133524-69-3

Basic information

• Product Name: N-Deboc-Docetaxel
• Synonyms: N-Deboc-Docetaxel;N-DesBoc Docetaxel;10-Desacetyl-N-debenzoylpaclitaxel;N-De(tert-butoxycarbonyl)-10-deacetyldocetaxel;N-Debenzoyl-10-deacetylpaclitaxel
• CAS NO: 133524-69-3
• Molecular Formula: C₃₈H₄₅NO₁₂
• Molecular Weight: 707.76
• Mol File: 133524-69-3.mol

Chemical Properties

• Boiling Point: 846.0±65.0 °C(Predicted)
• Appearance: /
• Density: 1.41±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 10.19±0.45(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: N-Deboc-Docetaxel(CAS DataBase Reference)
• NIST Chemistry Reference: N-Deboc-Docetaxel(133524-69-3)
• EPA Substance Registry System: N-Deboc-Docetaxel(133524-69-3)

Safety Data

• Hazardous Substances Data: 133524-69-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Deboc-Docetaxel is used as an impurity in the synthesis of Docetaxel for its antimitotic properties. It contributes to the development of Docetaxel, which is an antineoplastic agent used in the treatment of various types of cancer.

Upstream product

• 95603-45-5 7,10-di(2,2,2-trichloroethyloxy-carbonyl)-13-cinnamoyl-10-deacetyl baccatin III 
• 114915-20-7 Docetaxel 
• 850933-54-9 13-(3'-N-benzyloxycarbonylphenylisoserine)-10-deacetyl-7,10-dibenzyloxycarbonylbaccatin III 
• 159262-93-8 10-deacetylbaccatin III-13-O-[(4S,5R)-4-phenyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate] 
• 194864-02-3 C-7,C-10-dibenzyloxycarbonyl-10-deacetyl baccatin III 
• 132201-32-2 (2R,3S)-3-phenylisoserine hydrochloride 
• 157240-36-3 (2R,3S)-3-phenylisoserine methyl ester 
• 158810-74-3 (-)-(2R,3S)-methyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate 
• 195141-96-9 2'-(tert-butyldimethylsilyl)-7,10-di(triethylsilyl)docetaxel 
• 342613-14-3 2'-O-(tert-butyldimethylsilyl)docetaxel 
• 124605-42-1 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate 
• 32981-86-5 10-deacetylbaccatin III 
• 95603-44-4 7,10-di-(2,2,2-trichloroethyloxycarbonyl)-10-deacetylbaccatin III 
• 143615-03-6 (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid 

Downstream Products

• 114915-20-7 C₄₃H₅₃NO₁₄ 
• 78432-77-6 10-deacetyltaxol 
• 133524-71-7 C₄₃H₅₁NO₁₅ 
• 114915-20-7 Docetaxel 
• 940867-25-4 d₉-docetaxel 
• 1383561-40-7 d₉-docetaxel-2'-O-alaninate 
• 154044-50-5 N-de-tert-butoxycarbonyl-N-[2-(1,1,1-trifluoro-2-methyl)-propyloxycarbonyl]docetaxel 

Relevant articles and documents

Design and synthesis of taxane derivatives of valproic acid as potent and selective cytotoxic agents

Resistance to anticancer agents has important implications for cancer chemotherapy. Small changes in chemical structures of cytotoxic agents can alter their biological interactions that can be beneficial in overcoming the drug resistance problem. Valproic acid, a well-known antiepileptic drug is in advanced clinical studies for cancer treatment. In the present study, valproic acid was incorporated into the taxane moiety at various positions and the new analogs were evaluated for their in vitro cytotoxicity. The novel analog, Valprotaxel showed comparable cytotoxicity in head and neck, and colon cancer cell lines with remarkable improvement in selectivity for cancer cells compared to paclitaxel and docetaxel.

