123881-85-6 Usage
Description
(E)-5-<2-(ethoxycarbonyl)vinyl>uridine is a chemical compound that features a uridine molecule with a vinyl group and an ethoxycarbonyl group attached. The (E) designation signifies that the vinyl group is in the E configuration, where the substituents on the double bond are positioned on opposite sides. (E)-5-<2-(ethoxycarbonyl)vinyl>uridine holds promise in RNA biochemistry for studying and modifying RNA molecules, and it can be utilized as a building block in the synthesis of nucleoside analogs and other modified nucleic acid structures. Furthermore, it may have therapeutic potential in treating viral infections and specific types of cancer.
Uses
Used in RNA Biochemistry:
(E)-5-<2-(ethoxycarbonyl)vinyl>uridine is used as a research tool for studying the structure and function of RNA molecules. Its unique structure allows for the investigation of RNA interactions and modifications, which can lead to a better understanding of RNA biology and its role in various cellular processes.
Used in Synthesis of Nucleoside Analogs:
In the field of medicinal chemistry, (E)-5-<2-(ethoxycarbonyl)vinyl>uridine is used as a building block for the synthesis of nucleoside analogs. These analogs can have altered biological activities and can be used to develop new drugs with improved properties, such as higher potency, better selectivity, or reduced toxicity.
Used in Drug Development for Viral Infections:
(E)-5-<2-(ethoxycarbonyl)vinyl>uridine is used as a potential therapeutic agent for the treatment of viral infections. Its unique structure may allow it to interfere with viral replication or other essential viral processes, offering a new approach to combat viral diseases.
Used in Cancer Treatment:
In the field of oncology, (E)-5-<2-(ethoxycarbonyl)vinyl>uridine is used as a potential therapeutic agent for the treatment of certain types of cancer. Its ability to interact with RNA molecules may provide a novel strategy for targeting cancer cells and disrupting their growth and survival pathways.
Used in Pharmaceutical Industry:
(E)-5-<2-(ethoxycarbonyl)vinyl>uridine is used as a key intermediate in the development of new drugs for various therapeutic areas, including antiviral and anticancer treatments. Its unique chemical properties make it a valuable compound for the design and synthesis of innovative pharmaceuticals with improved efficacy and safety profiles.
Check Digit Verification of cas no
The CAS Registry Mumber 123881-85-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,3,8,8 and 1 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 123881-85:
(8*1)+(7*2)+(6*3)+(5*8)+(4*8)+(3*1)+(2*8)+(1*5)=136
136 % 10 = 6
So 123881-85-6 is a valid CAS Registry Number.
123881-85-6Relevant 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
Kumar, Rakesh,Xu, Lihua,Knaus, Edward E.,Wiebe, Leonard I.,Tovell, Dorothy R.,et al.
, p. 717 - 723 (2007/10/02)
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.
