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Synthesis and antitumor properties of new 2,4-dichlorophenoxy ethers

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Pharmaceutical Chemistry Journal Aims and scope

A series of new compounds incorporating 2,4-dichlorophenoxy nucleus have been synthesized. Reaction of 2,4-dichlorophenoxyacetic acid with thiosemicarbazide in the presence of phosphoryl chloride followed by treatment with phenacylbromides led to the formation of imidazo[2,1-b][1,3,4]thiadiazoles (3). Bischlorophenoxyallyl hydrazides (4) reacted with some of alkenes, azo dyes, aldehydes, and hydrazonoyl chlorides to produce pyrazoles, Schiff bases, and bis-diazo compounds, respectively. 1,3,4-Thiadiazole (10) was obtained by reaction of dichlorophenoxyallyl hydrazides (4b) with carbon disulphide followed by hydrazonoyl chlorides. All compounds were tested for their preliminarily antitumor activity on transplantable murine tumor cell line [Ehrlich ascites carcinoma (EAC)]. Compound 2-{2-[2-(2,4-dichlorophenoxy)acetyl]hydrazono}-N'-(4-fluorophenyl)propanehydrazonoyl chloride (8c) has remarkably decreased the viable EAC cell count as indicated by Trypan Blue dye exclusion test (3%) in comparison to the well known antitumor agent 5-FU (0%).

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References

  1. Y. N. Shi, Y. C. Lu, J. X. Fang, and Y. L. Hua, Chem. J. Univ. (Chinese), 16, 1710 – 1713 (1995).

    CAS  Google Scholar 

  2. M. Kitagawa, K. Yamamoto, S. Katakura, H. Kanno, and K. Yamada, Chem. Pharm. Bull., 39, 2681 – 2690 (1991).

    PubMed  CAS  Google Scholar 

  3. B. R. Baker and J. A. Hurlbut, J. Med. Chem., 12, 677 – 680 (1969).

    Article  PubMed  CAS  Google Scholar 

  4. P. K. Jain and S. K. Srirastara, J. Indian Chem. Soc., 69, 402 – 409 (1992).

    CAS  Google Scholar 

  5. Y. J. Li, Y. J. Dai, and J. C. Chen, Chem. J. Chin. Univ. (Chinese), 9, 584 – 591 (1988).

    CAS  Google Scholar 

  6. N. F. Eweiss and A. A. Bahajaj, J. Heterocycl. Chem., 24, 1173 – 1182 (1987).

    Article  CAS  Google Scholar 

  7. B. F. Abdel-Wahab, H. A. Abdel-Aziz, and E. M. Ahmed, Arch. Pharm., 341, 734 – 739 (2008).

    Article  CAS  Google Scholar 

  8. S. Rollas, S. Karakus, B. B. Durgun, M. Kiraz, and H. Erdeniz, Farmaco, 51, 811 – 814 (1996).

    PubMed  CAS  Google Scholar 

  9. M. Mamolo, L. Vio, and E. Banfi, Farmaco, 51, 71 – 74 (1996).

    PubMed  CAS  Google Scholar 

  10. B. F. Abdel-Wahab, H. A. Abdel-Aziz, and E. M. Ahmed, Eur. J. Med. Chem., 44, 2632 – 2635 (2009).

    Article  PubMed  CAS  Google Scholar 

  11. M. Kidwai, P. Misra, R. Kumar, R. K. Saxena, R. Gupta, and S. Bradoo, Monatsh. Chem., 129, 961 – 965 (1998).

    CAS  Google Scholar 

  12. A. H. Mandour, N. M. Fawzy, T. H. El-Shihi, Z. E. El-Bazza, Pak. J. Sci. Ind. Res., 38, 402 – 405 (1995); Chem. Abstr. 127, 135773 (1997).

    CAS  Google Scholar 

  13. E. E. Chufan, J. C. Pedregosa, O. N. Badini, and L. Bruno-Blanch, Farmaco, 54, 838 – 841 (1999).

    Article  PubMed  CAS  Google Scholar 

  14. K. Y. Lee, J. M. Kim, and J. N. Kim, Tetrahedron Lett., 44, 6737 – 6740 (2003).

    Article  CAS  Google Scholar 

  15. V. B. Jadhav, M. V. Kulkarni, V. P. Rasal, S. S. Biradar, M. D. Vinay, Eur. J. Med. Chem., 43, 1721 – 1729 (2008).

    Article  PubMed  CAS  Google Scholar 

  16. T. Wei, J. Chen, and Y. Zhang, Huaxue Shijie 35, 522 – 524(1994); Chem. Abstr., 122, 265298 (1996).

    CAS  Google Scholar 

  17. J. Chan, T. Wei, X. Wang, and S. Yang, Chinese Chem. Lett., 4, 5 – 8 (1993); Chem. Abstr., 120, 269783 (1995).

    CAS  Google Scholar 

  18. M. Amirthe and S. Kumar, Indian J. Heterocycl. Chem., 14, 51 – 54 (2004), Chem. Abstr., 142, 261478 (2005).

    Google Scholar 

  19. S. Singh, L. D. S. Yadav, and H. Singh, Bokin Bobai 8, 385 – 388 (1980), Chem. Abstr., 94, 103250 (1982).

    CAS  Google Scholar 

  20. X. Qian, R. Zhang, G. Song, and H. Yu, CN 1250049; Chem. Abstr., 134, 4937 (2001).

  21. W. Shi, X. Qian, R. Zhang, and G. Song, J. Agric. Food Chem., 49, 124 – 130 (2001).

    Article  PubMed  CAS  Google Scholar 

  22. J. Matysiak, A. Nasulewicz, M. Pelczynska, M. Switalska, I. Jaroszewicz, and A. Opolski, Eur. J. Med. Chem., 41, 475 – 482 (2006).

    Article  PubMed  CAS  Google Scholar 

  23. M. S. Karthikeyan, B. S. Holla, and N. S. Kumari, Eur. J. Med. Chem., 42, 30 – 36 (2007).

    Article  PubMed  CAS  Google Scholar 

  24. M. Amir and S. Kumar, Indian J. Chem., 44B, 2532 – 2537 (2005).

    CAS  Google Scholar 

  25. S. N. Shetty and B. Kalluraya, Chim. Acta Turcica, 19, 135 – 139 (1992), Chem. Abstr., 118, 169045 (1994).

    CAS  Google Scholar 

  26. F. Badria, M. Ameen, and M. Akl, Z. Naturforsch., 62c, 656 – 660 (2007).

    Google Scholar 

  27. S. I. Mostafa and F. A. Badria, Metal Based Drugs, 723634 (2008).

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Authors and Affiliations

  1. Applied Organic Chemistry Department, National Research Center, Dokki, Giza, Egypt

    B. F. Abdel-Wahab & M. Farghaly

  2. Pharmacognosy Departments, Faculty of Pharmacy, Mansoura University, Mansoura, 35516, Egypt

    F. A. Badria

Authors
  1. B. F. Abdel-Wahab
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  2. M. Farghaly
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  3. F. A. Badria
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Correspondence to B. F. Abdel-Wahab.

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Abdel-Wahab, B.F., Farghaly, M. & Badria, F.A. Synthesis and antitumor properties of new 2,4-dichlorophenoxy ethers. Pharm Chem J 45, 30–35 (2011). https://doi.org/10.1007/s11094-011-0555-5

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  • DOI: https://doi.org/10.1007/s11094-011-0555-5

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