148930-30-7

Upstream product

• 33069-62-4 taxol 
• 501-53-1 benzyl chloroformate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 160237-26-3 C₆₂H₆₆NO₁₈P 
• 160237-33-2 C₆₂H₆₆NO₁₈P 
• 160334-75-8 C₄₉H₅₇NO₂₂P₂ 
• 160237-31-0 C₅₅H₆₉NO₁₄SSi 
• 160237-09-2 C₄₈H₅₄NO₁₈P 
• 160237-11-6 C₄₈H₅₄NO₁₈P 
• 160237-25-2 BMS-184476 
• 160237-32-1 C₄₉H₅₅NO₁₄S 
• 148930-55-6 7-O-(triethylsilyl)paclitaxel 

Downstream Products

• 148930-57-8 2'-benzyloxycarbonyl-7-triethylsilyl taxol 
• 160237-27-4 C₅₇H₆₁NO₁₆S 
• 560060-72-2 C₆₉H₇₄N₂O₁₉ 
• 500782-55-8 2'-Z-7-Z-gly-paclitaxel 
• 220167-86-2 7-O-(6-aminohexanoyl)paclitaxel 
• 560060-76-6 C₅₅H₅₈N₂O₁₅ 
• 560060-77-7 7-O-(4-(4-aminophenyl)butyroyl)paclitaxel 
• 33069-62-4 taxol 
• 148930-55-6 7-O-(triethylsilyl)paclitaxel 
• 160237-32-1 C₄₉H₅₅NO₁₄S 

Relevant academic research and scientific papers

Synthesis and biological evaluation of a biotinylated paclitaxel with an extra-long chain spacer arm

A biotinylated paclitaxel derivative with an extra-long chain (LC-LC-biotin) spacer arm was synthesized using an improved synthetic reaction sequence. The biotinylated paclitaxel analogue retained excellent microtubule stabilizing activity in vitro. Furth

Synthesis and characterization of novel natural product-Gd(III) MRI contrast agent conjugates

Several novel gadolinium chelates conjugated with paclitaxel, colchicine and thyroxine have been prepared as MRI contrast agents targeted to tubulin and thyroxine-binding globulin, respectively.

Modulating paclitaxel bioavailability for targeting prostate cancer

Four novel water-soluble peptide-paclitaxel conjugates were designed and synthesized as prostate-specific antigen (PSA)-activated prodrugs for prostate cancer therapy. These prodrugs were composed of a peptide, HSSKLQ or SSKYQ, each of which is selectively cleavable by PSA; a self-immolative linker, either para-aminobenzyl alcohol (PABS) or ethylene diamine (EDA); and the parent drug, paclitaxel. Introduction of a PABA or EDA linker between the peptide and paclitaxel in prodrugs 2-5 resulted in products with an increased rate of hydrolysis by PSA. The stability of prodrugs 2 and 3, with the PABA linker, was poor in the serum-containing medium because of the weak carbonate bond between the PABA and paclitaxel; however, this disadvantage was overcome by introducing a carbamate bond using an EDA linker in prodrugs 4 and 5. Thus, the incorporation of an EDA linker increased both the stability and PSA-mediated activation of these prodrugs. The cytotoxicity of each prodrug, as compared to paclitaxel, was determined against a variety of cell lines, including the PSA-secreting CWR22Rv1 prostate cancer cell line. The EDA-derived prodrug of paclitaxel 5 was stable and capable of being efficiently converted to an active drug that killed cells specifically in the presence of PSA, suggesting that this prodrug and similarly designed PSA-cleavable prodrugs may have potential as prostate cancer-specific therapeutic agents.

Antitumor agents. 256. Conjugation of paclitaxel with other antitumor agents: Evaluation of novel conjugates as cytotoxic agents

Sixteen different taxoid conjugates were prepared by linking various anticancer compounds, including camptothecin (CPT), epipodophyllotoxin (EP), colchicine (COL), and glycyrrhetinic acid (GA), at the 2′- or 7-position on paclitaxel (TXL, 1) through an ester, imine, amine, or amide bond. Newly synthesized conjugates were evaluated for cytotoxic activity against replication of several human tumor cell lines. Among them, TXL-CPT conjugates, 8-10, were more potent than TXL itself against the human prostate carcinoma cell line PC-3 (ED50 = 14.8, 3.1, 19.4 nM compared with 55.5 nM), and conjugate 10 was also 8-fold more active than TXL against the LN-CAP prostate cancer cell line. These compounds also possessed anti-angiogenesis ability as well as lower inhibitory effects against a normal cell line (MRC-5). Thus, conjugates 8-10 are possible antitumor drug candidates, particularly for prostate cancer.

Paclitaxel delivery systems: The use of amino acid linkers in the conjugation of paclitaxel with carboxymethyldextran to create prodrugs

Paclitaxel was bound via its hydroxyl group to carboxymethyldextran (CMDex, 150 kDa) by means of an amino acid linker; the linker was introduced into the 2′- or 7-hydroxyl group of the paclitaxel through an ester bond. These conjugates - CMDex-2′-paclitax

Design and synthesis of a water-soluble taxol analogue: Taxol-sialyl conjugate

Glycosidation, using the methylthio derivative of N-acetylneuraminic acid 3, of linker alcohol 4 in DME with 'long-range participation' produced the α-glycosyl linkage with high stereoselectivity. The α-linked sialic acid 2 was introduced in taxol without protection of the alcohol functionality in sialic acid.

Synthesis and antitumor evaluation of paclitaxel phosphonooxymethyl ethers: A novel class of water soluble paclitaxel pro-drugs

The synthesis, pharmacokinetic properties, and antitumor evaluation of novel paclitaxel phosphonooxymethyl ether derivatives 8-11 and salts thereof is described. These compounds exhibit improved water solubility as compared to paclitaxel (1) and upon incubation with plasma and alkaline phosphatase they readily release parent drug. The in vivo antitumor evaluation of compounds 8-11 established them as suitable pro-drugs of paclitaxel.

Fluoro taxols

This invention relates to a fluorinated taxol of formula I STR1 in which R1 is --CORz in which Rz is RO-- or R; Rg is C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycl

THE CHEMISTRY OF TAXANES: REACTIONS OF TAXOL AND BACCATIN DERIVATIVES WITH LEWIS ACIDS IN APROTIC AND PROTIC MEDIA

Several Lewis acids were shown to cleanyl open the oxetane ring of taxol and baccatin derivatives.The reaction is shown to proceed via anchimeric assistance by the C-4 acetate group.Several minor products, including a novel derivative possessing a bridged C-ring, were also isolated.A mechanistric rationale is provides for all compounds formed.When taxol derivatives were treated with Lewis acids in methanol, ester cleavage reactions were observed.We provide conditions that are selective for C-10 acetate cleavage and for C-13 side-chain methanolysis.

Fluoro taxols

This invention relates to a fluorinated taxol of formula I STR1 in which R1 is benzoyl or t-butyloxycarbonyl; R2 is acetoxy, hydrogen or hydroxy; and the wavy line indicates either the α- or the β-configuration. Further provided by t