Abstract
Substituted isoquinolin-1-ones (1) were synthesized to test theirin vitro anticancer activity. 3-Biphenyl-N-methylisoquinolin-1-one (7) showed the most potent anticancer activity against five different human cancer cell lines.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Berdel, W. E. and Munder, P. G., Antitumor Analogs of PAF, In Snyder, F. (Ed).Platelet-Activating Factor and Related Lipid Mediators. Plenum Press, New York, pp. 449–467, 1987.
Berry, J. M. and Threadgill, M. D., Labeled compounds of interest as antitumor agents. V. Syntheses of [18O]-5-methylisoquinolinone and 1-(furan-2-yl-[18O]-methoxy) -5-methylisoquinoline.J. Labelled Compd. Radiopharm., 38, 935–940 (1996).
Brunton, V. C. and Workman, P.,Br. J. Cancer, 67, 989 (1993).
Cheon, S. H., Park, J. S., Jeong, S. H., Chung, B. H., Choi, B. G., Cho, W. J., Kang, B. H., and Lee, C. O., Synthesis and Structure-Activity Relationship Studies of 2,3-Dihydroimidazo[2,1-a]isoquinoline Analogs as Antitumor Agents.Arch. Pharm. Res., 20, 138–143 (1997).
Cheon, S. H., Park, J. S., Chung, B. H., Choi, B. G., Cho, W. J., Choi, S. U., and Lee, C. O., Synthesis and structure-activity relationship studies of substituted isoquinoline analogs as antitumor agent.Arch. Pharm. Res., 21, 193–197 (1998).
Cheon, S. H., Lee, J. Y., Chung, B. H., Choi, B. G., Cho, W. J., and Kim, T. S., Studies on the synthesis and in vitro antitumor activity of the isoquinolone derivatives. ynthesis and structure-activity relationship studies of substituted isoquinoline analogs as antitumor agent.Arch. Pharm. Res., 22, 179–183 (1999).
Cho, W. J., Yoo, S. J., Chung, B. H., Choi, B. G., Cheon, S. H., Whang, S. H., Kim, S. K., Kang, B. H., and Lee, C. O., Synthesis of Benzo[c]phenanthridine Derivatives and their in Vitro Antitumor Activities.Arch. Pharm. Res., 19, 321–325 (1996).
Danhauser-Riedl, S., Felix, S. B., Houlihan, W. J., Zafferani, M., Steinhauser, G., Oberberg, D., Kalvelage, H., Busch, R., Rastetter, J., and Berdel, W. F.,Cancer Res., 51, 43 (1991)
Dive, C., Watson, J. V., and Workman, P., Multiparametric Flow Cytometry of the Modulation of Tumor Cell Membrane Permeability by Developmental Antitumor Ether Lipid SRI 62–834 in EMT6 Mouse Mammary Tumor and HL6O Human Promyelocytic Leukemia cells.Cancer Res., 51, 799–806 (1990).
Houlihan, W. J. and Parrino, V. A., Directed Lithiation of 2-Phenyl- and 2-(o-methylphenyl)imidazoline.J. Org. Chem., 47, 5177–5180 (1982).
Houlihan, W. J., Cheon, S. H., Parrino, V. A., Handley, D. A., and Larson, D. A., Structural Modification of 5-Aryl-2,3-dihydroimidazo[2,1-a] isoquinoline Platelet Activating Factor Receptor Antagonists.J. Med. Chem., 36, 3098–3102 (1993).
Houlihan, W. J., Munder, P. G., Handley, D. A., Cheon, S. H., and Parrino, V. A., Antitumor Activity of 5-Aryl-2,3-dihydroimidazo[2,1-a] isoquinolines.J. Med. Chem., 38, 234–240 (1995a).
Houlihan, W. J., Munder, P. G., Handley, D. A., and Nemecek, C. A., Priclinical Pharmacology and Possible Mechanism of Action of the Novel Antitumor Agent 5-(4′-Piperidinomethylphenyl)-2, 3-dihydroimidazo[2,1-a]isoquinoline.Arzneim.-Forsch./Drug Res., 45(II), 1133–1137 (1995b).
Hutchinson, J. H., Cook, J. J., Brashear, K. M., Breslin, M. J., Class, J. D., Gould, R. J., Halczenko, W., Holahan, M. A., and Lynch, R. J., Non-peptide glycoprotein IIb/ IIIa antagonists. 11. Design and in vivo evaluation of 3,4-dihydro-1(1H)-isoquinolinone-based antagonists and ethyl ester prodrugs.J. Med. Chem., 39, 4583–4591 (1996).
Modest, E. J., Berens, M. E., Piantadosi, C., and Noseda, A., Pharmacological Effects and Anticancer Activity of New Ether Phospholipid Analogs, In Kabara, J. J. (Ed). ThePharm.acological Effect of lipids III, Role of Lipids in Cancer Research. The American Oil Chemists’ Society, Champaign, IL, pp. 330–337, 1989.
Munder, P. G. and Westphal, O., Antitumoral and Other Biomedical Activities of Synthetic Ether Lysophospholipids, In Waksman, B. H. (Ed).1939–1989: Fifty Years Progress in Allergy. Karger, New York, pp. 206–235, 1990.
Noseda, A., Godwin, P. L., and Modest, E. J., Effects of Antineoplastic Ether Lipids on Model and Biological Membranes,Biochim. Biophys. Acta, 945, 92–100 (1988).
Poindexter, G. S., Convenient preparation of 3′-substituted-1 (2H)-isoquinolines.J. Org. Chem., 47, 3787–3788 (1982).
Rubinstein, L. V., Shoemaker, R. H., Paul, K. D., Simon, R. M., Tosini, S., Skehan, P., Scudiero, D., Monks, A., and Boyd, M. R.,J. Natl. Cancer Inst., 82, 1113 (1990).
Seewald, M. J., Olsen, R. A., Sehgal, I., Melder, D. C., Modest, E. J., and Powis, G., Inhibition of Growth Factor-Dependent Inositol Phosphate Ca2+ Signaling by Antitumor Ether Lipid Analogues.Cancer Res., 50, 4458–4463 (1990).
Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J. B., Vistica, D. T., Warren, J. T., Bokesch, H., Kenny, S., and Boyd, M. R.,J. Natl. Cancer Inst., 82, 1107 (1990).
Still, W. C., Kahn, M., and Mitra, A. J.,J. Org. Chem., 43, 2923 (1978)
Uberall, F., Oberhuber, H., Maly, K., Zaknun J., Demuth, L., and Grunicke, H. H., Hexadecylphosphocholine Inhibits Inositol Phosphate Formation and Protein Kinase C Activity.Cancer Res., 51, 807–812 (1991).
Watson, C. Y., Whish, W. J. D., Treadgill, M. D., Synthesis of 3-substituted benzamides and 5-substituted isoquinolin-1 (2H)-ones and preliminary evaluation as inhibitors of poly(ADP-ribose)polymerase (PARP).Bioorg. Med. Chem., 6, 721–734 (1998).
Workman, P., Antitumor Ether Lipids: Endocytosis as a Determination of Cellular Sensitivity. CancerCells, 3, 315–317 (1991).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Cheon, S.H., Park, J.S., Lee, J.Y. et al. Structure-activity relationship studies of isoquinolinone type anticancer agent. Arch Pharm Res 24, 276–280 (2001). https://doi.org/10.1007/BF02975091
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02975091