$\require{mediawiki-texvc}$

연합인증

연합인증 가입 기관의 연구자들은 소속기관의 인증정보(ID와 암호)를 이용해 다른 대학, 연구기관, 서비스 공급자의 다양한 온라인 자원과 연구 데이터를 이용할 수 있습니다.

이는 여행자가 자국에서 발행 받은 여권으로 세계 각국을 자유롭게 여행할 수 있는 것과 같습니다.

연합인증으로 이용이 가능한 서비스는 NTIS, DataON, Edison, Kafe, Webinar 등이 있습니다.

한번의 인증절차만으로 연합인증 가입 서비스에 추가 로그인 없이 이용이 가능합니다.

다만, 연합인증을 위해서는 최초 1회만 인증 절차가 필요합니다. (회원이 아닐 경우 회원 가입이 필요합니다.)

연합인증 절차는 다음과 같습니다.

최초이용시에는
ScienceON에 로그인 → 연합인증 서비스 접속 → 로그인 (본인 확인 또는 회원가입) → 서비스 이용

그 이후에는
ScienceON 로그인 → 연합인증 서비스 접속 → 서비스 이용

연합인증을 활용하시면 KISTI가 제공하는 다양한 서비스를 편리하게 이용하실 수 있습니다.

Triazenoindazoles and Triazenopyrazolopyridines: Design, Synthesis, and Cytotoxic Activity

Archives of pharmacal research : a publication of the Pharmaceutical Society of Korea, v.33 no.6, 2010년, pp.813 - 819  

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

Abstract AI-Helper 아이콘AI-Helper

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...

주제어

참고문헌 (21)

  1. Cancer Res. C. V. Catapano 47 4884 1987 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. Eur. J. Med. Chem. G. Cirrincione 29 889 1994 10.1016/0223-5234(94)90112-0 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. J. Med. Chem. A. S. Clark 38 1493 1995 10.1021/jm00009a010 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. Eur. J. Med. Chem. G. Daidone 39 219 2004 10.1016/j.ejmech.2003.11.012 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. Eur. J. Med. Chem. P. Diana 34 353 1999 10.1016/S0223-5234(99)80085-3 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. Anticancer Res. P. Diana 19 2127 1999 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. J. Pharmacol. Exp. Ther. G. E. Housholder 179 386 1971 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. Bioorg. Med. Chem. L.-J. Huang 14 528 2006 10.1016/j.bmc.2005.08.032 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. Indian J. Chem. A. M. Kamal El-Dean 30B 878 1991 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. J. Heterocycl. Chem. M. Kocevar 15 1175 1978 10.1002/jhet.5570150721 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. V. S. Lucas 382 1982 Chemotherapy of melanoma 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. J. Org. Chem. K. Lukin 71 8166 2006 10.1021/jo0613784 Lukin, K., Hsu, M. C., Femando, D., and Leanna, M. R., New practical synthesis of indazoles via condensation of o-fluorobenzaldehydes and their o-methyloximes with hydrazine. J. Org. Chem., 71, 8166-8172 (2006). 

  14. Cancer Chemother. Rep. N. S. Mizuno 56 465 1972 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. Eur. J. Med. Chem. D. Raffa 44 165 2008 10.1016/j.ejmech.2008.03.023 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. Y. Shealy 173 1995 Cancer Chemotherapic Agents 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. J. Natl. Cancer Inst. P. Skehan 82 1107 1990 10.1093/jnci/82.13.1107 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 anti-cancer-drug screening. J. Natl. Cancer Inst., 82, 1107-1112 (1990). 

  18. Toxicol. Appl. Pharmacol. J. L. Skiba 18 707 1971 10.1016/S0041-008X(71)80026-1 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. Eur. J. Med. Chem. A. Tontini 31 735 1996 10.1016/0223-5234(96)85884-3 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. Biomarkers J. H. M. Delft van 1 94 1996 10.3109/13547509609088676 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. Bioorg. Med. Chem. G.-D. Zhu 15 2441 2007 10.1016/j.bmc.2007.01.010 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). 

관련 콘텐츠

섹션별 컨텐츠 바로가기

AI-Helper ※ AI-Helper는 오픈소스 모델을 사용합니다.

AI-Helper 아이콘
AI-Helper
안녕하세요, AI-Helper입니다. 좌측 "선택된 텍스트"에서 텍스트를 선택하여 요약, 번역, 용어설명을 실행하세요.
※ AI-Helper는 부적절한 답변을 할 수 있습니다.

선택된 텍스트

맨위로