N.A. Dangroo et al. / European Journal of Medicinal Chemistry 120 (2016) 160e169
167
4
.1.6.15. (1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl)methyl acetyl
a
-
(m, 2H, OCH
CH eCH), 2.59e2.63 and 2.53e2.59 (m, 1H each, AreCH
2.29e2.32 (m, 1H, CH eCHeCO), 2.29 (s, 3H, CH eCO), 2.17 (s, 3H,
AreCH ), 1.96e2.02 and 1.31e1.38 (m, 1H each, CH eCH eCH),
1.99e2.05 (m, 1H, CH eCHeCH ), 1.91 (s, 3H, AreCH ), 1.25 (d, 3H,
CHe); C NMR (125 MHz CDCl 176.01, 169.89,
2
e), 2.70e2.74 and 2.45e2.51 (m, 1H each, Are-
ꢀ
1
desmotroposantonoate (19). White solid; m.p:165 C. H NMR
2
2
eCH ),
2
1
(
400 MHz CDCl
3
)
d
8.15 (s, 1H, eNCHe), 7.94e7.95 (m, 1H, Ar eH),
3
3
1
1
7
.44e7.46 (m, 1H, Ar eH), 7.28e7.35 (m, 2H, 2ꢁ Ar eH), 6.66 (s, 1H,
3
2
2
AreH), 5.33 (m, 2H, OCH
AreCH
2
e), 2.70e2.74 and 2.49e2.54 (m, 1H each,
2
2
3
13
2
eCH), 2.61e2.67 and 2.53e2.58 (m, 1H each, AreCH
.27e2.33 (m, 1H, CH eCHeCO), 2.29 (s, 3H, CH eCO), 2.15 (s, 3H,
), 1.96e2.01 and 1.29e1.38 (m, 1H each, CH eCH eCH),
eCHeCH ), 1.87 (s, 3H, AreCH ), 1.25 (d, 3H,
CHe); C NMR (125 MHz CDCl 176.00, 169.90,
54.36,152.36,156.55,143.41, 135.92,134.64,132.83,130.45,125.29,
25.11, 124.92, 121.17, 120.28, 117.17, 117.01, 57.32, 44.32, 36.99,
2
eCH
2
),
J ¼ 7.9 Hz, CH
3
3
) d
2
3
3
146.56, 142.81, 135.92, 134.70, 134.65, 132.81, 130.90, 130.81, 128.59,
127.98, 127.80, 125.94, 125.42, 120.29, 57.37, 44.26, 36.99, 31.97,
26.99, 25.50, 20.87, 19.49, 14.15, 11.7. HRMS m/z calcd for
AreCH
3
2
2
1.99e2.05 (m, 1H, CH
2
2
3
13
[MþH]þ 482.1841, found 482.1879.
J ¼ 7.9 Hz, CH
3
3
)
d
26 3 4
C H28ClN O
1
1
4.1.6.20. (1-(4-hydroxyphenyl)-1H-1,2,3-triazol-4-yl)methyl acetyl
ꢀ
1
3
C
2.02, 27.11, 25.49, 20.86, 19.48, 14.10, 11.65. HRMS m/z calcd for
a
-desmotroposantonoate (24). White solid; m.p:153 C. H NMR
þ
26
H
28FN
3
O
4
[MþH] 466.2137, found 466.2157.
