Abstract
A series of yakuchinone B1f and its analogs1a-e was synthesized and evaluated for free radical scavenging, suppression of LPS-induced NO generation, cytotoxicity and anti-excitotoxicity in vitro. Compound1c exhibited potent anti-excitotoxicity, while all compounds1a-f showed considerable effects of free radical scavenging, suppression of LPS-induced NO generation, and cytotoxicity in microglia.
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Arty, I. S., Timmerman, H., Samhoedi, M., Sastrohamidjojo, Sugiyanto, and van der Goot, H., Synthesis of benzylidene-acetophenones and their inhibition of lipid peroxidation.Eur. J. Med. Chem., 35, 449–457 (2000).
Bicking, J. B., Robb, C. M., Watson, L. S., and Cragoe, E. J. Jr., (Vinylaryloxy)acetic acids. A new class of diuretic agents. 2. (4-(3-Oxo-1-alkenyl)phenoxy)acetic acids.J. Med. Chem., 19, 544–547 (1976).
Bocchini, V., Mazzolla, R., Barluzzi, R., Blasi, E., Sick, P., and Kettenmann, H., An immortalized cell line expresses properties of activated microglial cells.J. Neurosci. Res., 31, 616–621 (1992).
Connor, D. T. and Flynn, D. L., Preparation of diarylalkenones as lipoxygenase inhibitors. (Warner-Lambert Co., Ltd., U.S.A.)USP 4959503, 1–20 (1990).
Dess, D. B. and Martin, J. C., Readily accessible 12-l-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones.J. Org. Chem., 48, 4155–4156 (1983).
Green, L. C., Wagner, D. A., Glogowski, J., Skipper, P. L., Wishnok, J. S., and Tannenbaum, S. R., Analysis of nitrate, nitrite, and [15N]nitrate in biological fluids.Anal. Biochem., 126, 131–138 (1982).
Hogale, M. B., Dhore, N. P., Shelar, A. R., and Pawar, P. K., Synthesis and biological activity of some urethane derivatives of chalcones.Oriental. J. Chem., 2, 55–57 (1986).
Huang, M. T., Lou, Y. R., Ma, W., Newmark, H. L., Reuhl, K. R., and Conney, A. H., Inhibitory effects of dietary curcumin on forestomach, duodenal, and colon carcinogenesis in mice.Cancer Res., 54, 5841–5847 (1994).
Jung, J. C., Kache, R., Vines, K. K., Zheng, Y. S., Bijoy, P., Valluri, M., and Avery, M. A., Total Syntheses of Epothilones B and D.J. Org. Chem., 69, 9269–9284 (2004).
Kiuchi, F., Goto, Y., Sugimoto, N., Akao, N., Kondo, K., and Tsuda, Y., Studies on crude drugs effective on visceral larva migrans. XVI. Nematocidal activity of turmeric: synergistic action of curcuminoids.Chem. Pharm. Bull., 41, 1640–1643 (1993).
Ley, S. V., Norman, J., Griffith, W. P., and Marsden, S. P., Tetrapropylammonium perruthenate, Pr4N+RuO4-, TPAP: a catalytic oxidant for organic synthesis.Synthesis, 639–666 (1994).
Mancuso, A. J., Huang, S.-L., and Swern, D., Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide “activated” by oxalyl chloride.J. Org. Chem., 43, 2480–2482 (1978).
Murakami, S., Kijima, H., Isobe, Y., Muramatsu, M., Aihara, H., Otomo, S., Baba, K., and Kozawa, M., Inhibition of gastric hydrogen ion-potassium ATPase by chalcone derivatives, xanthoangelol and 4-hydroxyderricin from Angelica keiskei Koidzumi.J. Pharm. Pharmacol., 42, 723–726 (1990).
Ninomiya, Y., Shimma, N., and Ishitsuka, H., Comparative studies on the antirhinovirus activity and the mode of action of the rhinovirus capsid-binding agents, chalcone amides.Antiviral Res., 13, 61–74 (1990).
Ohishi, K., Aiyama, R., Hatano, H., Yoshida, Y., Wada, Y., Yokoi, W., Sawada, H., Watanabe, and Yokokura, T., Structure-activity relationships of N-(3,5-dimethoxy-4-n-octyloxycinnamoyl)-N′-(3,4-dimethylphenyl)piperazine and analogues as inhibitors of acyl-CoA: cholesterol O-acyltransferase.Chem. Pharm. Bull., 49, 830–839 (2001).
Ohtsu, H., Xiao, Z., Ishida, J., Nagai, M., Wang, H.-K., Itokawa, H., Su, C.-Y., Shih, C., Chiang, T., Chang, E., Lee, Y., Tsai, M.-Y., Chang, C., and Lee, K.-H., Antitumor Agents. 217. Curcumin Analogues as Novel Androgen Receptor Antagonists with Potential as Anti-Prostate Cancer Agents.J. Med. Chem. 45, 5037–5042 (2002).
Perrin, D. D., Armarego, L. F., and Perrin, D. R.,Purification of Laboratory Chemicals. 2nd ed. Pergamon Press: New York, (1980).
Samaha, H. S., Kelloff, G. J., Steele, V., Rao, C. V., and Reddy, B. S., Modulation of apoptosis by sulindac, curcumin, phenylethyl-3-methylcaffeate, and 6-phenylhexyl isothiocyanate: apoptotic index as a biomarker in colon cancer chemoprevention and promotion.Cancer Res., 57, 1301–1305 (1997).
Sreejayan, Rao, M. N., Curcuminoids as potent inhibitors of lipid peroxidation.J. Pharm. Pharmacol., 46, 1013–1016 (1994).
Srimal, R. C. and Dhawan, B. N., Pharmacology of diferuloyl methane (curcumin), a nonsteroidal antiinflammatory agent.J. Pharm. Pharmacol., 25, 447–452 (1973).
Yoon, J. W., Ahn, H., Ryu, J.-H., and Kim, H.-D., Synthesis of yakuchinone derivatives and their inhibitory activities on nitric oxide synthesis.Yakhak Hoechi, 45, 16–22 (2001).
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Oh, S., Jang, S., Kim, D. et al. Synthesis and evaluation of biological properties of benzylideneacetophenone derivatives. Arch Pharm Res 29, 469–475 (2006). https://doi.org/10.1007/BF02969418
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DOI: https://doi.org/10.1007/BF02969418