245657-90-3

Basic information

• Product Name: 7,10,13-tris(triethylsilyl)-2-debenzoyl-2-(m-fluorobenzoyl)-10-deacetylbaccatin III
• Synonyms: 7,10,13-tris(triethylsilyl)-2-debenzoyl-2-(m-fluorobenzoyl)-10-deacetylbaccatin III
• CAS NO: 245657-90-3
• Molecular Weight: 905.377
• Mol File: 245657-90-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 7,10,13-tris(triethylsilyl)-2-debenzoyl-2-(m-fluorobenzoyl)-10-deacetylbaccatin III(CAS DataBase Reference)
• NIST Chemistry Reference: 7,10,13-tris(triethylsilyl)-2-debenzoyl-2-(m-fluorobenzoyl)-10-deacetylbaccatin III(245657-90-3)
• EPA Substance Registry System: 7,10,13-tris(triethylsilyl)-2-debenzoyl-2-(m-fluorobenzoyl)-10-deacetylbaccatin III(245657-90-3)

Safety Data

• Hazardous Substances Data: 245657-90-3(Hazardous Substances Data)

Upstream product

• 994-30-9 triethylsilyl chloride 
• 194720-19-9 7,10,13-tris(triethylsilyl)-10-deacetylbaccatin III 
• 32981-86-5 10-deacetylbaccatin III 
• 455-38-9 3-fluorobenzoic acid 
• 204580-30-3 10-O-deacetyl-2-O-debenzoyl-7,10,13-O-tris(triethylsilyl)baccatin III 

Downstream Products

• 926306-83-4 3'-dephenyl-3'-(2,2-difluoroethenyl)-2-debenzoyl-2-(3-fluorobenzoyl)-10-methoxycarbonyldocetaxel 
• 926306-82-3 3'-dephenyl-3'-(2,2-difluoroethenyl)-2-debenzoyl-2-(3-fluorobenzoyl)-10-dimethyl-carbamoyldocetaxel 
• 926306-81-2 3'-dephenyl-3'-(2,2-difluoroethenyl)-2-debenzoyl-2-(3-fluorobenzoyl)-10-propanoyldocetaxel 
• 926306-80-1 3'-dephenyl-3'-(2,2-difluoroethenyl)-2-debenzoyl-2-(3-fluorobenzoyl)-10-cyclopropanecarbonyldocetaxel 
• 926306-79-8 3'-dephenyl-3'-(2,2-difluoroethenyl)-2-debenzoyl-2-(3-fluorobenzoyl)-10-acetyldocetaxel 
• 1007094-37-2 C₃₇H₅₁FO₁₂Si 
• 1007094-36-1 C₃₈H₅₄FNO₁₁Si 
• 1007094-35-0 10-O-cyclopropanecarbonyl-10-O-deacetyl-2-O-debenzoyl-2-O-(3-fluorobenzoyl)-7-O-triethylsilylbaccatin III 
• 245657-96-9 2-debenzoyl-2-(3-fluorobenzoyl)-7-triethylsilylbaccatin III 
• 259522-69-5 7-triethylsilyl-2-debenzoyl-2-(3-fluorobenzoyl)-10-deacetyl-10-propanoylbaccatin III 
• 1031784-02-7 7-TES-2-(3-fluorobenzoyl)-2-debenzoyl-10-deacetylbaccatin III 
• 926307-02-0 2-(3-fluorobenzoyl)-2-debenzoyl-10-deacetylbaccatin III 

Relevant articles and documents

Synthesis and biological evaluation of novel 3′-difluorovinyl taxoids

A series of 3′-difluorovinyl taxoids with C10 modifications, as well as those with C2 and C10 modifications, were strategically designed to block the metabolism by cytochrome P-450 3A4 enzyme and synthesized. These novel difluorovinyl taxoids were evaluated for their cytotoxicity against drug-sensitive human breast (MCF7), multidrug-resistant (MDR) human ovarian (NCI/ADR), human colon (HT-29) and human pancreatic (PANC-1) cancer cell lines. 3′-Difluorovinyl taxoids exhibit several to 16 times better activity against MCF7, HT-29 and PANC-1 cell lines and up to three orders of magnitude higher potency against NCI/ADR cell line as compared to paclitaxel. Structure-activity relationship study shows the critical importance of the C2 modifications on the activity against MDR cancer cell line, while the C10 modifications have a rather minor effect on the potency with some exceptions. The effect of the C2 modifications on potency against MCF7 cell line increases in the following order: H 3. Among the twenty five 3′-difluorovinyl taxoids evaluated, eight taxoids exhibited less than 100 pM IC50 values against MCF7 cell line. Difluorovinyl taxoids induced GTP-independent tubulin polymerization much faster than paclitaxel. Then, the resulting microtubules were stable to Ca2+-induced depolymerization, indicating strong stabilization of microtubules. Molecular modeling study indicated that a difluorovinyl taxoid binds to β-tubulin in a manner that is consistent with the REDOR-Taxol structure. The difluorovinyl group appears to mimic the isobutenyl group to some extent, but with very different electronic property, which may account for the unique activities of difluorovinyl taxoids.

Design, synthesis, and biological evaluation of new-generation taxoids

Novel second-generation taxoids with systematic modifications at the C2, C10, and C3′N positions were synthesized and their structure-activity relationships studied. A number of these taxoids exhibited exceptionally high potency against multidrug-resistan

Synthesis and structure-activity relationships of new second-generation taxoids

A series of second-generation taxoids bearing a substituent on the C-2-benzoyl group and modifications at C-3'/C-10 positions was synthesized. These taxoids exhibited 2-3 orders of magnitude higher potency than that of paclitaxel against drug-resistant human breast cancer cell lines. It is also noteworthy that three taxoids showed almost no difference in activity against drug-resistant and drug-sensitive cell lines, which are categorized as 'advanced second generation taxoids'.