115437-21-3

Usage

Uses

Used in Pharmaceutical Industry:
7-O-(TRIETHYLSILYL) BACCATIN III is used as a key precursor in the production of Paclitaxel for its application in cancer treatment. 7-O-(TRIETHYLSILYL) BACCATIN III plays a crucial role in the synthesis process, enabling the development of an effective chemotherapeutic agent that targets various types of cancer.
As a precursor to Paclitaxel, 7-O-(TRIETHYLSILYL) BACCATIN III is instrumental in the creation of a drug that has been widely used to treat different forms of cancer, including ovarian, breast, and lung cancer. Its significance in the pharmaceutical industry lies in its contribution to the development of life-saving medications.

Upstream product

• 115437-18-8 7-triethylsilyl-10-deacetylbaccatin III 
• 75-36-5 acetyl chloride 
• 150665-56-8 7-O-triethylsilyl-13-keto baccatin III 
• 150541-99-4 7,13-O,O-Bis(triethylsilyl)baccatin III 
• 175982-36-2 (4S,4aS,6R,9S,11S,12S,12aR)-11,12-(Carbonyldioxy)-4a,8,13,13-tetramethyl-1-methylene-5-oxo-4,9-bis(triethylsiloxy)-1,2,3,4,4a,5,6,9,10,11,12,12a-dodecahydro-7,11-methanobenzocyclodecen-6-yl acetate 
• 175982-38-4 (2S,4S,4aS,6R,9S,11S,12S,12aS)-2-Bromo-11,12-(carbonyldioxy)-4a,8,13,13-tetramethyl-1-methylene-5-oxo-4,9-bis(triethylsiloxy)-1,2,3,4,4a,5,6,9,10,11,12,12a-dodecahydro-7,11-methanobenzocyclodecen-6-yl acetate 
• 175982-37-3 (4S,4aS,6R,9S,11S,12S,12aS)-1-Bromomethyl-11,12-(carbonyldioxy)-4a,8,13,13-tetramethyl-5-oxo-4,9-bis(triethylsiloxy)-3,4,4a,5,6,9,10,11,12,12a-decahydro-7,11-methanobenzocyclodecen-6-yl acetate 
• 175982-40-8 1,2-O,O-Carbonyl-7,13-O,O-bis(triethylsilyl)-4-deacetyl-2-debenzoylbaccatin III 
• 175982-39-5 (1S,2S,4S,4aS,6R,9S,11S,12S,12aR)-2-Bromo-11,12-(carbonyldioxy)-1-hydroxy-1-hydroxymethyl-4a,8,13,13-tetramethyl-5-oxo-4,9-bis(triethylsiloxy)-1,2,3,4,4a,5,6,9,10,11,12,12a-dodecahydro-7,11-methanobenzocyclodecen-6-yl acetate 
• 175982-31-7 1,2-O,O-Carbonyl-7,13-O,O-bis(triethylsilyl)-2-debenzoylbaccatin III 
• 178626-24-9 2-bromo-5-(triethylsilyloxy)pentene 
• 150542-00-0 2-Debenzoyl-7,13-bis(triethylsilyl)baccatin III 
• 172481-24-2 7-(triethylsilyl)-13-(trifluoromethanesulfonyl)baccatin III 
• 135365-62-7 1-hydroxy-7β-triethylsilyloxy-9-oxo-10β-acetyloxy-5β,20-epoxytax-11-ene-2α,4,13α-triyl 4-acetate 2-benzoate 13-[(2R,3S)-3-benzoylamino-2-triethylsilyloxy-3-phenylpropanoate] 

Downstream Products

• 155588-18-4 C₄₁H₅₄N₂O₁₁SSi 
• 160237-83-2 7-(triethylsilyl)baccatin III 13--(2'R,3'S)-3'-phenylisoserinate> 
• 160239-19-0 7-O-(triethylsilyl)baccatrin III 13-O-<(2R,3S)-N-benzoyl-2-O-(tert-butyldimethylsilyl)-3-cyclohexylisoserinate> 
• 172481-24-2 7-(triethylsilyl)-13-(trifluoromethanesulfonyl)baccatin III 
• 175441-47-1 C₄₂H₆₆O₁₁Si₃ 
• 189190-72-5 13-β-chloro-7-(triethylsilyl)-A-nor-baccatin III 
• 214605-46-6 C₅₄H₆₅NO₁₄Si 
• 253327-59-2 C₅₃H₆₂INO₁₃Si 
• 253327-56-9 C₅₉H₇₈INO₁₄Si₂ 
• 326923-31-3 C₆₂H₈₄N₄O₁₄Si₂ 
• 326923-32-4 C₆₉H₈₉NO₁₅Si₂ 
• 326923-34-6 C₆₄H₈₄F₃N₃O₁₄Si₂ 
• 534572-18-4 (7-TES-baccatin III)-13-yl (5R)-2-phenylspiro[cyclopropane-1',4-oxazoline]-5-carboxylate 
• 534572-16-2 (7-TES-baccatin III)-13-yl (5S)-2-phenylspiro[cyclopropane-1',4-oxazoline]-5-carboxylate 

