Browse > Article

Solid Phase Synthesis of 3-(4-Hydroxyphenyl）coumarin: Preliminary Experiments for Combinatorial Synthesis of Substituted 3-Phenylcoumarin Derivatives  

Bae, Hoon (Department of Chemistry and Biochemistry, Florida State University)
Kim, Hak-Sung (Wonkwang University, College of Pharmacy)
Publication Information
Archives of Pharmacal Research / v.27, no.8, 2004 , pp. 811-815 More about this Journal
Abstract
Coumarin and its derivatives occur widely in nature. Many attempts were made for synthesis of various coumarin derivatives because of their interesting biological activities. In this study, solid phase synthetic approach of 3-(4-hydroxyphenyl)coumarin was achieved for combinatorial synthesis of substituted 3-phenylcoumarin analogues. Starting from 4-hydroxyphenylacetic acid methyl ester, release of 3-(4-hydroxypnehyl)coumarin from polymer support was accom-plished.
Keywords
Polymer-supported; Solid phase; Coumarin; 3-Phenylcoumarin; 3-Phenylchrome-none; Arylcoumarin; 3-(4-Hydroxyphenylcoumarin;
Citations & Related Records

Times Cited By Web Of Science : 1  (Related Records In Web of Science)
Times Cited By SCOPUS : 1
연도 인용수 순위
1 Bradshaw, J. S., Gebhard, J. S., and Jones, B. A., Formation of ethers by the reductive desulfurization of thiono esters. J. Org. Chem., 48, 1127-1129 (1983)   DOI
2 Chen, B., Duan, H., Lee, K.-H., Honda, G., Itoh, M., Kodzhimatov, O. K., Takeda, Y., Takaishi, Y., and Zhou, P., Coumarins and bicoumarin from Ferula sumbul: anti-HIV activity and inhibition of cytokine release. Phytochemistry, 53, 689-697 (2000)   DOI   ScienceOn
3 Crawford, I. M. and Shaw, J. A., Perkin coumarin synthesis. J. Chem. Soc., Abst., 3435-3459 (1953)
4 Fukuda, T., Hatano, T., Miyase, T., Noro, T., and Okuda, T., Phenolic constituents of licorice. III. Structures of glicoricone and licofuranone, and inhibitory effects of licorice constit-uents on monoamine oxidase. Chem. Pharm. Bull., 39, 1238-1243 (1991)   DOI   PUBMED   ScienceOn
5 Fylaktakidou, K., Hadjipavlou- Litina, D. J., Litinas, E. K., Nicolaides, D. N., and Papageorgiou, G., Synthesis of some pyrano[2,3-g]chromene-2,7-diones and furo[2,3-g]chromen-6-ones. Heterocyclic Chem., 35, 9196 (1998)
6 Newman M. S., Olson D. R., and Sankaran V., Phenolic and ketonic tautomers in polycyclic aromatic hydrocarbons. J. Am. Chem. Soc., 98, 3237-3242 (1976)   DOI   PUBMED
7 Khalmuradov, M. A. and Saidkhodzhaev, A. I., Coumarins of Zeravschania regeliana. Chem. Nat. Compd., 35, 364 (1999)   DOI   ScienceOn
8 Apers, S., De Bruyne, T., Pieters, L. A., and Vlietinck, A. J., Plant-derived leading compounds for chemotherapy of human immunodeficiency virus (HIV) infection. Planta Med., 64(2), 97-109 (1998)   DOI   ScienceOn
9 Furukawa, H., Gao, G., Ito, C., Koshimizu, K., Murakami, A., Ohigashi, H., Omura, M., Takahashi, D., and Yano, M., 1,1-Dimethylallylcoumarins potently suppress both lipopolysac-charide- and interferon-gamma-induced nitric oxide gener-ation in mouse macrophage RAW 264.7 cells. Bioorg. Med. Chem. Lett., 10, 59-62 (2000)   DOI   PUBMED   ScienceOn
10 Jegadeesan, M. and Kamalam, M., Estimation of bioactive principle, wedelolactone in Wedelia chinensis (Osbeck), Merr. Indian Drugs, 36, 484-486 (1999)
11 Bal-Tembe, S., Joshi, D. D., and Lakdawala, A. D., Isolation of the antiinflammatory principle of Heracleum candicans. Indian J. Chem., Sect. B : Org. Chem. Include. Med. Chem., 35B(5), 518-519 (1996)
12 Beauchamp, P. S., D'Souza, A. M., Kamat, S, P., and Paknikar, S. K., A convenient one-pot synthesis of 4-methyl-3-phenyl-, 3-aryl- and 3-aryl-4- phenylcoumarins. J. Chem. Res., Synop., 5, 242-246 (2002)
13 Botta, B., Botta, M., Delle, M. G., Kuge, T., Kusano, A., Nikaido, T., Ohmoto, T., and Saitoh, T., Inhibition of adenosine 3',5'-cyclic monophosphate phosphodiesterase by flavonoids from licorice roots and 4-arylcoumarins. Chem. Pharm. Bull., 39, 930-933 (1991)   DOI   PUBMED   ScienceOn
14 Celia do Nascimento, Mors, W B., Pereira, B. M. R., M., Parente, J. P., and Pereira, N. A., Pharmacological screening of plants recommended by folk medicine as snake venom antidotes; IV. Protection against jararaca venom by isolated constituents. Planta Med., 60(2), 99-100 (1994)   DOI   ScienceOn
15 Fall, Y., Santana, L., Teijeira, M., Teran, C., and Uriarte, E., Synthesis of new 4-cyclohexylcoumarin derivatives. Synthesis, 5, 643-645 (2000)
16 Gaudry, M, Henot, F., Pinard, E., and Thellend, A., Asymmetric total synthesis (+)-pisatin, a phytoalexin from garden peas (Pisum sativum L.). Tetraheron Lett., 39, 2739-2742 (1998)   DOI   ScienceOn
17 Delgado, H. P., Garcia-Argaez, A. N., Martinez-Vazquez, M., Ramirez Apan, T. O., and Velazquez, G., Anti-inflammatory activity of coumarins from Decatropis bicolor on TPA ear mice model. Planta Med., 66, 279-281 (2000)   DOI   ScienceOn
18 Naser-Hijazi, B., Stolze, B., and Zanker, K. S., Second Proceedings of the International Society of Coumarin Investigators, Springer: Berlin, 1994
19 Gafner, S., Hostettmann, K., Lu, H., Tan, R. X., Wolfender, J. L., Yang, L., Yu, T. T., and Zheng, W. F., Mono- and sesquiterpenes and antifungal constituents from Artemisia species. Planta Med., 65, 64-67 (1999)   DOI   PUBMED   ScienceOn
20 Maier, W., Nimtz, M., Schmidt, J., Strack, D., and Wray, V., Secondary products in mycorrhizal roots of tobacco and tomato. Phytochemistry, 54, 473-479 (2000)   DOI   ScienceOn
21 Abad, M. J., Bermejo, P., Silvan, A. M., Sollhuber, M., and Villar, A., Antiinflammatory activity of coumarins from Santolina oblongifolia. J. Nat. Prod., 59(12), 1183-1185 (1996)   DOI   ScienceOn
22 Chung, H. S., Hyun, J. W., Kang, S. S., Kim, B. K., Paik, W. H., Park, J. G., Sung, M. S., and Yang, Y. M., The cytotoxicity of psoralidin from Psoralea corylifolia. Planta Med., 62(4), 353-354 (1996)   DOI   ScienceOn