Synthesis of 2-phenylbenzofuran derivatives and selective binding activities on estrogen receptor

Chemical and Pharmaceutical Bulletin

Volumn 60, Issue 2, 2012, Pages 270-274

  Zhang, Ping ^a   Yang, Yewei ^a   Zheng, Xiaoliang ^a   Huang, Wenhai ^a,b   Ma, Zhen ^a   Shen, Zhengrong ^a  

^a INSTITUTE OF MATERIA MEDICA   (China)

^b ZHEJIANG UNIVERSITY   (China)

Author keywords

2 phenylbenzofuran; Binding affinity; Diol; Estrogen receptor; Selectivity

Indexed keywords

2 (3,4 DIMETHOXYPHENYL) 6 METHOXY BENZOFURAN; 2 (3,4 DIMETHOXYPHENYL)BENZOFURAN; 2 (4 BROMOPHENYL) 6 METHOXY BENZOFURAN; 2 (4 BROMOPHENYL)BENZOFURAN; 2 (4 METHOXYPHENYL)BENZOFURAN; 2 [2 (3,4 DIMETHOXYPHENYL) 3 HYDROXYPROPENYL] 5 METHOXYPHENOL; 2 [2 (3,4 DIMETHOXYPHENYL) 3 HYDROXYPROPENYL]PHENOL; 2 [2 (4 BROMOPHENYL) 3 HYDROXYPROPENYL] 5 METHOXYPHENOL; 2 [2 (4 BROMOPHENYL) 3 HYDROXYPROPENYL]PHENOL; 2 [3 HYDROXY 2 (4 METHOXYPHENYL)PROPENYL] 5 METHOXYPHENOL; 2 [3 HYDROXY 2 (4 METHOXYPHENYL)PROPENYL]PHENOL; 2 PHENYLBENZOFURAN DERIVATIVE; 3 PHENYLCOUMARIN; 4 (BENZOFURANYL)PHENOL; 6 METHOXY 2 (4 METHOXYPHENYL)BENZOFURAN; BENZOFURAN DERIVATIVE; COUMARIN; ESTROGEN RECEPTOR; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL ANALYSIS; MOLECULAR DOCKING; PURIFICATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

BENZOFURANS; ESTROGEN RECEPTOR ALPHA; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHENOLS; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP; TIME FACTORS;

EID: 84863064864     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.60.270     Document Type: Article

References (28)

1. Ziegert R. E., Toräng J., Knepper K., Bräse S., J. Comb. Chem., 7, 147-169 (2005).
2. De Luca L., Nieddu G., Porcheddu A., Giacomelli G., Curr. Med. Chem., 16, 1-20 (2009).
3. Pang J. Y., Xu Z. L., Chin. J. Org. Chem., 25, 25-33 (2005).
4. Pu W. C., Wang F., Wang C., Chin. J. Org. Chem., 31, 155-165 (2011).
5. Dean F. M., Sargent M. V., Comprehensive Heterocyclic Chemistry, 4, 531-597 (1984).
6. Ni G., Zhang Q. J., Zheng Z. F., Chen R. Y., Yu D. Q., J. Nat. Prod., 72, 966-968 (2009).
7. Dat N. T., Jin X. J., Lee K., Hong Y. S., Kim Y. H., Lee J. J., J. Nat. Prod., 72, 39-43 (2009).
8. Pacher T., Seger C., Engelmeier D., Vajrodaya S., Hofer O., Greger H., J. Nat. Prod., 65, 820-827 (2002).
9. Akgul Y. Y., Anil H., Phytochemistry, 63, 939-943 (2003).
10. Jiang X. Z., Liu W. L., Zhang W., Jiang F. Q., Gao Z., Zhuang H., Fu L., Eur. J. Med. Chem., 46, 3526-3530 (2011).
11. Thompson L. U., Rickard S. E., Orcheson L. J., Seidl M. M., Carcinogenesis, 17, 1373-1376 (1996).
12. Hutchinson S. A., Luetjens H., Scammells P. J., Bioorg. Med. Chem. Lett., 7, 3081-3084 (1997).
13. Scammells P. J., Baker S. P., Beauglehole A. R., Bioorg. Med. Chem., 6, 1517-1524 (1998).
14. Iwasaki T., Kondo K., Kuroda T., Moritani Y., Yamagata S., Sugiura M., Kikkawa H., Kaminuma O., Ikezawa K., J. Med. Chem., 39, 2696-2704 (1996).
15. Collini M. D., Kaufman D. H., Manas E. S., Harris H. A., Henderson R. A., Xu Z. B., Unwalla R. J., Miller C. P., Bioorg. Med. Chem. Lett., 14, 4925-4929 (2004).
16. Kinoshita T., Ichinose K., Heterocycles, 65, 1641-1654 (2005).
17. "Technical Bulletin," Akzo Nobel (Asia) Co., Ltd., Shanghai, 2006, pp. 1-14.
18. See the supplemental information.
19. Cassidy A., Hanley B., Lamuela-Raventos R. M., J. Sci. Food Agric., 80, 1044-1062 (2000).
20. Waibel M., De Angelis M., Stossi F., Kieser K. J., Carlson K. E., Katzenellenbogen B. S., Katzenellenbogen J. A., Eur. J. Med. Chem., 44, 3412-3424 (2009).
21. Xiao C. F., Tao L. Y., Sun H. Y., Wei W., Chen Y., Fu L. W., Zou Y., Chin. Chem. Lett., 21, 1295-1298 (2010).
22. Bertini S., Calderone V., Carboni I., Maffei R., Martelli A., Martinelli A., Minutolo F., Rajabi M., Testai L., Tuccinardi T., Ghidoni R., Macchia M., Bioorg. Med. Chem., 18, 6715-6724 (2010).
23. Ma Z., Wang Z. Y., Zheng X. L., Shen Z. R., Hu Y. Z., Chin. JMAP, 24, 362-365 (2007).
24. Pike A. C. W., Brzozowski A. M., Hubbard R. E., Bonn T., Thorsell A.-G., Engström O., Ljunggren J., Gustafsson J.-Å., Carlquist M., EMBO J., 18, 4608-4618 (1999).
25. Mosselman S., Polman J., Dijkema R., FEBS Lett., 392, 49-53 (1996).
26. Zhou H. B., Sheng S., Compton D. R., Kim Y., Joachimiak A., Sharma S., Carlson K. E., Katzenellenbogen B. S., Nettles K. W., Greene G. L., Katzenellenbogen J. A., J. Med. Chem., 50, 399-403 (2007).
27. Minutolo F., Macchia M., Katzenellenbogen B. S., Katzenellenbogen J. A., Med. Res. Rev., 31, 364-442 (2011).
28. Alexi X., Kasiotis K. M., Fokialakis N., Lambrinidis G., Meligova A. K., Mikros E., Haroutounian S. A., Alexis M. N., J. Steroid Biochem. Mol. Biol., 117, 159-167 (2009).