Y.-R. Wu et al.: Synthesis and AChE inhibitory activity of N-glycosyl benzofuran derivativesꢁ
ꢁ165
5-Methyl-N-(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahy-
dro-2H-pyran-3-yl)benzofuran-2-carboxamide (5b)
HGlu), 3.68−3.63 (m, 2H, OH) 3.54−3.50 (m, 1H, OH), 3.46–
3.42 (m, 1H, OH), 3.22−3.18 (m, 1H, HGlu); ESI-HRMS (m/z):
calcd for C16H19NO8Na+ [M+Na]+: 376.1003; Found: 376.1015.
Yield 77%; mp 189–190°C; IR (cm−1): 3403, 3060, 2345,
1588, 1437, 1201, 792; 1H NMR: 7.92 (d, J = 8.0 Hz, 1H, NH),
7.56 (m, 2H, ArH), 7.30 (d, J = 8.5 Hz, 1H, ArH), 7.17 (d, 5-Fluoro-N-(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-
J = 4.0 Hz, 1H, ArH), 6.61 (d, J = 4.0 Hz, 1H, HGlu), 5.09 (t,
J = 3.5 Hz, 1H, HGlu), 5.02 (d, J = 5.5 Hz, 1H, HGlu), 4.85 (d,
2H-pyran-3-yl)benzofuran-2-carboxamide (5f)
J = 5.5 Hz, 1H, HGlu), 3.84−3.80 (m, 1H, HGlu), 3.75−3.71 (m, Yield 76%; mp 132–133°C; IR (cm−1): 3421, 3009, 2401, 1573,
1H, OH) 3.67−3.64 (m, 2H, OH), 3.53–3.49 (m, 1H, OH), 1438, 1213, 791; 1H NMR : 8.06 (d, J = 8.0 Hz, 1H, NH), 7.63
3.22−3.16 (m, 1H, HGlu), 2.42 (s, 3H, C-H); ESI-HRMS (m/z): (s, 1H, ArH), 7.61 (d, J = 8.0 Hz, 1H, ArH), 7.21 (s, 1H, ArH),
calcd for C16H20NO7+ [M + H]+: 338.1234; Found: 338.1244.
7.10 (m, 1H, ArH), 6.61 (d, J = 4.0 Hz, 1H, HGlu), 5.09 (t, J =
4.0 Hz, 1H, HGlu), 5.02 (d, J = 5.5 Hz, 1H, HGlu), 4.85 (d, J = 6.0
Hz, 1H, HGlu), 3.85−3.81 (m, 1H, HGlu), 3.74−3.70 (m, 1H, OH),
3.65−3.62 (m, 2H, OH), 3.53–3.46 (m, 1H, OH), 3.24−3.18
(m, 1H, HGlu); ESI-HRMS (m/z): calcd for C15H16FNO8Na+
[M+Na]+: 364.0803; Found: 364.0811.
7-Methoxy-N-(2,4,5-trihydroxy-6-(hydroxymethyl)
tetrahydro-2H-pyran-3-yl)benzofuran-2-carboxamide (5c)
Yield 64%; mp 265–266°C; IR (cm−1): 3412, 3050, 2344,
1
1583, 1424, 1254, 780; H NMR: 8.07 (d, J = 6.5 Hz, 1H,
Acknowledgments: This work was supported by the Post-
graduate Research and Practice Innovation Program of
Jiangsu Province (KYCX18-2580, KYCX19-2277, KYCX19-
2281), Open-end Funds of Jiangsu Key Laboratory of
Marine Biotechnology (HS2014007), Project 521 Funded
by Lianyungang (LYG52105-2018023), A Project Funded
by the Priority Academic Program Development of
Jiangsu Higher Education Institutions (PAPD) and Public
Science and Technology Research Funds Projects of Ocean
(201505023).
NH), 7.20 (s, 1H, ArH), 7.12 (m, 2H, ArH), 6.94 (d, J = 8.5
Hz, 1H, ArH), 6.56 (d, J = 4.0 Hz, 1H, HGlu), 5.09 (t, J = 3.5
Hz, 1H, HGlu), 5.02 (d, J = 5.5 Hz, 1H, HGlu), 4.85 (d, J = 5.5
Hz, 1H, HGlu), 3.94 (s, 3H, −OCH3) 3.84−3.80 (m, 1H, HGlu),
3.75−3.71 (m, 1H, OH) 3.67−3.64 (m, 2H, OH), 3.53–3.49 (m,
1H, OH), 3.22−3.16 (m, 1H, HGlu); ESI-HRMS (m/z): calcd for
C16H19NO8Na+ [M+Na]+: 376.1003; Found: 376.1009.
6-Methoxy-N-(2,4,5-trihydroxy-6-(hydroxymethyl)
tetrahydro-2H-pyran-3-yl)benzofuran-2-carboxamide (5d)
Yield 68%; mp 168–169°C; IR (cm−1): 3377, 3010, 2340, 1606,
1437, 1197, 812; 1H NMR: 8.30 (d, J = 9.0 Hz, 1H, NH), 7.73 (d,
J = 8.5 Hz, 1H, ArH), 7.56 (s, 1H, ArH), 7.27 (d, J = 1.5 Hz, 1H,
ArH), 6.98 (m, 1H, ArH), 6.61 (d, J = 6.0 Hz, 1H, HGlu), 5.09
(t, J = 4.0 Hz, 1H, HGlu), 5.07 (d, J = 5.5 Hz, 1H, HGlu), 4.85 (d,
J = 5.5 Hz, 1H, HGlu), 3.84 (s, 3H, −OCH3) 3.83−3.80 (m, 1H,
HGlu), 3.75−3.71 (m, 1H, OH) 3.67−3.64 (m, 2H, OH), 3.53–3.49
(m, 1H, OH), 3.22−3.16 (m, 1H, HGlu); ESI-HRMS (m/z): calcd
for C16H19NO8Na+ [M+Na]+: 376.1003; Found: 376.1015.
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Yield 72%; mp 181–182°C; IR (cm−1): 3420, 3017, 2360, 1579,
1
1436, 1208, 780; H NMR: 7.90 (d, J = 3.5 Hz, 1H, NH), 7.60
(d, J = 9.0 Hz, 1H, ArH), 7.55 (s, 1H, ArH), 7.27 (d, J = 3.0 Hz,
1H, ArH), 7.07 (m, 1H, ArH), 6.60 (d, J = 4.5 Hz, 1H, HGlu),
5.09 (t, J = 3.5 Hz, 1H, HGlu), 5.01 (d, J = 5.5 Hz, 1H, HGlu), 4.84
(d, J = 5.5 Hz, 1H, HGlu), 3.81 (s, 3H, −OCH3) 3.73−3.70 (m, 1H,
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Unauthenticated
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