One-pot synthesis and antiproliferative evaluation of pyrazolo[3,4-d] pyrimidine derivatives

Tetrahedron

Volumn 68, Issue 47, 2012, Pages 9658-9664

  Huang, Yu Ying ^a   Wang, Li Ya ^a   Chang, Chun Hsi ^a   Kuo, Yueh Hsiung ^a   Kaneko, Kimiyoshi ^b   Takayama, Hiroyuki ^b   Kimura, Masayuki ^b   Juang, Shin Hun ^a   Wong, Fung Fuh ^a  

^a CHINA MEDICAL UNIVERSITY   (Taiwan)

^b NIHON PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

5 Aminopyrazoles; Antiproliferative activity; One pot synthesis; Pyrazolo 3,4 d pyrimidines

Indexed keywords

1 (2 CHLOROPHENYL) 3 (4 CHLOROPHENYL) 1H PYRAZOLO[3,4 D] PYRIMIDINE; 1 (2 CHLOROPHENYL) 3 PHENYL 1H PYRAZOLO[3,4 D]PYRIMIDINE; 1 (2 METHYLPHENYL) 3 PHENYL 1H PYRAZOLO[3,4 D]PYRIMIDINE; 1 (3 CHLOROPHENYL) 3 PHENYL 1H PYRAZOLO[3,4 D]PYRIMIDINE; 1 (3 METHYLPHENYL) 3 PHENYL 1H PYRAZOLO[3,4 D]PYRIMIDINE; 1 (3 NITROPHENYL) 3 PHENYL 1H PYRAZOLO[3,4 D]PYRIMIDINE; 1 (4 BROMOPHENYL) 3 PHENYL 1H PYRAZOLO[3,4 D]PYRIMIDINE; 1 (4 CHLOROPHENYL) 3 (4 CHLOROPHENYL) 1H PYRAZOLO[3,4 D] PYRIMIDINE; 1 (4 CHLOROPHENYL) 3 PHENYL 1H PYRAZOLO[3,4 D]PYRIMIDINE; 1 (4 METHOXYLPHENYL) 3 PHENYL 1H PYRAZOLO[3,4 D]PYRIMIDINE; 1,3 DIPHENYL 1H PYRAZOLO[3,4 D]PYRIMIDINE; 3 (4 CHLOROPHENYL) 1 (PYRIDIN 2 YL) 1H PYRAZOLO[3,4 D]PYRIMIDINE; 3 (4 CHLOROPHENYL) 1 PHENYL 1H PYRAZOLO[3,4 D]PYRIMIDINE; 3 (4 METHOXYLPHENYL) 1 PHENYL 1H PYRAZOLO[3,4 D]PYRIMIDINE; 3 (4 METHYLPHENYL) 1 (PYRIDIN 2 YL) 1H PYRAZOLO[3,4 D]PYRIMIDINE; 3 (4 METHYLPHENYL) 1 PHENYL 1H PYRAZOLO[3,4 D]PYRIMIDINE; 3 METHYL 1 (PYRIDIN 2 YL) 1H PYRAZOLO[3,4 D]PYRIMIDINE; 3 METHYL 1 PHENYL 1H PYRAZOLO[3,4 D]PYRIMIDINE; 3 PHENYL 1 (PYRIDIN 2 YL) 1H PYRAZOLO[3,4 D]PYRIMIDINE; 3 TERT BUTYL 1 (PYRIDIN 2 YL) 1H PYRAZOLO[3,4 D]PYRIMIDINE; 3 TERT BUTYL 1 PHENYL 1H PYRAZOLO[3,4 D]PYRIMIDINE; BROMIDE; CHLORINE; FORMAMIDE; METHYL GROUP; PHENYL GROUP; PHOSPHORUS DERIVATIVE; PYRAZOLE DERIVATIVE; PYRAZOLO[3,4 D]PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA CELL LINE; LUNG CARCINOMA; NASOPHARYNX CANCER; ONE POT SYNTHESIS; PRIORITY JOURNAL; T CELL LEUKEMIA;

EID: 84867522126     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.09.054     Document Type: Article

References (23)

