tenofovir CAS NO.147127-20-6

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Nucleoside antivirals are synthetic nucleotide analogues with simple chemical structure and easy modification and synthesis. They are the fastest developing antivirals. A series of new antivirals with high efficiency and low toxicity have been or will be used in the treatment of HIV infection and HBV infection. Nucleoside analogues can be divided into purines and pyrimidines according to drug structure types, and are mainly divided into anti-retroviral (RT) drugs, anti-hepatitis drugs, anti-herpes virus drugs and anti-other viral drugs according to drug effects. Tenofovir is an acyclic nucleoside antiviral drug that inhibits HBV polyenzyme polymerization and HIV reverse transcriptase. Tenofovir's active component, Tenofovir bisphosphonates, inhibits viral polymerase by directly and competitively binding to natural deoxyribose substrates, and terminates strands by intercalation into human DNA. Is the first nucleotide analogue to be approved by the US Food and Drug Administration (FDA) for the treatment of HIV-1 infection. Tenofovir, one of the drugs in the AIDS cocktail, has been shown to improve protection against the immunodeficiency virus, which is similar to the human AIDS virus, in monkeys. Pharmacokinetics Tenofovir is almost not absorbed through the gastrointestinal tract, so it is esterified and salted into tenofovir fumarate. Tenofovir ester is water soluble and can be rapidly absorbed and degraded into the active substance Tenofovir, which is then converted into the active metabolite Tenofovir bisphosphonate. Tenofoveda blood peak within 1 to 2 hours after administration. Bioavailability of tenofovir increased by about 40% when taken with food Chemicalbook. The intracellular half-life of tenofovir bisphosphonates is about 10h and can be administered once a day. Since the drug is not metabolized by the CYP450 enzyme system, there is little possibility of interaction with other drugs caused by this enzyme. The drug is excreted mainly through the glomerular filtration and active tubule transport system, and about 70% ~ 80% of the drug is excreted in its original form through urine. Indications for the treatment of HIV, HBV infection. This product is used in combination with other reverse transcriptase inhibitors for the treatment of HIV-1 infection and hepatitis B. Preparation method Diethyl phosphite, paraformaldehyde and triethylamine were dissolved in toluene and reacted under nitrogen protection. After the reaction was complete, it was cooled and slowly added p-toluenesulfonyl chloride and triethylamine to get p-toluenesulfonoxymethyl phosphonate. Under nitrogen protection, will (S) - glycidyl, palladium  carbon, 5% ethanol mixed with sodium hydroxide solution, hydrogenation, get a (R) - 1, 2 - propylene glycol. (R)-1, 2-propylene glycol carbonate was obtained by adding diethyl carbonate and ethanol sodium solution. It is dissolved in dimethylformamide with adenine, diethyl p-toluenesulfonoxymethyl phosphonate and sodium hydroxide to obtain (R)-9- [2- (diethylphosphonyl methoxy) propyl] adenine. It was dissolved in acetonitrile, trimethylsilane bromide, detenofovir crude, recrystallized to obtain pure product. Tenofovir was mixed with 1-methyl-2-pyrrolidone and triethylamine to react with chloromethyl propyl carbonate, and then acidified with fumaric acid to obtain tenofovir divalyl oxymethyl fumarate.