Synthesis of dihydrobenzofuran neoligans licarin a and dihydrocarinatin as well as related triazolylglycosides

Abstract

Two natural dihydrobenzofuran neolignans licarin A(1) and dihydrocarinatin(2) were systhesized from isoeugenol with Ag₂O-catalyzed biomimetic oxidative coupling as the key step. Four novel dihydrobenzofuran triazolylglycoside(3–6) were achieved in good yields via Cu(I)-catalyzed azide-alkyne cycloadditions of licarin A terminal alkynes with different azide acetylated sugar and deacetylation with sodium methoxide in anhydrous methanol. The structures of all the compounds synthesized were determined by elemental analysis, MS, ¹H NMR and ¹³C NMR. And the inhibition activity of synthesized compounds on α-glucosidase was determined by in vitro experiments. The results show that triazolyglycosides 3, 4, 5 and 6 show moderate inhibitory activity on α-glucosidase.

Keywords

Dihydrobenzofuran / Licarin A / Dihydrocarinatin / Triazolylglycoside

References

[1] Macda S, Masuda H, Tokoroyama T. Chem. Pharm. Bull., 1994, 42: 2500.

[2] Juhász L, Kürti L, Antus S. J. Nat. Prod., 2000, 63: 866.

[3] Achenbach H, Grob J, Dominguez X A, Cano G, Star J V, Brussolo L D C, Munoz G, Salgado F, Lopez L. Phytochemistry, 1987, 26: 1159.

[4] Marques M O M, Yoshida M, Gottlieb O R. Phytochemistry, 1992, 31: 4380.

[5] Barros L F L, Barison A, Salvador M J, Mello-Silva R, Cabral E C, Eberlin M N, Stefanello M E A. J. Nat. Prod., 2009, 72: 1529.

[6] Fan H F, Ren Y M, Wu X L, Wang Q A. J. Chem. Res., 2010, 34(4): 233.

[7] Wu Z, Liang Z Y, Li W, Ren Y M, Wang Q A. Chem. Res. Chinese Universities, 2011, 27(6): 949.

[8] Gyorgydeak Z, Thiem J. Adv. Carbohydr. Chem. Biochem., 2006, 60: 103.

[9] Hanessian S, Saavedra O M, Mascitti V, Marterer W, Dehriein R. Tetrahedron, 2001, 57: 3267.

[10] Zhao J Z, Zhang X Q, Wu X, Xing Z B, Yue A Q, Shao H W. Chem. Res. Chinese Universities, 2013, 29(1): 71.

[11] Wang E C, Wein Y S, Kuo Y H. Tetrahedron Lett., 2006, 47: 9195.

[12] Matsui T, Yoshimoto C, Osajima K, Oki T, Osajima Y. Biosci. Biotechnol. Biochem., 1996, 60: 2019.

[13] Liu Y, Zhao H, Liu S, Liu Z Q. Chem. J. Chinese Universities, 2013, 34(4): 813.

[14] Moussouni S, Saru M L, Loannou E, Mansour M, Detsi A, Roussis V, Kefalas P. Tetrahedron Lett., 2011, 52: 1165.

[15] Pieters L, van Dyck S, Gao M, Bai R, Hamel E, Vlietinck A, Lemiere G. J. Med. Chem., 1999, 42: 5475.

[16] Juhasz L, Kurti L, Antus S. J. Nat. Prod., 2000, 63: 866.

[17] Pellissier H. Tetrahedron, 2004, 60: 5123.

[18] Zhang X, Simmons C G, Corey D R. Bioorg. Med. Chem. Lett., 2001, 11: 1269.

[19] Kolb H C, Finn M G, Sharpless K B. Angew. Chem. Int. Ed., 2001, 40: 2004.

[20] Rostovtsev V V, Green L G, Fokin V V, Sharpless K B. Angew. Chem. Int. Ed., 2002, 41: 2596.