Synthesis 2014; 46(05): 660-668
DOI: 10.1055/s-0033-1340499
paper
© Georg Thieme Verlag Stuttgart · New York

Regioselective and Facile Synthesis of 7,9-Dialkyl-8-oxopurines from 7,9-Dialkyl-7,8-dihydropurines: Total Synthesis of Heteromines I and J

Tomáš Tobrman*
Department of Organic Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic   Fax: +420(220)444288   tomas.tobrman@vscht.cz
,
Dalimil Dvořák
Department of Organic Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic   Fax: +420(220)444288   tomas.tobrman@vscht.cz
› Author Affiliations
Further Information

Publication History

Received: 21 October 2013

Accepted after revision: 09 December 2013

Publication Date:
09 January 2014 (online)


Abstract

A novel protocol for the synthesis of 6-halo-8-oxo-7,8-dihydro-9H-purines based on the oxidation of 7,9-dialkyl-7,8-dihydro-9H-purines has been developed. The presented methodology was used as a key step in the synthesis of heteromines I and J.

Supporting Information

 
  • References

  • 1 Zelnik R, Haraguchi M, Matida AK, Lavie D, Frolow F, Weisb AL. J. Chem. Soc., Perkin Trans. 1 1986; 2051
  • 2 Fu W.-W, Tan C.-H, Zhuang P.-Y, Yang S.-M, Luo H.-F, Tan J.-J, Liu P, Zhu D.-Y. Heterocycles 2011; 83: 1405
    • 3a Lindsay BS, Almeida AM. P, Smith CJ, Berlinck RG. S, da Rocha RM, Ireland CM. J. Nat. Prod. 1999; 62: 1573
    • 3b Makarieva TN, Guzii AG, Dmitrenok AS, Dmitrenok PS, Krasokhin VB, Stonik VA. Nat. Prod. Commun. 2006; 9: 711

      Selected reviews on oxidative DNA cleavage:
    • 4a Breen AP, Murphy JA. Free Radical Biol. Med. 1995; 18: 1033
    • 4b Kasai H, Nishimura S In Oxidative Stress: Oxidants and Antioxidants . Sies H. Academic Press; San Diego: 1991: 99-116
    • 4c Kryston TB, Georgiev AB, Pissis P, Georgakilas AG. Mutat. Res. 2011; 711: 193
    • 4d Cooke MS, Evans MD, Dizdaroglu M, Lunec J. FASEB J. 2003; 17: 1195