(400 MHz CDCl
3
)
d
8.03 (s, 1H, eNCHe), 8.00 (d, J ¼ 8 Hz, 1H,
1
1
1
Ar eH), 7.40 (t, J ¼ 8 Hz, 1H, Ar eH), 7.10 (d, J ¼ 8 Hz, 1H, Ar eH),
1
4
.1.6.16. (1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methyl acetyl
a-
6.97 (d, J ¼ 8 Hz, 1H, Ar eH), 6.65 (s, 1H, AreH), 5.31e5.38 (m, 2H,
desmotroposantonoate (20). White solid; m.p:134 C. 1H NMR
400 MHz CDCl
8.03 (s, 1H, eNCHe), 7.69 (d, J ¼ 8 Hz, 2H, 2ꢁ
ꢀ
eCH),
), 2.29e2.32
eCO), 2.18 (s, 3H, AreCH ),
eCH), 1.99e2.05 (m,
), 1.23 (d, J ¼ 7 Hz, 3H,
2 2
OCH e), 2.65e2.74 and 2.45e2.51 (m, 1H each, AreCH
(
3
)
d
2.51e2.63 and 2.53e2.59 (m, 1H each, AreCH
(m, 1H, CH eCHeCO), 2.29 (s, 3H, CH
1.96e2.02 and 1.31e1.38 (m, 1H each, CH
1H, CH eCHeCH ), 1.91 (s, 3H, AreCH
CH CHe); C NMR (125 MHz CDCl
2 2
eCH
1
1
Ar eH), 7.50 (d, J ¼ 12 Hz, 2H, 2ꢁ Ar eH), 6.66 (s, 1H, AreH), 5.33
m, 2H, OCH ), 2.70e2.74 and 2.45e2.51 (m, 1H each, AreCH eCH),
.59e2.63 and 2.53e2.59 (m, 1H each, AreCH eCH ), 2.29e2.32
m, 1H, CH eCHeCO), 2.31 (s, 3H, CH eCO), 2.17 (s, 3H, AreCH ),
eCH eCH), 1.99e2.05 (m,
), 1.25 (d, 3H, J ¼ 7.9 Hz,
176.11, 169.89, 146.56,
3
3
3
(
2
(
2
2
2
3
eCH
2
2
2
2
2
13
3
3
3
3
3
)
d
176.16,170.31,158.45,146.48,
1.96e2.02 and 1.31e1.38 (m, 1H each, CH
2
2
143.36, 137.30, 135.82, 134.68, 132.84, 130.59, 125.32, 122.16, 120.17,
116.30, 110.28, 108.72, 56.94, 44.37, 37.05, 32.05, 26.94, 25.47, 20.86,
1
CH
H, CH
2
eCHeCH
2
), 1.94 (s, 3H, AreCH
3
1
3
[MþH]þ
3
CHe); C NMR (125 MHz, CDCl
3
)
d
29 3 5
19.45, 14.10, 11.68. HRMS m/z calcd for C26H N O
464.3245, found 464.3262.
144.45, 135.83, 135.34, 134.74, 132.80, 130.00 (2CH), 125.34, 121.99,
1
21.76 (2CH), 120.31, 57.36, 44.33, 37.02, 32.04, 26.93, 25.50, 20.84,
19.47, 14.16, 11.65. HRMS m/z calcd for C26
H
28 ClN
3
O
4
[MþH]þ
4.1.6.21. (1-
(3,4-methylenedioxyphenyl)-1H-1,2,3-triazol-4-yl)
4
82.1841, found 482.1827.
