4-epi-6-Oxodocetaxel - 162784-72-7

4-epi-6-Oxodocetaxel

Catalog Number: EVT-339619
CAS Number: 162784-72-7
Molecular Formula: C43H51NO14
Molecular Weight: 805.9 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
4-epi-6-Oxodocetaxel is a semi-synthetic derivative of docetaxel, a widely used chemotherapy drug for the treatment of various cancers. It is a member of the taxane family of compounds, which are known for their potent anticancer activity. 4-epi-6-Oxodocetaxel has been shown to exhibit superior efficacy and reduced toxicity compared to docetaxel, making it a promising candidate for further development as an anticancer agent.
Applications in Various Fields
In medical research, 4-epi-6-Oxodocetaxel has been studied extensively for its role in drug development. Several clinical trials have been conducted to evaluate its safety and efficacy in the treatment of various types of cancer, and it has shown promise as a potential alternative to docetaxel. In environmental research, 4-epi-6-Oxodocetaxel has been studied for its effects on ecosystems and its potential role in pollution management. In industrial research, 4-epi-6-Oxodocetaxel has been used in manufacturing processes to improve product quality and efficiency, with a focus on health and safety considerations.

Properties

CAS Number

162784-72-7

Product Name

4-epi-6-Oxodocetaxel

IUPAC Name

[(1S,2S,3R,4S,7R,9R,10S,15S)-4-acetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11,12-dioxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate

Molecular Formula

C43H51NO14

Molecular Weight

805.9 g/mol

InChI

InChI=1S/C43H51NO14/c1-22-26(55-37(51)32(48)30(24-15-11-9-12-16-24)44-38(52)58-39(3,4)5)20-43(53)35(56-36(50)25-17-13-10-14-18-25)33-41(8,34(49)31(47)29(22)40(43,6)7)27(46)19-28-42(33,21-54-28)57-23(2)45/h9-18,26-28,30,32-33,35,46,48,53H,19-21H2,1-8H3,(H,44,52)/t26-,27+,28+,30-,32+,33-,35-,41+,42-,43+/m0/s1

InChI Key

ZOLQDWANVNOXBK-JSBGVCCUSA-N

SMILES

CC1=C2C(=O)C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)OC(C)(C)C)O)O)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)O)C

Synonyms

(2b,5b,7a,13a)-4-Acetoxy-13-(((2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl)oxy)-1,7-dihydroxy-9,10-dioxo-5,20-epoxytax-11-en-2-yl Benzoate

Canonical SMILES

CC1=C2C(=O)C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)OC(C)(C)C)O)O)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)O)C

Isomeric SMILES

CC1=C2C(=O)C(=O)[C@@]3([C@@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)OC(C)(C)C)O)O)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)O)C
Method of Synthesis or Extraction
The synthesis of 4-epi-6-Oxodocetaxel involves several steps, including the isolation of precursor compounds and the modification of their chemical structure. The most commonly used method for the synthesis of 4-epi-6-Oxodocetaxel is a multi-step process that involves the use of various reagents and catalysts. The efficiency and yield of this method depend on several factors, including the quality of the starting materials, the reaction conditions, and the expertise of the chemist. Environmental and safety considerations are also important factors to consider when synthesizing 4-epi-6-Oxodocetaxel, as some of the reagents and solvents used in the process can be hazardous to human health and the environment.
Chemical Structure and Biological Activity
The chemical structure of 4-epi-6-Oxodocetaxel is similar to that of docetaxel, with the addition of an oxo group at the C6 position. This modification has been shown to enhance the potency and selectivity of the compound, as well as reduce its toxicity. The mechanism of action of 4-epi-6-Oxodocetaxel involves the inhibition of microtubule dynamics, which leads to cell cycle arrest and apoptosis. The biological targets of 4-epi-6-Oxodocetaxel include cancer cells, as well as normal cells that are actively dividing. The bioactivity and potency of 4-epi-6-Oxodocetaxel have been demonstrated in several preclinical studies, and it has shown promise in the treatment of various types of cancer, including breast, lung, and prostate cancer.
Biological Effects
The biological effects of 4-epi-6-Oxodocetaxel on cell function and signal transduction are complex and multifaceted. In addition to its effects on microtubule dynamics, 4-epi-6-Oxodocetaxel has been shown to modulate several signaling pathways that are involved in cell proliferation, survival, and apoptosis. The potential therapeutic and toxic effects of 4-epi-6-Oxodocetaxel depend on several factors, including the dose, duration of treatment, and the type of cancer being treated. While 4-epi-6-Oxodocetaxel has shown promise in preclinical studies, further research is needed to fully understand its therapeutic potential and potential side effects.
Future Perspectives and Challenges
Despite its promising potential, there are several limitations to the use and study of 4-epi-6-Oxodocetaxel. One of the main challenges is the complexity of its synthesis, which can limit its availability and increase its cost. Additionally, further research is needed to fully understand its therapeutic potential and potential side effects, as well as its effects on the environment. However, with continued research and development, 4-epi-6-Oxodocetaxel has the potential to become an important tool in the fight against cancer and other diseases.

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