Citation: Shahnaz Rostamizadeh, Masoomeh Nojavan, Reza Aryan, Hamid Sadeghian, Mahdieh Davoodnejad. A novel and efficient synthesis of pyrazolo[3, 4-d]pyrimidine derivatives and the study of their anti-bacterial activity[J]. Chinese Chemical Letters, ;2013, 24(07): 629-632. shu

A novel and efficient synthesis of pyrazolo[3, 4-d]pyrimidine derivatives and the study of their anti-bacterial activity

  • Corresponding author: Shahnaz Rostamizadeh, 
  • Received Date: 20 February 2013
    Available Online: 11 April 2013

  • In this work 4-amino-6-aryl-2-phenyl pyrimidine-5-carbonitrile derivatives were synthesized through a one-pot, three-component reaction of an aldehyde, malononitrile and benzamidine hydrochloride, in the presence of magnetic nano Fe3O4 particles as a catalyst under solvent-free conditions. 3-Amino-6-aryl-2-phenylpyrazolo[3,4-d]pyrimidine derivatives were prepared through an efficient and environmentally friendly reaction between 4-amino-6-aryl-2-phenylpyrimidine-5-carbonitrile derivatives and hydrazine hydrate and their antibacterial activity has been evaluated.
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    1. [1]

      [1] M. Soth, S. Abbot, A. Abubakari, et al., 3-Amino-pyrazolo[3,4-d]pyrimidines as p38α kinase inhibitors: design and development to a highly selective lead, Bioorg. Med. Chem. Lett. 21 (2011) 3452-3456.

    2. [2]

      [2] E. Dreassi, A.T. Zizzari, M. Mori, et al., 2-Hydroxypropyl-β-cyclodextrin strongly improves water solubility and anti-proliferative activity of pyrazolo[3,4-d]pyrimidines Src-Abl dual inhibitors, Eur. J. Med. Chem. 45 (2010) 5958-5964.

    3. [3]

      [3] F. Gattal, F. Perotti, L. Gradoni, et al., Synthesis of some 1-(dihydroxypropyl)pyrazolo[3, 4-d]pyrimidines and in vivo evaluation of their antileishmanial and antitrypanosomal activity, Eur. J. Med. Chem. 25 (1990) 419-424.

    4. [4]

      [4] M. Bakavoli, G. Bagherzadeh, M. Vaseghifar, et al., Molecular iodine promoted synthesis of new pyrazolo[3,4-d]pyrimidine derivatives as potential antibacterial agents, Eur. J. Med. Chem. 45 (2010) 647-650.

    5. [5]

      [5] H.B. Cottam, C.R. Petrie, P.A. McKernan, et al., Synthesis and biological activity of certain 3,4-disubstituted pyrazolo[3,4-d]pyrimidine nucleosides, J. Med. Chem. 27 (1984) 1119-1127.

    6. [6]

      [6] R.J. Gillespie, I.A. Cliffe, C.E. Dawson, et al., Antagonists of the human adenosine A2A receptor. Part 3: design and synthesis of pyrazolo[3,4-d]pyrimidines, pyrrolo[2,3-d]pyrimidines and 6-arylpurines, Bioorg. Med. Chem. Lett. 18 (2008) 2924-2929.

    7. [7]

      [7] R.R. Schmidt,Neuesynthese von pyrimidinderivaten, Chem. Ber. 98(1965) 346-351.

    8. [8]

      [8] J. Quiroga, J. Trilleras, B. Insuasty, et al., Microwave-assisted synthesis of pyrazolo[3,4-d]pyrimidines from 2-amino-4,6-dichloropyrimidine-5-carbaldehyde under solvent-free conditions, Tetrahedron Lett. 49 (2008) 3257-3259.

    9. [9]

      [9] S. Boyd, L. Campbell, W. Liao, et al., A one step synthesis of 1-alkylpyrazolo[5,4- d]pyrimidines, Tetrahedron Lett. 49 (2008) 7395-7397.

    10. [10]

      [10] J.C. Verheijen, D.J. Richard, K. Curran, et al., Discovery of 4-morpholino-6-aryl-1Hpyrazolo[3,4-d]pyrimidines as highly potent and selective ATP-competitive inhibitors of the mammalian target of rapamycin (mTOR): optimization of the 6-aryl substituent, J. Med. Chem. 52 (2009) 8010-8024.

    11. [11]

      [11] M.T. Cocco, C. Congiu, V. Onnis, Transformation of 6-methylthiopyrimidines. Preparation of new pyrimidine derivatives and fused azolopyrimidines, J. Heterocycl. Chem. 37 (2000) 707-710.

    12. [12]

      [12] M. Rehwald, K. Gewald, Syntheses of thieno[2,3-d]pyrimidines and aminopyrimidines from 2-alkoxy-5-cyano-4-thioxopyrimidine intermediates, Heterocycles 48 (1998) 1157-1167.

    13. [13]

      [13] T.M.C. Tan, F. Yang, H. Fu, M.S. Raghavendra, Y. Lam, Traceless solid-phase synthesis and biological evaluation of purine analogs as inhibitors of multidrug resistance protein 4, J. Comb. Chem. 9 (2007) 210-218.

    14. [14]

      [14] J. Ahmadi, S. Sadjadi, M. Hosseinpour, Granulated copper oxide nanocatalyst: a mild and efficient reusable catalyst for the one-pot synthesis of 4-amino-5- pyrimidinecarbonitriles under aqueous conditions, Monatsh. Chem. 142 (2011) 1163-1168.

    15. [15]

      [15] H. Sheibani, A.S. Saljoogi, A. Bazgir, Three-component process for the synthesis of 4-amino-5-pyrimidinecarbonitriles under thermal aqueous conditions or microwave irradiation, Arkivoc (ⅱ) (2008) 115-123.

    16. [16]

      [16] A.M. Abdelfaitah, S.M. Hijssain, A.M. El-Reedy, N.M. Yousif, Reactions with asubstituted monitriles. A novel synthesis of arylpyrimidines, Tetrahedron 39 (1983) 3197-3199.

    17. [17]

      [17] E. Salfrán, C. Seoaneb, M. Suárez, et al., One-step synthesis of aminopyrimidines from 5-oxo-4H-benzopyrans, J. Heterocycl. Chem. 41 (2004) 509-516.

    18. [18]

      [18] S.J. de Melo, L.C. dos Santos, E.P.S. Falco, et al., Synthesis of new 4-amino-2,6- diarylpyrimidine-5-carbonitriles, J. Chem. Res. Synop. (2002) 216-217.

    19. [19]

      [19] R.V. Rothenburg, Verhalten des Hydrzinhydrates gegen die nitro-, nitroso-und isonitrosogruppe, Chem. Ber. 26 (1893) 2060-2061.

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