1. T.El-S. Ali Eur. J. Med. Chem. 44 2009 4385 4392
2. M. Bakavoli, G. Bagherzadeh, M. Vaseghifar, A. Shiri, M. Mehdi Pordel, M. Mashreghi, P. Pordeli, and M. Araghi Eur. J. Med. Chem. 45 2009 647 650
3. B.S. Holla, M. Mahalinga, M.S. Karthikeyan, P.M. Akberali, and N.S. Shetty Bioorg. Med. Chem. 14 2006 2040 2047
4. A.H. Shamroukh, A.E. Rashad, and H.H. Sayed Phosphorous, Sulfur Silicon Relat. Elem. 180 2005 2347 2360
5. A. Kumar, I. Ahmad, B.S. Chhikara, R. Tiwari, D. Mandal, and K. Parang Bioorg. Med. Chem. Lett. 21 2011 1342 1346
6. M.M. Ghorab, F.A. Ragab, S.I. Alqasoumi, A.M. Alafeefy, and S.A. Aboulmag Eur. J. Med. Chem. 45 2010 171 178
7. S. Schenone, O. Bruno, F. Bondavalli, A. Ranise, L. Mosti, G. Giulia Menozzi, P. Paola Fossa, S. Donnini, A. Santoro, M. Ziche, F. Manetti, and M. Botta Eur. J. Med. Chem. 39 2004 939 946
8. E.R. EI-Bendary, and F.A. Badria Arch. Pharm. (Weinheim, Ger.) 333 2000 99 103
9. H. Liu, H.Q. Wang, and Z.J. Liu Bioorg. Med. Chem. Lett. 17 2007 2203 2209
10. J.H. Chern, K.S. Shia, T.A. Hsu, C.L. Tai, C.C. Lee, Y.C. Lee, C.S. Chang, S.N. Tseng, and S.R. Shih Bioorg. Med. Chem. Lett. 14 2004 2519 2525
11. A.E. Rashad, M.I. Hegab, R.E. Abdel-Megeid, N. Fathalla, and F.M.E. Abdel-Megeid Eur. J. Med. Chem. 44 2009 3285 3291
12. J.M. Quintela, C. Peinador, L. Gonzalez, I. Devesa, M.L. Ferrandiz, M.J. Alcaraz, and R. Riguera Bioorg. Med. Chem. 11 2003 863 868
13. A. Bendich, P.J. Russell, and J.J. Fox J. Am. Chem. Soc. 76 1954 6073 6077
14. D.C. Miller, W. Klute, A. Calabrese, and A.D. Brown Bioorg. Med. Chem. Lett. 19 2009 6144 6147
15. M. Chebib, and R.J. Quinn Bioorg. Med. Chem. 5 1997 311 322
16. M. Chebib, and R.J. Quinn Bioorg. Med. Chem. Lett. 5 1995 2409 2412
17. O. Moukha-Chafiq, M.L. Taha, H.B. Lazrek, C. Pannecouque, M. Witvrouw, E. DeClercq, J.L. Barascut, and J.L. Imbach Nucleosides Nucleotides Nucleic Acids 20 2001 1797 1810
18. F. Rigueiroa, S. Teixeiraa, A.M. Salaheldinb, A.M.F. Oliveira-Camposb, L.M. Rodriguesb, F. Peixotoc, and M.M. Oliveira Biochim. Biophys. Acta 1777 2008 S10.17
19. P. Molina, A. Arques, and M.V. Vinader Tetrahedron Lett. 28 1987 4451 4454
20. M.N. Jachak, A.B. Avhale, V.J. Medhane, and R.B. Toche J. Heterocycl. Chem. 43 2006 1169 1175
21. E.-S.A. Aly, M.A. Abdo, and A.A. El-Gharably Afinidad 61 2004 510 515
22. A. Simay, K. Takacs, K. Horvath, and P. Dvortsak Acta Chim. Acad. Sci. Hung. 105 1980 127 139
23. W.-N. Su, T.-P. Lin, K.-M. Cheng, K.-C. Sung, S.-K. Lin, and F.F. Wong J. Heterocycl. Chem. 47 2010 831 837