Chinese Journal of Organic Chemistry >
Synthesis and Biological Activity of BenzodihydrofuranNeolignans and Their Mannich Base Derivatives
Received date: 2015-02-03
Revised date: 2015-03-09
Online published: 2015-03-17
Supported by
Project supported by the National“Twelfth Five-Year”Plan for Science & Technology Support (No. 2012BAD31B02) and the Hunan Provincial Natural Science Foundation of China (No. 14JJ2048).
The natural benzodihydrofuran neolignans licarin A (1) was synthesized from isoeugenol through biomimetic oxidative coupling. Then licarin A (1) was transformed into another benzodihydrofuran compound 2-(3'-methoxy-4'-hydroxy)- phenyl-3-methyl-5-formylvinyl-7-methoxy-2,3-benzodihydrofuran (2) through 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidative reaction. Based on Mannich reaction of 1 or 2 with viarious secondary amines and formaldehyde in acidic alcohol system under microwave-assistanced, eleven new benzodihydrofuran neolignan Mannich base derivatives 3～13 were synthesized. All the synthetic compounds were tested for antiproliferation activity against human cervical carcinoma Hela cells by the standard CCK-8 method. The results showed that most of the target compounds exhibited moderate to potent antiproliferation activity against Heala cells. Among them, compound 2 (IC50 0.438 μmol/L) and compound 9 (IC50 8.358 μmol/L) displayed the strongest antiproliferation activity against Hela cells.
Shi Ling , Wang Caifang , Xu Yu , Wang Qiu'an . Synthesis and Biological Activity of BenzodihydrofuranNeolignans and Their Mannich Base Derivatives[J]. Chinese Journal of Organic Chemistry, 2015 , 35(7) : 1537 -1543 . DOI: 10.6023/cjoc201502003
[1] Achenbach, H.; Grob, J.; Dominguez, X. A.; Cano, G.; Star, J. V.; russolo, L. D. C.; Munoz, G.; Salgad, F.; Lopez, L. Phytochemstry 1987, 26, 1159.
[2] Barros, L. F. L.; Barison, A.; Salvador, M. T.; Mello-Silva, R.; Cabral, E. C.; Eberlin, M. N.; Stefanello, M. E. A. J. Nat. Prod. 2009, 72, 1529.
[3] Wang, E. C.; Wein, Y. S.; Kuo, Y. H. Tetrahedron Lett. 2006, 47(52), 9195.
[4] Joshi, D.; Field, J.; Murphy, J.; Abdelrahim, M.; Schonherr, H.; Sparrow, J. R.; Ellestad, G.; Nakanishi, K.; Zask, A. J. Nat. Prod. 2013, 76, 450.
[5] Xu, S.-H.; Liu, H.-R.; Lou, D.-H.; Wang, Q.-A. Chin. J. Org. Chem. 2014, 34, 749 (in Chinese).(许守慧, 刘浩然, 娄定辉, 汪秋安, 有机化学, 2014, 34, 749.)
[6] Liu, H.-R.; Huang, X.-Q.; Lou, D.-H.; Liu, X.-J.; Liu, W.-K.; Wang, Q.-A. Bioorg. Med. Chem. Lett. 2014, 24, 4779.
[7] Duan, K.-K.; Liu, H.-R.; Fan, H.-Q.; Zhang, J.; Wang, Q.-A. J. Chem. Res. 2014, 38(7), 443.
[8] Liu, S.-Y.; Wang, G.-Q.; Liang, Z. Y.; Wang, Q.-A. Chem. Res. Chin. Univ., 2013, 29(6), 1119.
[9] Wu, Z.; Liang, Z. Y.; Li, W.; Ren, Y.-M.; Wang, Q.-A. Chem. Res. Chin. Univ. 2011, 27(6), 949.
[10] Daquino, C.; Rescifina, A.; Spatafora, C.; Tringali, C. Eur. J. Org. Chem, 2009, 6289.
[11] Peng, Y.-Q.; Dou, R.-L.; Song, G.-H. Synlett 2005, 2245.
/
| 〈 |
|
〉 |
