Pharmaceuticals 2020, 13, 375
11 of 16
0
A7: Synthesis of (E)-3-(furan-2”-yl)-1-[4 -(trifluoromethyl)phenyl]prop-2-en-1-one: Yield: 80%;
◦
−1
m.p. 72 C; R = 0.71 (30% Ethyl acetate in Hexane); FT-IR (KBr, cm ): 1658 (C=O), 1514 (CH=CH),
631 (C=C Ar), 3111 (Ar C-H stretching), 1254 (-CF ), 1700 (C-O); H NMR (400 MHz, CDCl , ppm),
.75 (1H, d, J = 16.1 Hz, -CO-CH=), 8.14 (1H, d, J = 16.1 Hz, Ar-CH=), 7.59–8.12 (4H, m, C-2 , 3 , 5 , 6 ,
Ar-H), 6.52–7.53 (3H, m, C-3”, 4”, 5”, Ar-H); ESI-MS: 227.68 [M + H] .
A8: Synthesis of (E)-3-(4”-chlorophenyl)-1-[4 -(trifluoromethyl)phenyl]prop-2-en-1-one: Yield:
0%; m.p. 68 C; R = 0.72 (30% Ethyl acetate in Hexane); FT-IR (KBr, cm ): 1656 (C=O), 1609 (C=C
Ar), 1505 (CH=CH), 1247 (-CF ), 3001 (Ar C-H stretching), 841 (C-Cl); H NMR (400 MHz, CDCl ,
: 7.78 (1H, d, J = 16.3 Hz, -CO-CH=), 8.14 (1H, d, J = 16.2 Hz, Ar-CH=), 7.77–8.13 (4H, m, C-2 ,
, 5 , 6 , Ar-H), 7.43–7.61 (4H, m, C-2”, 4”, 5”, 6”, Ar-H); ESI-MS: 311.62 [M + H] .
A9: Synthesis of (E)-3-(4”-nitrophenyl)-1-[4 -(trifluoromethyl)phenyl]prop-2-en-1-one: Yield: 61%;
m.p. 82 C; R = 0.7 (30% Ethyl acetate in Hexane); FT-IR (KBr, cm ): 1654 (C=O), 1621 (C=C Ar),
512 (CH=CH), 1252 (-CF ), 3010 (Ar C-H stretching), 1430 (NO ); H NMR (400 MHz, CDCl , ppm):
δ: 7.85 (1H, d, J = 17 Hz, -CO-CH=), 8.11 (1H, d, J = 16 Hz, Ar-CH=), 7.68–7.82 (4H, m, C-2 , 3 , 5 , 6 ,
Ar-H), 8.12–8.32 (4H, m, C-2”, 3”, 5”, 6”, Ar-H); ESI-MS: 322.11 [M + H] .
A10: Synthesis of (E)-3-(1”H-pyrrol-2-yl)-1-[4 -(trifluoromethyl)phenyl]prop-2-en-1-one: Yield:
0%; m.p. 75 C; R = 0.68 (30% Ethyl acetate in Hexane); FT-IR (KBr, cm ): 1650 (C=O), 1501 (CH=CH)
618 (C=C Ar), 1242 (-CF ), 1370 (C-N), 3115 (Ar C-H stretching); H NMR (400 MHz, CDCl , ppm),
.77 (1H, d, J = 16 Hz, -CO-CH=), 8.11 (1H, d, J = 16 Hz, Ar-CH=), 7.74–8.23 (4H, m, C-2 , 3 , 5 , 6 ,
Ar-H), 6.08–6.96 (3H, m, C-3”, 4”, 5”, Ar-H), 9.93 (1H, s, -NH); ESI-MS: 266.23 [M + H] .
B1: Synthesis of (E)-3-(2”,3”-dichlorophenyl)-1-[4 -(trifluoromethoxy)phenyl]prop-2-en-1-one:
Yield: 86%; m.p. 70 C; R = 0.8 (30% Ethyl acetate in Hexane); FT-IR (KBr, cm ): 1664 (C=O),
f
1
1
7
δ
0
:
3
3
0
0
0
+
0
◦
−1
1
9
f
3
3
0
ppm):
δ
0
0
0
+
3
0
◦
−1
f
1
1
3
2
3
0
0
0
0
+
0
◦
−1
8
1
7
,
f
1
δ
:
3
3
0
0
0
0
+
0
◦
−1
f
1
1
624 (Ar C=C), 1520 (CH=CH), 1242 (-CF ), 3023 (Ar C-H stretching), 1166 (-C-O-) 838 (C-Cl); H NMR
3
(
7
400 MHz, CDCl , ppm),
δ
0
: 7.58 (1H, d, J = 16.3 Hz, CO-CH=), 8.03 (1H, d, J = 16.3 Hz, Ar-CH=),
3
0
0
0
+
.64–8.22 (4H, m, C-2 , 3 , 5 , 6 , Ar-H), 6.97–7.62 (3H, m, C- 4”, 5”, 6”, Ar-H); ESI-MS: 362.12 [M + H] .
