127911-92-6

Basic information

• Product Name: Uridine, 2'-deoxy-5-(2-iodo-1-methoxyethyl)-
• CAS NO: 127911-92-6
• Molecular Formula: C12H17IN2O6
• Molecular Weight: 412.181
• Mol File: 127911-92-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Uridine, 2'-deoxy-5-(2-iodo-1-methoxyethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Uridine, 2'-deoxy-5-(2-iodo-1-methoxyethyl)-(127911-92-6)
• EPA Substance Registry System: Uridine, 2'-deoxy-5-(2-iodo-1-methoxyethyl)-(127911-92-6)

Safety Data

• Hazardous Substances Data: 127911-92-6(Hazardous Substances Data)

Usage

General Description

Uridine, 2'-deoxy-5-(2-iodo-1-methoxyethyl)- is a modified form of uridine, a naturally occurring nucleoside that is essential for the synthesis of RNA. This chemical compound contains a deoxyribose sugar and a modified ethyl group, replacing the hydroxyl group at the 5'-position of the sugar. The addition of an iodine atom and a methoxyethyl group to the uridine molecule can potentially alter its biological activity and pharmacological properties, making it a potential candidate for pharmaceutical research and drug development. This modified uridine compound may be used in studying nucleic acid structure and function, as well as in the development of novel nucleoside analogs for therapeutic purposes.

Upstream product

• 55520-67-7 5-vinyl-2'-deoxyuridine 
• 67-56-1 methanol 

Downstream Products

• 15176-29-1 edoxudine 

Relevant articles and documents

Synthesis and Antiviral and Cytotoxic Activity of Iodohydrin and Iodomethoxy Derivatives of 5-Vinyl-2'-deoxyuridines, 2'-Fluoro-2'-deoxyuridine, and Uridine

A series of new 5-(1-hydroxy-2-iodoethyl)-2'-deoxyuridine and uridine cpmpounds (11, 16) was synthesized by the regiospecific addition of HOI to the vinyl substituent of 5-vinyl-2'-deoxyuridine (10a), 5-vinyl-2'-fluoro-2'-deoxyuridine (10b), 5-vinyl-uridine (10c), and (E)-5-(2-iodovinyl)-2'-deoxyuridine (4b).Treatment of the iodohydrins 11a-c with methanolic sulfuric acid afforded the corresponding 5-(1-methoxy-2-iodoethyl) derivatives (12a-c).In contrast, reaction of 5-(1-hydroxy-2-iodoethyl)-2'-deoxyuridine (11a) with sodium carbonate in methanol afforded a mixture of 5-(1-hydroxy-2-methoxyethyl)-2'-deoxyuridine (13) and 2,3-dihydro-3-hydroxy-5-(2'-deoxy-β-D-ribofuranosyl)furanopyrimidin-6(5H)-one (14).The most active compound, 5-(1-methoxy-2-iodoethyl)-2'-deoxyuridine (12a, ID50 = 0.1 μg/mL) which exhibited antiviral activity (HSV-1) 100-fold higher than that of the 5-(1-hydroxy-2-iodoethyl) analogue (11a), was less active than IVDU or acyclovir (ID50 = 0.01 - 0.1 μg/mL range).The C-5 substituent in the 2'-deoxyuridine series was a determinant of cytotoxic activity, as determined in the in vitro L1210 screen, where the relative activity order was CH(OH)CHI2 (16) > CH(OH)CH2I (11a) ca.CH(OH)CH2OMe (13).The 2'-substituent was also a determinant of cytotoxic activity in the 5-(1-hydroxy-2-iodoethyl) (11a-c) and 5-(1-methoxy-2-iodoethyl) series of compounds, where the relative activity profile was 2'-deoxyuridine > 2'-fluoro-2'-deoxyuridine > uridine (11a > 11b 11c; 12a > 12b > 12c).The most active cytotoxic agent (16), possessing a 5-(1-hydroxy-2,2-diiodoethyl) substituent (ED50 = 0.77 μg/mL), exhibited an activity approaching that of melphalan (ED50 = 0.15 μg/mL).All compounds tested, except for 13 and 14, exhibited high affinity (Ki = 0.035 - 0.22 mM range relative to deoxyuridine, Ki = 0.125) for the murine NBMPR-sensitive erthyrocyte nucleoside transport system, suggesting that these iodohydrins are good permeants of cell membranes.