Synthesis of novel 3-[(1-glycosyl-1H-1,2,3-triazol-4-yl)- methylamino]ket-2-en-1-ones

Article abstract of DOI:10.1007/s10593-018-2274-2

[Figure not available: see fulltext.] Nine 3-[(1-β-D-ribofuranosyl- and 3-[(1-β-D-glucopyranosyl-1H-1,2,3-triazol-4-yl)methylamino]ket-2-en-1-ones have been synthesized by copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction between propargylamine

Full text of DOI:10.1007/s10593-018-2274-2

DOI 10.1007/s10593-018-2274-2
Chemistry of Heterocyclic Compounds 2018, 54(3), 362–368
Synthesis of novel 3-[(1-glycosyl-1H-1,2,3-triazol-4-yl)-
methylamino]ket-2-en-1-ones
Banty Kumar1,2, Jyotirmoy Maity1, Amit Kumar1,
Vinod Khatri1, Bhawani Shankar1, Ashok K. Prasad1*
1 Bioorganic Laboratory, Department of Chemistry, University of Delhi,
Delhi 110 007, India; e-mail: ashokenzyme@gmail.com
2 Rajdhani College, Department of Chemistry, University of Delhi,
Delhi 110 007, India; e-mail: bantykumar881@gmail.com
Published in Khimiya Geterotsiklicheskikh Soedinenii,
2018, 54(3), 362–368
Submitted January 20, 2018
Accepted March 20, 2018
N
N
N
O
HO
HO
NH
O
67–68%
R
overall yield
OH
HO
O
HN
4 examples
R
C CH
CH
Ph
R1
HO
N
N
O
O
NH
N
R = Ph, Me(CH2)9, Me(CH2)4, Me(CH2)3,
3-MeC6H4OCH2, 3-MeC6H4
54–71%
overall yield
HO
OH
5 examples
R
Nine 3-[(1-β-D-ribofuranosyl- and 3-[(1-β-D-glucopyranosyl-1H-1,2,3-triazol-4-yl)methylamino]ket-2-en-1-ones have been synthesized
by copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction between propargylamine derivatives and 1-azido-2,3,5-tri-O-benzoyl-
β-D-ribofuranose or 2,3,4,6-tetra-O-acetyl-1-azido-β-D-glucopyranose, followed by deprotection of the resulting tri-O-benzoyl- or tetra-
O-acetyl-1-β-D-glycosyltriazoles in good yields. The precursor propargylamine derivatives were synthesized by Sonogashira reaction of
substituted acetylenes and benzoyl chloride followed by Michael-type addition of propargylamine to the resulting substituted alkynes in
good yields. The precursor azido sugars, 1-azido-2,3,5-tri-O-benzoyl-β-D-ribofuranose and 2,3,4,6-tetra-O-acetyl-1-azido-β-D-gluco-
pyranose, were synthesized by azidation of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose and β-D-glucopyranose pentacetate,
respectively, with azidotrimethylsilane in the presence of tin(IV) chloride. All products were unambiguously characterized on the basis
of the spectral data analysis.
Keywords: N-glycoconjugates, CuAAC reaction, Sonogashira reaction.
Carbohydrates and glycoconjugates are involved in
numerous biologically and pathologically significant regu-
latory processes,1 such as immune response, cell-cell
recognition, interaction of pathogen and host, cell
adhesion,2 cancer and metastasis,3 inflammation,4 etc. Due
to their prominent role in biology and medicine, efforts are
being directed toward the development of novel
carbohydrate-based scaffolds with desirable properties.
Further, due to the relevance of the click chemistry in the
recent past, 1,2,3-triazole cycle has emerged as a promising
heterocyclic aglycon moiety. There are ample examples in
the literature on glycosyl triazoles and broad spectrum of
their chemical and biological significance.5,6 They are
reported as inhibitors of galectin proteins,7 glycogen
phosphorylase,8 carbonic anhydrase,9 sweet almond
β-glucosidase10 and as anticancer agents.11 Herein, we
report the synthesis of novel 3-[(1-glycosyl-1H-1,2,3-
triazol-4-yl)methylamino]ket-2-en-1-ones via copper-
catalyzed azide–alkyne cycloaddition (CuAAC) reaction of
1-azido-2,3,5-tri-O-benzoyl-β-D-ribofuranose or 1-azido-
2,3,4,6-tetra-O-acetyl-β-D-glucopyranose to 1-phenyl-
3-propargylaminoprop-2-en-1-ones in good to excellent
yield.
The precursors for the synthesis of the targeted
3-[(1-glycosyl-1H-1,2,3-triazol-4-yl)methylamino]ket-2-en-
1-ones are 1-phenyl-3-propargylaminopropenones 4a–f,
1-azido-2,3,5-tri-O-benzoyl-β-D-ribofuranose (5) and
2,3,4,6-tetra-O-acetyl-1-azido-β-D-glucopyranose (6). The
alkyne precursors, i.e., 1,3-diphenyl-3-(prop-2-yn-1-ylamino)-
prop-2-en-1-one (4a), 1-phenyl-3-(prop-2-yn-1-ylamino)-
tridec-2-en-1-one (4b), 1-phenyl-3-(prop-2-yn-1-ylamino)-
oct-2-en-1-one (4c), 1-phenyl-3-(prop-2-yn-1-ylamino)hept-
0009-3122/18/54(3)-0362©2018 Springer Science+Business Media, LLC
362

Chemistry of Heterocyclic Compounds 2018, 54(3), 362–368
Scheme 1. Synthesis of 3-[(1-glycosyl-1H-1,2,3-triazol-4-yl)methylamino]ket-2-en-1-ones 9a–d, 10b–f
Table 1. Substituents and yields of compounds 3a–f, 4a–f, 7a–d, 8b–f, 9a–d, and 10b–f
Com-
pound
Com-
pound
Com-
pound
Com-
pound
Com-
pound
Com-
pound
R
Yield, %
Yield, %
Yield, %
Yield, %
Yield, %
Yield, %
Ph
78
78
75
72
79
74
96
93
95
93
80
50
80
82
84
86
–
–
–
84
83
81
79
–
–
–
3a
3b
3c
3d
3e
3f
4a
4b
4c
4d
4e
4f
7a
7b
7c
7d
–
9a
9b
9c
9d
–
Me(CH2)9
82
87
83
85
65
80
79
85
82
83
8b
8c
8d
8e
8f
10b
10c
10d
10e
10f
Me(CH2)4
Me(CH2)3
3-MeC6H4OCH2
4-MeC6H4
–
–
–
–
2-en-1-one (4d), 4-(3-methylphenoxy)-1-phenyl-3-(prop-
2-yn-1-ylamino)but-2-en-1-one (4e), 3-(4-methylphenyl)-
1-Azido-2,3,5-tri-O-benzoyl-β-D-ribofuranose (5) was
synthesized by the azidation of commercially available
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose with azido-
trimethylsilane in the presence of tin(IV) chloride
following literature procedure in 88% yield.12 The copper-
catalyzed cycloaddition of 1-azido-2,3,5-tri-O-benzoyl-
β-D-ribofuranose (5) to propargylamine derivatives 4a–d in
THF and H2O, followed by debenzoylation of the resulting
3-{[1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-1H-1,2,3-
triazol-4-yl]methylamino}ket-2-en-1-ones 7a–d with
NaOMe in MeOH led to the formation of 1,3-diphenyl-
3-[(1-β-D-ribofuranosyl-1H-1,2,3-triazol-4-yl)methylamino]-
prop-2-en-1-one (9a), 1-phenyl-3-[(1-β-D-ribofuranosyl-
1H-1,2,3-triazol-4-yl)methylamino]tridec-2-en-1-one (9b),
1-phenyl-3-[(1-β-D-ribofuranosyl-1H-1,2,3-triazol-4-yl)methyl-
amino]oct-2-en-1-one (9c), and 1-phenyl-3-[(1-β-D-ribo-
furanosyl-1H-1,2,3-triazol-4-yl)methylamino]hept-2-en-1-one
(9d) in 67–68% overall yields.
