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논문 상세정보

Abstract

Aiming at the development of anticancer agents by modification of phenolic benzo[c]phenanthridine alkaloid, additional hydroxyl group was put on C10 position of fagaridine (1) by a biomimetic synthetic procedure to afford 10-hydroxyfagaridine (12). All of the synthetic intermediates were also screened in vitro antitumor activities against five different cell lines as well as 12. Among them the representative cytotoxic results are shown as follows; P-quinone (11) $[ED_50;(A549=0.22; {\mu}g/ml)$, $(HCT;15=0.21 {\mu}g/ml)$, fagaridine (1) $(HCT;15=0.41 {\mu}g/ml)$, olefin (6) $(HCT; 15=0.06 {\mu}g/ml)$, acetal (7) $(SKMEL-2=0.07 {\mu}g/ml)$, dihydrofagaridne (10) $(A549=0.38 {\mu}g/ml)$, 10-hydroxyfagaridine (12) $(A 549=0.45{\mu}g/mi)$. From these observation three main remarks can be drawn; (i) the iminium part of benzo[c]phenanthridine is not essential for showing acitvities, (ii) the additional hydroxyl group did not contribute to enhance the cytotoxicity, (iii) the 3-arylisoquinolin-1(2H)-one derivatives were found to display significant in vitro antitumor activity.

참고문헌 (15)

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  2. Kobayashi,F.;Yokumoto,H.;Suzuki,M.;Tsubaki,M. , Chem. Abstr. / v.118,pp., 1993
  3. Rubinstein,L.V.;Shoemaker,R.H.;Paul,K.D.;Simon,R.M.;Tosini,S.;Skehan,P.;Scudiero,D.;Monks,A.;Boyd,M.R. , J. Natl. Cancer Inst. / v.82,pp.1113, 1990
  4. Synthesis and Antitumor Activity of Structural Analogues of the Anticancer Benzophenanthridine Alkaloid Fagaronine Chloride , Cushman,M.;Moham,P. , J. Med. Chem. / v.28,pp.1031-1036, 1985
  5. Synthesis and Evaluation of New 6-Amino-substututud Benzo[c]phenanthridine Derivatives , Janain,Y.L.;Croisy,A.;Riou,J.F.;Bisagni,E. , J. Med. Chem. / v.36,pp.3686-3692, 1993
  6. Skehan,P.;Storeng,R.;Scudiero,D.;Monks,A.;McMahon,J.B.;Vistica,D.T.;Warren,J.T.;Bokesch,H.;Kenney,S.;Boyd,M.R. , J. Natl. Cancer Inst. / v.82,pp.1107, 1990
  7. Hanaoka,M.;Mukai,C. , Studies in Natural Products Chemistry / v.14,pp.769-803, 1994
  8. Pharmacological Activity of Benzophenanthridine and Phenanthridine Alkaloids , Simeon,S.;Rios,J.L.;Villar,A. , Pharmazie / v.44,pp.593-597, 1989
  9. Transformation of Protopine and Protoberberine Alkaloid to Benzo[c]phenanthridine Alkaloid , Onda,M.;Yonezawa,K.;Abe,K. , Chem. Pharm. Bull. / v.19,pp., 1971
  10. Biomimetic Introduction of an Oxy Functionality at the C10 Position in the Benzo[c]phenanthridine Skeleton : Synthesis of 2,3,7,8,10- Pentaoxygenated Benzo[c]phenanthridine Alkaloids, Chelilutine and Sanguilutine , Hanaoka,M.;Cho,W.J.;Yoshida,S.;Mukai,C. , Chem. Pharm. Bull. / v.39,pp.1163-1166, 1991
  11. Utilization of Protopine and Related Alkaloids. XI. , Onda,M.;Yamaguchi,H. , Chem. Pharm. Bull. / v.27,pp.2076-2083, 1979
  12. Synthesis of Fagaridine, A Phenolic Benzo[c]phenanthridine Alkaloids , Hanaoka,M.;Yamagishi,H.;Mukai,C. , Chem. Pharm. Bull. / v.33,pp.1763-1765, 1985
  13. Sufness,M.;Douros,J.;De Vita,V.T.(ed.);Jr.Busch,H.(ed.) , Methods in Cancer Research / v.,pp.474, 1979
  14. A First Synthesis of Isofagaridine : Topoisomerase I Inhibitor , Cho,W.J.;Hanaoka,M. , Arch. Pharm. Res. / v.19,pp.240-242, 1996
  15. A Biomimetic Synthesis of Oxychelerythrine, Dihydrochelerythrine and Chelerythrine from Berberine , Hanaoka,M.;Motonishi,T.;Mukai,C. , J. Chem. Soc. Perkin Trans. / v.1,pp.2253-2256, 1986

이 논문을 인용한 문헌 (1)

  1. 2002. "Two -week Oral Toxicity Study of 1- (4-methylpiperazinyl) -3- phenylisoquinoline (CWJ-a-5) in sprague-Dawley (SD) Rats" Journal of toxicology and public health : an official journal of the Korean Society of Toxicology, 18(1): 47~57 

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