153695-19-3

Usage

Chemical Structure

Synthetic derivative of taxol
Azide group linked to the 3'-position of the benzoylphenylisoserine side chain

Purpose

Used in chemotherapy
Employed in targeted drug delivery systems
Utilized in biological studies

Key Features

Contains an azide group
Allows for bioorthogonal labeling
Facilitates conjugation to other molecules

Applications

Medicinal chemistry
Cancer research

Significance

Versatile tool for drug development
Valuable for biological studies
Offers potential therapeutic applications

Upstream product

• 53053-08-0 4-azidobenzoic acid N-hydroxysuccinimide ester 
• 133524-70-6 13-(O-2R-hydroxy-3S-amine-phenylpropionyl)-baccatin III 
• 14848-01-2 4-azidobenzoyl chloride 
• 326923-28-8 (3R,4S)-1-(4-Azido-benzoyl)-4-phenyl-3-triisopropylsilanyloxy-azetidin-2-one 
• 6427-66-3 4-azidobenzoic acid 
• 160237-83-2 7-(triethylsilyl)baccatin III 13--(2'R,3'S)-3'-phenylisoserinate> 
• 155399-27-2 7-(triethylsilyl)baccatin III 13- 
• 155399-25-0 (3R,4S)-1-(benzyloxycarbonyl)-3-<(tert-butyldimethylsilyl)oxy>-4-phenyl-2-azetidinone 
• 132127-30-1 (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one 
• 132127-31-2 (3R,4S)-3-triisopropylsilyloxy-4-phenylazetidin-2-one 
• 326923-31-3 C₆₂H₈₄N₄O₁₄Si₂ 

Relevant academic research and scientific papers

Characterization of Two Taxol Photoaffinity Analogues Bearing Azide and Benzophenone-Related Photoreactive Substituents in the A-Ring Side Chain

Taxol is a structurally novel and clinically effective antitumor drug, which, unlike other antimitotic agents, induces the assembly of tubulin into microtubules.To characterize the binding site(s) of taxol on the microtubule, taxol-based photoaffinity rea

Synthesis of taxol, analogs and intermediates with variable A-nng side chains

An efficient protocol for the synthesis of taxol, taxol analogs, and their intermediates is described. The process includes the attachment of the taxol A-ring side chain to baccatin III and for the synthesis of taxol and taxol analogs with variable A-ring side chain structures. A rapid and highly efficient esterification of O-protected isoserine and 3-phenylisoserine acids having N-benzyoloxycarbonyl groups to the C-13 hydroxyl of 7-O-protected baccatin III is followed by a deprotection-acylation sequence to make taxol, calphalomanninne and various analogs, including photoaffinity labeling candidates.

Direct, efficient and selective tritiations of paclitaxel and photoaffinity taxoids

Radiolabeled paclitaxel and three photophore-bearing derivatives were prepared by organoiridium-mediated direct tritium exchange under both catalytic and stoichiometric conditions. The resulting tritiated taxoids had specific activities ranging from 53 to 195 Ci/mmol. (C) 2000 Elsevier Science Ltd.

Synthesis of a photoaffinity taxol analogue and its use in labeling tubulin

A photoaffinity analogue of taxol, N-([3,5-3H]-4-azidobenzoyl)-N- debenzoyltaxol (7), was synthesized and used to photolabel microtubules. Approximately 20% of the noncovalently bound analogue becomes covalently bound upon irradiation at 300 nm. Incorporated label was stable to a 50% ethanol solution and sodium dodecyl sulfate. About 80% of the incorporated label was found in the β-subunit and 20% in the α-subunit. Incorporation did not occur into unpolymerized tubulin, consistent with the fact that taxol binds only to polymerized tubulin, and was decreased by the presence of taxol. Little or no nonspecific labeling occurs. This analogue is currently being used to identify taxol binding site(s) on tubulin.