Home Amines 24967-27-9
24967-27-9,MFCD00135810
Catalog No.:AA002PXV

24967-27-9 | 1,3-Dehydro-2-deoxy-N-acetylneuraminicacid

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  • Technical Information
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Technical Information
Catalog Number:
AA002PXV
Chemical Name:
1,3-Dehydro-2-deoxy-N-acetylneuraminicacid
CAS Number:
24967-27-9
Molecular Formula:
C11H17NO8
Molecular Weight:
291.2546
MDL Number:
MFCD00135810
SMILES:
OC[C@H]([C@H]([C@@H]1OC(=C[C@@H]([C@H]1NC(=O)C)O)C(=O)O)O)O
Properties
Properties
 
Form:
Solid  
MP:
227-228℃  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
409  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
6  
Rotatable Bond Count:
5  
XLogP3:
-2.5  

Literature

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Title: Pyrrolidinobenzoic acid inhibitors of influenza virus neuraminidase: the hydrophobic side chain influences type A subtype selectivity.

Journal: Bioorganic & medicinal chemistry 20120715

Title: Molecular modeling of T. rangeli, T. brucei gambiense, and T. evansi sialidases in complex with the DANA inhibitor.

Journal: Chemical biology & drug design 20120701

Title: NEU1 and NEU3 sialidase activity expressed in human lung microvascular endothelia: NEU1 restrains endothelial cell migration, whereas NEU3 does not.

Journal: The Journal of biological chemistry 20120504

Title: Receptor-binding specificity of the human parainfluenza virus type 1 hemagglutinin-neuraminidase glycoprotein.

Journal: Glycobiology 20120201

Title: Inhibitor selectivity of a new class of oseltamivir analogs against viral neuraminidase over human neuraminidase enzymes.

Journal: Bioorganic & medicinal chemistry 20110501

Title: Syntheses of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid analogues modified by N-sulfonylamidino groups at the C-4 position and biological evaluation as inhibitors of human parainfluenza virus type 1.

Journal: Bioorganic & medicinal chemistry 20110401

Title: A single amino acid mutation at position 170 of human parainfluenza virus type 1 fusion glycoprotein induces obvious syncytium formation and caspase-3-dependent cell death.

Journal: Journal of biochemistry 20110201

Title: Real time enzyme inhibition assays provide insights into differences in binding of neuraminidase inhibitors to wild type and mutant influenza viruses.

Journal: PloS one 20110101

Title: Inhibition of human neuraminidase 3 (NEU3) by C9-triazole derivatives of 2,3-didehydro-N-acetyl-neuraminic acid.

Journal: Bioorganic & medicinal chemistry letters 20101215

Title: Carbocycles related to oseltamivir as influenza virus group-1-specific neuraminidase inhibitors. Binding to N1 enzymes in the context of virus-like particles.

Journal: Journal of medicinal chemistry 20101028

Title: Analogs of zanamivir with modified C4-substituents as the inhibitors against the group-1 neuraminidases of influenza viruses.

Journal: Bioorganic & medicinal chemistry 20100601

Title: Complexity in influenza virus targeted drug design: interaction with human sialidases.

Journal: Journal of medicinal chemistry 20100408

Title: 'Click chemistry' synthesis of a library of 1,2,3-triazole-substituted galactose derivatives and their evaluation against Trypanosoma cruzi and its cell surface trans-sialidase.

Journal: Bioorganic & medicinal chemistry 20100401

Title: The effect of neuraminidase blocker on gabazine-induced seizures in rat hippocampus.

Journal: Fiziolohichnyi zhurnal (Kiev, Ukraine : 1994) 20100101

Title: Human sialidase inhibitors: design, synthesis, and biological evaluation of 4-acetamido-5-acylamido-2-fluoro benzoic acids.

Journal: Bioorganic & medicinal chemistry 20090701

Title: Efficient method for the preparation of peracetylated Neu5Ac2en by flash vacuum pyrolysis.

Journal: The Journal of organic chemistry 20090605

Title: Sialic acid: a preventable signal for pneumococcal biofilm formation, colonization, and invasion of the host.

