RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2016; 48(07): 1029-1045
DOI: 10.1055/s-0035-1561287
DOI: 10.1055/s-0035-1561287
paper
Synthesis of Fluorescent 2-Substituted 6-(Het)aryl-7-deazapurine Bases {4-(Het)aryl-pyrrolo[2,3-d]pyrimidines} by Aqueous Suzuki–Miyaura Cross-Coupling Reactions
Weitere Informationen
Publikationsverlauf
Received: 16. November 2015
Accepted after revision: 20. November 2015
Publikationsdatum:
11. Januar 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201607/lookinside/thumbnails/ss-2015-z0663-op_10-1055_s-0035-1561287-1.jpg)
Abstract
A series of 4-(het)aryl-pyrrolo[2,3-d]pyrimidines [6-(het)aryl-7-deazapurine bases] bearing a H, NH2, CH3, F, or Cl group at the 2-position and either H or F at the 5-position (position 7 of 7-deazapurine) were prepared in a single step by the aqueous Suzuki–Miyaura cross-coupling reactions of the corresponding 6-chloro-7-deazapurines with (het)arylboronic acids. Unlike their ribonucleoside derivatives, which are potent cytostatics, the deazapurine bases did not show significant biological activity but most of them exerted bright fluorescence with emission maxima 368–468 nm and high quantum yields up to 0.83.
Key words
nucleobases - deazapurines - pyrrolo[2,3-d]pyrimidines - Suzuki cross-coupling - arylationSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561287.
- Supporting Information
-
References
- 1 For a review, see: Tumkevicius S, Dodonova J. Chem. Heterocycl. Comp. 2012; 48: 258
- 2a Lawhorn BG, Philp J, Zhao Y, Louer C, Hammond M, Cheung M, Fries H, Graves AP, Shewchuk L, Wang L, Cottom JE, Qi H, Zhao H, Totoritis R, Zhang G, Schwartz B, Li H, Sweitzer S, Holt DA, Gatto GJ. Jr, Kallander LS. J. Med. Chem. 2015; 58: 7431
- 2b Henderson JL, Kormos BL, Hayward MM, Coffman KJ, Jasti J, Kurumbail RG, Wager TT, Verhoest PR, Noell GS, Chen Y, Needle E, Berger Z, Steyn SJ, Houle C, Hirst WD, Galatsis P. J. Med. Chem. 2015; 58: 419
- 2c O’Brien NJ, Brzozowski M, Buskes MJ, Deady LW, Abbott BM. Bioorg. Med. Chem. 2014; 22: 3879
- 3a Tumkevicius S, Dodonova J, Kazlauskas K, Masevisius V, Skardziute L, Jursenas S. Tetrahedron Lett. 2010; 51: 3902
- 3b Urbonas RV, Poskus V, Bucevicius J, Dodonova J, Tumkevicius S. Synlett 2013; 24: 1383
- 3c Dodonova J, Tumkevicius S. RSC Adv. 2014; 4: 35966
- 3d Dodonova J, Skardziute L, Kazlauskas K, Jursenas S, Tumkevicius S. Tetrahedron 2012; 68: 329
- 3e Prieur V, Rubio-Martınez J, Font-Bardia M, Guillaumet G, Pujol MD. Eur. J. Org. Chem. 2014; 1514
- 3f Prieur V, Heindler N, Rubio-Martinez J, Guillaumet G, Pujol MD. Tetrahedron 2015; 71: 1207
- 3g Krömer M, Klečka M, Slavětínská L, Klepetářová B, Hocek M. Eur. J. Org. Chem. 2014; 7203
- 3h Klečka M, Poštová Slavětínská L, Hocek M. Eur. J. Org. Chem. 2015; 7943
- 4 Nauš P, Pohl R, Votruba I, Džubák P, Hajdúch M, Ameral R, Birkuš G, Wang T, Ray AS, Mackman R, Cihlar T, Hocek M. J. Med. Chem. 2010; 53: 460
- 5 Perlíková P, Konečný P, Nauš P, Snášel J, Votruba I, Džubák P, Pichová I, Hajdúch M, Hocek M. Med. Chem. Commun. 2013; 4: 1497
- 6 Malnuit V, Slavětínská L, Nauš P, Džubák P, Hajdúch M, Stolaříková J, Snášel J, Pichová I, Hocek M. ChemMedChem 2015; 10: 1079
- 7a Nauš P, Perlíková P, Pohl R, Hocek M. Collect. Czech. Chem. Commun. 2011; 76: 957
- 7b Perlíková P, Jornet Martínez N, Slavětínská L, Hocek M. Tetrahedron 2012; 68: 8300
- 8a Western EC, Daft JR, Johnson EM, Gannett PM, Shaughnessy KH. J. Org. Chem. 2003; 68: 6767
- 8b Čapek P, Pohl R, Hocek M. Org. Biomol. Chem. 2006; 4: 2278
- 9 Čapek P, Vrábel M, Hasník Z, Pohl R, Hocek M. Synthesis 2006; 3515
- 10 Molander GA, Canturk B, Kennedy LE. J. Org. Chem. 2009; 74: 973
- 11 Wang XJ, Seth PP, Ranken R, Swayze EE, Migawa MT. Nucleosides, Nucleotides Nucleic Acids 2004; 23: 161
- 12 West RA, Beauchamp L. J. Org. Chem. 1961; 26: 3809
- 13 Babu YS, Chand P, Kotian PL, Kumar VS. US Patent WO2010/14930 A2, 2010
- 14 Kimoto M, Mitsui T, Yokoyama S, Hirao I. J. Am. Chem. Soc. 2010; 132: 4988
- 15a Tainaka K, Tanaka K, Ikeda S, Nishiza K, Unzai T, Fujiwara Y, Saito I, Okamoto A. J. Am. Chem. Soc. 2007; 129: 4776
- 15b Riedl J, Pohl R, Ernsting NP, Orsag P, Fojta M, Hocek M. Chem. Sci. 2012; 3: 2797
- 15c Weinberger M, Berndt F, Mahrwald R, Ernsting NP, Wagenknecht H.-A. J. Org. Chem. 2013; 78: 2589
- 15d Barthes NP. F, Karpenko IA, Dziuba D, Spadafora M, Auffret J, Demchenko AP, Mely Y, Benhida R, Michel BY, Burger A. RSC Adv. 2015; 5: 33536
- 15e Saito Y, Suzuki A, Okada Y, Yamasaka Y, Nemoto N, Saito I. Chem. Commun. 2013; 49: 5684
- 15f Saito Y, Suzuki A, Yamauchi T, Saito I. Tetrahedron Lett. 2015; 56: 3034
- 15g Dumat B, Bood M, Wranne MS, Lawson CP, Larsen AF, Preus S, Streling J, Gradén H, Wellner E, Grøtli M, Wilhelmsson LM. Chem. Eur. J. 2015; 21: 4039
- 16a Brouwer AM. Pure Appl. Chem. 2011; 83: 2213
- 16b Würth C, Grabolle M, Pauli J, Spieles M, Resch-Genger U. Nature Protocols 2013; 8: 1535
- 17 Melhuish WH. J. Phys. Chem. 1961; 65: 229
For examples, see: