4
Journal of Chemical Research 00(0)
ArH), 7.42 (d, J=2.0Hz, 1H,ArH), 7.10 (dd, J=8.5, 2.5Hz, H-5GlcN, H-6bGlcN), 2.38 (s, 3H, CH ), 2.00 (s, 3H, CH ),
3
3
GlcN
1
H, ArH), 5.34 (t, J=9.5Hz, 1H, H-1 ), 5.22 (t, 1.98 (s, 3H, CH ), 1.94 (s, 3H, CH ), 1.73 (s, 3H, CH );
3 3 3
GlcN
GlcN
+
J=10.0Hz, 1H, H-3 ), 4.88 (t, J=10.0Hz, 1H, H-4 ), ESI-HRMS (m/z): calcd for C H N NaO [M+Na] :
2
2
27
3
9
GlcN
4
3
3
.22 (dd, J=12.0, 4.0Hz, 1H, H-6a ), 4.03−3.93 (m, 500.1640; found: 500.1636.
H, H-2 , H-5 , H-6b ), 2.00 (s, 3H, CH ), 1.98 (s,
GlcN
GlcN
GlcN
3
H, CH ), 1.94 (s, 3H, CH ), 1.73 (s, 3H, CH ); ESI-HRMS Declaration of conflicting interests
3
3
3
+
(
m/z): calcd for C H ClN NaO [M+Na] : 520.1093;
21 24 3 9
The author(s) declared no potential conflicts of interest with
respect to the research, authorship, and/or publication of this
found: 520.1091.
2
-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D- article.
glucopyranosyl)amino-6-methyl-1, 3-benzoxazole (5e):
Light yellow solid; yield 0.81g (92%); m.p. 62–64°C; IR Funding
−
1
1
(
cm ): 3415, 1748, 1638, 1585, 1244, 1113, 1044, 918; H
The author(s) disclosed receipt of the following financial sup-
port for the research, authorship, and/or publication of this arti-
cle: This work was supported by the Postgraduate Research and
NMR (500MHz, DMSO-d ): δ=8.75 (d, J=9.5Hz, 1H,
NH), 8.07 (d, J=9.0Hz, 1H, NH), 7.25 (s, 1H, ArH), 7.21
6
(
(
4
1
d, J=8.0Hz, 1H, ArH), 6.99 (d, J=8.0Hz, 1H, ArH), 5.33 Practice Innovation Program of Jiangsu Province (KYCX19-
GlcN
GlcN
t, J=9.5Hz, 1H, H-1 ), 5.22 (t, J=10.0Hz, 1H, H-3 ), 2277, KYCX19-2281), the Open-End Funds of Jiangsu Key
GlcN
.88 (t, J=9.5Hz, 1H, H-4 ), 4.22 (dd, J=12.5, 8.0Hz, Laboratory of Marine Biotechnology (HS2014007), Project 521
H, H-6aGlcN), 4.02−3.91 (m, 3H, H-2GlcN, H-5
GlcN
funded by Lianyungang (LYG52105-2018023), a project
funded by the Priority Academic Program Development of
Jiangsu Higher Education Institutions (PAPD), and the Public
Science and Technology Research Funds Projects of Ocean
,
GlcN
H-6b ), 2.36 (s, 3H, CH ), 2.00 (s, 3H, CH ), 1.98 (s, 3H,
CH ), 1.94 (s, 3H, CH ), 1.73 (s, 3H, CH ); ESI-HRMS
(
3
3
3
3
3
+
m/z): calcd for C H N NaO [M+Na] : 500.1640;
22 27 3 9
(
201505023).
found: 500.1637.
2
-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-
ORCID iD
glucopyranosyl)amino-4-methyl-1, 3-benzoxazole (5f):
Yu-Ran Wu
Light yellow solid; yield 0.80g (91%); m.p. 68–71°C; IR
−
1
1
(
cm ): 3419, 1748, 1639, 1591, 1243, 1125, 1045, 915; H
References
NMR (500MHz, DMSO-d ): δ=8.78 (d, J=10.0Hz, 1H,
6
NH), 8.07 (d, J=9.0Hz, 1H, NH), 7.24 (d, J=8.0Hz, 1H,
1. Terencio MC, Ferrandiz ML, Carceller MC, et al. Biomed
Pharmacother 2016; 79: 120.
2. Fu M, Qin C, Li W, et al. Carbohydr Polym 2013; 91:
390.
ArH), 7.00 (d, J=7.5Hz, 1H, ArH), 6.96 (t, J=7.5Hz, 1H,
GlcN
ArH), 5.36 (t, J=10.0Hz, 1H, H-1 ), 5.24 (t, J=10.0Hz,
GlcN
GlcN
1
H, H-3 ), 4.88 (t, J=10.0Hz, 1H, H-4 ), 4.22 (dd,
GlcN
), 4.02−3.95 (m, 3H, H-2GlcN
3. Li Y, Chen L, Liu Y, et al. Sci Rep 2018; 8: 5624.
J=12.5, 4.5Hz, 1H, H-6a
H-5 , H-6b ), 2.39 (s, 3H, CH ), 2.00 (s, 3H, CH ),
,
4
5
6
. Mubarak AD, Lewis OF, Gopinath V, et al. Microb
Pathogenesis 2018; 114: 323.
. Zahedipour F, Dalirfardouei R, Karimi G, et al. Biomed
Pharmacother 2017; 95: 1051.
GlcN
GlcN
3
3
1
.98 (s, 3H, CH ), 1.94 (s, 3H, CH ), 1.73 (s, 3H, CH );
3 3 3
+
ESI-HRMS (m/z): calcd for C H N NaO [M+Na] :
2
2
27
3
9
5
00.1640; found: 500.1636.
. Wang L, Wu YR, Ren ST, et al. Heterocycl Commun 2018;
2
-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-
2
4: 333.
glucopyranosyl)amino-5-methyl-1, 3-benzoxazole (5g):
7. Yin L, Wang L, Liu XJ, et al. Heterocycl Commun 2017; 23:
231.
8. Liu XJ, Wang L, Yin L, et al. J Chem Res 2017; 41: 571.
Light yellow solid; yield 0.80g (91%); m.p. 68–70°C; IR
−
1
1
(
cm ): 3416, 1748, 1639, 1591, 1243, 1127, 1045, 916; H
9
. Haneda S, Gan Z, Eda K, et al. Organometallics 2007; 26:
551.
0. Shavaleev NM, Scopelliti R, Gumy F, et al. Inorg Chem
009; 48: 6178.
1. Boyle KE, Mac MKS, Ellis DA, et al. Bioorg Med Chem Lett
010; 20: 1854.
2. Jeyanthi P and Pazhanisamy P. Synthesis 2010; 2: 1170.
NMR (500MHz, DMSO-d ): δ=8.79 (d, J=9.5Hz, 1H,
6
6
NH), 8.08 (d, J=9.0Hz, 1H, NH), 7.29 (d, J=8.0Hz, 1H,
1
1
1
ArH), 7.15 (s, 1H, ArH), 6.87 (d, J=8.0Hz, 1H, ArH), 5.34
2
GlcN
(
t, J=10.0Hz, 1H, H-1 ), 5.22 (t, J=10.0Hz, 1H,
GlcN
GlcN
H-3 ), 4.88 (t, J=10.0Hz, 1H, H-4 ), 4.22 (dd,
2
J=12.5, 4.0Hz, 1H, H-6a ), 4.02−3.92 (m, 3H, H-2GlcN
GlcN
,
GlcN
GlcN
H-5 , H-6b ), 2.35 (s, 3H, CH ), 2.00 (s, 3H, CH ),
3
3
13. Malapati P, Krishna VS, Nallangi R, et al. Eur J Med Chem
1
.98 (s, 3H, CH ), 1.94 (s, 3H, CH ), 1.73 (s, 3H, CH );
3 3 3
2018; 145: 23.
+
ESI-HRMS (m/z): calcd for C H N NaO [M+Na] : 14. Kakkar S, Tahlan S, Lim SM, et al. Chem Cent J 2018; 12:
2
2
27
3
9
5
00.1640; found: 500.1637.
92.
2
-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D- 15. Singh H, Kumar M, Nepali K, et al. Eur J Med Chem 2016;
1
16: 102.
6. Wei H, Ruan J and Zhang X. RSC Adv 2016; 6: 10846.
17. Ramprasad J, Nayak N and Dalimba U. Eur J Med Chem
015; 106: 75.
8. Liu WW, Li QX, Cheng FC, et al. Heterocycl Commun 2014;
0: 333.
glucopyranosyl)amino-7-methyl-1, 3-benzoxazole (5h):
1
Light pink solid; yield 0.83g (94%); m.p. 63–65°C; IR
−
1
1
(
cm ): 3426, 1748, 1639, 1588, 1242, 1127, 1046, 913; H
2
NMR (500MHz, DMSO-d ): δ=8.85 (d, J=9.5Hz, 1H,
6
1
NH), 8.07 (d, J=9.0Hz, 1H, NH), 7.16 (d, J=8.0Hz, 1H,
2
ArH), 7.07 (t, J=7.5Hz, 1H, ArH), 6.89 (d, J=7.5Hz, 1H,
1
2
9. Yin L, Cheng FC, Li QX, et al. J Chem Res 2016; 40: 545.
0. Ellman GL, Courtney KD, Andres V, et al. Biochem
Pharmacol 1961; 7: 88.
GlcN
ArH), 5.35 (t, J=10.0Hz, 1H, H-1 ), 5.23 (t, J=10.0Hz,
GlcN
GlcN
1
H, H-3 ), 4.88 (t, J=10.0Hz, 1H, H-4 ), 4.22 (dd,
J=12.5, 4.5Hz, 1H, H-6a ), 4.02−3.92 (m, 3H, H-2GlcN
GlcN
,
21. Shetab-Boushehri SV. EXCLI J 2018; 17: 798.