Total synthesis and biological evaluation of methylgerambullone

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 1, 2010, Pages 52-55

  Moon, Jong Taik ^a   Ha, Sung Hoon ^a   Lee, So Hyung ^a   Kwon, Tae Hui ^a   Oh, Chun Rim ^b   Kim, Young Deuk ^b   Kim, Jungahn ^a   Choo, Dong Joon ^a   Lee, Jae Yeol ^a  

^a Korea Basic Science Institute (KBSI)   (South Korea)

^b DongWoo Syntech Co Ltd   (South Korea)

Author keywords

Guinea pig ileum; Methylgerambullone; Natural product; Relaxation

Indexed keywords

ACETYLCHOLINE; METHYLGERAMBULLONE; SPASMOLYTIC AGENT; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BIOLOGICAL ACTIVITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG SYNTHESIS; GLYCOSMIS ANGUSTIFOLIA; GUINEA PIG; ILEUM CONTRACTION; MEDICINAL PLANT; MITSUNOBU REACTION; NONHUMAN; SMOOTH MUSCLE CONTRACTION; SMOOTH MUSCLE RELAXATION;

ACETYLCHOLINE; ACRYLAMIDES; ANIMALS; BIOLOGICAL PRODUCTS; GUINEA PIGS; ILIUM; MUSCLE RELAXATION; MUSCLE, SMOOTH; RUTACEAE; SULFONES;

CAVIA; GLYCOSMIS;

EID: 72049098757     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.11.040     Document Type: Article

References (14)

1. Greger H., Hofer O., Zechner G., Hadacek F., and Wurz G. Phytochemistry 37 (1994) 1305
2. Jeong S.I., Lee S., Kim K.J., Keum K.S., Choo Y.K., Choi B.K., and Jung K.Y. J. Pharm. Pharmacol. 57 (2005) 1653
3. Umbreit M.A., and Sharpless K.B. J. Am. Chem. Soc. 99 (1977) 5526
4. 2 at -10 °C in 89% yield.
5. Ikegami F., Sekine T., Duangteraprecha S., Matsushita N., Matsuda N., Ruangrungsi N., and Murakoshi I. Phytochemistry 28 (1989) 881
6. 1H NMR as follows: for cis-isomer (14), δ 7.20 and 5.87, J = 10.1 Hz; for trans-isomer (15), δ 7.88 and 5.66, J = 14.8 Hz.
7. Lepore S.D., and He Y. J. Org. Chem. 68 (2003) 8261
8. Clarke P.A., and Cridland A.P. Org. Lett. 7 (2005) 4221
9. Perry N.B., Foster L.M., Lorimer S.D., May B.C.H., and Weavers R.T. J. Nat. Prod. 59 (1996) 729
10. Baek S.H., Perry N.B., and Weavers R.T. J. Nat. Prod. 61 (1998) 1143
11. Barhate N.B., Shinde P.D., Mahajan V.A., and Wakharkar R.D. Tetrahedron Lett. 43 (2002) 6031
12. Takano S., Hatakeyama S., and Ogasawara K. J. Chem. Soc., Chem. Commun. (1977) 68
13. +: 434.2001, found 434.2007.
14. Fatehi M., Farifteh F., and Fatehi-Hassanabad Z. J. Ethnopharmacol. 91 (2004) 321