148579-93-5

Basic information

• Product Name: 4-ForMyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate
• Synonyms: 4-ForMyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate;MHAQOFAFDHVKQE-UHFFFAOYSA-N
• CAS NO: 148579-93-5
• Molecular Formula: C₂₀H₂₁NO₁₃
• Molecular Weight: 483.37964
• Product Categories: Aromatics, Carbohydrates & Derivatives
• Mol File: 148579-93-5.mol
• Article Data: 31

Chemical Properties

• Melting Point: 180-182 °C
• Boiling Point: 582.6±50.0 °C(Predicted)
• Appearance: /
• Density: 1.44±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 4-ForMyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ForMyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate(148579-93-5)
• EPA Substance Registry System: 4-ForMyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate(148579-93-5)

Safety Data

• Hazardous Substances Data: 148579-93-5(Hazardous Substances Data)

Usage

Description

4-ForMyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate is a complex organic compound that serves as an essential intermediate in the synthesis of various pharmaceutical agents. It is characterized by its unique chemical structure, which includes a nitrophenyl group, a glucopyranosiduronic acid moiety, and a methyl ester functional group. The compound's structure allows it to be a versatile building block in the development of novel therapeutics, particularly in the field of cancer treatment.

Uses

Used in Pharmaceutical Industry:
4-ForMyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate is used as a key intermediate in the synthesis of Camptothecin-based anticancer therapy. Camptothecin is a potent chemotherapeutic agent that has demonstrated significant efficacy against various types of cancer, including colorectal, ovarian, and lung cancer. The compound's unique structure enables the development of Camptothecin analogs with improved pharmacological properties, such as enhanced solubility, stability, and bioavailability.
In the synthesis of Camptothecin-based anticancer therapy, 4-ForMyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate plays a crucial role in the formation of the final therapeutic agent. Its chemical reactivity allows for the introduction of various functional groups and modifications, which can lead to the development of more effective and targeted cancer treatments. By utilizing this compound as a starting material, researchers can explore new strategies for the design and synthesis of novel anticancer drugs, potentially improving patient outcomes and overall survival rates.

Upstream product

• 3011-34-5 4-hydroxy-3-nitrobenzaldehyde 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 57820-69-6 (3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 63-29-6 D-glucurono-6,3-lactone 
• 6919-98-8 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranuronic acid methy ester 
• 90151-04-5 4-hydroxy-2-nitrobenzaldehyde 
• 3082-96-0 methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate 
• 3082-95-9 2,3,4-Tri-O-acetyl-β-D-glucopyranuronic acid methylester 

Downstream Products

• 148579-94-6 (25,3R,45,55,65)-2-(4-(hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 866611-70-3 methyl 1-(4-(2-bromoethylcarbamoyloxymethyl)-2-nitrophenyl)-β-D-glucopyronuronate 
• 870701-97-6 methyl 1-(4-(2-hydroxyethylcarbamoyloxymethyl)-2-nitrophenyl)-β-D-glucopyronuronate 
• 866611-65-6 (2S,3R,4S,5S,6S)-2-(4-(((1H-imidazole-1-carbonyl)oxy)methyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 866611-67-8 methyl 1-(4-(2-bromoethylcarbamoyloxymethyl)-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyronuronate 
• 870701-96-5 methyl 1-(4-(2-hydroxyethylcarbamoyloxymethyl)-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyronuronate 
• 866611-74-7 methyl 1-(4-(2-(1-(1,4,7,10-tetraazacyclododecyl))ethylcarbamoyloxymethyl)-2-nitrophenyl)-β-D-glucopyronuronate 
• 1053628-49-1 (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-hydroxymethyl-2-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid 
• 637330-32-6 methyl [2-nitro-4-(hydroxymethyl)phenyl-β-D-glucopyranosid]uronate 
• 637330-34-8 methyl [2-nitro-4-(O-tert-butyldiphenylsilylmethyl)phenyl-β-D-glucopyranosid]uronate 
• 637330-37-1 benzyl [(2-nitro-4-hydroxymethylphenyl)-2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosid]uronate 
• 637330-35-9 methyl {[2-nitro-4-(O-tert-butyldiphenylsilylmethyl)phenyl]-2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosid}uronate 
• 637330-38-2 benzyl [(2-nitro-4-(4-nitrophenoxycarbonyloxymethyl)phenoxy)-2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosid]uronate 
• 637330-41-7 N,N'-dimethyl-N-benzyl-[4-(2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)uronate-3-nitrobenzoyloxycarbonyl]ethylenediamine carbamoyl chloride 

Relevant articles and documents

Design, synthesis and in vitro evaluation of β-glucuronidase-sensitive prodrug of 5-aminolevulinic acid for photodiagnosis of breast cancer cells

Treatment of cancer cells by clinically approved hexyl ester of 5-aminolevulinic acid (ALA-Hex) induces accumulation of fluorescent porphyrins in tumors. This allows fluorescence photodiagnosis (PD) of bladder cancer by blue light illumination. However, PD of other cancers is hampered by acute toxicity of the compound limiting its use to local applications. We have designed and synthesized a new prodrug of ALA-Hex that tackles the stability-activity paradox of amino-modified 5-ALA prodrugs. The glucuronide prodrug Glu-ALA-Hex demonstrates excellent stability under physiological conditions and activation in the presence of the target enzyme. β-glucuronidase-triggered release of 5-ALA is programmed to yield fluorescence in tumor environment with elevated β-glucuronidase activity, a characteristic of many solid tumors. Glu-ALA-Hex produces similar levels of fluorescence as ALA-Hex in breast cancer MCF7 cells in vitro but with much lower non-specific cell toxicity.

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