Relevant academic research and scientific papers

A chemoselective approach to functionalize the C-10 position of 10- deacetylbaccatin III. Synthesis and biological properties of novel C-10 Taxol analogues

A chemoselective approach to functionalize the C-10 position of 10- deacetyl baccatin III, a key intermediate for the semi-synthesis of paclitaxel, is described. The chemistry provides an easy access to a variety of C-10 hydroxyl derivatives, such as, eth

Total Synthesis of Paclitaxel

The total synthesis of paclitaxel (Taxol) is described. Double Rubottom oxidation of the bis(silyl enol ether) derived from a tricarbocyclic diketone effectively installed a bridgehead olefin and C-5/C-13 hydroxy groups in a one-step operation. The novel Ag-promoted oxetane formation smoothly constructed the tetracyclic framework of paclitaxel.

Fluorinated taxane compound, preparation method therefor and application of fluorinated taxane compound

The invention discloses a fluorinated taxane compound, a preparation method therefor and an application of the fluorinated taxane compound. The compound has a structural general formula represented bya formula I. Proven by pharmacological experiments, compared with paclitaxel, a series of fluorinated taxane derivatives synthesized by the method have cytotoxicity superior to that of the paclitaxelto a multidrug-resistant human mammary cancer cell line MCF-7/Adr and an ovarian cancer cell line NCI/Adr and represent cytotoxicity superior to that of the paclitaxel to a colon cancer cell line HCT-116 with overexpressed neoplasm stem cells.

Novel crystalline forms of anticancer compound CX1409 and preparation method and application of novel crystalline forms of anticancer compound CX1409

The invention relates to the field of compounds, in particular to two novel crystalline forms of an anticancer compound CX1409. A crystalline form A of the anticancer compound CX1409 is determined byusing a powder X-ray diffraction method, wherein characteristic diffraction peaks are shown at 4.3 degree, 8.7 degree, 11.0 degree, 12.5 degree, 13.0 degree, 14.1 degree, 15.4 degree, 17.4 degree, 18.4 degree, 19.6 degree, 20.1 degree, 20.8 degree, 21.7 degree, 27.0 degree, 29.0 degree, 30.6 degree and 31.4 degree in an X-ray powder diffraction spectrum expressed by a diffraction angle of 2 theta+/-0.3 degree; a crystalline form B of the anticancer compound CX1409 is determined by using the powder X-ray diffraction method, wherein characteristic diffraction peaks are shown at 4.9 degree, 5.4degree, 5.8 degree, 6.4 degree, 8.0 degree, 9.4 degree and 12.9 degree in an X-ray powder diffraction spectrum expressed by a diffraction angle of 2 theta +/-0.3 degree. The above two crystalline forms are not reported, outlines of the two crystalline forms are clear, and the two crystalline forms can be perfectly reproduced; besides, the two crystalline forms have the advantages of being good instability of preparation and high in yield and purity, can be applied to anti-tumor drugs, and have wide application prospects.

Anticancer compound CX1409 dihydrate and DMSO solvate of the new crystal and its preparation method and application (by machine translation)

The invention relates to the field of compound, in particular to anti-cancer compounds CX1409 of the dihydrate and DMSO solvate of the two new crystalline form, wherein the anticancer compound CX1409 dihydrate crystalline forms of powder X-ray diffraction for C assay measuring, in order to 2 θ ± 0.3 ° diffraction of said X-ray powder diffraction spectrum in the 5.0 °, 5 . 8°, 10 . 4°, 12 . 8°, 13 . 6°, 15 . 2°, 18 . 6°, 20 . 0°, 20 . 7°, 21 . 6°, 22 . 1° and 22.8 ° for display at the feature diffraction peak. Anticancer compound CX1409 of DMSO solvate crystalline forms of powder X-ray diffraction for D assay measuring, in order to 2 θ ± 0.3 ° diffraction of said X-ray powder diffraction spectrum in the 8.1 °, 8 . 6°, 11 . 1°, 11 . 4°, 12 . 4°, 13 . 0°, 13 . 8°, 14 . 2°, 14 . 8°, 15 . 3°, 15 . 8°, 17 . 2°, 18 . 0°, 18 . 2°, 19 . 7°, 20 . 0° and 22.3 ° for display at the feature diffraction peak. The above two kinds of crystalline form has not been reported, the contours thereof are clear, and can be perfectly reproducing, and has good stability, high yield, purity is high, can be used as the use of the antineoplastic, it has broad application prospects. (by machine translation)

