139110-70-6

Basic information

• Product Name: Zanamivir
• Synonyms: D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID, 5-(ACETYLAMINO)-4-[(AMINOIMINOMETHYL)AMINO]-2,6-ANHYDRO-3,4,5-TRIDEOXY-;D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID, 5-(ACETYLAMINO)-4-AMINO-2,6-ANHYDRO-3,4,5-TRIDEOXY-, METHYL ESTER, 7,8,9-TRIACETATE;Zanamivir Amine Triacetate Methyl Ester;5-(AcetylaMino)-4-aMino-2,6-anhydro-3,4,5-trideoxy-;5-(Acetylamino)-4-amino-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester 7,8,9-triacetate
• CAS NO: 139110-70-6
• Molecular Formula: C₁₈H₂₆N₂O₁₀
• Molecular Weight: 430.407
• Product Categories: Amines;Heterocycles;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 139110-70-6.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 554.841°C at 760 mmHg
• Flash Point: 289.358°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.518
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol, Water
• CAS DataBase Reference: Zanamivir(CAS DataBase Reference)
• NIST Chemistry Reference: Zanamivir(139110-70-6)
• EPA Substance Registry System: Zanamivir(139110-70-6)

Safety Data

• Hazardous Substances Data: 139110-70-6(Hazardous Substances Data)

Usage

Chemical Properties

Low Melting Yellow Solid

Uses

A synthetic precursor of Zanamivir (Z148000), as antiviral agents against influenza virus.

InChI:InChI=1/C18H26N2O10/c1-8(21)20-15-12(19)6-13(18(25)26-5)30-17(15)16(29-11(4)24)14(28-10(3)23)7-27-9(2)22/h6,12,14-17H,7,19H2,1-5H3,(H,20,21)/t12-,14+,15+,16+,17?/m0/s1

Upstream product

• 73960-72-2 methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 
• 1372800-41-3 N-((4R,5R,6R,7R)-6,7,8-tris(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)oct-1-en-4-yl)acetamide 
• 1372800-42-4 N-((3R,4R,5R,6R)-5,6,7-tris(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)-1-oxoheptan-3-yl)acetamide 
• 1372800-43-5 (5R,6R,7R,8R,E)-methyl 5-acetamido-7,8,9-tris(benzyloxy)-2,6-bis((tert-butyldimethylsilyl)oxy)non-2-enoate 
• 1372800-46-8 C₂₅H₂₉NO₁₂ 
• 1372800-32-2 (4S,5R,E)-1-((4-methoxybenzyl)oxy)-5-nitroocta-2,7-dien-4-ol 
• 1372800-34-4 tert-butyl ((4R,5S,E)-5-hydroxy-8-((4-methoxybenzyl)oxy)octa-1,6-dien-4-yl)carbamate 
• 1372800-35-5 (4R,5S)-tert-butyl 4-allyl-5-((E)-3-((4-methoxybenzyl)oxy)prop-1-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1372800-36-6 (4R,5S)-tert-butyl 4-allyl-5-((E)-3-hydroxyprop-1-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1372800-37-7 (4R,5R)-tert-butyl 4-allyl-5-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1372800-38-8 (4R,5R)-tert-butyl 4-allyl-2,2-dimethyl-5-((1R,2R)-1,2,3-trihydroxypropyl)oxazolidine-3-carboxylate 
• 1372800-39-9 (4R,5R)-tert-butyl 4-allyl-2,2-dimethyl-5-((1S,2R)-1,2,3-tris(benzyloxy)propyl)oxazolidine-3-carboxylate 
• 1372800-40-2 N-((4R,5R,6S,7R)-6,7,8-tris(benzyloxy)-5-hydroxyoct-1-en-4-yl)acetamide 
• 107020-87-1 methyl (5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-2,3,4,5-tetradeoxy-D-glycero-D-galacto-non-2-enpyranosyl)onate 

Downstream Products

• 392712-32-2 methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-(4'-hydroxyphenyl)acetamino-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate 
• 1236306-91-4 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-(2-nitrobenzenesulfonamido)-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester 
• 1304780-13-9 methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-[2-(4-fluorophenyl)-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonate 
• 1304780-11-7 methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-[2-cyclohexenyl-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonate 
• 1228216-82-7 methyl 5-acetamido-4-cyanamido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate 
• 139110-80-8 zanamivir 

Relevant articles and documents

The synthesis of 2,3-didehydro-2,4-dideoxy-4-guanidinyl-N- acetylneuraminic acid: A potent influenza virus sialidase inhibitor

The synthesis of a number of 5-acetamido-2,6-anhydro-3,5-dideoxy-D-galacto-non-2-enonic acid (Neu5Ac2en, 1) analogues has received considerable attention over the past decade. We have recently reported the design and biological evaluation of 5-acetamido-4-amino-2,6-anhydro-3,4,5-trideoxy-D-glucero-D-galacto-no n-2- enonic acid (4-amino-Neu5Ac2en, 2) and 5-acetomido-2,6-anhydro-4-guanidino- 3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid (4-guanidino-Neu5Ac2en, 3) as influenza virus sialidase inhibitors. The synthetic strategy that we adopted for the preparation of 3 required the introduction of nitrogen at C-4 of 1.

SMALL MOLECULE LIGAND-TARGETED DRUG CONJUGATES FOR ANTI-INFLUENZA CHEMOTHERAPY AND IMMUNOTHERAPY

Disclosed herein is a small molecule targeted drug conjugate for anti-influenza chemotherapy and immunotherapy. The disclosed drug conjugate may form an adaptor to recruit additional CAR T cells or other immune cells for precise elimination of influenza virus-infected cells in a subject. Concurrently administered antibodies or pre-existing immunity in influenza-virus infected subject works well with the targeted conjugate to eliminate virus infected cells, saving valuable time for rescuing late stage patients.

Synthesis of novel pentacyclic triterpene-Neu5Ac2en derivatives and investigation of their: In vitro anti-influenza entry activity

Sialic acid derivatives, analogs, and their conjugates are important pharmacophores. Modification of the C-4 hydroxyl group of sialic acid can lead to derivatives, such as zanamivir, with potent anti-influenza activities. Herein, we described the synthesis of C-4-modified sialic acid derivatives via conjugation with naturally derived pentacyclic triterpenes, which are active ingredients of traditional Chinese medicine, and the evaluation of their in vitro anti-influenza virus activity in MDCK cells. Interestingly, a set of configurational isomers was obtained during the de-O-acetylation reaction of two pentacyclic triterpene-sialic acid conjugates under Zemplén conditions, and a mechanism was proposed. Owing to the attachment of the Neu5Ac2en moiety, all synthesized conjugates displayed lower hydrophobicity than their parent compounds. In comparison with ursane- and lupane-type triterpenes, oleanane-type triterpene-functionalized Neu5Ac2en conjugates were most promising. The insertion of a (1,2,3-triazol-4-yl)-methyl between the amide bond and Neu5Ac2en caused a substantial decrease in activity. Compound 15a exhibited the highest inhibitory activity (IC50 = 8.3 μM) and selectivity index (SI = 22.7). Further studies involving hemagglutination inhibition and neuraminidase inhibition suggested that compound 15a inhibited virus-induced hemagglutination with no effect on the enzymatic activity of neuraminidase, indicating that the antiviral activity appeared to be mediated via interaction with hemagglutinin at the initial stage of viral infection.