The preparation and evaluation of 1-substituted 1,2,3,4-tetrahydro- and 3,4-dihydro-β-carboline derivatives as potential antitumor agents

Chemical and Pharmaceutical Bulletin

Volumn 53, Issue 1, 2005, Pages 32-36

  Shen, Ya Ching ^a   Chen, Ching Yeu ^a   Hsieh, Pei Wen ^a   Duh, Chang Yih ^a   Lin, Yat Min ^a   Ko, Chin Lien ^a  

^a NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

Author keywords

1,2,3,4 tetrahydro carboline; 3,4 dihydro carboline; Antitumor agent

Indexed keywords

1 (2' FLUORENYL) 3,4 DIHYDRO BETA CARBOLINE; 1 (2' FLUOROFENYL) 1,2,3,4 TETRAHYDRO BETA CARBOLINE; 1 (2',4' DIMETHOXYLPHENYL 3,4 DIHYDRO BETA CARBOLINE; 1 (2',4' DIMETHOXYPHENYL) 1,2,3,4 TETRAHYDRO BETA CARBOLINE; 1 (2',5' DIMETHOXYLPHENYL) 1,2,3,4 DIHYDRO BETA CARBOLINE; 1 (2',5' DIMETHOXYPHENYL) 1,2,3,4 TETRAHYDRO BETA CARBOLINE; 1 (3',4' DIMETHOXYLPHENYL) 3,4 DIHYDRO BETA CARBOLINE; 1 (3',4' DIMETHOXYPHENYL) 1,2,3,4 TETRAHYDRO BETA CARBOLINE; 1 (3',4',5' TRIMETHOXYLPHENYL) 3,4 TETRAHYDRO BETA CARBOLINE; 1 (3',4',5' TRIMETHOXYPHENYL) 1,2,3,4 TETRAHYDRO BETA CARBOLINE; 1 (3',5' DIMETHOXYLPHENYL) 3,4 DIHYDRO BETA CARBOLINE; 1 (3',5' DIMETHOXYPHENYL) 1,2,3,4 TETRAHYDRO BETA CARBOLINE; 1 (4' BROMOPHENYL) 1,2,3,4 TETRAHYDRO BETA CARBOLINE; 1 (4' BROMOPHENYL) 3,4 DIHYDRO BETA CARBOLINE; 1 (4' CHLOROPHENYL) 1,2,3,4 TETRAHYDRO BETA CARBOLINE; 1 (4' CHLOROPHENYL) 3,4 DIHYDRO BETA CARBOLINE; 1 (4' N DIETHYLPHENYL) 1,2,3,4 TETRAHYDRO BETA CARBOLINE; 1 (4' N DIETHYLPHENYL) 3,4 DIHYDRO BETA CARBOLINE; 1 (4' N DIMETHYLPHENYL) 1,2,3,4 TETRAHYDRO BETA CARBOLINE; 1 (4' N DIMETHYLPHENYL) 3,4 DIHYDRO BETA CARBOLINE; 1 (4' NITROPHENYL) 1,2,3,4 TETRAHYDRO BETA CARBOLINE; 1 (4' NITROPHENYL) 3,4 DIHYDRO BETA CARBOLINE; 1 (6' NITRO 1' PIPEROYL) 1,2,3,4 TETRAHYDRO BETA CARBOLINE; 1 (6' NITRO 1' PIPEROYL) 3,4 DIHDYRO BETA CARBOLINE; 1 (9' ETHYL 3' CARBAZOLE) 1,2,3,4 TETRAHYDRO BETA CARBOLINE; 1 (9' ETHYL 3' CARBAZOLE) 3,4 DIHYDRO BETA CARBOLINE; 3,4 DIHYDRO BETA CARBOLINE; BETA CARBOLINE DERIVATIVE; TRYPTOLINE; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; CARBOLINE DERIVATIVE;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL LINE; COLON ADENOCARCINOMA; CORRELATION ANALYSIS; CYTOTOXICITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA P 388; LUNG ADENOCARCINOMA; NASOPHARYNX CARCINOMA; NONHUMAN; DRUG SCREENING; METHODOLOGY; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CARBOLINES; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS;