0
B2: Synthesis of (E)-3-(3”-chlorophenyl)-1-[4 -(trifluoromethoxy)phenyl]prop-2-en-1-one: Yield:
◦
−1
8
1
4%; m.p. 65 C; R = 0.81 (30% Ethyl acetate in Hexane); FT-IR (KBr, cm ): 1648 (C=O), 1607 (Ar C=C),
f
1
512 (CH=CH), 1232 (-CF3), 3015 (Ar C-H stretching), 1156 (-C-O-), 840 (C-Cl); H NMR (400 MHz,
CDCl , ppm), δ: 7.37 (1H, d, J = 16.3 Hz, -CO-CH=), 8.02 (1H, d, J = 16.2 Hz, Ar-CH=), 7.70–8.22 (4H,
3
0
0
0
0
+
m, C-2 , 3 , 5 , 6 , Ar-H), 7.05–7.68 (4H, m, C-3”, 4”, 5”, 6”, Ar-H); ESI-MS: 343.58 [M + H] .
B3: Synthesis of (E)-3-(1”H-indol-3”-yl)-1-[4 -(trifluoromethoxy)phenyl]prop-2-en-1-one: Yield:
5%; m.p. 67 C; R = 0.74 (30% Ethyl acetate in Hexane); FT-IR (KBr, cm ): 1651 (C=O), 1602 (Ar
0
◦
−1
4
f
C=C), 1595 (CH=CH), 1521 (C-N), 3681 (-NH), 1206 (-OCF ), 3362 (Ar C-H stretching), 1248 (-C-O-);
3
1
H NMR (400 MHz, CDCl , ppm):
δ 7.53 (1H, d, J = 16.3 Hz, -CO-CH=), 8.05 (1H d, J = 15.9, Ar-CH=),
3
0 0 0 0
.78 (1H, s, -NH), 7.38–8.02 (4H, m, C-2 , 3 , 5 , 6 , Ar-H), 7.05–7.66 (5H, m, C-2”, 4”, 5”, 6”, 7”, Ar-H);
8
13
0
C NMR (125 MHz, CDCl3, ppm): 189.97 (C-1), 125.33 (C-2), 137.37 (C-3), 130.23 (C-1 ), 130.71
C-2 and 6 ), 121.88 (C-3 and 5 ), 139.61 (C-4 ), 121.88 (C-4, ), 112.08 (C-1”), 123.63 (C-2”), 137.35
C-4”),114.41 (C-5”), 120.47 (C-6”), 122.69 (C-7”), 117.81 (C-8”), 123.63 (C-9”); ESI-MS: 332.20 [M + H] ;
0
0
0
0
0
0
(
(
+
1
9
F NMR (376 MHz, CDCl ): δ, 58.64 (3F, s).
3
0
B4: Synthesis of (E)-3-(2”-nitrophenyl)-1-[4 -(trifluoromethoxy)phenyl]prop-2-en-1-one: Yield:
6%; m.p. 69 C; R = 0.87 (30% Ethyl acetate in Hexane); FT-IR (KBr, cm ): 1640 (C=O), 1632 (Ar C=C),
504 (CH=CH),1232 (-CF ), 3012 (Ar C-H stretching), 1126 (-C-O-), 1462 (NO ); H NMR (400 MHz,
◦
−1
5
1
f
1
3
2
CDCl , ppm):
δ
: 7.85 (1H, d, J = 17 Hz, -CO-CH=), 8.28 (1H, d, J = 16 Hz, Ar-CH=), 8.27–8.51 (4H, m,
3
0
0
0
0
+
C-2 , 3 , 5 , 6 , Ar-H), 7.05–8.25 (4H, m, C-3”, 4”, 5”, 6”, Ar-H); ESI-MS: 338.08 [M + H] .
0
B5: Synthesis of (E)-3-(3”-nitrophenyl)-1-[4 -(trifluoromethoxy)phenyl]prop-2-en-1-one: Yield:
◦
−1
5
5%; m.p. 71 C; R = 0.72 (30% Ethyl acetate in Hexane); FT-IR (KBr, cm ): 1659 (C=O), 1626 (Ar C=C),
f
1
1
532 (CH=CH), 1248 (-CF ), 3019 (Ar C-H stretching), 1127 (-C-O-), 1448 (NO ); H NMR (400 MHz,
3
2
CDCl , ppm):
δ
: 7.06 (1H, d, J = 16.3 Hz, CO-CH=), 8.05 (1H, d, J = 16.2 Hz, Ar-CH=), 7.76–8.03 (4H,
3
0
0
0
0
+
m, C-2 , 3 , 5 , 6 , Ar-H), 7.08–7.79 (4H, m, C-2”, 4”, 5”, 6”, Ar-H); ESI-MS: 338.35 [M + H] .