Synthesis and cytotoxic activities of a new benzo[c]phenanthridine alkaloid, 7-hydroxynitidine, and some 9-oxygenated benzo[c]phenanthridine derivatives

被引:108
作者
Nakanishi, T [1 ]
Suzuki, M [1 ]
机构
[1] Nippon Kayaku Co Ltd, Pharmaceut Grp, Kita Ku, Tokyo 1158588, Japan
关键词
D O I
10.1021/ol990775g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A new benzo[c]phenanthridine alkaloid, 7-hydroxynitidine, was synthesized by a novel synthetic procedure, The cytotoxic activity of this compound against HeLa S3 cells was strong, but not greater than those of its mother compounds, nitidine and NK109, We also synthesized other 9-oxygenated benzo[c]phenanthridine alkaloids, 7-methoxynitidine, 9-demethylnitidine, nitidine, and fagaronine, and tested their cytotoxic activities. These results suggest that the 7-hydroxy group enhances antitumor activity and an 8- or 9-hydroxy group weakens this activity.
引用
收藏
页码:985 / 988
页数:4
相关论文
共 12 条
  • [1] BERNARD AM, 1989, SYNTHESIS-STUTTGART, P287
  • [2] REDUCTION OF SCHIFF BASES .3. REDUCTION WITH DIMETHYLAMINE BORANE
    BILLMAN, JH
    MCDOWELL, JW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (05) : 1437 - &
  • [3] CLARK JH, 1976, TETRAHEDRON LETT, V41, P3361
  • [4] CORDELL GA, 1976, HETEROCYCLES, V4, P393
  • [5] HANAOKA M, 1992, CHEM ABSTR 718D, V116
  • [6] ISHII H, 1985, CHEM PHARM BULL, V33, P4139
  • [7] Synthesis of NK109, an anticancer benzo[c]phenanthridine alkaloid
    Nakanishi, T
    Suzuki, M
    Mashiba, A
    Ishikawa, K
    Yokotsuka, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13) : 4235 - 4239
  • [8] Revision of the structure of fagaridine based on the comparison of UV and NMR data of synthetic compounds
    Nakanishi, T
    Suzuki, M
    [J]. JOURNAL OF NATURAL PRODUCTS, 1998, 61 (10): : 1263 - 1267
  • [9] Structural considerations of NK109, an antitumor benzo[c]phenanthridine alkaloid
    Nakanishi, T
    Suzuki, M
    Saimoto, A
    Kabasawa, T
    [J]. JOURNAL OF NATURAL PRODUCTS, 1999, 62 (06): : 864 - 867
  • [10] A REVIEW OF THE CHEMISTRY OF THE ANTI-TUMOR BENZO[C]PHENANTHRIDINE ALKALOIDS NITIDINE AND FAGARONINE AND OF THE RELATED ANTI-TUMOR ALKALOID CORALYNE
    PHILLIPS, SD
    CASTLE, RN
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1981, 18 (02) : 223 - 232