Antagonizing NOD2 Signaling with Conjugates of Paclitaxel and Muramyl Dipeptide Derivatives Sensitizes Paclitaxel Therapy and Significantly Prevents Tumor Metastasis

A noncleavable paclitaxel (PTX) and N-acetylmuramyl-l-alanyl-d-isoglutamine (MDP) derivative conjugate, 22 (DY-16-43), and its analogues were prepared and characterized as antagonists of NOD2 signaling. This conjugate enhanced the antitumor and antimetastatic efficacy of PTX in Lewis lung carcinoma (LLC) tumor-bearing mice. This work first describes a molecular strategy that enables the sensitization of a chemotherapeutic response via antagonizing NOD2 inflammatory signaling and suggests NOD2 antagonist as potential adjunct in treating non-small-cell lung cancer (NSCLC).

Methods for preparing semi-synthetic paclitaxel and intermediate thereof

The invention relates to methods for preparing semi-synthetic paclitaxel and an intermediate thereof. The method for preparing the semi-synthetic paclitaxel comprises the following steps: dissolving 10-DABIII (10-deacetylbaccatinIII) into pyridine, protecting hydroxyl on position-7 carbon on the 10-DABIII with triethyl silicyl to obtain an intermediate I, acetylating hydroxyl on position-10 carbon of the intermediate I to obtain an intermediate II, reacting the intermediate II, a side-chain radical compound and 4-dimethylaminopyridine in an organic solvent to prepare an intermediate III, and reacting the intermediate III with trifluoroacetic acid under an acidic condition to obtain a crude paclitaxel product. The preparation methods are simple and easy for industrialization; the active hydroxyl of the raw material 10-DABIII is effectively protected, so that fewer byproducts are finally generated, and a prepared paclitaxel product has high molar yield of 70 to 81 percent and high paclitaxel purity of 99.5 to 99.9 percent; the residual rate of the raw material in the steps of synthesizing the intermediate II and synthesizing the paclitaxel is low, side reactions are reduced, and the raw material is high in reaction selectivity and utilization rate; the product can be directly used as a raw material for the medical field of treatment of ovarian cancer, breast cancer and the like.

A process for the preparation of paclitaxel

The invention discloses a preparation method of paclitaxel. A side chain which performs condensation reaction on 13-hydroxyl of 7-TES-barca III is di(3R, 4S)-1-benzoyl-3-hydroxyl-4-phenylazepane-2-butanone. According to the preparation method, a new side chain is used for performing condensation reaction; a new preparation method is expanded, the quantity of reaction byproducts is small, and the yield is high.

Ferrocenyl Paclitaxel and Docetaxel Derivatives: Impact of an Organometallic Moiety on the Mode of Action of Taxanes

A series of ferrocenyl analogues and derivatives of paclitaxel and docetaxel were synthesised and assayed for their antiproliferative/cytotoxic effects, impact on the cell cycle distribution and ability to induce tubulin polymerisation. The replacement of the 3′-N-benzoyl group of paclitaxel with a ferrocenoyl moiety, in particular, led to formation of an analogue that was at least one order of magnitude more potent in terms of antiproliferative activity than the parent compound (IC50values of 0.11 versus 1.11 μm, respectively), but still preserved the classical taxane mode of action, that is, microtubule stabilisation leading to mitotic arrest. Molecular docking studies revealed an unexpected binding pocket in the tubulin structure for the ferrocenoyl group introduced in the paclitaxel backbone.

A structure-based design of new C2- and C13-substituted taxanes: Tubulin binding affinities and extended quantitative structure-activity relationships using comparative binding energy (COMBINE) analysis

Ten novel taxanes bearing modifications at the C2 and C13 positions of the baccatin core have been synthesized and their binding affinities for mammalian tubulin have been experimentally measured. The design strategy was guided by (i) calculation of interaction energy maps with carbon, nitrogen and oxygen probes within the taxane-binding site of β-tubulin, and (ii) the prospective use of a structure-based QSAR (COMBINE) model derived from an earlier series comprising 47 congeneric taxanes. The tubulin-binding affinity displayed by one of the new compounds (CTX63) proved to be higher than that of docetaxel, and an updated COMBINE model provided a good correlation between the experimental binding free energies and a set of weighted residue-based ligand-receptor interaction energies for 54 out of the 57 compounds studied. The remaining three outliers from the original training series have in common a large unfavourable entropic contribution to the binding free energy that we attribute to taxane preorganization in aqueous solution in a conformation different from that compatible with tubulin binding. Support for this proposal was obtained from solution NMR experiments and molecular dynamics simulations in explicit water. Our results shed additional light on the determinants of tubulin-binding affinity for this important class of antitumour agents and pave the way for further rational structural modifications. The Royal Society of Chemistry 2013.