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A. Masunari, L. C. Tavares / Bioorg. Med. Chem. 15 (2007) 4229–4236
7.49 (d, 1H, H , J = 4.32 Hz); 2.88 (septet, 1H, CH,
J = 6.87 Hz); 1.14 (d, 6H, 2CH , J = 6.87 Hz).
IR (KBr): m 3350 (mN–H); 3020 (mC–H); 1657 (mC@O); 1598
and 1474 (mC@C); 1571 (dN–H); 1542 (mN@O ass.); 1453
3
3
(
dCH2 ); 1373 (dCH3 ); 1340 (mN@O sim.); 729 (dC–H); 645
1
3
C NMR: d 164.15 (C ); 153.80 (C ); 151.62 (C );
(mC–S).
9
6
2
1
and C ); 130.40 (C and C ); 128.76 (C ); 127.36
47.73 (C ); 141.76 (C ); 131.39 (C ); 131.31 (C
13 5 10 12
1
H NMR: d 11.86 (s, 1H, H ); 8.63 (s, 1H, H ); 8.11 (d,
1
4
11
15
4
8
6
(
C ); 34.32 (CH); 24.45 (2CH ).
3
1H, H , J = 4.35 Hz); 7.72 (d, 2H, H and H15,
J = 7.50 Hz); 6.60 (d, 2H, H12 and H , J = 7.50 Hz);
3
4 11
14
EA: Calcd C, 56.77%; H, 4.76%; N, 13.24%. Experimen-
tal: C, 57.02%; H, 4.81%; N, 13.29%.
7.51 (d, 1H, H , J = 4.35 Hz); 6.41 (t, 1H, NH,
3
J = 5.22 Hz), 3.07 (dd, 2H, CH2, J = 6.91 Hz,
0
J = 5.22 Hz); 1.54 (quintet, 2H, CH , J = 6.91 Hz);
2
4
.1.8. 4-Propoxy-benzoic acid [(5-nitro-thiophen-2-yl)-
methylene]-hydrazide (C H O N S) (8). Dark-yellow
1.39 (sextet, 2H, CH , J = 6.91 Hz); 0.91 (t, 3H, CH ,
2
J = 6.91 Hz).
3
1
5
15
4
3
amorphous solid. Yield: 93%; mp 195.7–197.2 °C.
1
3
C NMR: d 164.18 (C ); 153.18 (C ); 151.16 (C );
9
6
2
IR (KBr): m 3290 (mN–H); 3105 (mC–H); 1659 (mC@O); 1607
and 1507 (mC@C); 1571 (dN–H); 1528 (mN@O ass.); 1470
148.47 (C ); 139.86 (C ); 131.43 (C ); 130.52 (C
13 5 10 12
and C ); 129.62 (C and C ); 126.29 (C ); 119.18
14
11
15
4
(
d
CH2 ); 1391 (dCH3 ); 1337 (mN@O sim.); 1256 (mC–O); 729
(C ); 42.87 (CH ); 31.50 (CH ); 20.63 (CH ); 14.64
2
3
2
2
(
dC–H); 680 (mC–S).
(CH3).
1
H NMR: d 12.12 (s, 1H, H ); 8.67 (s, 1H, H ); 8.13 (d,
EA: Calcd C, 52.74%; H, 4.98%; N, 15.37%. Experimen-
tal: C, 52.85%; H, 4.69%; N, 15.47%.
8
6
1
J = 8.54 Hz); 7.07 (d, 2H, H12 and H , J = 8.54 Hz);
H, H , J = 4.29 Hz); 7.90 (d, 2H, H11 and H15,
4
14
7
J = 6.94 Hz); 1.76 (sextet, 2H, CH , J = 6.94 Hz); 0.99
.56 (d, 1H, H , J = 4.29 Hz); 4.02 (t, 2H, CH ,
4.1.11. 4-Butyl-benzoic acid [(5-nitro-thiophen-2-yl)-
methylene]-hydrazide (C H O N S) (11). Dark-yellow
3
2
2
16 17
3
3
(
t, 3H, CH , J = 6.94 Hz).
3
amorphous solid. Yield: 98%; mp 175.8–179.2 °C.
1
3
C NMR: d 161.80 (C ); 150.67 (C ); 147.04 (C );
IR (KBr): m 3250 (mN–H); 3110 (mC–H); 1652 (mC@O); 1610
and 1490 (mC@C); 1557 (dN–H); 1534 (mN@O ass.); 1465
(dCH2 ); 1393 (dCH3 ); 1339 (mN@O sim.); 729 (dC–H); 656
(mC–S).
9
6
2
1
and C ); 124.63 (C and C ); 124.58 (C ); 114.25
40.50 (C ); 130.60 (C ); 129.80 (C ); 129.41 (C
13 5 10 12
1
4
11
15
4
(
C ); 69.28 (CH ); 21.95 (CH ); 10.35 (CH ).