1-phenyl-3-(prop-2-yn-1-ylamino)prop-2-en-1-one
(4f)
were synthesized by Sonogashira reaction between benzoyl
chloride (1) and acetylenes 2a–f in THF, followed by
Michael-type addition of propargylamine to the resulting
disubstituted acetylenes 3a–f in MeOH in acceptable
overall yields (Scheme 1). We would like to mention that
when Sonogashira reaction was carried out with benzoyl
chloride (1) and phenylacetylene (2a) in the presence of
PdCl2(PPh3)2, NaHCO3, CuI, and MeOH at room tempe-
rature, we obtained product 3a with only 50% yield. How-
ever, product 3a was obtained in 78% yield when the same
reaction was performed in the presence of PdCl2(PPh3)2
(0.01 equiv), Et3N (1 equiv), CuI (0.03 equiv), and THF at
room temperature. In the present work, all the reactions
were carried out under modified reaction conditions to
afford alkyne precursors 4a–f in 50–96% yields (Table 1).
363

Chemistry of Heterocyclic Compounds 2018, 54(3), 362–368
1-Azido-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose (6)
4c,14 4d,18 4f,14 5,12 and 613 were in agreement with the
was synthesized by acetylation of glucose with acetic
anhydride in DMF in the presence of catalytic amount of
4-dimethylaminopyridine (DMAP), followed by selective
anomeric azidation of the resulting β-D-glucopyranose
pentacetate with azidotrimethylsilane in the presence of
tin(IV) chloride following literature procedure in 80%
overall yield.13 Further, copper-catalyzed cycloaddition of
1-azido-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose (6) to pro-
pargylamine derivatives 4b–f in THF and H2O, followed
by deacetylation of the resulting 3-{[1-(2',3',4',6'-tetra-
O-acetyl-β-D-glucopyranosyl)-1H-1,2,3-triazol-4-yl]methyl-
amino}ket-2-en-1-one 8b–f with NaOMe in MeOH led to
the formation of 3-[(1-β-D-glucopyranosyl-1H-1,2,3-triazol-
literature reported.
1-Phenyltridec-2-yn-1-one (3b). Benzoyl chloride (1)
(281 mg, 2 mmol), PdCl2(PPh3)2 (14 mg, 0.02 mmol), and
Et3N (202 mg, 2 mmol) were stirred in anhydrous THF for
10 min under nitrogen atmosphere at room temperature.
Then CuI (11 mg, 0.06 mmol) was added into the reaction
mixture, which was stirred for 10 min, followed by
addition of decylacetylene 2b (266 mg, 1.6 mmol). The
stirring was continued at room temperature for 6–8 h. After
completion of the reaction, solvent was removed under
reduced pressure and reaction mixture was extracted with
EtOAc (3×20 ml). The combined EtOAc solution was
washed with aqueous 0.1 N HCl solution followed by
saturated NH4Cl solution. Finally, EtOAc layer was dried
over anhydrous Na2SO4 and concentrated to dryness under
reduced pressure. Resulting crude was purified by column
chromatography, eluent petroleum ether – EtOAc, 10:1.
Yield 421 mg (78%), light-yellow sticky solid. IR spectrum,
ν, cm–1: 700, 750, 910, 1263, 1314, 1454, 1642, 2202,
4-yl)methylamino]-1-phenyltridec-2-en-1-one
(10b),
3-[(1-β-D-glucopyranosyl-1H-1,2,3-triazol-4-yl)methylamino]-
1-phenyloct-2-en-1-one (10c), 3-[(1-β-D-glucopyranosyl-
1H-1,2,3-triazol-4-yl)methylamino]-1-phenylhept-2-en-1-one
(10d),
3-[(1-β-D-glucopyranosyl-1H-1,2,3-triazol-4-yl)-
methylamino]-4-phenoxy-1-phenylbut-2-en-1-one (10e),
and 3-[(1-β-D-glucopyranosyl-1H-1,2,3-triazol-4-yl)methyl-
amino]-3-(4-methylphenyl)-1-phenylprop-2-en-1-one (10f)
in 54–71% overall yields.
1
2925. H NMR spectrum, δ, ppm (J, Hz): 0.86 (3H, t,
J = 6.9, CH2(CH2)8CH3); 1.25 (12H, s, (CH2)3(CH2)6CH3);
1.41–1.50 (2H, m, (CH2)2CH2(CH2)6CH3); 1.62–1.70 (2H, m,
CH2CH2(CH2)7CH3); 2.48 (2H, t, J = 7.2, CH2(CH2)8CH3);
7.44–7.48 (2H, m, H Ph); 7.56–7.60 (1H, m, H Ph); 8.11–
8.14 (2H, m, H Ph). 13C NMR spectrum, δ, ppm: 14.2;
19.3; 22.8; 27.9; 29.1; 29.4; 29.6; 32.0; 79.8; 97.0; 128.6;
128.7; 129.6; 134.0; 137.0; 178.4. Found, m/z: 271.2061
[M+H]+. C19H27O. Calculated, m/z: 271.2062.
The structure of all synthesized compounds 3a–f, 4a–f,
5, 6, 7a–d, 8b–f, 9a–d, and 10b–f was unambiguously
established on the basis of their spectral (1H and 13C NMR,
IR, and HRMS) analysis.
Four novel 1-β-D-ribofuranosyl-1H-1,2,3-triazol-4-yl)-
methylamino]ket-2-en-1-ones and five 1-β-D-gluco-
pyranosyl-1H-1,2,3-triazol-4-yl)methylamino]ket-2-en-1-ones
have been synthesized in moderate to good yields by
copper-catalyzed azide-alkyne cycloaddition reaction
between 1-phenyl-3-(prop-2-yn-1-ylamino)ket-2-en-1-ones
and 1-azido-2,3,5-tri-O-benzoyl-β-D-ribofuranose or 2,3,4,6-
tetra-O-acetyl-1-azido-β-D-glucopyranose followed by
deprotection of the resulting penultimate compounds.