methyl acetyl
a
-desmotroposan- tonoate (25). White solid; m.p:
ꢀ
1
156 C. H NMR (400 MHz CDCl ) d 7.94 (s, 1H, eNCHe), 7.24 (d,
3
1
1
4
.1.6.17. (1-(2-cyanophenyl)-1H-1,2,3-triazol-4-yl)methyl acetyl
a
-
J ¼ 8 Hz, 1H, Ar eH), 7.10 (d, J ¼ 4 Hz, 1H, Ar eH), 6.89 (d, J ¼ 8 Hz,
ꢀ
1
1
desmotroposantonoate (21). White solid; m.p:143 C, H NMR
400 MHz CDCl 8.25 (s, 1H, eNCHe), 7.79e7.86 (m, 3H, 3x
1H, Ar eH), 6.66 (s, 1H, AreH), 6.07 (s, 2H, eOCH
(m, 2H, OCH e), 2.60e2.70 and 2.48e2.51 (m, 1H each, Are-
CH eCH), 2.48e2.52 and 2.53e2.59 (m, 1H each, AreCH eCH ),
2.31e2.35 (m, 1H, CH eCHeCO), 2.29 (s, 3H, CH eCO), 2.15 (s, 3H,
AreCH ), 1.96e2.01 and 1.33e1.38 (m, 1H each, CH eCH eCH),
1.99e2.01 (m, 1H, CH eCHeCH ), 1.85 (s, 3H, AreCH ), 1.25 (d,
CHe); C NMR (125 MHz CDCl 176.10, 169.89,
2
Oe), 5.28e5.36
(
3
)
d
2
1
1
1
Ar eH), 7.60e7.64 (m, 1H, Ar eH), 6.66 (s, 1H, Ar eH), 5.33 (s, 2H,
OCH e), 2.70e2.75 and 2.50e2.54 (m, 1H each, AreCH eCH),
.63e2.68 and 2.53e2.56 (m, 1H each, AreCH eCH ), 2.29e2.38
m, 1H, CH eCHeCO), 2.31 (s, 3H, CH eCO), 2.16 (s, 3H, AreCH ),
eCH eCH),1.97e2.01 (m,
), 1.28 (d, 3H, J ¼ 8.0 Hz,
175.93, 169.88, 146.55,
43.91, 138.37, 135.95, 134.66, 134.39,134.37, 132.85, 129.71, 125.53,
25.41, 124.33, 120.27, 115.53, 106.76, 57.23, 44.25, 36.96, 32.01,
2
2
2
2
2
3
3
2
2
2
3
2
2
(
3
3
3
2
2
3
13
1
.99e2.02 and 1.36e1.42 (m, 1H each, CH
2
2
J ¼ 7 Hz, 3H, CH
3
3
) d
1
CH
H, CH
2
eCHeCH
2
), 1.99 (s, 3H, AreCH
3
148.66, 148.15, 146.55, 143.48, 135.88, 134.67, 132.81, 131.34, 125.38,
122.34, 120.29, 114.31, 108.53, 102.81, 102.16, 57.46, 44.32, 37.01,
32.04, 27.14, 25.49, 20.85, 19.48, 14.13, 11.68. HRMS m/z calcd for
1
3
3
CHe); C NMR (125 MHz CDCl ) d
3
1
1
[MþH]þ 492.2129, found 492.2097.
27 29
C H N
3
O
6
2
C
7.13, 25.48, 20.87, 19.48, 14.04, 11.76. HRMS m/z calcd for
þ
27
H
28
N
4
O
4
[MþH] 473.2183, found 473.2177.
4.1.6.22. (1-(2-chloropyridin-4-yl)-1H-1,2,3-triazol-4-yl)methyl
ꢀ
1
acetyl
a
-desmotroposantono- ate (26). White solid; m.p: 152 C. H
4
.1.6.18. (1-(3-cyanophenyl)-1H-1,2,3-triazol-4-yl)methyl acetyl
a
-
NMR (400 MHz CDCl ) d
3
8.79 (s, 1H, eNCHe), 8.10 (dd J ¼ 4.5, 4 Hz,
ꢀ
1
1
1
1
desmotroposantonoate (22). White solid; m.p: 126 C. H NMR
2H, 2ꢁ Ar eH), 7.52 (d, J ¼ 8.5 Hz, 1H, Ar eH), 6.66 (s, 1H, Ar eH),
