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    South African Journal of Chemistry

    On-line version ISSN 1996-840XPrint version ISSN 0379-4350

    S.Afr.j.chem. (Online) vol.62  Durban  2009

     

    RESEARCH ARTICLE

     

    Synthesis and cytotoxicity screening of some novel benzofuranoyl-pyrazole derivatives against liver and cervix carcinoma cell lines

     

     

    Magdy I. El-Zahar; Somaia S. Abd El-Karim; Manal M. Anwar

    Therapeutical Chemistry Department, National Research Centre, Dokki, Cairo, Egypt

     

     


    ABSTRACT

    A series of new pyrazole, thiazole and thiazolinone derivatives incorporated into benzofuran were synthesized by using 3-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-4-carboxaldehyde as starting material. A total of 41 novel compounds were synthesized. Some of these synthesized compounds were evaluated for cytotoxicity activity against HEPG2 (liver carcinoma cell line) and HELA (cervix carcinoma cell line). The tested compounds (1, 2c, 7c, 8b, 9b, 13b and 14b) showed better activities at low concentration against the commonly used human carcinoma cell lines. A detailed synthesis, spectroscopic data and cytotoxicity screening for the new compounds are described.

    Key words: Pyrazole, thiazolinone, benzofuran, benzofuranoyl-pyrazoles, cytotoxic screening, HEPG2, HELA


     

     

    Full text available only in PDF format.

     

    Acknowledgements

    The authors express deepest thanks to Professor Dr Samia Shoman, head of the Pharmacology Unit, National Cancer Institute, Cairo University, for carrying out the anticancer screening, and the staff of the Central Services Laboratory, National Research Centre, Dokki, Cairo, Egypt.

     

    References

    1 B. Jojart, T.A. Martenik and A. Marki, J. Comp.-Aided Molec. Design, 2005, 19, 341-356.         [ Links ]

    2 J.M. Grisar, F.N. Bolkenius, M.A. Petty and J. Verne, J. Med. Chem., 1995, 38, 453-58.         [ Links ]

    3 S.S. Sangapure and R. Basawaraj, Ind. J. Pharm. Sci, 2004, 66, 221-225.         [ Links ]

    4 W.M. Luo, Q.S. Yu, M. Zhan and D. Parrish, J. Med. Chem., 2005, 48, 986-994.         [ Links ]

    5 M. Ono, M.P. Kung C. Hou and H.F. Kung, Nucl. Med. Biol., 2002, 29, 633-642.         [ Links ]

    6 M. Cowart, R. Faghihi, M.P. Curtis and G.A. Gfesser, J. Med. Chem., 2005, 48, 38-55.         [ Links ]

    7 M.E. Page, J.F. Cryan, A. Sullivan, A. Dalvi, B. Saucy, D.R. Manning and I. Lucki, J. Pharm. Exp. Therap., 2002, 302, 1220-1227.         [ Links ]

    8 A.F. Abdel-Magid, B.E. Maryanoff, S.J. Mehrman, M.H. Parker and A.B. Reitz, U.S. Pat. Appl. US 276, 528, 2006.         [ Links ]

    9 K.M. Dawood, H. Abdel-Gawad, E.A. Ragab, M. Ellithey and H.A. Mohamed, Bioorg. Med. Chem., 2006, 14, 3672-3680.         [ Links ]

    10 S. Pautus, S.W. Yee, M. Jayne, M.P. Coogan and C. Simons, Bioorg. Med. Chem., 2006, 14, 3643-3653.         [ Links ]

    11 H. Ichiro, S. Reiko, A. Toshinori, F. Hidehiko, N. Shunji and S. Yuichi, Bioorg. Med. Lett., 2004, 14, 4383-4387.         [ Links ]

    12 S.K. Lee, B. Cui, R.P. Mehta, A.D. Kinghorn and J.M. Pezzuto, Chem. Bio. Interactions, 1998, 115, 215-228.         [ Links ]

    13 R.S. Mohammed, K.V Tai, W.Y. Sook, B.J. Nathan, J.E. Peter and S. Claire, J. Med. Chem., 2006, 49, 1016-1022.         [ Links ]