Synthesis of compounds 4b,e (General method). The
corresponding benzoylacetylene 3b,e (2 mmol) was heated
with propargylamine (132 mg, 2.4 mmol) in MeOH at 60°C
for 3–5 h. After completion of the reaction, MeOH was
removed under reduced pressure. The crude product thus
obtained was extracted with EtOAc (3×40 ml), combined
EtOAc solution was washed with saturated NaCl solution
and dried over anhydrous Na2SO4. After removal of the
solvent under reduced pressure, crude product was purified
by column chromatography, eluent petroleum ether –
EtOAc, 10:1.
Experimental
IR spectra were recorded on a PerkinElmer model 2000
1
FT-IR spectrometer in KBr pellets. H and 13C NMR
spectra were recorded on a Jeol alpha-400 spectrometer
(400 and 100 MHz, respectively) in CDCl3 (compounds 3b,
4b,e, 7a–d, 8b–f) and in MeOH-d4 (compounds 9a–d, 10b–f)
with TMS as internal standard. The NH group signals in
1H NMR spectra recorded in CDCl3 were verified by D2O
exchange method. HRMS analysis was carried out using an
Agilent G6530AA LC Q-TOF mass spectrometer. Melting
points were determined on a Buchi M-560 instrument and
are uncorrected. The optical rotation was measured on a
Rudolph autopol II automatic polarimeter using 589 nm
wavelength light. TLC was performed on precoated Merck
silica gel 60F254 plates, visualization under UV light and
with 5% H2SO4 solution in EtOH. Silica gel (100–
200 mesh) was used for column chromatography.
1-Phenyl-3-(prop-2-yn-1-ylamino)tridec-2-en-1-one (4b).
Yield 605 mg (93%), red solid, mp 48–50°C. IR spectrum,
1
ν, cm–1: 667, 748, 1215, 1587, 2926, 3016, 3306. H NMR
spectrum, δ, ppm (J, Hz): 0.87 (3H, t, J = 6.1, CH3);
1.26 (12H, s, CH2CH2CH2(CH2)6CH3); 1.37–1.45
(2H, m, CH2CH2CH2(CH2)6CH3); 1.59–1.68 (2H, m,
CH2CH2(CH2)7CH3); 2.31 (1H, t, J = 2.5, ≡CH); 2.34–2.42
(2H, m, CH2(CH2)8CH3); 4.08 (2H, dd, J = 6.1, J = 2.5,
CH2NH); 5.74 (1H, s, =CH); 7.36–7.43 (3H, m, H Ph);
7.85 (2H, d, J = 7.9, H Ph); 11.47 (1H, s, NH). 13C NMR
spectrum, δ, ppm: 14.2; 22.8; 28.2; 29.4; 29.6; 29.7; 32.0;
32.2; 32.3; 72.5; 79.2; 92.2; 127.1; 128.3; 130.7; 140.4;
168.3; 188.8. Found, m/z: 326.2487 [M+H]+. C22H32NO.
Calculated, m/z: 326.2484.
All solvents, reagents, and adsorbents used were
purchased from Sigma-Aldrich Chemicals (New Delhi,
India) and SD Fine Chemicals (New Delhi, India),
solvents were distilled before use. The physical and
spectral data of known compounds 3a,14 3c–f,14–17 4a,15
4-(3-Methylphenoxy)-1-phenyl-3-(prop-2-yn-1-ylamino)-
but-2-en-1-one (4e). Yield 488 mg (80%), white sticky
solid. IR spectrum, ν, cm–1: 692, 772, 1160, 1258, 1604,
2920, 3050, 3287. 1H NMR spectrum, δ, ppm (J, Hz): 2.34
(4H, s, CH3, ≡CH); 4.19 (2H, dd, J = 6.1, J = 2.3, CH2NH);
364

Chemistry of Heterocyclic Compounds 2018, 54(3), 362–368
4.80 (2H, s, OCH2); 6.04 (1H, s, =CH); 6.76–6.89 (3H, m,
1-Phenyl-3-{[1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-
1H-1,2,3-triazol-4-yl]methylamino}oct-2-en-1-one (7c).
H Ar); 7.20 (1H, t, J = 7.7, H Ar); 7.36–7.49 (3H, m,
H Ar); 7.86 (2H, d, J = 7.1, H Ar); 11.06 (1H, br. s, NH).
13C NMR spectrum, δ, ppm: 21.6; 32.7; 66.8; 72.8; 79.2;
92.6; 111.7; 115.8; 122.9; 127.3; 128.4; 129.5; 131.3;
139.8; 140.0; 157.9; 160.2; 190.2. Found, m/z: 306.1489
[M+H]+. C20H20NO2. Calculated, m/z: 306.1494.
32
Yield 1.25 g (84%), sticky brown solid, [α]D –29.25
(c 0.1, MeOH). IR spectrum, ν, cm–1: 668, 743, 1266, 1728,
1
3020. H NMR spectrum, δ, ppm (J, Hz): 0.90 (3H, t,
J = 6.8, CH3); 1.31–1.39 (4H, m, CH2CH2(CH2)2CH3);
1.57–1.64 (2H, m, CH2CH2(CH2)2CH3); 2.37 (2H, t,
J = 7.8, CH2(CH2)3CH3); 4.55–4.66 (3H, m, CH2NH,
5'-CH2A); 4.78 (1H, dd, J = 12.2, J = 3.3, 5'-CH2B); 4.86–
4.89 (1H, m, 3'-CH); 5.73 (1H, s, =CH); 6.13–6.18 (1H, m,
2'-CH); 6.26–6.29 (1H, m, 4'-CH); 6.38 (1H, d, J = 3.1,
1'-CH); 7.34–7.44 (10H, m, H Ph); 7.50–7.59 (3H, m,
H Ph); 7.79 (1H, s, H triazole); 7.82–7.85 (1H, m, H Ph);
7.92–8.09 (6H, m, H Ph); 11.76 (1H, t, J = 5.8, NH).
13C NMR spectrum, δ, ppm: 14.0; 22.5; 28.0; 31.7; 32.5;
38.7; 63.9; 71.8; 75.2; 81.3; 90.4; 92.1; 121.5; 127.1; 128.3;
128.6; 128.7; 129.4; 129.9; 130.0; 130.7; 133.4; 133.8; 133.9;
140.4; 146.0; 165.1; 165.2; 166.2; 168.8; 188.6. Found, m/z:
743.3081 [M+H]+. C43H43N4O8. Calculated, m/z: 743.3081.
1-Phenyl-3-{[1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-
1H-1,2,3-triazol-4-yl]methylamino}hept-2-en-1-one (7d).
