Nucleic acid related compounds. 28. 2′-amino-araA [9-(2-amino-2-deoxy-β-D-arabinofuranosyl)adenine]. Synthesis via nucleoside-aziridine or azido intermediates and biological effects.
✍ Scribed by Morris J. Robins; S.D. Hawrelak
- Publisher
- Elsevier Science
- Year
- 1978
- Tongue
- French
- Weight
- 247 KB
- Volume
- 19
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Naturally occurring nucleosides, nucleoside antibiotics, and their analogues are compounds of increasing importance and interest as antitumor and antiviral agents.
3 In particular, araA (9-8-g-arabinofuranosyladenine, 1) exerts inhibi--4 tory activity against various tumor lines and against DNA viruses. Clinical evaluation of 1 is in progress and appears promising in the treatment of certain herpes viral infections. 5 However, araA has extremely limited solubility in water and it also suffers rapid enzymatic deamination to 9-8-D-arabinofuranosylhypoxanthine which then undergoes enzymatic glycosyl cleavage to the natural metabolite, hypoxanthine. 6 The 2'-amino-2'-deoxy ribo analogue of adenosine has been synthesized 7,8 and the corresponding guanosine 2 '-amino analogue has been isolated as an antibiotic' and synthesized. 8 However, no examples of 2'-amino-2'-deoxy arabino