Summary
Various 2’-azido- and 2’-aminoarabinofuranosyl purine and pyrimidine nucleosides have been synthesized. Among these, the derivatives of cytosine and of adenine inhibit the growth of some tumor cell lines in vitro and in vivo. 2’-Azidoarabinofuranosyl cytosine also interferes with the replication of herpes simplex virus types I and II. Whereas 2’-azidoara-C is resistant to deamination by a partially purified CdR deaminase from KB cells, the adenine derivatives are substrates for aminohydrolases partially purified from calf and mouse intestines. Both azido- and aminoara-C are phosphorylated by partially purified CdR kinases from leukemia L1210 and from human AML blast cells. The accumulated data encourage exploration of the clinical utility of the more potent of these analogues.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Bobek, M (1979) 2’-Azido-2’-deoxy- and 2’-amino-2’-deoxy-D-arabinofuranosyl purine nucleosides. Carbohydr Res 70:263–273
Bobek M, Bloch A, Berkowitz P, Bardos TJ (1977) Synthesis and antitumor activity of 1,2-dihydro-l-(2-deoxy-β-D-erythro-pentofuranosyl)-2-oxo-5-methylpyrazine 4-oxide, a structural analogue of thymidine. J Med Chem 20:458–460
Bobek M, Cheng YC, Bloch A (1978) Novel arabinofuranosyl derivatives of cytosine resistant to enzymatic deamination and possessing potent antitumor activity. J Med Chem 21:597
Bobek M, Martin V (1978) The synthesis of anomeric 3-0-acetyl-5-Obenzoyl-2-azi- do-2-deoxy-D-arabinofuranosyl chlorides. Versatile sugar intermediates for the synthesis of 2’-azido-2’-deoxy- and 2’-amino-2’-deoxy-β-D-arabinofuranosyl nucleosides. Tetrahedron Lett 22:1919–1922
Cheng YC, Domin B, Lee LS (1977) Human deoxycytidine kinase. Purification and characterization of the cytoplasmic and mitochondrial isozymes derived from blast cells of acute leukemia patients. Biochem Biophys Acta 481:481–492
Cheng YC, Domin BA, Sharma RA, Bobek M (1976) Antiviral action and cellular toxicity of four thymidine analogues: 5-ethyl-, 5-vinyl-, 5-propyl-, and 5-allyl-2’-deoxyuridine. Antimicrob Agents Chemother 10:119–122
Ho DHW, Carter CF, Loo TL (1975) Tetrahydrouridine in the uptake and metabolism of arabinosylcytosine by human acute myelocytic leukemia cells. Proc Am Assoc Cancer Res 16:57
LePage GA, Worth LS, Kimball AP (1976) Enhancement of the antitumor activity of arabinofuranosyladenine by 2’-deoxycoformycin. Cancer Res 36:1481–1485
Ranganathan R, Larwood D (1978) Facile conversion of adenosine into new 2’-substi- tuted-2’-deoxy-arabinofuranosyladenine derivatives: Stereospecific synthesis of 2’-azi- do-2’-deoxy-, 2’-amino-2’-deoxy-, and 2’-mercapto-2’-deoxy-β-D-arabinofuranosylade- nines. Tetrahedron Lett 45:4341–4344
Robins MJ, Hawrelak SD (1978) 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. Tetrahedron Lett 39:3653–3656
Unger FM, Christian R, Waldstatten P (1979) Azido- und Diazido-Derivative von Arabinonukleosiden. Tetrahedron Lett 7:605–608
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1980 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Bobek, M., Cheng, YC., Mihich, E., Bloch, A. (1980). Synthesis, Biologic Effects, and Biochemical Properties of Some 2’-Azido- and 2’-Amino-2’-Deoxyarabinofuranosyl Pyrimidines and Purines. In: Mathé, G., Muggia, F.M. (eds) Cancer Chemo- and Immunopharmacology. Recent Results in Cancer Research, vol 74. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-81488-4_11
Download citation
DOI: https://doi.org/10.1007/978-3-642-81488-4_11
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-81490-7
Online ISBN: 978-3-642-81488-4
eBook Packages: Springer Book Archive