Synthesis of compounds 7a–d, 8b–f (General method).11
1-Azido-2,3,5-tri-O-benzoyl-β-D-ribofuranose (5) or 2,3,4,6-
tetra-O-acetyl-1-azido-β-D-glucopyranose (6) (2 mmol) and
the corresponding propargylamine 4a–f (1.6 mmol) were
dissolved in a minimum amount of THF. CuSO4·5H2O
(79.17 mg, 0.32 mmol) and sodium ascorbate (122.30 mg,
0.64 mmol) were dissolved separately in minimum amount
of water and added to above solution. The reaction mixture
was stirred at room temperature under nitrogen atmosphere.
After completion of the reaction, solvent was removed
under reduced pressure and reaction mixture was extracted
with EtOAc (3×120 ml). Combined EtOAc layer was dried
over anhydrous Na2SO4 and concentrated under reduced
pressure. The crude products thus obtained were purified
by column chromatography, eluent petroleum ether –
EtOAc, 10:3.
32
Yield 1.25 g (86%), sticky brown solid, [α]D –143.80
(c 0.1, MeOH). IR spectrum, ν, cm–1: 667, 747, 1215, 1728,
2980, 3050. 1H NMR spectrum, δ, ppm (J, Hz): 0.97 (3H, t,
J = 7.3, CH3); 1.37–1.46 (2H, m, CH2CH2CH2CH3); 1.55–
1.63 (2H, m, CH2CH2CH2CH3); 2.38 (2H, t, J = 7.8,
CH2(CH2)2CH3); 4.55–4.69 (3H, m, CH2NH, 5'-CH2A);
4.78 (1H, dd, J = 12.3, J = 3.3, 5'-CH2B); 4.87 (1H, dd,
J = 9.2, J = 4.8, 3'-CH); 5.73 (1H, s, =CH); 6.12–6.19 (1H,
m, 2'-CH); 6.25–6.30 (1H, m, 4'-CH); 6.38 (1H, d, J = 3.1,
1'-CH); 7.32–7.46 (10H, m, H Ph); 7.49–7.61 (3H, m,
H Ph); 7.78 (1H, s, H triazole); 7.83 (1H, d, J = 7.0, H Ph);
7.85–8.09 (6H, m, H Ph); 11.75 (1H, t, J = 5.7, NH).
13C NMR spectrum, δ, ppm: 13.8; 22.7; 30.4; 32.2; 38.7;
63.9; 71.8; 75.2; 81.3; 90.3; 92.1; 121.5; 127.1; 128.3;
128.6; 128.7; 129.4; 129.9; 130.0; 130.7; 133.4; 133.7;
133.9; 140.4; 146.0; 165.1; 165.2; 166.2; 168.8; 188.6.
Found, m/z: 729.2912 [M+H]+.C42H41N4O8. Calculated, m/z:
729.2924.
1,3-Diphenyl-3-{[1-(2',3',5'-tri-O-benzoyl-β-D-ribo-
furanosyl)-1H-1,2,3-triazol-4-yl]methylamino}prop-2-en-
1-one (7a). Yield 1.20 g (80%), white solid, mp 102–104°C,
32
[α]D +0.41 (c 0.1, MeOH). IR spectrum, ν, cm–1: 710,
1
752, 1575, 1735, 2924, 3434. H NMR spectrum, δ, ppm
(J, Hz): 4.41–4.54 (2H, m, CH2NH); 4.59 (1H, dd,
J = 12.2, J = 4.8, 5'-CH2A); 4.78 (1H, dd, J = 12.2, J = 3.6,
5'-CH2B); 4.86 (1H, q, J = 4.6, 3'-CH); 5.83 (1H, s, =CH);
6.13 (1H, t, J = 5.5, 2'-CH); 6.23–6.27 (1H, m, 4'-CH);
6.38 (1H, d, J = 3.3, 1'-CH); 7.33–7.59 (17H, m, H Ph);
7.69 (1H, s, H triazole); 7.85–7.90 (2H, m, H Ph); 7.92–
7.96 (2H, m, H Ph); 7.96–8.02 (4H, m, H Ph); 11.55 (1H, t,
J = 6.0, NH). 13C NMR spectrum, δ, ppm: 40.0; 63.8; 71.8;
75.2; 81.3; 90.3; 94.6; 121.3; 127.2; 127.9; 128.3; 128.6;
128.7; 128.8; 129.8; 129.9; 130.0; 131.0; 133.4; 133.8;
133.9; 135.1; 140.1; 146.1; 165.1; 165.2; 166.2; 166.5;
189.1. Found, m/z: 749.2625 [M+H]+. C44H37N4O8.
Calculated, m/z: 749.2611.
1-Phenyl-3-{[1-(2',3',4',6'-tetra-O-acetyl-β-D-gluco-
pyranosyl)-1H-1,2,3-triazol-4-yl]methylamino}tridec-2-en-
1-one (8b). Yield 1.15 g (82%), cream-colored solid,
mp 140–141°C, [α]D32 –40.86 (c 0.1, MeOH). IR spectrum,
ν, cm–1: 699, 750, 1041, 1217, 1516, 1753, 2980, 3699,
1-Phenyl-3-{[1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-
1H-1,2,3-triazol-4-yl]methylamino}tridec-2-en-1-one (7b).
32
Yield 1.33 g (82%), sticky brown solid, [α]D –44.88
(c 0.1, MeOH). IR spectrum, ν, cm–1: 709, 803, 1093, 1120,
1267, 1601, 1729, 2358, 2925, 3063, 3443. 1H NMR
spectrum, δ, ppm (J, Hz): 0.85 (3H, s, CH3); 1.24 (14H, s,
CH2CH2(CH2)7CH3); 1.59 (2H, s, CH2CH2(CH2)7CH3);
2.33–2.39 (2H, m, CH2(CH2)8CH3); 4.54–4.67 (3H, m,
CH2NH, 5'-CH2A); 4.76 (1H, d, J = 12.0, 5'-CH2B); 4.85
(1H, s, 3'-CH); 5.71 (1H, s, =CH); 6.13 (1H, s, 2'-CH); 6.26
(1H, s, 4'-CH); 6.36 (1H, s, 1'-CH); 7.31–7.45 (10H, m,
H Ph); 7.47–7.59 (3H, m, H Ph); 7.75–7.86 (3H, m, H Ph);
7.89–8.05 (5H, m, H Ph); 11.73 (1H, s, NH). 13C NMR
spectrum, δ, ppm: 14.2; 22.7; 28.3; 29.4; 29.6; 32.0; 32.5; 38.7;
63.8; 71.8; 75.2; 81.3; 90.4; 92.1; 121.5; 127.0; 128.2; 128.6;
128.7; 129.4; 129.9; 130.0; 130.7; 133.4; 133.7; 133.9;
140.4; 146.0; 165.1; 165.2; 168.8; 188.6. Found, m/z:
813.3840 [M+H]+. C48H53N4O8. Calculated, m/z: 813.3863.
