본문 바로가기
HOME> 논문 > 논문 검색상세

논문 상세정보

Archives of pharmacal research : a publication of the Pharmaceutical Society of Korea v.33 no.6, 2010년, pp.813 - 819   SCIE
본 등재정보는 저널의 등재정보를 참고하여 보여주는 베타서비스로 정확한 논문의 등재여부는 등재기관에 확인하시기 바랍니다.

Triazenoindazoles and Triazenopyrazolopyridines: Design, Synthesis, and Cytotoxic Activity

Abdel-Hakeem, Maha    (Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Cairo University  );
  • 초록

    Several triazenoindazoles 3a-e and triazinopyrazolopyridines 6a-i were prepared through the reaction of the corresponding 3-amino-4-chloroindazole and 3-aminopyrazolopyridine diazonium salts 2 and 5 with a number of secondary amines. All compounds were evaluated for their in vitro cytotoxic activity on three cell lines, HepG2, MCF7, and HeLa. Most compounds inhibited cell growth with $IC_{50}$ less than $0.1\;{\mu}M$ . Compound 6d was the most potent, with an $IC_{50}$ of $0.03\;{\mu}M$ against HepG2 and $0.05\;{\mu}M$ against MCF7 and HeLa cells.


  • 주제어

    Triazenoindazole .   Triazenopyrazolopyridine .   Cytotoxic activity.  

  • 참고문헌 (21)

