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V. Raparti et al. / European Journal of Medicinal Chemistry 44 (2009) 3954–3960
1585 (C]N); 1459 (C]C); 1108 (C–O–C). 1H NMR chemical shifts at
(300 MHz, CDCl3, ppm): 3.3 (t, 4H, CH2); 3.7 (t, 4H, CH2);); 6.28–
d
6.33 (dd, 1H, furanyl, J3,4 ¼ 3.5 Hz, J3,5 ¼ 0.8 Hz); 6.38–6.44 (dd, 1H,
furanyl J3,5 ¼ 3.5 Hz, J4,5 ¼ 3.5 Hz); 6.52–6.59 (m, 4H, phenyl); 7.36–
7.42 (dd, 1H, furanyl, J3,5 ¼ 0.8 Hz, J4,5 ¼ 3.7 Hz); 8.66 (s, 1H, CH);
11.12 (bs, 1H, NH). Mass spectra of compound exhibited molecular
ion peak at m/z 354 (Mþ), 355 (M þ 1) Anal. Calcd for C16H17O3N3: C,
64.21; H, 5.84; N, 16.05. Found: C, 64.83; H, 5.04; N, 16.83.
4.5.2. 4-(Morpholin-4-yl)-N0-(3-nitrobenzylidene)benzohydrazide
Yield: 87.5% (solid); mp 157–159 ꢃC. FTIR (KBr) cmꢀ1: 3288 (N–
H); 3065 (Ar C–H); 2976 (C–H); 2862 (N]CH); 1698 (C]O); 1605
(C]N); 1532 (asymm NO2); 1460 (C]C); 1347 (symm NO2); 1111
(C–O–C). 1H NMR chemical shifts at (300 MHz, CDCl3,
d ppm): 3.22
(t, 4H, CH2); 3.62 (t, 4H, CH2); 6.94–7.1 (m, 4H, phenyl); 7.22–7.29
(m, 4H, phenyl); 8.86 (s, 1H, CH); 11.28 (bs, 1H, NH). Mass spectra of
compound exhibited molecular ion peak at m/z 354 (Mþ), 355
(M þ 1) Anal. Calcd for C18H18O4N4: C, 61.01; H, 5.08; N, 15.81.
Found: C, 61.55; H, 5.86; N, 15.12.
Fig. 1. Overlain of all 4-(morpholin-4-yl)-N0-(arylidene)benzohydrazides aligned using
alignment tool of V-Life MDS.
4.5.7. 4-(Morpholin-4-yl)-N0-(4-(N,N-dimethylamino)benzylidene)
benzohydrazide
4.5.3. 4-(Morpholin-4-yl)-N0-(4-chlorobenzylidene)benzohydrazide
Yield: 85.5% (solid); mp 216–218 ꢃC. FTIR (KBr) cmꢀ1: 3380 (N–
H); 3092 (Ar C–H); 2982 (C–H); 2864 (N]CH); 1701 (C]O); 1615
(C]N); 1462 (C]C); 1116 (C–O–C); 766 (C–Cl). 1H NMR chemical
Yield: 92.1% (solid); mp 165–167 ꢃC. FTIR (KBr) cmꢀ1: 3245 (N–
H); 3061(Ar C–H); 2975 (C–H); 2830 (N]CH); 1680 (C]O); 1572
(C]N); 1454 (N (CH3)2); 1446 (C]C); 1105 (C–O–C). 1H NMR
chemical shifts at (300 MHz, CDCl3,
d ppm): 3.27 (t, 4H, CH2); 3.54
shifts at (300 MHz, CDCl3,
d ppm): 3.26 (t, 4H, CH2); 3.79 (t, 4H,
(t, 4H, CH2); 7.1–7.18 (m, 4H, phenyl); 7.2–7.34 (m, 4H, phenyl); 8.45
(s, 1H, CH); 10.6 (bs, 1H, NH). Mass spectra of compound exhibited
molecular ion peak at m/z 352 (Mþ), 353 (M þ 1). Anal. Calcd for
C20H24O2N4: C, 68.18; H, 6,82; N, 15.09. Found: C, 68.70; H, 6.42; N,
15.52.
CH2); 7.20-7.23 (m, 4H, phenyl); 7.50-7.68 (m, 4H, phenyl); 8.91
(s, 1H, CH); 11.36 (bs, 1H, NH). Mass spectra of compound exhibited
molecular ion peak at m/z 343.5 (Mþ), 344.5 (M þ 1). Anal. Calcd for
C18H18O2N3Cl: C, 62.88; H, 5.24; N, 12.33. Found: C, 62.24; H, 5.06;
N, 12.19.
4.5.8. 4-(Morpholin-4-yl)-N0-(4-
methylbenzylidene)benzohydrazide
4.5.4. 4-(Morpholin-4-yl)-N0-(4-fluorobenzylidene)benzohydrazide
Yield: 85.6% (solid); mp 216–218 ꢃC. FTIR (KBr) cmꢀ1: 3289 (N–
H); 3085 (Ar C–H); 2986 (C–H); 2868 (N]CH); 1705 (C]O); 1621
(C]N); 1465 (C]C); 1231 (C–F); 1120 (C–O–C). 1H NMR chemical
Yield: 63.9% (solid); mp 138–140 ꢃC. FTIR (KBr) cmꢀ1: 3244 (N–
H); 3059 (Ar C–H); 2981 (C–H); 2896 (N]CH); 1678 (C]O); 1569
(C]N); 1450 (C]C); 1108 (C–O–C), 741 (C–H). 1H NMR chemical
shifts at (300 MHz, CDCl3,
d ppm): 3.32 (t, 4H, CH2); 3.81 (t, 4H,
shifts at (300 MHz, CDCl3,
d ppm): 3.12 (t, 4H, CH2); 3.48 (t, 4H,
CH2); 7.49–7.58 (m, 4H, phenyl); 7.68–7.79 (m, 4H, phenyl); 8.95
(s, 1H, CH); 12.1 (bs, 1H, NH). Mass spectra of compound exhibited
molecular ion peak at m/z 327 (Mþ), 328 (M þ 1). Anal. Calcd for
C18H18O2N3F: C, 66.06; H, 5.51; N, 12.84. Found: C, 66.28; H, 5.66;
N, 12.13.