3743. H NMR spectrum, δ, ppm (J, Hz): 0.86 (3H, t,
1
J = 6.6, CH3); 1.27 (12H, s, (CH2CH2CH2(CH2)6CH3); 1.36–
1.41 (2H, m, CH2CH2CH2(CH2)6CH3) 1.59–1.65 (2H, m,
CH2CH2(CH2)7CH3); 1.87 (3H, s, OCOCH3); 2.01 (3H, s,
OCOCH3); 2.06 (6H, d, J = 7.6, 2OCOCH3); 2.34–2.41
(2H, m, CH2(CH2)8CH3); 3.95–4.01 (1H, m, 5'-CH); 4.13
(1H, dd, J = 12.4, J = 1.5, 6'-CH2A); 4.28 (1H, dd, J = 12.6,
J = 4.9, 6'-CH2B); 4.66 (2H, dd, J = 6.1, J = 2.3, CH2NH);
5.22 (1H, t, J = 9.7, 4'-CH); 5.36–5.45 (2H, m, 2',3'-CH);
5.76 (1H, s, =CH); 5.83 (1H, d, J = 8.9, 1'-CH); 7.35–7.44
(3H, m, H Ph); 7.77 (1H, s, H triazole); 7.85 (2H, dd,
J = 7.6, J =1.4, H Ph); 11.74 (1H, t, J = 5.9, NH). 13C NMR
spectrum, δ, ppm: 14.2; 20.3; 20.6; 20.8; 22.8; 28.3; 29.4;
29.6; 32.0; 32.5; 38.7; 61.6; 67.7; 70.4; 72.7; 75.3; 85.9;
92.1; 120.4; 127.0; 128.3; 130.7; 140.4; 146.2; 168.8;
365

Chemistry of Heterocyclic Compounds 2018, 54(3), 362–368
168.9; 169.4; 170.0; 170.7; 188.7. Found, m/z: 699.3605
67.7; 70.5; 72.6; 75.2; 85.9; 92.3; 111.8; 115.8; 120.5;
122.8; 127.2; 128.4; 129.5; 131.2; 139.8; 139.9; 146.0;
157.9; 160.7; 169.0; 169.4; 170.0; 170.7; 190.0. Found, m/z:
679.2629 [M+H]+. C34H39N4O11. Calculated, m/z: 679.2615.
3-(4-Methylphenyl)-1-phenyl-3-{[1-(2',3',4',6'-tetra-
O-acetyl-β-D-glucopyranosyl)-1H-1,2,3-triazol-4-yl]me-
thylamino}prop-2-en-1-one (8f). Yield 842 mg (65%),
[M+H]+. C36H51N4O10. Calculated, m/z: 699.3605.
1-Phenyl-3-{[1-(2',3',4',6'-tetra-O-acetyl-β-D-gluco-
pyranosyl)-1H-1,2,3-triazol-4-yl]methylamino}oct-2-en-
1-one (8c). Yield 1.09 g (87%), white solid, mp 142–143°C,
32
[α]D –43.65 (c 0.1, MeOH). IR spectrum, ν, cm–1: 597,
735, 1044, 1238, 1577, 1746, 2929, 3088. 1H NMR
spectrum, δ, ppm (J, Hz): 0.88 (3H, t, J = 6.8, CH3); 1.30–
1.38 (4H, m, CH2CH2(CH2)2CH3); 1.57–1.64 (2H, m,
CH2CH2(CH2)2CH3); 1.85 (3H, s, OCOCH3); 1.99 (3H, s,
OCOCH3); 2.03 (3H, s, OCOCH3); 2.05 (3H, s, OCOCH3);
2.34–2.39 (2H, m, CH2(CH2)3CH3); 3.94–3.98 (1H, m,
6'-CH2A); 4.07–4.14 (1H, m, 6'-CH2B); 4.26 (1H, dd,
J = 12.6, J = 4.9, 5'-CH); 4.65 (2H, dd, J = 6.0, J = 2.4,
CH2NH); 5.20 (1H, t, J = 9.5, 4'-CH); 5.34–5.45 (2H, m,
2',3'-CH); 5.74 (1H, s, =CH); 5.82 (1H, d, J = 8.8, 1'-CH);
7.33–7.42 (3H, m, H Ph); 7.75 (1H, s, H triazole); 7.83
(2H, d, J = 7.7, H Ph); 11.73 (1H, t, J = 5.7, NH). 13C NMR
spectrum, δ, ppm: 14.0; 20.3; 20.6; 20.8; 22.5; 27.9; 31.7;
32.4; 38.7; 61.5; 67.7; 70.4; 72.7; 75.2; 85.9; 92.1; 120.3;
127.0; 128.3; 130.7; 140.3; 146.2; 168.8; 168.9; 169.4;
170.7; 188.7. Found, m/z: 629.2810 [M+H]+. C31H41N4O10.
Calculated, m/z: 629.2823.
32
white solid, mp 156–158°C, [α]D –70.35 (c 0.1, MeOH).
IR spectrum, ν, cm–1: 753, 1039, 1218, 1749, 2924, 3020,
1
3500. H NMR spectrum, δ, ppm (J, Hz): 1.87 (3H, s,
OCOCH3); 2.01 (3H, s, OCOCH3); 2.05 (3H, s, OCOCH3 );
2.07 (3H, s, OCOCH3); 2.39 (3H, s, CH3); 3.94–4.02 (1H, m,
6'-CH2A); 4.13 (1H, dd, J = 12.7, J = 1.5, 5'-CH); 4.29 (1H,
dd, J = 12.6, J = 4.9, 6'-CH2B); 4.50–4.59 (2H, m, CH2NH);
5.23 (1H, t, J = 9.5, 4'-CH); 5.36–5.49 (2H, m, 2',3'-CH);
5.84 (2H, d, J = 8.3, =CH, 1'-CH); 7.24 (2H, d, J = 7.5,
H Ar); 7.32–7.45 (5H, m, H Ph); 7.75 (1H, s, H triazole); 7.87
(2H, d, J = 1.4, H Ar); 11.57 (1H, t, J = 6.1, NH). 13C NMR
spectrum, δ, ppm: 20.3; 20.6; 20.8; 21.5; 40.6; 61.6; 67.7;
70.3; 72.7; 75.2; 85.8; 94.5; 120.2; 127.2; 127.9; 128.3;
129.5; 131.0; 132.2; 140.1; 146.6; 166.9; 169.0; 169.4;
170.1; 170.7; 189.1. Found, m/z: 649.2504 [M+H]+.
C33H37N4O10. Calculated, m/z: 649.2510.
1-Phenyl-3-{[1-(2',3',4',6'-tetra-O-acetyl-β-D-gluco-
pyranosyl)-1H-1,2,3-triazol-4-yl]methylamino}hept-2-en-
1-one (8d). Yield 1.02 g (83%), cream-colored solid, mp 164–
166°C, [α]D32 –61.02 (c 0.1, MeOH). IR spectrum, ν, cm–1:
Synthesis of compounds 9a–d, 10b–f (General method).
