Antiviral Nucleosides: Chiral Synthesis and Chemotherapy by C.K. Chu

By C.K. Chu

• updated assessment at the chemistry and biology of nucleosides • sleek artificial method • finished assurance of antiviral nucleosidesThis e-book summarizes the new advances in nucleosides chemistry and chemotherapy over the last 10-15 years. It covers lately came upon nucleoside antiviral brokers, their healing elements and biochemistry, and in addition large stories on their chiral synthesis.

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O-" N f—OH -o 116(L-0ddC) 117(L-F-0ddC) Figure 47. P-L-Dioxolane cytosine and 5-fluorocytosine. ^^^ L-OddC is currently undergoing phase II clinical trials against leukemia and solid tumors. L-OddC t dCyd kinase L-OddC-MP - ^ L-OddC-DP L-OddC-TP dCyd deaminase L-OddU: inactive Inhibition of DNA polymerase a, p, y: Incorporation into HepG2 DNA chain and chain termination antitumor activity against various solid tumor cell lines Figure 48. ^'^b Among purine derivatives, p-2,6-diaminopurine dioxolanes, DAPD (118) and its enantiomer, L-DAPD (119), display potent anti-HIV and anti-HBV activities (Figure 49).

HO-i N^N^NH, 101[(-)-CBV] N H^N^N^N 102[(+)-CBV] Figure 38. Carbovir and its (+) isomer. pOH Recent Advances in Antiviral 31 Nucleosides Incorporation into proviral DNA/chain termination or Inhibition of HIV RT/ chain termination (-)-CBV (+)-CBV (-)-CBV-MP ^ (-)-CBV-DP \ / GMP \ / 5-nucleotidase w/ kinase vy ^ (+)-CBV-MP (+)-CBV-DP (-)-CBV-TP No interaction with DNA polymerase a, p and y Figure 39. ^^ Its cytotoxicity is low in various human T-cells and bone marrow cells. In addition, toxicity common to other dideoxynucleosides such as peripheral neuropathy and hematopoietic toxicity has not been detected during preclinical studies.

0 |LiM for HBV and HIV, respectively). However, both compounds inhibited cell growth at concentrations below 20 |iM. Nevertheless, L-d4FC did not exhibit significant inhibition of mt-DNA at 100 |LiM. ^^^ The combination of its resistance profile, rapid uptake and conversion to the active triphosphate, and intracellular half-life of 13 to 17 h^^^ make D-d4FC a promising anti-HIV candidate. Both D- and L-d4FC are currently undergoing clinical trials. Inhibition of HIV-1 RT/ chain ternnination TK d4T d4TTP d4TDP d4TMP ratelimiting Incorporation into cellular DNA or inhibition of DNA polymerase y Figure 31.

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