69075-47-4

5''-Ethynyl-2''-deoxycytidine (EdC) is a nucleoside analog that inhibits replication of the herpes simplex virus-1 (HSV-1) KOS strain (ID₅₀ = 0.2 μg/mL). It also reduces virus-induced cytopathogenicity of HSV-1, HSV-2, and vaccinia virus strains in PRK cells (MICs = 0.2-0.4, 1-2, and 5 μg/ml, respectively). EdC is an inhibitor of thymidylate synthetase, selectively reducing DNA incorporation of [1'',2''-³H]deoxyuridine over [CH₃-³H]deoxythymidine in PRK cells (ID₅₀s = 3 and 120 μg/ml, respectively). It inhibits thymidine synthetase in and reduces proliferation of L1210 cells, an effect which is reversed by addition of deoxythymidine (ID₅₀s = 4.4 and 1,000 μg/ml, respectively). EdC has been used to monitor DNA synthesis and cellular replication via click chemistry conjugation of the ethynyl group to an azido group of various fluorochromes.

5-Ethynyl-2’-deoxycytidine is an lower toxicity analog of 2’-deoxycytidine, a metabolic labeling probe for DNA synthesis. 5-Ethynyl-2’-deoxycytidine is most commonly used when thymidine analogs is undesirable.

reaction type: click chemistry

1) 5-Iodo-2’3’5’-oxo-triacetyluridine (15 g, 30.23 mmol, 1eq) was dissolved in 200 ml of CH2Cl2:(C2H5)3N1:1 mixed solution, to which was added under the protection of N2 (PPh3)2PdCl2 (1.59 g, 2.27 mmol. 0.075eq), CuI (0.86g, 4.52mmol, 0.

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