 (Ph3PCH=CH2+) also appear above 23 mA.

Cited by 21 publications

References 9 publications

Development and pharmacologic characterization of deoxybromophospha sugar derivatives with antileukemic activity

Development and pharmacologic characterization of deoxybromophospha sugar derivatives with antileukemic activity

5-Thiopyranoses. Part 12. Sulphur participation in displacement reactions of sulphonate esters of 5-thio-D-allose, 5-thio-D-altrose, and 5-thio-D-glucose derivatives

Methods for Introducing Atoms Other than Oxygen into Sugar Rings

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