Journal: The Journal of infectious diseases 20090515

Title: Discovery of novel inhibitors of Trypanosoma cruzi trans-sialidase from in silico screening.

Journal: Bioorganic & medicinal chemistry letters 20090201

Title: Crystal structure of the NanB sialidase from Streptococcus pneumoniae.

Journal: Journal of molecular biology 20081212

Title: Limited inhibitory effects of oseltamivir and zanamivir on human sialidases.

Journal: Antimicrobial agents and chemotherapy 20081001

Title: Structure of the catalytic domain of Streptococcus pneumoniae sialidase NanA.

Journal: Acta crystallographica. Section F, Structural biology and crystallization communications 20080901

Title: 2-Deoxy-2,3-didehydro-N-acetylneuraminic acid analogs structurally modified by thiocarbamoylalkyl groups at the C-4 position: Synthesis and biological evaluation as inhibitors of human parainfluenza virus type 1.

Journal: Bioorganic & medicinal chemistry 20080715

Title: Membrane type sialidase inhibits the megakaryocytic differentiation of human leukemia K562 cells.

Journal: Biochimica et biophysica acta 20080501

Title: Investigation into an efficient synthesis of 2,3-dehydro-N-acetyl neuraminic acid leads to three decarboxylated sialic acid dimers.

Journal: Carbohydrate research 20080407

Title: Photoaffinity labeling of sialidase with a biotin-conjugated phenylaminodiazirine derivative of 2,3-didehydro-2-deoxy-N-acetylneuraminic acid.

Journal: Biological & pharmaceutical bulletin 20080301

Title: Design, synthesis, and biological evaluation of human sialidase inhibitors. Part 1: selective inhibitors of lysosomal sialidase (NEU1).

Journal: Bioorganic & medicinal chemistry letters 20080115

Title: Sialidase activity in Mycoplasma synoviae.

Journal: Avian diseases 20071201

Title: Role of sialidase in Mycoplasma alligatoris-induced pulmonary fibroblast apoptosis.

Journal: Veterinary microbiology 20070331

Title: Synthesis and evaluation of 4-O-alkylated 2-deoxy-2,3-didehydro-N-acetylneuraminic acid derivatives as inhibitors of human parainfluenza virus type-3 sialidase activity.

Journal: Bioorganic & medicinal chemistry letters 20070315

Title: STD NMR spectroscopy and molecular modeling investigation of the binding of N-acetylneuraminic acid derivatives to rhesus rotavirus VP8* core.

Journal: Glycobiology 20070101

Title: 2-Deoxy-2,3-didehydro-N-acetylneuraminic acid analogues structurally modified at the C-4 position: synthesis and biological evaluation as inhibitors of human parainfluenza virus type 1.

Journal: Bioorganic & medicinal chemistry 20061201

Title: Preparation of a fluorous protecting group and its application to the chemoenzymatic synthesis of sialidase inhibitor.

Journal: Chemical communications (Cambridge, England) 20060807

Title: Insights from modeling the 3D structure of H5N1 influenza virus neuraminidase and its binding interactions with ligands.

Journal: Biochemical and biophysical research communications 20060609

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: A QSAR study on influenza neuraminidase inhibitors.

Journal: Bioorganic & medicinal chemistry 20060215

Title: Structural analysis of a designed inhibitor complexed with the hemagglutinin-neuraminidase of Newcastle disease virus.

Journal: Glycoconjugate journal 20060201

Title: A sialidase mutant displaying trans-sialidase activity.

Journal: Journal of molecular biology 20050128

Title: Crystal structure of the human cytosolic sialidase Neu2. Evidence for the dynamic nature of substrate recognition.

Journal: The Journal of biological chemistry 20050107

Title: Reduction in the adherence of Pseudomonas aeruginosa to human buccal epithelial cells with neuraminidase inhibition.

Journal: Polish journal of microbiology 20050101

Title: Structural analogs of sialic acid interfere with the binding of erythrocyte binding antigen-175 to glycophorin A, an interaction crucial for erythrocyte invasion by Plasmodium falciparum.

Journal: Molecular and biochemical parasitology 20041101

Title: Sialic acid recognition by Vibrio cholerae neuraminidase.