FLUORESCENT RHODAMINE DYES WITH ENHANCED CELL PERMEABILITY

The invention relates to novel fluorescent rhodamine dyes with enhanced cell permeability which are rhodamine 4′-isomers having the following general structural formula A: wherein Z is selected from O(alkyl), O(aryl), S(aryl), S(O)(alkyl), S(O)(aryl), S(O)2(alkyl), S(O)2(aryl), S(O)2(-O-alkyl), S(O)2(-O-aryl), S(O)2NH(alkyl), S(O)2NH(aryl), S(O)2N(alkyl)2, S(O)2N(aryl)2, S(O)2N(alkyl)(aryl), C(O)O(alkyl), C(O)O(aryl), C(O)(alkyl), C(O)(aryl), P(O)OH(-NH-alkyl), P(O)OH(-O-alkyl), P(O)OH(-NH-aryl), P(O)OH(-O- aryl), P(O)(-O-alkyl)2, P(O)(-NH-alkyl)2, P(O)OH(-N(alkyl)2), P(O)OH(-N(aryl)2), P(O)(-N(aryl)2)2, P(O) (-N(alkyl)2)(-N(alkyl)2), P(O)(-O-aryl)2, P(O)(-NH-aryl)2, P(O)(-O-alkyl)(-O-aryl), P(O)(-NH-alkyl)(-O-aryl), P(O)(- O-alkyl)(-NH-aryl), P(O)(-NH-alkyl)(-NH-aryl), C(O)OH, C(O)NH(alkyl), C(O)NH(aryl), CON(alkyl)2, CON(aryl)2, in particular C(O)OH, C(O)NH(alkyl), C(O)NH(aryl), CON(alkyl)2, CON(aryl)2, C(O)O(alkyl) and C(O)O(aryl), or any group which is neither Cl, NH2 or NO2 and which induces a neighboring group effect via steric, ionic or bonding interactions with the adjacent carboxyl group resulting in a shift of the equilibrium between zwitterionic form and spirolactone form towards the spirolactone form. The invention further relates to 4′-isomer derivatives and probes comprising such 4′-isomers coupled to at least one reactive group or ligand which is capable to interact with or bind to other molecules, wherein said reactive group or ligand may be coupled to the rhodamine 4′-isomer fluorophore either directly or via a linker. Another aspect of the invention relates to the use of these compounds and conjugates as labels in microscopic, spectroscopic and other imaging techniques and/or as cell permeable substances penetrating through membranes of living and fixed cells in vivo or in vitro.

Azoacetylenes for the Synthesis of Arylazotriazole Photoswitches

We report a modular approach toward novel arylazotriazole photoswitches and their photophysical characterization. Addition of lithiated TIPS-acetylene to aryldiazonium tetrafluoroborate salts gives a wide range of azoacetylenes, constituting an underexplored class of stable intermediates.In situdesilylation transiently leads to terminal arylazoacetylenes that undergo copper-catalyzed cycloadditions (CuAAC) with a diverse collection of organoazides. These include complex molecules derived from natural products or drugs, such as colchicine, taxol, tamiflu, and arachidonic acid. The arylazotriazoles display near-quantitative photoisomerization and long thermalZ-half-lives. Using the method, we introduce for the first time the design and synthesis of a diacetylene platform. It permits implementation of consecutive and diversity-oriented approaches linking two different conjugants to independently addressable acetylenes within a common photoswitchable azotriazole. This is showcased in the synthesis of several photoswitchable conjugates, with potential applications as photoPROTACs and biotin conjugates.

SILICON-SUBSTITUTED RHODAMINE DYES AND DYE CONJUGATES

Silicon-substituted rhodamine compounds are disclosed herein. Also described herein are SiR dyes comprising at least one vinyl group attached to the Si atom (10 position) of the SiR dye. Derivatives, functionalized versions, conjugates, kits, related synthetic methods and uses of SiR compounds also are provided. Silicon-rhodamine (SiR) dyes can provide bright fluorescence at far red wavelengths and exhibit good photostability. The compounds described herein can be useful for fluorescent labeling and detection of biological samples.

NOVEL TUNABLE PHOTOACTIVATABLE SILICON RHODAMINE FLUOROPHORES

The invention relates to a compound characterized by general formula (100), wherein R1 and R6 are H or F, R2, R3, R4 and R5 can be any substituent, R7, R8, RN1/s

Synthesis, cytotoxic activity and binding model analysis of novel isoxazole-docetaxel analogues with C3′-N modification

Structure–activity relationship (SAR) studies confirm that modifications at C-3′ position can lead to the development of highly potent novel taxoids. We designed and synthesized a series of novel isoxazole-docetaxel analogues A1–A5 by introducing isoxazol

Novel taxane anti-tumor compound as well as synthesis method and application thereof

The invention discloses a novel taxane anti-tumor compound shown in a structural formula (I). 10-DAB (10-deacetylbaccatin) is adopted as a raw material, and is condensed with phenylisoserine (side chain) with protected 3'-NH2 and 2'-OH in the presence of condensing agents DCC and DMAP after 7-OH and 10-OH are protected, the side chain and a protecting group on a baccatin ring are simultaneously removed in the presence of zinc powder, and coupling is performed with substituted phenylisoxazole in an alkaline medium to obtain a target product. The compound has relatively high anti-tumor activity. (The structural formula (I) is shown in the description.).

MULTI-ARM POLYMERIC PRODRUG CONJUGATES OF TAXANE-BASED COMPOUNDS

Among other aspects, provided herein are multi-arm polymeric prodrug conjugates of taxane-based compounds and/or fluorinated forms thereof. Methods of preparing such conjugates as well as methods of administering the conjugates are also provided. Upon administration to a patient, release of the taxane-based compound is achieved.

PRODRUG COMPOSITIONS, PRODRUG NANOPARTICLES, AND METHODS OF USE THEREOF

The present invention encompasses prodrug compositions, nanoparticles comprising one or more prodrugs, and methods of use thereof.

DEUTERATED AND/OR FLUORINATED TAXANE DERIVATIVES

The invention relates to (among other things) deuterated and/or fluorinated docetaxel and cabazitaxel and derivatives thereof, as well as compositions comprising each of the foregoing.