CH2); 6.94–7.16 (m, 4H, phenyl); 7.32–7.45 (m, 4H, phenyl); 8.48 (s,
1H, CH); 10.71 (bs, 1H, NH). Mass spectra of compound exhibited
molecular ion peak at m/z 323 (Mþ), 324 (M þ 1). Anal. Calcd for
C19H21O2N3: C, 70.58; H, 6.50; N, 13.00. Found: C, 70.02; H, 6.72; N,
13.66.
4.5.5. 4-(Morpholin-4-yl)-N0-(4-
4.5.9. 4-(Morpholin-4-yl)-N0-(3-phenylallylidene)benzohydrazide
Yield: 88.1% (solid); mp 186–188 ꢃC. FTIR (KBr) cmꢀ1: 3269 (N–
H); 3076 (Ar C–H); 2988 (C–H); 2856 (N ¼ CH); 1688 (C]O); 1582
(C]N); 1462 (C]C); 1113 (C–O–C). 1H NMR chemical shifts at
hydroxybenzylidene)benzohydrazide
Yield: 81.8% (solid); mp 148–150 ꢃC. FTIR (KBr) cmꢀ1: 3289 (O–
H); 3255 (N–H); 3056 (Ar C–H); 2974 (C–H); 2830 (N]CH); 1670
(C]O); 1569 (C]N); 1449 (C]C); 1106 (C–O–C). 1H NMR chemical
(300 MHz, CDCl3,
d ppm): 3.34 (t, 4H, CH2); 3.58 (t, 4H, CH2); 6.95-
shifts at (300 MHz, CDCl3,
d ppm): 3.26 (t, 4H, CH2); 3.51 (t, 4H,
6.98 (d, 1H, J ¼ 6.5 Hz, CH]CH-Ph); 7.43-7.48 (m, 4H, phenyl);
7.55–7.61 (d, 1H, J ¼ 2.2 Hz, N]CH–CH); 8.71 (s, 1H, CH); 10.09 (bs,
1H, NH). Mass spectra of compound exhibited molecular ion peak at
m/z 335 (Mþ), 336 (M þ 1). Anal. Calcd for C20H21O2N3: C, 71.64; H,
6.27; N, 12.54. Found: C, 71.05; H, 6.42; N, 12.88.
CH2); 6.94–7.16 (m, 4H, phenyl); 7.39–7.46 (m, 4H, phenyl); 8.42
(s, 1H, CH); 10.12 (bs, 1H, NH). Mass spectra of compound exhibited
molecular ion peak at m/z 325 (Mþ), 326 (M þ 1). Anal. Calcd for
C18H19O3N3: C, 66.46; H, 5.85; N, 12.92. Found: C, 66.12; H, 5.05;
N, 12.21.
4.5.10. 4-(Morpholin-4-yl)-N0-(3,4,5-trimethoxybenzylidene)
benzohydrazide
4.5.6. 4-(Morpholin-4-yl)-N0-(4-
methoxybenzylidene)benzohydrazide
Yield: 74.1% (solid); mp 209–211 ꢃC. FTIR (KBr) cmꢀ1: 3272 (N–
H); 3079 (Ar C–H); 2992 (C–H); 2864 (N]CH); 1690 (C]O); 1594
(C]N); 1464 (C]C); 1176 (Ar C–O); 1116 (C–O–C). 1H NMR chem-
Yield: 73.9% (solid); mp 233–235 ꢃC. FTIR (KBr) cmꢀ1: 3265 (N–
H); 3072 (Ar C–H); 2982 (C–H); 2844 (N]CH); 1678 (C]O); 1672
(C]N); 1451 (C]C); 1174 (Ar C–O); 1109 (C–O–C). 1H NMR chem-
ical shifts at (300 MHz, CDCl3, d ppm): 3.38 (t, 4H, CH2); 3.59 (t, 4H,
ical shifts at (300 MHz, CDCl3, d ppm): 3.36 (t, 4H, CH2); 3.66 (t, 4H,
CH2); 7.4–7.46 (m, 4H, phenyl); 7.65–7.68 (m, 4H, phenyl); 8.76 (s,
1H, CH); 11.22 (bs, 1H, NH). Mass spectra of compound exhibited
molecular ion peak at m/z 339 (Mþ), 340 (M þ 1). Anal. Calcd for
C21H25O5N3: C, 63.16; H, 6.27; N, 10.53. Found: C, 63.78; H, 6.89; N,
10.84.
CH2); 6.91–7.12 (m, 4H, phenyl); 7.31–7.36 (m, 4H, phenyl); 8.65
(s, 1H, CH); 11.2 (bs, 1H, NH). Mass spectra of compound exhibited
molecular ion peak at m/z 339 (Mþ), 340 (M þ 1). Anal. Calcd for
C19H21O3N3: C, 67.26; H, 6.19; N, 12.38. Found: C, 67.02; H, 6.82;
N, 12.76.