4152-77-6

Usage

Uses

Used in Pharmaceutical Industry:
5'O-Tritylinosine is used as an allosteric inhibitor for inhibiting angiogenic enzyme thymidine phosphorylase (TPase) for the purpose of blocking the conversion of thymidine to thymine. This action has potential applications in the development of anti-cancer therapies, as angiogenesis is a critical process in tumor growth and metastasis.
Additionally, 5'O-Tritylinosine is used as an inhibitor to prevent the binding of fibroblast growth factor 2 (FGF2) to FGF receptor 1, which can help in limiting the growth and neovascularization of tumors. This application is particularly relevant in the context of cancer treatments, where inhibiting angiogenesis can lead to reduced tumor growth and improved patient outcomes.
Furthermore, 5'O-Tritylinosine's ability to reduce endothelial cell migration without impacting proliferation suggests potential applications in wound healing and tissue regeneration, where controlled cell migration is essential for proper tissue repair.

Upstream product

• 76-83-5 trityl chloride 
• 58-63-9 Inosine 

Downstream Products

• 911430-78-9 1-allyl-5'-O-tritylinosine 

Relevant academic research and scientific papers

Tricyclanos: Conformationally constrained nucleoside analogues with a new heterotricycle obtained from a d-ribofuranose unit

A novel type of nucleoside analogue in which the sugar part is replaced by a new tricycle, 3,7,10-trioxa-11-azatricyclo[5.3.1.05,11]undecane has been prepared by substrate-controlled asymmetric synthesis. 1,5-Dialdehydes obtained from properly protected or unprotected uridine, ribothymidine, cytidine, inosine, adenosine and guanosine by metaperiodate oxidation reacted readily with tris(hydroxymethyl)aminomethane to provide the corresponding tricyclic derivatives with three new stereogenic centers. Through a double cyclisation cascade process the tricyclic compounds were obtained in good to high yields, with very high diastereoselectivity. Formation of one stereoisomer, out of the eight possible, was observed in all cases. The absolute configuration of the new stereotriad-containing tricyclic systems was aided by conventional NMR experiments followed by chemical shift calculations using an X-ray crystal structure as reference that was in good agreement with H-H distances obtained from a new ROESY NMR method. The synthesis was compatible with silyl, trityl and dimethoxytrityl protecting groups. A new reagent mixture containing ZnCl2, Et3SiH and hexafluoroisopropanol was developed for detritylation of the acid-sensitive tricyclano nucleosides.

In search of flavivirus inhibitors: Evaluation of different tritylated nucleoside analogues

Following up on a hit that was identified in a large scale cell-based antiviral screening effort, a series of triphenylmethyl alkylated nucleoside analogues were synthesized and evaluated for their in vitro antiviral activities against the dengue virus (DENV) and the yellow fever virus (YFV). Hereto, trityl moieties were attached at various positions of the sugar ring combined with subtle variations of the heterocyclic base. Several triphenylmethyl modified nucleosides were uncovered being endowed with submicromolar in vitro antiviral activity against the YFV. The most selective inhibitor in this series was 3′,5′-bis-O-tritylated-5-chlorouridine (1b) affording a selectivity index of over 90, whereas the 3′,5′-bis-O-tritylated inosine congener (5b) displayed the highest activity, but proved more toxic. The finding of these lipophilic structures being endowed with high antiviral activity for flaviviruses, should stimulate the interest for further structureeactivity research.

Microwave-assisted selective 5′-O-trityl protection of inosine derivatives

The efficient microwave-assisted synthesis of 5′-O-trityl inosine derivatives is described. The reported protocol allows the protection of inosine derivatives in significantly higher yields and shorter reaction times than the standard thermal conditions.