(E)-5-(2-Carbomethoxyvinyl)-2'-deoxyuridine - CAS 86163-17-9
Category:
Nucleosides
Product Name:
(E)-5-(2-Carbomethoxyvinyl)-2'-deoxyuridine
Catalog Number:
86163-17-9
CAS Number:
86163-17-9
Molecular Weight:
312.28
Molecular Formula:
C13H16N2O7
COA:
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MSDS:
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Structure\Application:
2'-Deoxy-Nucleosides
Chemical Structure
CAS 86163-17-9 (E)-5-(2-Carbomethoxyvinyl)-2'-deoxyuridine

Related 2'-Deoxy-Nucleosides Products


Reference Reading


1.Antiherpes activity of some novel analogues of (E)-5-(2-bromovinyl)-2'-deoxyuridine (E-BrVUdR) in two different cell lines.
Reefschläger J, Bärwolff D, Herrmann G, Langen P. Acta Virol. 1984 Jan;28(1):1-10.
In a series of 5-vinyl-2'-deoxyuridine (VUdR) analogues (5-(2-X-vinyl)-UdRs) the (E)-5-(2-bromovinyl)-UdR (E-BrVUdR) proved the most potent inhibitor of plaque formation of two herpes simplex virus type 1 (HSV-1) strains in human embryonic lung fibroblast (HELF) and African green monkey kidney (Vero) cell cultures. The (Z)-5-(2-bromovinyl)-UdR (Z-BrVUdR) isomer and the 5-(2,2-dibromovinyl)-UdR (Br2VUdR) analogue were 10-20 times less efficient, whereas the (E)-5-(2-cyanovinyl)-UdR (CNVUdR) and the (E)-5-(2-carboxyvinyl)-UdR (COOHVUdR) derivative were only marginally active (10(3)-10(4) times less than E-BrVUdR). The antiherpes potential of the 5-(2-X-vinyl)-UdRs was compared with that of 5-iodo-, 5-fluoro-, 5-formyl- and 5-ethyl-UdR (IUdR, FUdR, fUdR, EUdR) as well as of 9-(2-hydroxyethoxymethyl)guanine (acyclovir, ACV), 2'-fluoro-5-iodo-1-beta-D-arabinofuranosyl(ara)-cytosine (FIAC), 2'-fluoro-5-methylarauracil (FMAU), arabinosylthymine (araT) and (E)-5-(2-bromovinyl)- and 5-vinyl-araU (BrVaraU, VaraU).
2.Synthesis, antiviral and cytotoxic activity of 2'-deoxyuridines, 2'-fluoro-2'-deoxyuridines and 2'-arabinouridines containing 5-(1-hydroxy-2-halo-2-ethoxycarbonylethyl)-, 5-(1-hydroxy-2-iodo-2- carboxyethyl)- and 5-[1-hydroxy (or methoxy)-2-iodoethyl] substituents.
Kumar R1, Wiebe LI, Knaus EE, Allen TM, Tempest ML. Drug Des Discov. 1992 Feb;8(3):179-89.
The 5-[1-hydroxy-2-chloro-2-(ethoxycarbonyl)ethyl]-2'-deoxyuridine (7) and 5-[1-hydroxy-2-bromo-2-(ethoxycarbonyl)ethyl]-2'- fluoro-2'-deoxyuridine/uridine nucleosides (8, 9) were synthesized by the regiospecific addition of HOX (X = Br or Cl) to the vinyl substituent of the respective (E)-5-[2-(ethoxycarbonyl)-vinyl]-2'-deoxyuridines (6a-b) and uridine (6c). A related reaction of (E)-5-(2-carboxyvinyl)-2'-deoxyuridines (10a-b) and uridine (10c) with iodine and potassium iodate afforded the 5-(1-hydroxy-2-iodo-2-carboxyethyl) derivatives (11-13). 5-(1-Hydroxy-2-iodoethyl)-arabinouridine (18) was obtained by the reaction of (17) with iodine in the presence of the oxidizing agent iodic acid. Treatment of (18) with methanolic sulfuric acid afforded 5-(1-methoxy-2-iodoethyl)-arabinouridine (19) in 65% yield. Of the newly synthesized compounds, 7, 11 and 12 showed activity in vitro against HSV-1. The most active compound (12, ID50 = 0.1 microgram/ml) was 10 times less active than acyclovir (ID50 = 0.
3.Synthesis of 131I, 125I and 82Br labelled (E)-5-(2-halovinyl)-2'-deoxyuridines.
Samuel J, Knaus EE, Wiebe LI, Tyrrell DL. Int J Appl Radiat Isot. 1984 Nov;35(11):1049-52.
Radiohalogenated (E)-5-(2-iodovinyl)-2'-deoxyuridine (IVDU, 4) and (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU, 5) were synthesized by reaction of (E)-5-(2-carboxyvinyl)-2'-deoxyuridine (1) with radiolabelled iodide or bromide in the presence of chloramine-T. A "no-carrier-added" synthesis of [131I]IVDU was completed within 30 min providing a radiochemical yield of 65%. Alternatively, radioactive iodine was incorporated into IVDU using a halogen isotope exchange reaction catalyzed by cuprous ion. [82Br]BVDU was also prepared by direct neutron activation of unlabelled BVDU.
4.Synthesis and antiviral activity of (E)-5-(2-bromovinyl)uracil and (E)-5-(2-bromovinyl)uridine.
De Clercq E, Desgranges C, Herdewijn P, Sim IS, Jones AS, McLean MJ, Walker RT. J Med Chem. 1986 Feb;29(2):213-7.
(E)-5-(2-Bromovinyl)uracil (BVU) and (E)-5-(2-bromovinyl)uridine (BVRU) were synthesized starting from 5-formyluracil via (E)-5-(2-carboxyvinyl)uracil or starting from 5-iodouridine via (E)-5-(2-carbomethoxyvinyl)uridine and (E)-5-(2-carboxyvinyl)uridine, respectively. Depending on the choice of the cell system, BVU and BVRU exhibited a marked activity against herpes simplex virus type 1 (HSV-1) in vitro. Although BVU and BVRU were less potent than the reference compound (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU), their antiviral activity spectrum was remarkably similar to that of BVDU. The latter findings suggest that BVU and BVRU are metabolically converted to BVDU or a phosphorylated product thereof. In vivo, BVU protected mice against a lethal disseminated HSV-1 infection.