4152-77-6

Basic information

• Product Name: 5’O-Tritylinosine
• Synonyms: 5’O-Tritylinosine;KIN-59
• CAS NO: 4152-77-6
• Molecular Formula: C₂₉H₂₆N₄O₅
• Molecular Weight: 510.54054
• Mol File: 4152-77-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5’O-Tritylinosine(CAS DataBase Reference)
• NIST Chemistry Reference: 5’O-Tritylinosine(4152-77-6)
• EPA Substance Registry System: 5’O-Tritylinosine(4152-77-6)

Safety Data

• Hazardous Substances Data: 4152-77-6(Hazardous Substances Data)

Usage

Description

KIN59 is a purine riboside derivative that allosterically inhibits thymidine phosphorylase (TPase; IC50s = 44 and 67 μM for purified E. coli and human enzymes, respectively). Through this action, KIN59 blocks the conversion of thymidine to thymine. KIN59 inhibits TPase-induced angiogenesis in a chicken chorioallantoic membrane assay and reduces endothelial cell migration without impacting proliferation. KIN59 also inhibits the binding of fibroblast growth factor 2 (FGF2) to FGF receptor 1, preventing the growth and neovascularization of subcutaneous tumors induced by FGF2-transformed endothelial cells injected in immunodeficient nude mice.

Uses

Different sources of media describe the Uses of 4152-77-6 differently. You can refer to the following data:
1. 5’O-Tritylinosine acts as an allosteric inhibitor of angiogenic enzyme thymidine phosphorylase.
2. 5’-O-Tritylinosine acts as an allosteric inhibitor of angiogenic enzyme thymidine phosphorylase.

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.

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.