NaOMe (3–4 equiv) was added to a solution of protected
compounds 7a–d, 8b–f (0.1 mmol) in dry MeOH (4 ml),
and solution was stirred at room temperature till comple-
tion of the reaction. After that, the reaction mixture was
neutralized by the addition of Amberlite resin (H+ form) to
the solution, followed by filtration. The filtrate was
concentrated, washed with hexane, dried in air.
1
696, 755, 1041, 1225, 1593, 1751, 2925, 3020. H NMR
spectrum, δ, ppm (J, Hz): 0.94 (3H, t, J = 7.3, CH3); 1.38–
1.45 (2H, m, CH2CH2CH2CH3); 1.56–1.64 (2H, m,
CH2CH2CH2CH3); 1.87 (3H, s, OCOCH3); 2.01 (3H, s,
OCOCH3); 2.05 (3H, s, OCOCH3); 2.07 (3H, s, OCOCH3);
2.36–2.41 (2H, m, CH2(CH2)2CH3); 3.98 (1H, dd, J = 9.3,
J = 4.2, 6'-CH2A); 4.13 (1H, d, J = 12.3, 6'-CH2B); 4.28
(1H, dd, J = 12.6, J = 4.9, 5'-CH); 4.67 (2H, dd, J = 6.0,
J = 2.0, CH2NH); 5.22 (1H, t, J = 9.5, 4'-CH); 5.37–5.44
(2H, m, 2',3'-CH); 5.76 (1H, s, =CH); 5.83 (1H, d, J = 8.6,
1'-CH); 7.35–7.44 (3H, m, H Ph); 7.76 (1H, s, H triazole);
7.85 (2H, d, J = 6.6, H Ph); 11.75 (1H, t, J = 5.7, NH).
13C NMR spectrum, δ, ppm: 13.9; 20.3; 20.6; 20.8; 22.7;
30.3; 32.2; 38.7; 61.5; 67.7; 70.4; 72.7; 75.3; 85.9; 92.2;
120.4; 127.0; 128.3; 130.8; 140.4; 146.2; 168.8; 168.9;
169.4; 170.1; 170.7; 188.7. Found, m/z: 615.2659 [M+H]+.
C30H39N4O10. Calculated, m/z: 615.2666.
1,3-Diphenyl-3-[(1-β-D-ribofuranosyl-1H-1,2,3-triazol-
4-yl)methylamino]prop-2-en-1-one (9a). Yield 36 mg
25
(84%), sticky brown solid, [α]D –44.99 (c 0.02, MeOH).
IR spectrum, ν, cm–1: 696, 752, 1045, 1328, 1566, 1595,
1
2926, 3331. H NMR spectrum, δ, ppm (J, Hz): 3.31 (1H,
s, =CH); 3.69 (1H, dd, J = 12.1, J = 3.9, 5'-CH2A); 3.81
(1H, dd, J = 12.1, J = 3.0, 5'-CH2B); 4.13 (1H, d, J = 3.4,
4'-CH); 4.31 (1H, t, J = 4.7, 3'-CH); 4.47–4.50 (1H, m,
2'-CH); 4.53 (2H, s, CH2NH); 6.03 (1H, d, J = 3.6, 1'-CH);
7.42 (3H, dd, J = 13.9, J = 7.3, H Ph); 7.51 (5H, s, H Ph);
7.83 (2H, d, J = 7.1, H Ph); 8.12 (1H, s, H triazole).
13C NMR spectrum, δ, ppm: 30.7; 40.9; 62.8; 71.9; 77.1;
87.1; 87.2; 94.4; 94.5; 122.8; 128.1; 129.0; 129.5; 129.9;
131.1; 132.2; 136.3; 141.3; 168.5; 190.6. Found, m/z:
437.1801 [M+H]+. C23H25N4O5. Calculated, m/z: 437.1825.
1-Phenyl-3-[(1-β-D-ribofuranosyl-1H-1,2,3-triazol-4-yl)-
methylamino]tridec-2-en-1-one (9b). Yield 41 mg (83%),
4-(3-Methylphenoxy)-1-phenyl-3-{[1-(2',3',4',6'-tetra-
O-acetyl-β-D-glucopyranosyl)-1H-1,2,3-triazol-4-yl]methyl-
amino}but-2-en-1-one (8e). Yield 1.15 g (85%), cream-
32
colored solid, mp 179–181°C, [α]D –18.72 (c 0.1,
25
MeOH). IR spectrum, ν, cm–1: 692, 752, 1037, 1215, 1601,
1747, 2960, 3050, 3400. 1H NMR spectrum, δ, ppm (J, Hz):
1.85 (3H, s, OCOCH3); 1.99–2.08 (9H, m, 3OCOCH3); 2.32
(3H, s, CH3); 3.95–4.01 (1H, m, 6'-CH2A); 4.12 (1H, d,
J = 12.5, 5'-CH); 4.24–4.32 (1H, m, 6'-CH2B); 4.70–4.83 (4H,
m, OCH2, CH2NH); 5.19–5.27 (1H, m, 4'-CH); 5.40 (2H, d,
J = 6.6, 2',3'-CH); 5.83–5.87 (1H, m, 1'-CH); 6.05 (1H, s,
=CH); 6.75–6.82 (3H, m, H Ar); 7.15–7.19 (1H, m, H Ar);
7.37–7.43 (3H, m, H Ar); 7.77 (1H, s, H triazole); 7.85
(2H, d, J = 6.9, H Ar); 11.32 (1H, br. s, NH). 13C NMR
spectrum, δ, ppm: 20.2; 20.6; 20.8; 21.6; 39.0; 61.6; 66.9;
sticky yellow solid, [α]D –32.32 (c 0.02, MeOH).
IR spectrum, ν, cm–1: 769, 1045, 1099, 1597, 2854, 2924,
1
3400. H NMR spectrum, δ, ppm (J, Hz): 0.89 (3H, t,
J = 6.8, CH3); 1.29 (12H, s, CH2CH2CH2(CH2)6CH3); 1.41–
1.49 (2H, m, CH2CH2CH2(CH2)6CH3); 1.61–1.71 (2H, m,
CH2CH2(CH2)7CH3); 2.51 (2H, t, J = 8.0, CH2(CH2)8CH3);
3.35 (1H, s, =CH); 3.70 (1H, dd, J = 12.2, J = 4.2,
5'-CH2A); 3.82 (1H, dd, J = 12.2, J = 3.1, 5'-CH2B); 4.13–
4.16 (1H, m, 4'-CH); 4.33 (1H, t, J = 4.9, 3'-CH); 4.52 (1H,
t, J = 4.4, 2'-CH); 4.71 (2H, s, CH2NH); 6.06 (1H, d,
J = 3.9, 1'-CH); 7.37–7.46 (3H, m, H Ph); 7.79 (2H, d,
366

Chemistry of Heterocyclic Compounds 2018, 54(3), 362–368
J = 6.6, H Ph); 8.28 (1H, s, H triazole). 13C NMR spectrum,
MeOH). IR spectrum, ν, cm–1: 694, 746, 1047, 1583, 2927,
1
δ, ppm: 14.5; 23.7; 29.3; 30.4; 30.5; 30.7; 33.0; 33.3; 39.1;
62.8; 71.9; 77.1; 87.2; 94.5; 122.9; 127.9; 129.3; 131.8;
141.6; 168.8; 171.2; 189.7. Found, m/z: 501.3056 [M+H]+.