5.34 (s, 2H, OCH e), e), 2.64e2.73 and 2.38e2.51 (m, 1H each,
AreCH eCH), 2.55e2.59 and 2.48e2.52 (m,1H each, AreCH eCH ),
2.29e2.35 (m, 1H, CH eCHeCO), 2.29 (s, 3H, CH eCO), 2.15 (s, 3H,
AreCH ), 1.99e2.01 and 1.32e1.39 (m, 1H each, CH eCH eCH),
1.92e1.99 (m, 1H, CH eCHeCH ), 1.85 (s, 3H, AreCH ), 1.26 (d,
CHe); C NMR (125 MHz CDCl 176.09, 169.92,
1
(
400 MHz CDCl
3
)
d
8.08 (s, 1H, eNCHe), 8.06 (s, 1H, Ar eH), 7.99 (d,
2
1
1
J ¼ 8 Hz, 1H, Ar eH), 7.74 (d, J ¼ 8 Hz, 1H, Ar eH), 7.66e7.79 (m, 1H,
2
2
2
1
Ar eH), 6.66 (s, 1H, AreH), 5.31e5.38 (m, 2H, OCH
and 2.45e2.58 (m, 1H each, AreCH eCH), 2.59e2.63 and 2.47e2.53
), 2.31e2.35 (m, 1H, CH eCHeCO), 2.29
eCO), 2.15 (s, 3H, AreCH ), 1.96e2.01 and 1.31e1.42 (m,
H each, CH eCH eCH), 1.95e2.00 (m, 1H, CH eCHeCH ), 1.85 (s,
H, AreCH CHe); C NMR (125 MHz
), 1.26 (d, 3H, J ¼ 7.9 Hz, CH
175.93, 169.92, 146.57, 144.38, 137.38, 135.78, 134.75,
32.78, 132.23, 130.96, 125.34, 124.46, 123.72, 121.90, 120.34, 117.34,
2
e), 2.69e2.74
3
3
2
3
2
2
(
(
m, 1H each, AreCH
s, 3H, CH
2
eCH
2
3
2
2
3
1
3
3
3
J ¼ 8 Hz, 3H, CH
3
3
) d
1
3
CDCl
2
2
2
2
151.38, 146.96, 144.44, 141.13, 135.77, 134.74, 132.77, 132.58, 130.84,
128.35, 125.28, 122.01, 120.33, 57.20, 44.21, 36.98, 32.00, 26.85,
1
3
3
3
3
)
d
25.47, 20.86, 19.47, 14.16, 11.70. HRMS m/z calcd for C25
4 4
H27ClN O
1
[MþH]þ 483.1794, found 483.1793.
114.25, 57.27, 44.23, 37.01, 32.03, 26.86, 25.49, 20.86, 19.48, 14.19,
11.71. HRMS m/z calcd for C27
H
31
N
4
O
4
[MþH]þ 473.2183, found
4.1.6.23. (1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl acetyl a-
desmotroposantonoate (27). White solid; m.p:159 C. 1H NMR
400 MHz CDCl
8.61 (s, 1H, eNCHe), 8.31(dd, J ¼ 4.0 Hz, each,
ꢀ
473.2193.
(
3
) d
1
1
1
4
.1.6.19. (1-(2-chlorophenyl)-1H-1,2,3-triazol-4-yl)methyl acetyl
a-
1H, Ar eH), 8.19 (s, 1H, Ar eH), 8.17 (dd, J ¼ 8.0, 4.0 Hz, 1H, Ar eH),
7.75 (t, J ¼ 8 Hz, 1H), 6.65 (s, 1H, AreH), 5.35 (s, 2H, OCH e),
2.69e2.74 and 2.39e2.45 (m, 1H each, AreCH eCH), 2.54e2.68 and
2.42e2.53 (m, 1H each, AreCH eCH ), 2.29e2.35 (m, 1H,
desmotroposantonoate (23). White solid; m.p: 149 C. 1H NMR
ꢀ
2
(
400 MHz CDCl
3
)
d
8.10 (s, 1H, eNCHe), 7.64e7.69 (m, 2H, 2ꢁ
2
1
1
Ar eH), 7.45e7.55 (m, 2H, 2ꢁ Ar eH), 6.66 (s, 1H, AreH), 5.31e5.38
2
2