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Oligonucleotides as drugs - ATDBio - Oligo synthesis …

AZT was originally synthesized from thymidine by Horwitz and his coworkers

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Inspection of the approved antiviral agents in and (72-88) again with a Phase III compound (89) in trials for postherpetic pain, aptly demonstrates how the knowledge that modification of the sugar moiety could lead to novel bioactivities. Perhaps the best examples for this comment are two very early drugs in this section, vidarabine (72) and acyclovir (73). In the first case, the change of the sugar to arabinose (as mentioned earlier, this was coincidental with the reports of the Bergmann group, though whether Lee et al., had prior knowledge is unknown), yielded a compound that was designed to be an antitumor agent but gained fame as an anti-herpes simplex drug. Similarly, perhaps the most "famous" of these early nucleosides was azidothymidine (AZT; 74). Again this was synthesized as an antitumor agent but happened to be available as the HIV epidemic occurred and following testing at the US NCI, it turned out to be the first effective agent against HIV infection, even though it was quite toxic.

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A very efficient synthesis of 3′-azido-3′-deoxythymidine (4) (AZT) from thymidine is described. The key step is a one-pot transformation of thymidine into 2,3′-anhydro-5′-O-(4-methoxybenzoyl)-thymidine (2) which is isolated by direct crystallization. Further ring opening of 2 with the azide ion and 5′-O-deprotection afforded AZT in 73 % overall yield.

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Synthesis, Characterization, and In Vitro Assay of Folic Acid Conjugates of 3′-Azido-3′-Deoxythymidine (AZT): Toward Targeted AZT Based Anticancer Therapeutics

In a review in 1991, Suckling demonstrated how such structures evolved in the Wellcome laboratories, leading ultimately to molecules such as azidothymidine (74) or AZT, though no direct mention was made of the original "privileged structures from natural sources". Demonstrating an interesting temporal reversal where chemists synthesized a compound that was later found in nature, in 1960, Lee et al. reported the synthesis of arabinosyladenine (Ara-A or vidarabine, 72) as a potential antitumor agent, with a later report showing production by fermentation of S. antibioticus. Then it was isolated and purified from the Mediterranean gorgonian Eunicella cavolini by the Cimino et al. in 1984. To this list can be added cytarabine (Ara-C; 57), which was synthesized by Evans et al. following the reports of the early discoveries above. It was covered in work by Pizer and Cohen on its metabolism and on the potential mechanism as an antileukemic agent in the report by Chu and Fischer.

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