C27H41N4O5. Calculated, m/z: 501.3077.
3309. H NMR spectrum, δ, ppm (J, Hz): 0.95 (3H, t,
J = 7.0, CH3); 1.37–1.49 (4H, m, CH2CH2(CH2)2CH3); 1.64–
1.74 (2H, m, CH2CH2(CH2)2CH3); 2.53 (2H, t, J = 7.9,
CH2(CH2)3CH3); 3.46–3.62 (4H, m, =CH, 4'-CH, 6'-CH2);
3.71 (1H, dd, J = 12.2, J = 5.4, 5'-CH); 3.85–3.94 (2H, m,
2',3'-CH); 4.74 (2H, s, CH2NH); 5.62 (1H, d, J = 9.2,
1'-CH); 7.37–7.47 (3H, m, H Ph); 7.79 (2H, d, J = 6.7,
H Ph); 8.23 (1H, s, H triazole). 13C NMR spectrum, δ, ppm:
14.0; 22.5; 27.5; 31.6; 32.4; 38.4; 39.1; 61.0; 69.1; 72.8;
79.1; 88.0; 91.6; 122.7; 127.0; 127.1; 128.3; 128.4; 140.0;
144.0; 169.5; 171.6; 187.6. Found, m/z: 461.2456 [M+H]+.
C23H33N4O6. Calculated, m/z: 461.2400.
1-Phenyl-3-[(1-β-D-ribofuranosyl-1H-1,2,3-triazol-4-yl)-
methylamino]oct-2-en-1-one (9c). Yield 35 mg (81%),
sticky yellow-orange solid, [α]D25 –172.79 (c 0.02, MeOH).
IR spectrum, ν, cm–1: 694, 746, 1224, 1369, 1741, 2864,
1
3022. H NMR spectrum, δ, ppm (J, Hz): 0.95 (3H, t,
J = 7.0, CH3); 1.37–1.49 (4H, m, CH2CH2(CH2)2CH3); 1.63–
1.73 (2H, m, CH2CH2(CH2)2CH3); 2.53 (2H, t, J = 7.9,
CH2(CH2)3CH3); 3.35 (1H, s, =CH); 3.70 (1H, dd, J = 12.2,
J = 4.2, 5'-CH2A); 3.82 (1H, dd, J = 12.1, J = 3.2, 5'-CH2B);
4.12–4.15 (1H, m, 3'-CH); 4.32 (1H, t, J = 5.0, 4'-CH);
4.51 (1H, t, J = 4.5, 2'-CH); 4.73 (2H, s, CH2NH); 6.06
(1H, d, J = 3.9, 1'-CH); 7.35–7.48 (3H, m, H Ph); 7.77–
7.80 (2H, m, H Ph); 8.28 (1H, s, H triazole). 13C NMR
spectrum, δ, ppm: 14.3; 23.5; 29.0; 32.7; 33.3; 39.1; 62.8;
71.9; 77.1; 87.2; 87.3; 94.5; 122.9; 127.9; 129.3; 131.8;
141.7; 171.3; 189.8. Found, m/z: 431.2268 [M+H]+.
C22H31N4O5. Calculated, m/z: 431.2294.
3-[(1-β-D-Glucopyranosyl-1H-1,2,3-triazol-4-yl)methyl-
amino]-1-phenylhept-2-en-1-one (10d). Yield 38 mg
25
(85%), sticky orange solid, [α]D +8.41 (c 0.02, MeOH).
IR spectrum, ν, cm–1: 709, 752, 1068, 1095, 1577, 2927,
1
3329. H NMR spectrum, δ, ppm (J, Hz): 0.98 (3H, t,
J = 7.3, CH3); 1.44–1.52 (2H, m, CH2CH2CH2CH3); 1.61–
1.68 (2H, m, CH2CH2CH2CH3); 2.51 (2H, t, J = 7.8,
CH2(CH2)2CH3); 3.50–3.61 (4H, m, =CH, 4'-CH, 6'-CH2);
3.72 (1H, dd, J = 12.1, J = 5.0, 5'-CH); 3.92 (2H, dd,
J = 16.1, J = 6.9, 2',3'-CH); 4.72 (2H, s, CH2NH); 5.64
(1H, d, J = 9.2, 1'-CH); 7.36–7.44 (3H, m, H Ph); 7.79 (2H,
d, J = 6.6, H Ph); 8.21 (1H, s, H triazole). 13C NMR
spectrum, δ, ppm: 14.2; 23.6; 31.4; 33.0; 39.1; 62.3; 70.8;
74.0; 78.4; 81.1; 89.6; 123.4; 123.5; 127.9; 129.3; 131.8;
145.8; 171.2; 189.7. Found, m/z: 447.2219 [M+H]+.
C22H31N4O6. Calculated, m/z: 447.2244.
1-Phenyl-3-[(1-β-D-ribofuranosyl-1H-1,2,3-triazol-4-yl)-
methylamino]hept-2-en-1-one (9d). Yield 33 mg (79%),
sticky yellow-orange solid, [α]D25 –118.57 (c 0.02, MeOH).
IR spectrum, ν, cm–1: 694, 752, 1369, 1741, 2868, 3022,
1
3336. H NMR spectrum, δ, ppm (J, Hz): 0.98 (3H, t,
J = 7.2, CH3); 1.41–1.50 (2H, m, CH2CH2CH2CH3); 1.62–
1.66 (2H, m, CH2CH2CH2CH3); 2.51 (2H, t, J = 7.7,
CH2(CH2)2CH3); 3.35 (1H, s, =CH); 3.70 (1H, dd, J = 12.2,
J = 4.2, 5'-CH2A); 3.82 (1H, dd, J = 12.2, J = 3.1, 5'-CH2B);
4.14 (1H, dd, J = 7.9, J = 4.1, 3'-CH); 4.33 (1H, t, J = 4.9,
4'-CH); 4.52 (1H, t, J = 4.5, 2'-CH); 4.71 (2H, s, CH2NH);
6.06 (1H, d, J = 3.9, 1'-CH); 7.35–7.46 (3H, m, H Ph); 7.78
(2H, d, J = 8.0, H Ph); 8.28 (1H, s, H triazole). 13C NMR
spectrum, δ, ppm: 14.3; 23.5; 29.0; 32.7; 33.3; 39.1; 62.8;
71.9; 77.1; 87.2; 94.5; 122.9; 127.9; 129.3; 131.8; 141.7;
171.3; 189.8. Found, m/z: 417.1853 [M+H]+. C21H29N4O5.