    1. Catapano, C. V., Broggini, M., Erba, E., Ponti, M., Mariani, L., Citti, L., D'Incalci, M., In vitro and in vivo methazolastone- induced DNA damage and repair in L-1210 leukemia sensitive and resistant to chloronitrosoureas. Cancer Res., 47, 4884-4889 (1987). 
    2. Cirrincione, G., Almerico, A. M., Dattolo, G., Aiello, E., Diana, P., Grimaudo, S., Mingoia, F., Barraja, P., and Gancitano, R. A., 3-Triazenoindoles. Synthesis and Antileukemic Activity. Eur. J. Med. Chem., 29, 889-891 (1994). 
    3. Clark, A. S., Deans, B., Stevens, M. F. G., Tisdale, M. J., Wheelhouse, R. T., Denny, B. J., and Hartley, J. A., Antitumor imidazotetrazines 32. Synthesis of novel imidazotetrazinones and related bicyclic heterocycles to probe the mode of action of the antitumor drug Temozolomide. J. Med. Chem., 38, 1493-1504 (1995). 
    4. Daidone, G., Raffa, D., Maggio, B., Raimondi, M. V., Plescia, F., and Schillaci, D., Synthesis and antiproliferative activity of triazenoindazoles and trizenopyrazoles : A comparative study. Eur. J. Med. Chem., 39, 219-224 (2004). 
    5. Diana, P., Barraja, P., Lauria, A., Almerico, A. M., Cirrincione, G., Loi, A., Musiu, C., Pani, A., La Colla, P., and Marongiu, M., 2-Triazenopyrroles: synthesis and biological activity. Eur. J. Med. Chem., 34, 353-360 (1999). 
    6. Diana, P., Barraja, P., Lauria, A., Almerico, A. M., Cirrincione, G., Minnei, C., Longu, S., Congiu, D., Musiu, C., La Colla, P., and Marongiu, M., Synthesis and antiprolefrative activity of triazenothiophenes. Anticancer Res., 19, 2127-2131 (1999). 
    7. Housholder, G. E. and Loo, T. L., Disposition of 5-(3,3- dimethyl-1-triazeno)-imidazole-4-carboxamide, a new antitumor agent. J. Pharmacol. Exp. Ther., 179, 386-395 (1971). 
    8. Huang, L.-J., Shih, M.-L., Chen, H.-S., Pan, S.-L., Teng, C.- M., Fang-Yu, L., and Sheng-Chu, K., Synthesis of N2- (substituted benzyl)-3-(4-methylphenyl)indazoles as novel anti-angiogenic agents. Bioorg. Med. Chem., 14, 528-536 (2006). 
    9. Kamal El-Dean, A. M., Geies, A. A., and Mohamed, Th. A., Synthesis of some fused pyrazolo [3,4-b]pyridine heterocyclic compounds. Indian J. Chem., 30B, 878-882 (1991). 
    10. Kocevar, M., Stanovink, B., and Tisler, M., 3-Diazopyrazolo[ 3,4-b]pyridine, A versatile synthon for new Heterocyclic systems. J. Heterocycl. Chem., 15, 1175 (1978). 
    11. Larsen, I. K. and Kastrup, J. S., Textbook of drug design and discovery, Anticancer agents, Ed. Taylor and Francis, London and Newyork, 3rd. ed. Larsen, P. K., Liljefors T. Madsen, chapter 17, pp. 520-522, (2002). 
    12. Lucas, V. S. and Huang, A. T., Chemotherapy of melanoma, In H. F. Siegler (Ed.). Development in Oncology, Martinus Nijhoff, The Hague, The Netherlands, Vol. 5, pp. 382, (1982). 
    13. Lukin, K., Hsu, M. C., Femando, D., and Leanna, M. R., New practical synthesis of indazoles via condensation of ofluorobenzaldehydes and their o-methyloximes with hydrazine. J. Org. Chem., 71, 8166-8172 (2006). 
    14. Mizuno, N. S. and Humphrey, E. W., Metabolism of 5-(3,3- dimethyl-1triazeno)imidazole-4-carboxamide (NSC-45388) in human and animal tumor tissue. Cancer Chemother. Rep., 56, 465-472 (1972). 
    15. Raffa, D., Maggio, B., Cascioferro, S., Raimondi, M. V., Schillaci, D., Gallo, G., Daidone, G., Plescia, S., Meneghetti, F., Bombieri, G., Di Cristina, A., Piptone, R. M., Grimaudo, S., and Tolomeo, M., Synthesis and antiproliferative activity of 3-amino-N-phenyl-1H-indazole-1-carboxamides. Eur. J. Med. Chem., 44, 165-178 (2008). 
    16. Shealy, Y., Trizenylimidazoles, other triazenes, and imidazo [5,1-d]-1,2,3,5-tetrazin-4(3H)ones, In Foye, W. O. (Ed.). Cancer Chemotherapic Agents, ACS, Washington, pp. 173-174, (1995). 
    17. Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S., and Boyed, M. R., New colorimetric cytotoxic assay for anticancer- drug screening. J. Natl. Cancer Inst., 82, 1107-1112 (1990). 
    18. Skiba, J. L. and Bryan, G. T., Methylation of nucleic acid and urinary excretion of 14 C-labeled 7-methylguanine by rats and man after administration of 4(5)-(3,3-dimeyhyl-1- triazeno)-imidazole-5(4)-carboxamide. Toxicol. Appl. Pharmacol., 18 , 707-719 (1971). 
    19. Tontini, A., Diamantini, G., Balsamini, C., Tarzia, G., Perissin, L., and Rapozzi, V., Synthesis of 1-(isoxazol-3- yl)triazene derivatives. Antimetastatic activity of 3,3- dimethyl-1-(5-methylisoxazol-3-yl)triazene. Eur. J. Med. Chem., 31, 735-740 (1996). 
    20. van Delft, J. H. M., Luiten-Schuite, A., Souliotis, V. L., Kyrtopoulos, S. A., Ouwerkerk, J., Keizer, H. J., and Baan, R. A., N7-metylguanine and O6-methylguanine levels in DNA of white blood cells from cancer patients trated with dacarbazine. Biomarkers, 1, 94-98 (1996). 
    21. Zhu, G.-D., Gong, J., Gandhi, V. B., Woods, K., Luo, Y., Liu, X., Guan, R., Klinghofer, V., Johnson, E. F., Stoll, V. S., Mamo, M., Li, Q., Rosenberg, S. H., and Giranda, V. L., Design and synthesis of pyridine-pyrazolopyridine-based inhibitors of protein kinase B/Akt. Bioorg. Med. Chem., 15, 2441-2452 (2007). 

 활용도 분석

  • 상세보기

    amChart 영역
  • 원문보기

    amChart 영역

원문보기

무료다운로드
  • 원문이 없습니다.
유료다운로드

유료 다운로드의 경우 해당 사이트의 정책에 따라 신규 회원가입, 로그인, 유료 구매 등이 필요할 수 있습니다. 해당 사이트에서 발생하는 귀하의 모든 정보활동은 NDSL의 서비스 정책과 무관합니다.

원문복사신청을 하시면, 일부 해외 인쇄학술지의 경우 외국학술지지원센터(FRIC)에서
무료 원문복사 서비스를 제공합니다.

NDSL에서는 해당 원문을 복사서비스하고 있습니다. 위의 원문복사신청 또는 장바구니 담기를 통하여 원문복사서비스 이용이 가능합니다.

이 논문과 함께 출판된 논문 + 더보기