Subscribe to RSS
DOI: 10.1055/s-2002-31956
Synthesis and Cytostatic Activities of New 6-Substituted Purinylcarbonucleosides Derived from Indan [1]
Publication History
Publication Date:
03 June 2002 (online)
![](https://www.thieme-connect.de/media/synthesis/200208/lookinside/thumbnails/10.1055-s-2002-31956-1.jpg)
Abstract
A new series of 6-substituted purinylcarbonucleosides derivatives of indan, 8a-g and 10a-d, was synthesized from (±)-cis-1,3-indandimethanol acetate (5), which was prepared in three steps from benzonorbornadiene. 6-Chloropurine was introduced both by Mitsunobu reaction with 5 and by substitution of the mesylate 6. Suzuki-Miyaura reactions of the protected 6-chloropurine derivative 7 with substituted phenylboronic acids afforded 9a-d (protected purine derivatives with substituted phenyl rings at position 6); deprotection of the latter yielded the new series of purinylcarbonucleoside indan derivatives 10a-d. Treatment of compound 7 with R′H/NaOH afforded a parallel series 8a-g, with alkoxy or amino groups R′ at position 6 instead of substituted phenyl rings.
Key words
synthesis - antineoplastic agent - indan carbocyclic nucleoside - Mitsunobu reaction - Suzuki-Miyaura cross-coupling reaction
Part of this work was presented at the XIV International Round Table on Nucleosides, Nucleotides and their Biological Applications, San Francisco, USA, September 2000 and XII Congreso Nacional de la Sociedad Española de Química Terapéutica, Sevilla, Spain, September 2001.
-
2a
Cheson BD. Hematol. Cell. Ther. (Suppl. 2) 1996, 38: 109 -
2b
Bergmann L. Leukemia (Suppl. 2) 1997, 11: 29 - 3
Lambe CU.Averett DR.Paff MT.Reardon JE.Wilson JG.Krenitsky TA. Cancer Res. 1995, 55: 3352 - 4
Gibboney DS.French BT.Patrick DE.Trewin RW. Cancer Chemother. Pharmacol. 1989, 25: 189 - 5
Hocek M.Hol A.Votruba I.Dvoráková H. J. Med. Chem. 2000, 43: 1817 - 6
Fernández F.García-Mera X.Morales M.Rodríguez-Borges JE. Synthesis 2001, 239 - 7
Wittig G.Knauss E. Chem. Ber. 1958, 91: 895 -
8a
Mitsunobu O.Wata M.Sano T. J. Am. Chem. Soc. 1972, 94: 679 -
8b
Mitsunobu O. Synthesis 1981, 1 -
8c
Girard F.Lee MG.Agrofoglio LA. J. Heterocycl. Chem. 1998, 35: 911 - 9
Borcherding DR.Peet NP.Munson HR.Zhang H.Hoffman PF.Bowlin TL.Edwards CK. J. Med. Chem. 1996, 39: 2615 - 10
Cesnek M.Hocek M.Hol A. Collect. Czech. Chem. Commun. 2000, 65: 1357 - 11
Havelková M.Dvorak D.Hocek M. Synthesis 2001, 1704 - 12
Suzuki A. J. Organomet. Chem. 1999, 576: 147 ; and references therein - 13
De Clercq E. In Vivo and Ex Vivo Text Systems to Rationalize Drug Design and DeliveryCromelin D.Couvreur P.Duchene D. Editions de Sante; Paris: 1994.
References
Part of this work was presented at the XIV International Round Table on Nucleosides, Nucleotides and their Biological Applications, San Francisco, USA, September 2000 and XII Congreso Nacional de la Sociedad Española de Química Terapéutica, Sevilla, Spain, September 2001.