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)
  • Published : 2004.08.01

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

References

  1. 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) https://doi.org/10.1021/np960422f
  2. 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) https://doi.org/10.1055/s-2006-957384
  3. 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)
  4. 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)
  5. 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) https://doi.org/10.1248/cpb.39.930
  6. 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) https://doi.org/10.1021/jo00155a048
  7. 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) https://doi.org/10.1055/s-2006-959425
  8. 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) https://doi.org/10.1016/S0031-9422(99)00554-3
  9. 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) https://doi.org/10.1055/s-2006-957901
  10. Crawford, I. M. and Shaw, J. A., Perkin coumarin synthesis. J. Chem. Soc., Abst., 3435-3459 (1953)
  11. 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) https://doi.org/10.1055/s-2000-14894
  12. Fall, Y., Santana, L., Teijeira, M., Teran, C., and Uriarte, E., Synthesis of new 4-cyclohexylcoumarin derivatives. Synthesis, 5, 643-645 (2000)
  13. 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) https://doi.org/10.1248/cpb.39.1238
  14. 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) https://doi.org/10.1016/S0960-894X(99)00578-8
  15. 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)
  16. 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) https://doi.org/10.1055/s-1999-13965
  17. 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) https://doi.org/10.1016/S0040-4039(98)00299-8
  18. Jegadeesan, M. and Kamalam, M., Estimation of bioactive principle, wedelolactone in Wedelia chinensis (Osbeck), Merr. Indian Drugs, 36, 484-486 (1999)
  19. Khalmuradov, M. A. and Saidkhodzhaev, A. I., Coumarins of Zeravschania regeliana. Chem. Nat. Compd., 35, 364 (1999) https://doi.org/10.1007/BF02234865
  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) https://doi.org/10.1016/S0031-9422(00)00047-9
  21. Naser-Hijazi, B., Stolze, B., and Zanker, K. S., Second Proceedings of the International Society of Coumarin Investigators, Springer: Berlin, 1994
  22. 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) https://doi.org/10.1021/ja00427a031