134934-82-0Relevant 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.
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.
Syntheses of puromycin from adenosine and 7-deazapuromycin from tubercidin, and biological comparisons of the 7-aza/deaza pair
Robins, Morris J.,Miles, Robert W.,Samano, Mirna C.,Kaspar, Roger L.
, p. 8204 - 8210 (2007/10/03)
Protection (05′) of 2′,3′-anhydroadenosine with tert-butyldiphenylsilyl chloride and epoxide opening with dimethylboron bromide gave the 3′-bromo-3′-deoxy xylo isomer which was treated with benzylisocyanate to give the 2′-O-(N-benzylcarbamoyl) derivative. Ring closure gave the oxazolidinone, and successive deprotection concluded an efficient route to 3′-amino-3′-deoxyadenosine. Analogous treatment ofthe antibiotic tubercidin {7-deazaadenosine; 4-amino-7-(β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidine} gave 3′-amino-3′-deoxytubercidin. Trifluoroacetylation of the 3′-amino function, elaboration of the heterocyclic amino group into a (1,2,4-triazol-4-yl) ring with N,N′-bis-[(dimethylamino)methylene]hydrazine, and nucleophilic aromatic substitution with dimethylamine gave puromycin aminonucleoside [9-(3-amino-3-deoxy-β-D-ribofuranosyl)-6-(dimethylamino)purine] and its 7-deaza analogue. Aminoacylation [BOC-(4-methoxy-L-phenylalanine)] and deprotection gave puromycin and 7-deazapuromycin. Most reactions gave high yields at or below ambient temperature. Equivalent inhibition of protein biosynthesis in a rabbit reticulocyte system and parallel growth inhibition of several bacteria were observed with the 7-aza/deaza pair. Replacement of N7 in the purine ring of puromycin by "CH" has no apparent effect on biological activity.
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.
Synthesis of purine and pyrimidine 3′-amino-3′-deoxy- and 3′-amino-2′,3′-dideoxyxylonucleosides
Garcia-Alles, Luis F.,Magdalena, Julia,Gotor, Vicente
, p. 6980 - 6986 (2007/10/03)
A general procedure to obtain the 3′-aminoxylonucleosides 13a,b and 17a,b is presented. The synthetic scheme is based on the 5′ directed intramolecular nucleophilic substitution at the 3′-activated position of the nucleoside. The approach of the incoming group to this position takes place regio- and stereoselectively from the most hindered face of the nucleoside. The methodology presented is applicable to ribonucleosides and 2′-deoxyribonucleosides, regardless of their nitrogenated base.