Journal: The Journal of biological chemistry 20040924

Title: Saturation transfer difference (STD) 1H-NMR experiments and in silico docking experiments to probe the binding of N-acetylneuraminic acid and derivatives to Vibrio cholerae sialidase.

Journal: Proteins 20040801

Title: Localization of sialidase-positive cells expressing Mac-1 and immunoglobulin in the mouse thymus.

Journal: Glycoconjugate journal 20040101

Title: Investigation of neuraminidase-substrate recognition using molecular dynamics and free energy calculations.

Journal: Journal of medicinal chemistry 20031218

Title: Inhibition of influenza A virus sialidase activity by sulfatide.

Journal: FEBS letters 20031023

Title: Oxochromium(V) species formed with 2,3-dehydro-2-deoxy-N-acetylneuraminic or N-acetylneuraminic (sialic) acids: an in vitro model system of oxochromium(V) species potentially stabilized in the respiratory tract upon inhalation of carcinogenic chromium(VI) compounds.

Journal: Chemical research in toxicology 20030701

Title: The high resolution structures of free and inhibitor-bound Trypanosoma rangeli sialidase and its comparison with T. cruzi trans-sialidase.

Journal: Journal of molecular biology 20030124

Title: Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives.

Journal: Bioorganic & medicinal chemistry letters 20020805

Title: Synthesis and anti-influenza evaluation of polyvalent sialidase inhibitors bearing 4-guanidino-Neu5Ac2en derivatives.

Journal: Bioorganic & medicinal chemistry letters 20020805

Title: Computational 3-D modeling and site-directed mutation of an antibody that binds Neu2en5Ac, a transition state analogue of a sialic acid.

Journal: Proteins 20011201

Title: Thermal stability of the hemagglutinin-neuraminidase from Sendai virus evidences two folding domains.

Journal: FEBS letters 20010420

Title: Analysis of inhibitor binding in influenza virus neuraminidase.

Journal: Protein science : a publication of the Protein Society 20010401

Title: Inhibition of human parainfluenza virus type 1 sialidase by analogs of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid.

Journal: Glycoconjugate journal 20010401

Title: Synthesis of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid analogues modified at the C-4 and C-9 positions and their behaviour towards sialidase from influenza virus and pig liver membrane.

Journal: Carbohydrate research 20010115

Title: BCX-1812 (RWJ-270201): discovery of a novel, highly potent, orally active, and selective influenza neuraminidase inhibitor through structure-based drug design.

Journal: Journal of medicinal chemistry 20000921

Title: A novel approach to antiviral therapy for influenza.

Journal: The Journal of antimicrobial chemotherapy 19991101

Title: Potent inhibition of influenza sialidase by a benzoic acid containing a 2-pyrrolidinone substituent.

Journal: Journal of medicinal chemistry 19990701

Title: Dihydropyrancarboxamides related to zanamivir: a new series of inhibitors of influenza virus sialidases. 2. Crystallographic and molecular modeling study of complexes of 4-amino-4H-pyran-6-carboxamides and sialidase from influenza virus types A and B.

Journal: Journal of medicinal chemistry 19980312

Title: Design and synthesis of benzoic acid derivatives as influenza neuraminidase inhibitors using structure-based drug design.

Journal: Journal of medicinal chemistry 19971205

Title: A study of the active site of influenza virus sialidase: an approach to the rational design of novel anti-influenza drugs.

Journal: Journal of medicinal chemistry 19960119

Title: Structure-based inhibitors of influenza virus sialidase. A benzoic acid lead with novel interaction.

Journal: Journal of medicinal chemistry 19950818

Title: Structures of aromatic inhibitors of influenza virus neuraminidase.

Journal: Biochemistry 19950314

Title: 4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid is a highly effective inhibitor both of the sialidase (neuraminidase) and of growth of a wide range of influenza A and B viruses in vitro.

Journal: Antimicrobial agents and chemotherapy 19930701

Title: Rational design of potent sialidase-based inhibitors of influenza virus replication.

Journal: Nature 19930603

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Tags:24967-27-9 Molecular Formula|24967-27-9 MDL|24967-27-9 SMILES|24967-27-9 1,3-Dehydro-2-deoxy-N-acetylneuraminicacid