4704-15-8Relevant academic research and scientific papers
Adverse effects of alkali and acid on the anticoagulant potency of heparin, evaluated with methyl 2-deoxy-2-sulfamino-α-D-glucopyranoside 3-sulfate as a model compound
Liu, Zhengchun,Perlin, Arthur S.
, p. 29 - 36 (1992)
A variety of chemical modifications can induce a reduction in the anticoagulant activity of heparin.Among such modifications are the removal in alkaline solution of the 2-O-sulfonate group of α-L-idopyranosyluronic acid 2-sulfate residues (1) and, in a we
Regioselective sulfamoylation at low temperature enables concise syntheses of putative small molecule inhibitors of sulfatases
Miller, Duncan C.,Carbain, Benoit,Beale, Gary S.,Alhasan, Sari F.,Reeves, Helen L.,Baisch, Ulrich,Newell, David R.,Golding, Bernard T.,Griffin, Roger J.
supporting information, p. 5279 - 5284 (2015/05/13)
Regioselective sulfamoylation of primary hydroxyl groups enabled a 5-step synthesis (overall yield 17%) of the first reported small molecule inhibitor of sulfatase-1 and 2, ((2S,3R,4R,5S,6R)-4,5-dihydroxy-2-methoxy-6-((sulfamoyloxy)methyl)tetrahydro-2H-pyran-3-yl)sulfamic acid, which obviated the use of hydroxyl protecting groups and is a marked improvement on the reported 9-step synthesis (overall yield 9%) employing hazardous trifluoromethylsulfonyl azide. The sulfamoylation methodology was used to prepare a range of derivatives of 1, and inhibition data was generated for Sulf-2, ARSA and ARSB.
PROCESS FOR PREPARING HEPARINOIDS AND INTERMEDIATES USEFUL IN THE SYNTHESIS THEREOF
-
, (2013/02/28)
Processes are disclosed for the synthesis of the Factor Xa anticoagulant fondaparinux and related compounds. Protected pentasaccharide intermediates and efficient and scalable processes for the industrial scale production of fondaparinux sodium by conversion of the protected pentasaccharide intermediates via a sequence of deprotection and sulfonation reactions are provided.
Hybrid aminoglycoside antibiotics via tsuji palladium-catalyzed allylic deoxygenation
Hanessian, Stephen,Maianti, Juan Pablo,Matias, Rowena D.,Feeney, Lee Ann,Armstrong, Eliana S.
supporting information; experimental part, p. 6476 - 6479 (2012/02/14)
Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an R,β-unsaturated 6′- aldehyde and an allylic 3′-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol % Pd2(dba)3 and Bu3P granted access to a novel series of 3′,4′-dideoxy- 4′,5′-dehydro ring A hybrids. The neomycin-sisomicin hybrid exhibited superior in vitro antibacterial activity to the parent compound neomycin.
Synthesis of pseudo-disaccharide analogues of lipid A: Haptens for the generation of antibodies with glycosidase activity towards lipid A
Berg, Richard J.B.H.N. Van Den,Noort, Daan,Van Der Marel, Gijs A.,Van Boom, Jacques H.,Benschop, Hendrik P.
, p. 167 - 188 (2007/10/03)
In order to develop a generic treatment of sepsis caused by infections with Gram-negative bacteria, a series of pseudo-disaccharide analogues of lipid A (1-5) was synthesized. These adducts not only harbor a 2-acylaminodideoxynojirimycin unit mimicking th
Synthesis of heparin partial structures and their binding activities to platelets
Koshida, Shuhei,Suda, Yasuo,Sobel, Michael,Ormsby, Julie,Kusumoto, Shoichi
, p. 3127 - 3132 (2007/10/03)
A synthetic pentasaccharide corresponding to the antithrombin III-binding region in heparin was also found to bind to human platelets. To identify the platelet-binding site in the pentasaccharide which is expected to be a novel sequence in heparin responsible for its platelet-binding, five partial structures of this particular pentasaccharide were synthesized. In a competitive assay using [3H]-heparin, a trisaccharide, O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-α-D-glucopyranosyl)- (1→4)-O-(2-O-sulfo-α-L-idopyranosyluronic acid)-(1→4)-2-deoxy-2-sulfamido-6-O-sulfo-α-D-glucopyranose, was concluded to be a high-affinity site for heparin's binding to platelets.
In the search for new anticancer drugs. 27. Synthesis and comparison of anticancer activity in vivo of amino acids, carbohydrates, and carbohydrate- amino acid conjugates containing the [N'-(2-chloroethyl)-N'- nitrosoamino]carbonyl group
Sosnovsky,Gnewuch
, p. 989 - 998 (2007/10/02)
The [N'-(2-chloroethyl)-N'-nitrosoamino]carbonyl [(2- chloroethyl)nitrosocarbamoyl, CNC] moiety containing compounds CNC- glycinamide 2d, CNC-amino acid derivatives 7a-d, and carbohydrate-CNC-amino acid conjugates 13, 18, 22, 23, 27, and 28 were synthesized and evaluated in vivo for their anticancer activities against the murine lymphocytic leukemia P388 using the National Cancer Institute (NCI) protocol. The most active compound was 2d with a 520% increase in life span (%ILS) and 6/6 survivors after 60 days. The CNC-amino acid analogs 7a-d possessed high to moderate activities with maximum %ILS values of 270, 174, 141 and 132, respectively. Among the carbohydrate-CNC-amino acid derivatives the α-methyl glycoside derivatives 22 and 23 were most active with maximum %ILS values of 277 and 137, respectively, followed by the hemiacetal carbohydrate analogs 13 and 18 with %ILS values of 93 and 149, respectively, and the tetra-O-acetyl derivatives 27 and 28 with %ILS of 110 and 111, respectively. Compounds 7b, 18, 23 and 28 were then tested in vivo against the murine lymphoid leukemia L1210 using the NCI protocol. In this case, the hemiacetal type carbohydrate- CNC-amino analog 18 had the highest activity with a maximum %ILS value of 477 and 4/6 survivors on day 60, followed by 7b (275% ILS), 23 (152% ILS) and 28 (106% ILS). The lipophilicities of all CNC compounds were determined by the partition coefficient using the UV method. A correlation of %ILS values with log P values indicated, in general, an increase in cytotoxicity with a decrease in hydrophilicity for the carbohydrate-CNC-amino acid conjugates 13, 18, 22, 23 and the clinical drugs streptozotocin (1e), chlorozotocin (1f), and cymerin (1g).
Synthesis of the Aziridinopyrrolidine Substructure of the Antitumor Agents Azinomycin A and B
Coleman, Robert S.,Carpenter, Andrew J.
, p. 5813 - 5815 (2007/10/02)
A stereoselective synthesis of the central aziridinopyrrolidine substructure (19) of the antitumor agents azinomycin A and B is reported and featured as the key step an intramolecular Michael addition-elimination reaction between the aziridine and
