125084-71-1Relevant articles and documents
A new protecting group '3′,5′-O-sulfinyl' for xylo-nucleosides. A simple and efficient synthesis of 3′-amino-3′-deoxyadenosine (a puromycin intermediate), 2,2′-anhydro-pyrimidine nucleosides and 2′,3′-anhydro-adenosine
Takatsuki, Ken-Ichi,Yamamoto, Makoto,Ohgushi, Sumito,Kohmoto, Shigeo,Kishikawa, Keiki,Yamashita, Haruhiro
, p. 137 - 140 (2007/10/03)
We developed a new protecting group, the cyclic sulfite for the protection of the 3′,5′-dihydroxy group of nucleosides. Seven cyclic sulfites, 4a-c, 5a-b, and 6a-b were prepared in high yields from the corresponding xylo-uridines 1 and 2, and xylo-adenosines 3 with thionyl chloride, respectively. Synthesis of the puromycin intermediate 8 was carried out by deprotection of the sulfite moiety through an intramolecular cyclization of the 2′-α-carbamate 7.
Nucleotides: Part LIX: Synthesis, characterization, and biological activities of new potential antiviral agents: (2'-5')Adenylate trimer analogs containing 3'-deoxy-3'(hexadecanoylamino)adenosine at the 2'-terminus
Schirmeister-Tichy, Helga,Iacono, Kathryn T.,Muto, Nicholas F.,Homan, Joseph W.,Suhadolnik, Robert J.,Pfleiderer, Wolfgang
, p. 597 - 613 (2007/10/03)
Based upon 3'-amino-3'-deoxyadenosine (15), its protected 3'- hexadecanoylamino derivative 22 was chosen as starting material for the synthesis of a series of new modified 2'-5'-adenylate trimers 33-36 as potential antiviral agents. All (2'-5')A trimer analogs 33-36 inhibit HIV-1 replication as measured by the inhibition of syncytia formation and inhibition of HIV-1 reverse transcriptase activity. Compound 34 inhibits HIV- 1 reverse transcription by 100% and subsequently inhibits expression of HIV- 1 p24. However, compound 35 acts differently, since it does not inhibit HIV- 1 reverse transcription, HIV-1 integrase, or HIV-1 p24 expression. Therefore, 35 appears to exert its inhibitory effect at a later stage of HIV-1 replication, i.e., the budding process.
