Naturally occurring benzofuran: isolation, structure elucidation and total synthesis of 5-(3-hydroxypropyl)-7-methoxy-2-(3′-methoxy-4′-hydroxyphenyl)-3-benzo[b]furancarbaldehyde, a novel adenosine A1 receptor ligand isolated from salvia miltiorrhiza bunge (danshen)

作者: Zhen Yang , Po Ming Hon , Kuk Ying Chui , Zun Le Xu , Hson Mou Chang

DOI: 10.1016/S0040-4039(00)78908-8

关键词: ChemistryPhenolsSalvia miltiorrhizaTotal synthesisLigand (biochemistry)Biological activityBenzofuranBicyclic moleculeStereochemistryAdenosine A1 receptor

摘要: Abstract A naturally occurring benzofuran, namely 5-(3-hydroxypropyl)-7-methoxy-2-(3′-methoxy-4′-hydroxyphenyl)-3-benzo[ b ]furancarbaldehyde was isolated from the roots of S. miltiorrhiza Bunge “Danshen”. Its structure established by means spectroscopic methods as well a total synthesis. Both natural and synthetic compounds showed high potency (IC 50 = 17 nM 10 nM, respectively) in bovine adenosine 1 radioligand binding. The title compound root (Danshen) its

参考文章(13)
Robert M. Berne, Cardiac nucleotides in hypoxia: possible role in regulation of coronary blood flow American Journal of Physiology-Legacy Content. ,vol. 204, pp. 317- 322 ,(1963) , 10.1152/AJPLEGACY.1963.204.2.317
John W. Daly, Adenosine receptors: targets for future drugs Journal of Medicinal Chemistry. ,vol. 25, pp. 197- 207 ,(1982) , 10.1021/JM00345A001
R. D. Stephens, C. E. Castro, The Substitution of Aryl Iodides with Cuprous Acetylides. A Synthesis of Tolanes and Heterocyclics1 Journal of Organic Chemistry. ,vol. 28, pp. 3313- 3315 ,(1963) , 10.1021/JO01047A008
Hson Mou Chang, Kwok Ping Cheng, Tai Francis Choang, Hak Fun Chow, Kuk Ying Chui, Po Ming Hon, Fan Wah Lau Tan, Yun Yang, Zeng Pei Zhong, Structure elucidation and total synthesis of new tanshinones isolated from Salvia miltiorrhiza Bunge (Danshen) Journal of Organic Chemistry. ,vol. 55, pp. 3537- 3543 ,(1990) , 10.1021/JO00298A029
Wing-Tai Cheung, Maggie M. Shi, James D. Young, Chi-Ming Lee, Inhibition of radioligand binding to A1 adenosine receptors by bay k8644 and nifedipine Biochemical Pharmacology. ,vol. 36, pp. 2183- 2186 ,(1987) , 10.1016/0006-2952(87)90148-1
C. E. Castro, E. J. Gaughan, D. C. Owsley, Indoles, Benzofurans, Phthalides, and Tolanes via Copper(I) Acetylides Journal of Organic Chemistry. ,vol. 31, pp. 4071- 4078 ,(1966) , 10.1021/JO01350A045
Roger Adams, I. Levine, SIMPLIFICATION OF THE GATTERMANN SYNTHESIS OF HYDROXY ALDEHYDES Journal of the American Chemical Society. ,vol. 45, pp. 2373- 2377 ,(1923) , 10.1021/JA01663A020
R. L. Shriner, P. McCutchan, PREPARATION OF SOME METHYLATED GALLIC ACIDS Journal of the American Chemical Society. ,vol. 51, pp. 2193- 2195 ,(1929) , 10.1021/JA01382A033
Alexander Galat, A Synthesis of α,β-Unsaturated Esters Journal of the American Chemical Society. ,vol. 68, pp. 376- 377 ,(1946) , 10.1021/JA01207A009