      Recent examples:
    • 5a Kim SK, Kim JY, Baek AK, Moon BJ. Bioorg. Med. Chem. Lett. 2002; 12: 1977
    • 5b Kim SK, Yokoyama S, Takaku H, Moon BJ. Bioorg. Med. Chem. Lett. 1998; 8: 939
    • 5c Hamm ML, Billig K. Org. Biomol. Chem. 2006; 4: 4068
    • 5d Cadena-Amaro C, Delepierre M, Pochet S. Bioorg. Med. Chem. Lett. 2005; 15: 1069
    • 6a Sekine M, Okada K, Seio K, Kakeya H, Osada H, Sasaki T. Bioorg. Med. Chem. 2004; 12: 5193
    • 6b Sekine M, Okada K, Seio K, Obata T, Sasaki T, Kakeya H, Osada H. Bioorg. Med. Chem. 2004; 12: 6343
    • 6c Moriguchi T, Asai N, Okada K, Seio K, Sasaki T, Sekine M. J. Org. Chem. 2002; 67: 3290
    • 6d Sekine M, Okada K, Seio K, Kakeya H, Osada H, Obata T, Sasaki T. J. Org. Chem. 2004; 69: 314
    • 6e Taguchi H, Ohkubo A, Sekine M, Seio K, Kakeya H, Osada H, Sasaki T. Nucleosides, Nucleotides Nucleic Acids 2006; 25: 647
    • 6f Moriguchi T, Asai N, Wada T, Seio K, Sasaki T, Sekine M. Tetrahedron Lett. 2000; 41: 5881
    • 7a Ho CY, Kukla MJ. Bioorg. Med. Chem. Lett. 1991; 1: 531
    • 7b Kelley JL, Linn JA, Selway JW. T. J. Med. Chem. 1991; 34: 157
    • 7c Michael MA, Cottam HB, Smee DF, Robins RK, Kini GD. J. Med. Chem. 1993; 36: 3431
  • 8 Beck JP, Arvanitis AG, Curry MA, Rescinito JT, Fitzgerald LW, Gilligan PJ, Zaczek R, Trainor GL. Bioorg. Med. Chem. Lett. 1999; 9: 967
  • 9 Kumagai T, Okubo T, Kataoka-Okubo H, Chaki S, Okuyama S, Nakazato A. Bioorg. Med. Chem. 2001; 9: 1357
  • 10 Shao Y, Cole AG, Brescia M.-R, Qin L.-Y, Duo J, Stauffer M, Rokosz LL, McGuinness BF, Henderson I. Bioorg. Med. Chem. Lett. 2009; 19: 1399
    • 11a Kurimoto A, Hashimoto K, Nakamura T, Norimura K, Ogita H, Takaku H, Bonnert R, McInally T, Wada H, Isobe Y. J. Med. Chem. 2010; 53: 2964
    • 11b Nakamura T, Wada H, Kurebayashi H, McInally T, Bonnert R, Isobe Y. Bioorg. Med. Chem. Lett. 2013; 23: 669
    • 11c Weterings JJ, Khan S, van der Heden van Noort GJ, Melief CJ. M, Overkleeft HS, van der Burg SH, Ossendorp F, van der Marel GA, Filippov DV. Bioorg. Med. Chem. Lett. 2009; 19: 2249
    • 12a Kumata K, Yui J, Hatori A, Fujinaga M, Yanamoto K, Yamasaki T, Kawamura K, Wakizaka H, Nengaki N, Yoshida Y, Ogawa M, Fukumura T, Zhang M.-R. J. Med. Chem. 2011; 54: 6040
    • 12b Yamasaki T, Koike S, Hatori A, Yanamoto K, Kawamura K, Yui J, Kumata K, Ando K, Zhang M.-R. J. Radiat. Res. 2010; 51: 57
  • 13 Reitz AB, Goodman MG, Pope BL, Argentieri DC, Bell SC, Burr LE, Chourmouzis E, Come J, Goodman JH, Klaubert DH, Maryanoff BE, McDonnell ME, Rampulla MS, Schott MR, Chen R. J. Med. Chem. 1994; 37: 3561
    • 14a Hirota K, Kazaoka K, Niimoto I, Kumihara H, Sajiki H, Isobe Y, Takaku H, Tobe M, Ogita H, Ogino T, Ichii S, Kurimoto A, Kawakami H. J. Med. Chem. 2002; 45: 5419
    • 14b Hirota K, Kazaoka K, Sajiki H. Bioorg. Med. Chem. 2003; 11: 2715
  • 15 Yamazaki K, Yasuda N, Inoue T, Nagakura T, Kira K, Shinoda M, Saeki T, Tanaka I. J. Pharmacol. Exp. Ther. 2006; 319: 1253
    • 16a Ikehara M, Maruyama T. Tetrahedron 1975; 31: 1369
    • 16b Fujii T, Saito T, Mori S. Heterocycles 1988; 27: 1145
  • 17 Janeba Z, Holý A, Masojídková M. Collect. Czech. Chem. Commun. 2001; 66: 1393
    • 18a Dornow A, Hinz E. Chem. Ber. 1958; 91: 1834
    • 18b Goodman MG, Goodman JH. J. Immunol. 1994; 130: 4081
  • 19 Gaulon C, Dijkstra HP, Springer CJ. Synthesis 2005; 2227
    • 20a Kosaku H, Kazunori K, Itaru N, Hironao S. Heterocycles 2001; 55: 2279
    • 20b Zaki ME. E, Proença MF. Tetrahedron 2011; 67: 755
    • 21a Come J, Burr L, Chen R. Tetrahedron Lett. 1991; 32: 4823
    • 21b Koukal P, Dvořáková H, Dvořák D, Tobrman T. Chem. Pap. 2013; 67: 3
    • 22a Fujii T, Ogawa K, Saito T, Kobayashi K, Itaya T, Date T, Okamura K. Chem. Pharm. Bull. 1995; 43: 53
    • 22b Itaya T, Kanai T, Shimada M, Nishikawa T, Takada Y, Hozumi Y, Mori S, Saito T, Fujii T. Chem. Pharm. Bull. 1997; 45: 1601
    • 23a Kameyama K, Sako M, Hirota K, Yoshifumi M. Synthesis 1983; 849
    • 23b Lee JM, Niles JC, Wishnok JS, Tannenbaum SR. Chem. Res. Toxicol. 2002; 15: 7
    • 23c Madyastha KM, Sridhar GR. J. Chem. Soc., Perkin Trans. 1 1999; 677
  • 25 Maryška M, Chudíková N, Kotek V, Dvořák D, Tobrman T. Monatsh. Chem. 2013; 144: 501
  • 26 Spontaneous air oxidation of 6-methoxy-2-dimethylamino-7,9-dimethyl-7,8-dihydro-9H-purine to heteromine J along with other byproducts was reported: Lin Y.-L, Huang R.-L. J. Nat. Prod. 1997; 60: 982
  • 27 Havelková M, Hocek M, Česnek M, Dvořák D. Synlett 1999; 1145
  • 28 Kazunobu K, Richard C, Seiji Y, Taisuke U. EP 1,568,699, 2005
  • 29 Porcheddu A, Giacomelli G, Piredda I, Carta M, Nieddu G. Eur. J. Org. Chem. 2008; 5786
  • 30 Gundersen L.-L, Bakkestuen AK, Aasen AJ, Øverås H, Rise R. Tetrahedron 1994; 50: 9743
  • 31 McKenzie TC, Epstein JW. J. Org. Chem. 1982; 47: 4881
  • 32 Kim BY, Ahn JB, Lee HW, Kang SK, Lee JH, Shin JS, Ahn SK, Hong CI, Yoon SS. Eur. J. Med. Chem. 2004; 39: 433
  • 33 Zheng Q.-H, Liu X, Fei X, Wang J.-Q, Ohannesian DW, Erickson LC, Stone KL, Martinez TD, Miller KD, Hutchins GD. J. Labelled Compd. Radiopharm. 2002; 45: 1239