    14 R. Wojciech, M. Joanna and K.S. Martyna, Bioorg. Med. Chem, 2007, 15, 3201-3207.         [ Links ]

    15 C. Jyh-Haur, S. Kak-Shan and C. Chung-Ming, Bioorg. Med. Chem. Lett., 2004, 14, 1169-1172.         [ Links ]

    16 W.A. Zaghary, M.E. Heiba, M.M. Anwar and S.A. Hassan, Egypt. Pharm. J. NRC, 2005, 4, 145-156.         [ Links ]

    17 E.A. Soliman, M.I. El-Zahar, A.H. El-Masry and R.S. Gohar, Egypt. Pharm. J. NRC, 2004, 3, 69-85.         [ Links ]

    18 J.J. Bhatt, B.R. Shah, H.P. Shah, P.B. Trivedi, N.K. Undavia and N.C. Desai, Ind. J. Chem., 1994, 33B, 189-192.         [ Links ]

    19 R. Ottana, S. Carotti, R. Maccari, I. Landini, G. Chiricosta, B. Caciagli, M.Q. Vigrita and E. Mini, Bioorg. Med. Chem. Lett, 2005, 15, 3930-3933.         [ Links ]

    20 V. Gududuru, E. Hurh, J.T. Dalton and D.D. Miller, J. Med. Chem., 2005, 48, 2584-2588.         [ Links ]

    21 D.H. Jones, R. Slack, S. Squires and K.R. Wooldridge, J. Med. Chem., 1965, 8, 676-680.         [ Links ]

    22 S.P. Ackland, S.J. Clarke, P. Beale and G.J. Peters, Update Canc. Therap, 2006, 1, 403-427.         [ Links ]

    23 P. Noordhuis, U. Holwerda, C.L. Vander Witt, C.J. Van Groeningen, K. Smid and S. Meijer, Ann. Oncol., 2004, 15, 1025-1032.         [ Links ]

    24 E.D. Elliott, J. Am. Chem. Soc., 1951, 73, 754.         [ Links ]

    25 D.B. Kumar, G.K. Prakash, M.N. Kumaraswamy, B.P. Nandesh-warappa, B.S. Sherigara and K.M. Mahadevan, Ind. J. Chem., 2007, 46B, 336-343.         [ Links ]

    26 M.K. Bratenko, M.K. Panimarchuk, O.I. Chornous and V.A. Vovk, Russ. J. Org. Chem., 2005, 41, 98-102.         [ Links ]

    27 D.B. Kumar, G.K. Prakash, M.N. Kumaraswamy, B.P. Nandesh-warappa, B.S. Sherigara and K.M. Mahadevan, Ind. J. Chem., 2007, 46B, 336-343.         [ Links ]

    28 Z.M. Nofal, H.H. Fahmy and H.S. Mohamed, Arch. Pharm. Res., 2002, 25, 250-257.         [ Links ]

    29 H.S. Mei, S.S. Yu and L.W. Cheng, Chem. Pharm. Bull., 2007, 55, 1126-1135.         [ Links ]

    30 S. Bon, J. Pharm. Soc. Japan, 1953, 73, 533-537.         [ Links ]

    31 E. Bulka and H. Dinse, Z. Chem., 1966, 5, 376-378.         [ Links ]

    32 W. Shaozhone, C. Liya, S. Haijian, D. Yanmei, S. Jianwei and H. Yuefei, Chem. Pharm. Bull., 2005, 53, 67-71.         [ Links ]

    33 M.M. Kamel, K.Z. Gadalla, W.S. El-Hamouly and M.T. El-Wassimi, Z. Naturforsch., 1985, 40b, 661-663.         [ Links ]

    34 M.Y. Ebeid, A. El-Ansary, M.M. Kamel, E.M. Kassem, WA. Abdou and N. Zayed, Bull. Fac. Pharm. Cairo Univ., 1992, 30, 293-296.         [ Links ]

    35 N. Hamdy, Egypt. J. Chem, 2005, 48, 749-758.         [ Links ]

    36 J.H. Biliman and R.L. Schmidgall, J. Pharm. Sci., 1970, 59, 1191-1194.         [ Links ]

    37 M.I. El-Zahar, M.M. Kamel and M.M. Anwar, Die Pharmazie, 1994, 49, 616-617.         [ Links ]

    38 K.B. Bimal and F.B. Frederick, Bioorg. Med. Chem., 2001, 9, 593-605.         [ Links ]

    39 P. Skehan and R. Storeng, J. Nat. Canc. Inst, 1990, 82, 1107-1112.         [ Links ]

     

     

    Received 7 April 2009
    Revised 28 September 2009
    Accepted 26 October 2009

     

     

    * To whom correspondence should be addressed. E-mail: melzahar@hotmail.com