Browse > Article

Synthesis and Cytotoxic Activity-II, Aminoacetyl Derivatives  

You, Young-Jae (College of Pharmacy, Chungnam National University)
Kim, Yong (College of Pharmacy, Chungnam National University)
Nam, Nguyen-Hai (College of Pharmacy, Chungnam National University)
Ahm, Byung-Zun (College of Pharmacy, Chungnam National University)
Publication Information
YAKHAK HOEJI / v.46, no.5, 2002 , pp. 301-306 More about this Journal
Abstract
To increase the water solubility, sixteen lupane derivatives bearing aminoacetyl moiety at C3 were synthesized. Their cytotoxic activities against three cancer cell lines, SK-MEL-2, A549, and B16, were tested. Among them, six derivatives showed significant cytotoxic activity.
Keywords
Lupane; betulinic acid; cytotoxic activity; hydrophilicity;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Schmidt, M. L., Kuzmanoff, K. L., Ling-Indeck, L., Pezzuto, J. M. : Betulinic acid induces apoptosis in human neuroblastoma cell lines. Eur. J. Cancer 33, 2007 (1997)
2 Shin, D. J., You, Y. J., Ahn, B. Z. : 2-(1-Aminoacetyloxyalkyl)-1,4-dihydroxy-9,10-anthraquinone derivatives: synthesis and cytotoxic activity. J. Pharm. Soc. Korea 45, 133 (2001)
3 Kashiwada, Y., Hashimoto, F., Cosentino, L. M., Chen, C. H., Garrett, P. E., Lee, K. H. : Betulinic acid and dihydrobetulinic acid derivatives as potent anti-HIV agents. J. Med. Chem. 39, 1016 (1996)   DOI   ScienceOn
4 Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S., Boyd, M. R. : New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst. 82, 1107 (1990)   DOI   PUBMED
5 Yasukawa, K., Takido, M., Matsumoto, T., Takeuchi, M., Nakagawa, S. : Sterol and triterpene derivatives from plants inhibit the effects of a tumor promoter, and sitosterol and betulinic acid inhibit tumor formation in mouse skin two-stage carcinogenesis. Oncology 48, 72 (1991)
6 Inoue, H., Saito, H., Koshihara, Y., Murota, S. : Inhibitory effect of glycyrrhetinic acid derivatives on lipoxygenase and prostaglandin synthetase. Chem. Pharm. Bull. 34, 897 (1986)
7 Fujioka, T., Kashiwada, Y., Kilkuskie, R. E., Cosentino, L. M., Ballas, L. M., Jiang, J. B., Janzen, W. P., Chen, I. S., Lee, K. H. : Anti-AIDS agents, 11. Betulinic acid and platanic acid as anti-HIV principles from Syzigium claviflorum, and the anti-HIV activity of structurally related triterpenoids. J. Nat. Prod. 57, 243 (1994)
8 Ryu, S. Y., Choi, S. U., Lee, S. H., Lee, C. O., No, Z. S., Ahn, J. W. : Antitumor Triterpenes from Medicinal Plants, Arch. Pharm. Res. 17, 375 (1994)   DOI   ScienceOn
9 Yasukawa, K., Yu, S., Yamanouchi, S., Takido, M., Akihisa, T., Tamura, T. : Some lupane-type triterpenes inhibit tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skin. Phytomedicine 1, 309 (1995)
10 Pisha, E., Chai, H. B., Lee, I. S., Chagwedera, T. E., Farnsworth, N. R., Cordell, G. A., Beecher, C. W., Fong, H. H., Kinghorn, A. D., Brown, D. M. : Discovery of betulinic acid as a selective inhibitor of human melanoma that functions by induction of apoptosis. Nat. Med., 1(10), 1046 (1995)
11 Jeong, H. J., Chai, H. B., Park, S. Y., Kim, D. S. : Preparation of amino acid conjugates of betulinic acid with activity against human melanoma. Bioorg. Med. Chem. Lett. 9, 1201 (1999)   DOI   ScienceOn