125127-12-0Relevant articles and documents
Stereoselective and Divergent Aza-Adenosine and Aza-Guanosine Syntheses from Xylofuranose, the Key Fragments of a STING Cyclic Dinucleotide Agonist
Eastgate, Martin,Ortiz, Adrian,Rogers, Amanda,Schmidt, Michael A.,Xu, Zhongmin,Yuan, Changxia,Zhu, Jason
supporting information, (2021/07/31)
The stereoselective and divergent synthesis of two aza-nucleosides is reported. Starting from xylofuranose 9, aza-adenosine 2 was prepared in 13 steps and 7% overall yield, and aza-guanosine 3 was prepared in 13 steps and 7.8% overall yield. Compared to t
An efficient synthesis of 3′-amino-3′-deoxyguanosine from guanosine
Zhang, Lei,Cui, Zhiyong,Zhang, Biliang
, p. 703 - 710 (2007/10/03)
3′-Amino-3′-deoxyguanosine was synthesized from guanosine in eight steps and 58% overall yield. The 2′,3′-diol of 5′-O-[(tert-butyl)diphenylsilyl]-2-N-[(dimethylamino) methylidene]guanosine was reacted with α-acetoxyisobutyryl bromide and treated with 0.5N NH3 in MeOH to yield 9-[2′-O-acetyl-3′-bromo-5′-O-[(tertbutyl) diphenylsilyl]-3′-deoxy-β-D-xylofuranosyl]-2-N- [(dimethylamino)methylidene]guanine, which was reacted with benzyl isocyanate, NaH, and then 3.0N NaOH, and finally with Pd/C (10%) and HCO2NH4 in EtOH/AcOH to afford 3′-amino-3′-deoxyguanosine.
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.