Calculated, m/z: 417.2138.
3-[(1-β-D-Glucopyranosyl-1H-1,2,3-triazol-4-yl)methyl-
amino]-4-(3-methylphenoxy)-1-phenylbut-2-en-1-one (10e).
Yield 42 mg (82%), sticky yellow-brown solid,
25
[α]D +12.76 (c 0.02, MeOH). IR spectrum, ν, cm–1: 692,
1
765, 1070, 1257, 1595, 2918, 3327. H NMR spectrum,
δ, ppm (J, Hz): 2.11 (3H, s, CH3); 3.09 (2H, s, OCH2); 3.31–
3.38 (3H, m, 4'-CH, 6'-CH2); 3.50 (1H, dd, J = 11.9, J = 5.1,
5'-CH); 3.65–3.68 (3H, m, =CH, 2',3'-CH); 4.57 (2H, s,
CH2NH); 5.42 (1H, m, 1'-CH); 6.56–6.71 (3H, m, H Ar);
6.97 (1H, t, J = 7.7, H Ar); 7.21 (2H, dd, J = 15.3, J = 7.3,
H Ar); 7.56–7.64 (1H, m, H Ar); 7.99 (1H, s, H Ar), 8.05
(1H, s, H Ar); 8.31 (2H, s, H triazole). 13C NMR spectrum,
δ, ppm: 21.6; 39.3; 62.3; 67.4; 70.8; 74.0; 78.4; 81.1; 89.6;
112.8; 116.7; 123.5; 128.0; 128.4; 129.4; 130.4; 132.1;
132.3; 140.9; 141.2; 159.2; 163.5; 191.2. Found, m/z:
511.2168 [M+H]+. C26H31N4O7. Calculated, m/z: 511.2193.
3-[(1-β-D-Glucopyranosyl-1H-1,2,3-triazol-4-yl)methyl-
amino]-3-(4-methylphenyl)-1-phenylprop-2-en-1-one (10f).
3-[(1-β-D-Glucopyranosyl-1H-1,2,3-triazol-4-yl)methyl-
amino]-1-phenyltridec-2-en-1-one (10b). Yield 42 mg
25
(80%), sticky yellow solid, [α]D +11.52 (c 0.02, MeOH).
IR spectrum, ν, cm–1: 696, 738, 1055, 1095, 1585, 2856,
2922, 3329. 1H NMR spectrum, δ, ppm (J, Hz): 0.89 (3H, t,
J = 6.8, CH3); 1.30 (12H, s, CH2CH2CH2(CH2)6CH3); 1.41–
1.49 (2H, m, CH2CH2CH2(CH2)6CH3); 1.63–1.71 (2H, m,
CH2CH2(CH2)7CH3); 2.51 (2H, t, J = 7.8 , CH2(CH2)8CH3);
3.48–3.64 (4H, m, =CH, 4'-CH, 6'-CH2); 3.72 (1H, dd,
J =12.2, J = 5.0, 5'-CH); 3.84–3.97 (2H, m, 2',3'-CH); 4.72
(2H, s, CH2NH); 5.63 (1H, d, J = 9.2, 1'-CH); 7.34–7.46
(3H, m, H Ph); 7.79 (2H, d, J = 8.1, H Ph); 8.21 (1H, s,
H triazole). 13C NMR spectrum, δ, ppm: 14.5; 23.7; 29.2;
30.4; 30.6; 33.0; 33.2; 39.1; 62.2; 70.7; 74.0; 78.3; 81.0;
89.5; 123.5; 127.9; 129.4; 131.9; 134.3; 141.5; 145.8;
171.3; 189.7. Found, m/z: 531.3159 [M+H]+. C28H43N4O6.
Calculated, m/z: 531.3183.
25
Yield 40 mg (83%), sticky yellow solid, [α]D +6.46
(c 0.02, MeOH). IR spectrum, ν, cm–1: 758, 1222, 1739,
2970, 3022, 3356. 1H NMR spectrum, δ, ppm (J, Hz): 2.40
(3H, s, CH3); 3.49–3.60 (4H, m, =CH, 4'-CH, 6'-CH2), 3.72
(1H, dd, J = 12.1, J = 5.0, 5'-CH); 3.85–3.93 (2H, m, 2',3'-CH);
4.55 (2H, s, CH2NH); 5.61 (1H, d, J = 9.1, 1'-CH); 7.32
(2H, d, J = 7.5, H Ar); 7.37–7.46 (5H, m, H Ph); 7.81 (2H,
d, J = 7.7, H Ar); 8.09 (1H, s, H triazole). 13C NMR
spectrum, δ, ppm: 21.4; 40.9; 62.3; 70.8; 74.0; 78.4; 81.1;
89.6; 123.3; 128.0; 129.0; 129.4; 130.5; 132.2; 133.3;
141.3; 141.6; 146.1; 168.8; 190.3. Found, m/z: 481.2064
[M+H]+. C25H29N4O6. Calculated, m/z: 481.2087.
3-[(1-β-D-Glucopyranosyl-1H-1,2,3-triazol-4-yl)methyl-
amino]-1-phenyloct-2-en-1-one (10c). Yield 36 mg
25
(79%), sticky yellow-orange solid, [α]D +12.93 (c 0.02,
367

Chemistry of Heterocyclic Compounds 2018, 54(3), 362–368
1
Supplementary information file containing H and 13C
Zhang, H.-L.; Chen, G.-R.; Xu, S.; Liu, H. Carbohydr. Res.
2011, 346, 1320.
NMR data of all synthesized compounds is available at the
journal website at http://link.springer.com/journal/10593.
7. (a) Giguere, D.; Patnam, R.; Bellefleur, M.-A.; St-Pierre, C.;
Sato, S.; Roy, R. Chem. Commun. 2006, 22, 2379. (b) Tejler, J.;
Skogman, F.; Leffler, H.; Nilsson, U. J. Carbohydr. Res.
2007, 342, 1869.
8. Goyard, D.; Docsa, T.; Gergely, P.; Praly, J. P.; Vidal, S.
Carbohydr. Res. 2015, 402, 245.
We are grateful to University of Delhi for providing
financial support under DU-DST Purse grant to strengthen
research and development. We are also thankful to CIF-USIC,
University of Delhi for providing the NMR spectral and
HRMS recording facilities.
9. (a) Salmon, A. J.; Williams, M. L.; Maresca, A.; Supuran, C. T.;
Poulsen, S.-A. Bioorg. Med. Chem. Lett. 2011, 21, 6058.
(b) Wilkinson, B. L.; Innocenti, A.; Vullo, D.; Supuran, C. T.;
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Chang, Y.-T.; Kim, Y. K.; Chang, C.-W. T. Bioorg. Med.
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