79528-49-7

Basic information

• Product Name: Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside 3,4,6-triacetate
• Synonyms: Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside 3,4,6-triacetate
• CAS NO: 79528-49-7
• Molecular Weight: 527.552
• Mol File: 79528-49-7.mol
• Article Data: 29

Chemical Properties

• CAS DataBase Reference: Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside 3,4,6-triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside 3,4,6-triacetate(79528-49-7)
• EPA Substance Registry System: Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside 3,4,6-triacetate(79528-49-7)

Safety Data

• Hazardous Substances Data: 79528-49-7(Hazardous Substances Data)

Usage

General Description

Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside 3,4,6-triacetate is a complex chemical compound composed of a phenyl group attached to a glucopyranoside molecule. The presence of a thio group and multiple acetate groups make this compound highly reactive and potentially useful in a variety of chemical reactions. The isoindol-2-yl group adds further complexity and potential biological activity to the molecule. Overall, this compound is likely to have a range of interesting properties and applications in the fields of chemistry and biochemistry.

Upstream product

• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 4551-15-9 phenylthiotrimethylsilane 
• 17314-33-9 tributyltin phenyl sulfide 
• 136882-36-5 2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione 
• 75-36-5 acetyl chloride 
• 66-84-2 D-(+)-glucosamine hydrochloride 
• 85-44-9 phthalic anhydride 
• 1449790-68-4 phenyl 3,4-di-O-acetyl-2-deoxy-2-phthalimido-6-O-(N-phenylcarbamoyl)-1-thio-β-D-glucopyranoside 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-phthalimido-2-deoxy-α-D-glucopyranose 
• 108-98-5 thiophenol 
• 31505-45-0 2-deoxy-2-phthalimido-β-D-glucopyranose 
• 14131-63-6 D-glucosamine hydrochloride 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 31505-45-0 2-deoxy-2-phthalimido-D-glucopyranose 

Downstream Products

• 890016-25-8 benzyl [(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)]-(1->6)-3-[4-(2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-galactopyranosyl)]-2-deoxy-2-acetamido-α-D-galactopyranoside 
• 871111-40-9 phenyl 3-O-acetyl-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 371123-22-7 phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside 
• 225242-46-6 phenyl 3,4-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 

Relevant articles and documents

BIFUNCTIONAL COMPOUND AND ITS USE IN IMMUNOTHERAPY

The invention relates to a bifunctional compound that is, on one side, an agonist of the TLR4 and, on the other side, an important inhibitor of the PSMA. Said compound is useful in immunotherapy for the treatment and/or prevention of prostate cancer. Therefore, the invention also relates to the use of the compound and to the pharmaceutical composition comprising it.

Chemoenzymatic Synthesis of Glycoconjugates Mediated by Regioselective Enzymatic Hydrolysis of Acetylated 2-Amino Pyranose Derivatives

Highly regioselective deprotection of a series of 2-amino pyranose building blocks was achieved by enzymatic hydrolysis. These monodeprotected intermediates were successfully used in the synthesis of a variety of glycoconjugate derivatives with a core of glucosamine or galactosamine, including neo-glycoproteins and glycosphingolipids. The hydrolysis catalyzed by acetylxylan esterase from Bacillus pumilus (AXE) is suitable for the synthesis of neo-glycoproteins with an N-acetyl glucosamine core. The hydrolysis catalyzed by Candida rugosa lipase (CRL) was successfully applied in the preparation of new sialylated glycolipids starting from glucosamine building blocks protected as phthalimide. This chemoenzymatic approach can be used for the preparation of new glycoconjugate products with anticancer activity.

Design, synthesis and evaluation of cytotoxic properties of bisamino glucosylated antitumor ether lipids against cancer cells and cancer stem cells

Glycosylated antitumor ether lipids (GAELs) are a class of amphiphilic antitumor agents that kill cancer cells by a non-apoptotic pathway. Previous studies have shown that 2-amino-2-deoxy-d-gluco-based GAELs such as α-GLN and β-GLN show greatly improved antitumor activity against epithelial cancer cells and stem cells. To further optimize the bioactivity, we prepared a series of diamino-d-gluco-based GAELs and their analogs, and screened them against a panel of human epithelial cancer cell lines and cancer stem cells. Most of the new GAEL analogs are more potent than chlorambucil, cisplatin and salinomycin. The most potent bisamine-based GAEL analogs 1, 2, 4 and 8 showed 2- to 3-fold enhanced cytotoxicity against various cancer cell lines when compared to β-GLN, indicating that the addition of a second amino group enhances the cytotoxic effect. The effect of the most active dicationic GAELs 1 and 4 on cancer stem cells isolated from breast (BT-474) and prostate (DU-145) cell lines revealed that the two GAELs inhibited the formation of tumor spheres and resulted in >95% loss of viability of the cancer stem cells at 5 μM. Activity of GAEL 1 against BT-474 cancer stem cells is superior to that of salinomycin.