3 2 2 3
1
EA: Calcd C, 53.04%; H, 4.54%; N, 12.60%. Experimen-
tal: C, 52.08%; H, 4.60%; N, 12.31%.
H NMR: d 12.18 (s, 1H, H ); 8.67 (s, 1H, H ); 8.14 (d,
8
6
1H, H , J = 4.27 Hz); 7.83 (d, 2H, H and H15,
J = 7.90 Hz); 7.36 (d, 2H, H12 and H , J = 7.90 Hz);
4
11
14
4.1.9. 4-Butoxy-benzoic acid [(5-nitro-thiophen-2-yl)-
methylene]-hydrazide (C H O N S) (9). Dark-yellow
7.58 (d, 1H, H , J = 4.27 Hz); 2.65 (t, 2H, CH ,
2
J = 7.63 Hz); 1.57 (quintet, 2H, CH , J = 7.63 Hz);
2
3
1
6
17
4
3
amorphous solid. Yield: 97%; mp 200.5–201.6 °C.
1.32 (sextet, 2H, CH , J = 7.63 Hz), 0.90 (t, 3H, CH ,
2
J = 7.63 Hz).
3
IR (KBr): m 3360 (mN–H); 3075 (mC–H); 1643 (mC@O); 1607
and 1507 (mC@C); 1570 (dN–H); 1529 (mN@O ass.); 1466
1
3
C NMR: d 163.03 (C ); 151.61 (C ); 147.92 (C );
9
6
2
(
dCH2 ); 1384 (dCH3 ); 1339 (mN@O sim.); 1256 (mC–O); 729
dC–H); 679 (mC–S).
147.73 (C ); 141.71 (C ); 131.41 (C ); 131.12 (C
13 5 10 12
and C ); 130.43 (C and C ); 129.33 (C ); 128.67
(
14
11
15
4
(C3); 35.56 (CH2); 33.69 (CH2); 22.59 (CH2);
14.61(CH3).
1
H NMR: d 12.08 (s, 1H, H ); 8.64 (s, 1H, H ); 8.11 (d,
8
6
1
J = 8.39 Hz); 7.04 (d, 2H, H12 and H , J = 8.39 Hz);
H, H , J = 4.18 Hz); 7.87 (d, 2H, H11 and H15,
4
EA: Calcd C, 57.99%; H, 5.17%; N, 12.07%. Experimen-
tal: C, 58.32%; H, 5.30%; N, 12.77%.
14
7
J = 6.80 Hz); 1.70 (quintet, 2H, CH , J = 6.80 Hz);
.54 (d, 1H, H , J = 4.18 Hz); 4.03 (t, 2H, CH ,
3 2
2
1
J = 6.80 Hz).
.40 (sextet, 2H, CH , J = 6.80 Hz); 0.92 (t, 3H, CH ,
2
4.1.12. 4-Ethyl-benzoic acid [(5-nitro-thiophen-2-yl)-
methylene]-hydrazide (C H O N S) (12). Dark-yellow
3
1
4
13
3
3
amorphous solid. Yield: 94%; mp 207.2–208.5 °C.
1
3
C NMR: d 161.79 (C ); 150.65 (C ); 147.03 (C ); 140.46
9
6
2
(
and C ); 124.62 (C and C ); 114.24 (C ); 67.51
C ); 130.58 (C ); 129.76 (C ); 129.56 (C ); 129.40 (C
IR (KBr): m 3310 (mN–H); 3105 (mC–H); 1649 (mC@O); 1611
and 1503 (mC@C); 1567 (dN–H); 1544 (mN@O ass.);
14652(dCH2 ); 1376 (dCH3 ); 1342 (mN@O sim.); 730 (dC–H);
1
3
5
4
10
12
1
4
11
15
3
(
CH ); 30.61 (CH ); 18.69 (CH ); 13.69 (CH ).
2 2 2 3
6
60 (mC–S).
EA: Calcd C, 55.32%; H, 4.93%; N, 11.50%. Experimen-
tal: C, 56.09%; H, 5.16%; N, 11.57%.
1
H NMR: d 12.19 (s, 1H, H ); 8.68 (s, 1H, H ); 8.13 (d,
8
6
1
J = 7.80 Hz); 7.38 (d, 2H, H12 and H , J = 7.80 Hz);
H, H , J = 4.30 Hz); 7.84 (d, 2H, H and H15,
4 11
4.1.10. 4-Butylamine-benzoic acid [(5-nitro-thiophen-2-
yl)-methylene]-hydrazide (C H O N S) (10). Dark-red
14
7.58 (d, 1H, H , J = 4.30 Hz); 2.50 (q, 2H, CH ,
3
1
6
18
3
3
2
amorphous solid. Yield: 93%; mp 249.1–250.9 °C.
J = 7.54 Hz); 1.21 (t, 3H, CH , J = 7.54 Hz).
3