EID: 18744399049     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.53.32     Document Type: Article

References (24)

1. Blackman A. J., Matthews D. J., Narkowicz C. K., J. Nat. Prod., 50, 494-496 (1987).
2. Kearns P. S., Coll J. C., Rideout J. A., J. Nat. Prod., 58, 1075-1076 (1995).
3. Kobayashi J., Tsuda M., Kawasaki N., Sasaki T., Mikami Y., J. Nat. Prod., 57, 1737-1740 (1994).
4. McNulty J., Still I. W. J., Tetrahedron Lett., 36, 7965-7966 (1995).
5. Still I. W. J., McNulty J., Heterocycles, 29, 2057 (1989).
6. Nowak W., Gerlach Liebigs, Ann. Chem., 1993, 153-159 (1993).
7. Badre A., Boulanger A., Mansom A. E., Banaigs B., Combaut G., Francisco C., J. Nat. Prod., 57, 528-533 (1994).
8. Rinehart K. L., Jr., Kobayashi J., Harbour G. C., Gilmore J., Mascal M., Holt T. G., Shield L. S., Lafargue F., J. Am. Chem. Soc., 109, 3378-3387 (1987).
9. Crews P., Cheng X. C., Adamczeski M., Rodriguez J., Jaspars M., Schmitz F. J., Traeger S. C., Pordesimo E. O., Tetrahedron, 50, 13567-13574 (1994).
10. Sakai R., Kohmoto S., Higa T., Jefford C. W., Bernardinelli G., Tetrahedron Lett., 28, 5493-5496 (1987).
11. Munro M. H. G., Luibrand R. T., Blunt J. W., "Bioorganic Marine Chemstry," Vol. I, ed. by Scheuer P. J., Springer-Verlag, N.Y., 1987, pp. 103-105.
12. Ichiba T., Sakai R., Kohmoto S., Saucy G., Higa T., Tetrahedron Lett., 29, 3083-3086 (1988).
13. Higa T., "Studies in Natural Product Chemistry," Vol. 5, Part B, ed. by Atta-Ur-Rahman, Elsevier Co., New York, 1989, pp. 346-353.
14. Yousaf M., Hammond N. L., Peng J., Wahyuono S., McIntosh K. A., Charman W. N., Mayer A. M. S., Hamann M. T., J. Med. Chem., 47, 3512-3517 (2004).
15. Sakai R., Higa T., Jefford C. W., Bernardinelli G., J. Am. Chem. Soc., 108, 6404-6405 (1986).
16. Shen Y. C., Tai H. R., Duh C. Y., Chin. Pharm. J., 48, 1-10 (1996).
17. Valentine D., Jr., Scot J. W., Synthesis, 1978, 329-356 (1978).
18. Kawashima Y., Horiguchi A., Taguchi M., Tuyuki Y., Karasawa Y., Araki H., Hatayama, K., Chem. Pharm. Bull., 43, 783-787 (1995).
19. Tsuji R., Yamanaka M., Nishida A., Nakagawa M., Chem. Lett., 2002, 428 (2002).
20. Sui Z., Jihua G., Macielag M. J., Jiang W., Qiu Y., Kraft P., Bhattacharjee S., John T. M., Craig E., Haynes-Johnson D., Clancy J., Bioorg. & Med. Chem. Lett., 13, 761-765 (2003).
21. Kondo K., Shigemori H., Kikuchi Y., Ishibashi M., Sasaki T., Kobayashi J., J. Org. Chem., 57, 2480-2483 (1992).
22. Pezzuto J. M., Che C. T., Mc Pherson D. D., Zhu J. P., Topcu G., Erdelmeir C. A. J., Cordell G. A., J. Nat. Prod., 54, 1522-1530 (1991).
23. Tu L. C., Chou C. K., Chen C. Y., Chang Y. T., Shen Y. C., Yeh S. F., Biochimica et Biophysica Acta, 1672, 148-156 (2004).
24. Mosmann T., J. Immunol. Methods, 65, 55-63 (1983).