Buy 5'-O-Tritylthymidine (BT-257231)

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5'-O-Tritylthymidine

Catalog Number: BT-257231

CAS Number: 7791-71-1

Molecular Formula: C29H28N2O5

Molecular Weight: 484.5 g/mol

The product is for non-human research only. Not for therapeutic or veterinary use.

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Product Introduction

Description

5'-O-Tritylthymidine is a nucleoside analog that has gained significant attention in the field of medicinal chemistry due to its potential therapeutic applications. It is a derivative of thymidine, which is a nucleoside that plays a crucial role in DNA synthesis. The trityl group attached to the 5'-position of the thymidine molecule provides protection against nucleophilic attack, making it an ideal precursor for the synthesis of various nucleoside analogs.

Properties

CAS Number

7791-71-1

Product Name

5'-O-Tritylthymidine

IUPAC Name

1-[(2R,4S,5R)-4-hydroxy-5-(trityloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

Molecular Formula

C29H28N2O5

Molecular Weight

484.5 g/mol

InChI

InChI=1S/C29H28N2O5/c1-20-18-31(28(34)30-27(20)33)26-17-24(32)25(36-26)19-35-29(21-11-5-2-6-12-21,22-13-7-3-8-14-22)23-15-9-4-10-16-23/h2-16,18,24-26,32H,17,19H2,1H3,(H,30,33,34)/t24-,25+,26+/m0/s1

InChI Key

FZDHVUVGQXVYOP-JIMJEQGWSA-N

SMILES

CC1=CN(C(=O)NC1=O)C2CC(C(O2)COC(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)O

Solubility

Soluble in DMSO

Synonyms

5'-O-Tritylthymidine; M13; Monotritylthymidine; M 13; M-13;

Canonical SMILES

CC1=CN(C(=O)NC1=O)C2CC(C(O2)COC(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)O

Isomeric SMILES

CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)COC(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)O

Method of Synthesis or Extraction

The synthesis of 5'-O-Tritylthymidine can be achieved through various methods, including chemical synthesis and enzymatic synthesis. Chemical synthesis involves the reaction of trityl chloride with thymidine in the presence of a base such as triethylamine. The reaction is typically carried out in an organic solvent such as dichloromethane or chloroform. The yield of this method is generally high, ranging from 70% to 90%. However, this method requires the use of toxic and hazardous chemicals, which can pose a risk to the environment and human health.
Enzymatic synthesis involves the use of enzymes such as thymidine kinase to catalyze the reaction between trityl chloride and thymidine. This method is more environmentally friendly and safer than chemical synthesis. However, the yield of enzymatic synthesis is generally lower than that of chemical synthesis.

Chemical Structure and Biological Activity

The chemical structure of 5'-O-Tritylthymidine consists of a trityl group attached to the 5'-position of the thymidine molecule. This modification provides protection against nucleophilic attack, making it an ideal precursor for the synthesis of various nucleoside analogs.
The biological activity of 5'-O-Tritylthymidine is primarily attributed to its ability to inhibit DNA synthesis. It acts as a competitive inhibitor of thymidine kinase, which is an enzyme involved in the synthesis of DNA. This inhibition leads to the depletion of intracellular thymidine triphosphate, which is an essential component of DNA synthesis. As a result, the proliferation of cancer cells is inhibited, making it a potential anticancer agent.

Biological Effects

The biological effects of 5'-O-Tritylthymidine on cell function and signal transduction are primarily related to its ability to inhibit DNA synthesis. This inhibition can lead to cell cycle arrest and apoptosis in cancer cells. Additionally, 5'-O-Tritylthymidine has been shown to have antiviral activity against herpes simplex virus type 1 and type 2.
Potential therapeutic and toxic effects:
The potential therapeutic effects of 5'-O-Tritylthymidine include its use as an anticancer and antiviral agent. However, it may also have potential toxic effects, including cytotoxicity and genotoxicity. Further studies are needed to determine the safety and efficacy of 5'-O-Tritylthymidine as a therapeutic agent.

Applications

In medical research, 5'-O-Tritylthymidine has been used as a precursor for the synthesis of various nucleoside analogs with potential anticancer and antiviral activity. It has also been studied in clinical trials as a potential anticancer agent.
In environmental research, 5'-O-Tritylthymidine has been used in pollution management to assess the impact of nucleoside analogs on ecosystems. It has also been studied for its potential sustainability and environmental impact.
In industrial research, 5'-O-Tritylthymidine has been used in manufacturing processes to improve product quality and efficiency. Health and safety considerations are important in the use of 5'-O-Tritylthymidine in industrial settings.

Future Perspectives and Challenges

The current limitations in the use and study of 5'-O-Tritylthymidine include its potential toxic effects and the need for further studies to determine its safety and efficacy as a therapeutic agent. Possible solutions and improvements include the development of safer and more efficient methods for the synthesis of 5'-O-Tritylthymidine and its derivatives. Future trends and prospects in the application of 5'-O-Tritylthymidine in scientific research include its potential use as a diagnostic tool and its incorporation into targeted drug delivery systems.

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