✦ LIBER ✦

4-aza-7,9-dideazaadenosine, a new cytotoxic synthetic C-nucleoside analogue of adenosine

✍ Scribed by Shirish A. Patil; Brian A. Otter; Robert S. Klein

Book ID: 104214712
Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 323 KB
Volume: 35
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)73494-0

No coin nor oath required. For personal study only.

✦ Synopsis

The first synthesis of M , the pyrrolo[2,1-fl[1.2,4]triazinc C-nucleoside congener of adenosine is described. The key intexmediate ribofuranosyl pyrmle 4 is obtained by the direct C-ribosylation of pyrrolemagnesiumbromide with 2,3,5-t& 0-benzyl ribose followed by an acid-catalyzed dehydration. Vilsmeier formylation of 4 followed by N-amination and CHO --r CN conversion affords N-amino nitrile intermediate 2 which can be cyclized with formamidinc acetate to the blocked title compound 2. Hydrogenolytic debenzylation completes the synthesis. In vitro growth inhibitory activities of 1p against leukemic cell lines (0.8 -I5 TIM) are comparable to those of pdeazardenosine.

📜 SIMILAR VOLUMES

Synthesis and antiviral activity of a se

Synthesis and antiviral activity of a series of 1′-substituted 4-aza-7,9-dideazaadenosine C-nucleosides

✍ Aesop Cho; Oliver L. Saunders; Thomas Butler; Lijun Zhang; Jie Xu; Jennifer E. V 📂 Article 📅 2012 🏛 Elsevier Science 🌐 English ⚖ 363 KB

ChemInform Abstract: Synthesis and Antiv

ChemInform Abstract: Synthesis and Antiviral Activity of a Series of 1′-Substituted 4-Aza-7,9-dideazaadenosine C-Nucleosides.

✍ Aesop Cho; Oliver L. Saunders; Thomas Butler; Lijun Zhang; Jie Xu; Jennifer E. V 📂 Article 📅 2012 🏛 John Wiley and Sons ⚖ 32 KB

Synthesis of “9-deazaadenosine”; A new c

Synthesis of “9-deazaadenosine”; A new cytotoxic C-nucleoside isostere of adenosine

✍ Mu-Ill Lim; Robert S. Klein 📂 Article 📅 1981 🏛 Elsevier Science 🌐 French ⚖ 221 KB

Synthesis of 1,N 6 -etheno-2-aza-adenosi

Synthesis of 1,N 6 -etheno-2-aza-adenosine (2-aza-ε-adenosine): a new cytotoxic fluorescent nucleoside

✍ Tsou, K.C.; Yip, K.F.; Miller, E.E.; Lo, K.W. 📂 Article 📅 1974 🏛 Oxford University Press 🌐 English ⚖ 419 KB

ChemInform Abstract: A New C-Nucleoside

ChemInform Abstract: A New C-Nucleoside Analogue of Tiazofurin: Synthesis and Biological Evaluation of 2-β-D-Ribofuranosylimidazole-4-carboxamide (Imidazofurin).

✍ Palmarisa Franchetti; Stefano Marchetti; Loredana Cappellacci; Joel A. Yalowitz; 📂 Article 📅 2001 🏛 John Wiley and Sons ⚖ 33 KB 👁 2 views

ChemInform Abstract: Nucleosides and Nuc

ChemInform Abstract: Nucleosides and Nucleotides. Part 157. New Neplanocin Analogues. Part 9. A Practical Preparation of (6′R)-6′-C-Methylneplanocin A (RMNPA), a Potent Antiviral Agent, and the Determination of Its 6′-Configuration. Diastereoselective Deamination by Adenosine Deaminase.

✍ S. SHUTO; T. OBARA; S. YAGINUMA; A. MATSUDA 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB 👁 1 views