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M. Amir et al. / Bioorg. Med. Chem. Lett. 18 (2008) 918–922
Compound 2d: yield 93%, mp 166 ꢁC; IR (KBr, m cmꢀ1):
80.89; H, 6.06; N, 9.43. Found: C, 80.81; H, 6.13; N, 9.37.
Compound 3e: yield 64%, mp 104 ꢁC; IR (KBr, m cmꢀ1):
3231 (NH), 1590 (C@N); 1H NMR (CDCl3, d): 2.43 (s,
6H, (CH3)2), 3.18 (dd, JXM = 12.7 Hz, JXA = 4.7 Hz, 1H,
CH2 pyrazoline), 3.61 (dd, JMX = 12.7 Hz, JMA = 6.9 Hz,
1H, CH2 pyrazoline), 5.49 (dd, JAX = 4.7 Hz,
JAM = 6.9 Hz, 1H, CH pyrazoline), 7.16–7.82 (m, 13H,
ArH), 9.05 (br s, 1H, NH); MS: m/z 341 (M+); Anal. Calcd
for C23H23N3: C, 80.93; H, 6.74; N, 12.31. Found: C,
80.99; H, 6.71; N, 12.28.
1
1669 (C@O), 1599 (C@N); H NMR (CDCl3, d): 2.31 (s,
3H, CH3), 3.19 (dd, JXM = 13.44 Hz, JXA = 4.2 Hz, 1H,
CH2 pyrazoline), 3.75 (dd, JMX = 13.44 Hz, JMA = 5.7 Hz,
1H, CH2 pyrazoline), 5.50 (dd, JAX = 4.2 Hz,
JAM = 5.7 Hz, 1H, CH pyrazoline), 7.15–8.14 (m, 18H,
ArH); MS: m/z 416 (M+); Anal. Calcd for C29H24N2O: C,
83.65; H, 5.76; N, 6.73. Found: C, 83.53; H, 5.69; N, 6.78.
Compound 3f: yield 73%, mp 114 ꢁC; IR (KBr, m cmꢀ1):
1622 (C@O), 1569 (C@N), 1238(C–O–C); 1H NMR
(CDCl3, d): 3.03 (dd, JXM = 10.5 Hz, JXA = 5.6 Hz, 1H,
CH2 pyrazoline), 3.15 (dd, JMX = 10.5 Hz, JAM = 7.6 Hz,
1H, CH2 pyrazoline), 3.89 (s, 3H, OCH3), 4.94 (dd,
JAX = 5.6 Hz, JAM = 7.6 Hz, 1H, CH pyrazoline), 7.20–
7.87 (m, 18H, ArH); MS: m/z 432 (M+); Anal. Calcd for
C29H24N2O2: C, 80.55; H, 5.55; N, 6.48. Found: C, 80.62;
H, 5.59; N, 6.51.
Compound 2e: yield 88%, mp 164 ꢁC; IR (KBr, m cmꢀ1):
3273 (NH), 1590 (C@N); 1H NMR (CDCl3, d): 2.32 (s,
3H, CH3), 3.20(dd, JXM = 12.9 Hz, JXA = 4.7 Hz, 1H, CH2
pyrazoline), 3.77 (dd, JMX = 12.9 Hz, JMA = 6.9 Hz, 1H,
CH2 pyrazoline), 5.50 (dd, JAX = 4.7 Hz, JAM = 6.9 Hz,
1H, CH pyrazoline), 7.16–7.82 (m, 13H, ArH), 8.97 (br s,
1H, NH); MS: m/z 312 (M+); Anal. Calcd for C22H20N2:
C, 84.61; H, 6.41; N, 8.97. Found: C, 84.66; H, 6.39; N,
8.94.
Compound 2f: yield 85%, mp 158 ꢁC; IR (KBr, m cmꢀ1):
3260 (NH), 1610 (C@N),1255(C–O–C);1H NMR (CDCl3,
d): 3.19 (dd, JXM = 12.0 Hz, JXA = 4.7 Hz, 1H, CH2
pyrazoline), 3.89–3.99 (m, 4H, OCH3 & 1H of CH2
pyrazoline), 5.48 (dd, JAX = 4.7 Hz, JAM = 6.9 Hz, 1H,
CH pyrazoline), 7.14–8.01 (m, 13H, Ar-H), 8.90 (br s, 1H,
NH); MS: m/z 328 (M+). Anal. Calcd for C22H20N2O: C,
80.48; H, 6.09; N, 8.53. Found: C, 80.37; H, 6.14; N, 8.48.
Compound 2g: yield 83%, mp 128 ꢁC; IR (KBr, m cmꢀ1):
3235 (NH), 1583 (C@N), 1250(C–O–C); 1H NMR
(CDCl3, d): 3.22 (dd, JXM = 12.8 Hz, JXA = 4.8 Hz, 1H,
CH2 pyrazoline), 3.82–3.89 [m, 7H, (OCH3)2 & 1H of CH2
pyrazoline], 5.48 (dd, JAX = 4.8 Hz, JAM = 6.9 Hz, 1H, CH
pyrazoline), 6.77–7.83 (m, 12H, Ar-H), 8.99 (br s, 1H,
NH); MS: m/z 358 (M+); Anal. Calcd for C23H22N2O2: C,
77.09; H, 6.14; N, 7.82. Found: C, 77.01; H, 6.18; N, 7.89.
Compound 2h: yield 92%, mp 190 ꢁC; IR (KBr, m cmꢀ1):
3233 (NH), 1589 (C@N), 1256(C–O–C); 1H NMR
(CDCl3, d): 3.24 (dd, JXM = 12.8 Hz, JXA = 4.8 Hz, 1H,
CH2 pyrazoline), 3.82–3.89 [m, 10H, (OCH3)3 & 1H of
CH2 pyrazoline], 5.50 (dd, JAX = 4.8 Hz, JAM = 6.8 Hz,
1H, CH pyrazoline), 6.77–7.83 (m, 11H, ArH), 9.04 (br s,
1H, NH); MS: m/z 388 (M+); Anal. Calcd for
C24H24N2O3: C, 74.22; H, 6.18; N, 7.21. Found: C,
74.29; H, 6.22; N, 7.23.
Compound 3g: yield 73%, mp 98 ꢁC; IR (KBr, m cmꢀ1):
1647 (C@O), 1597 (C@N), 1234 (C–O–C); 1H NMR
(CDCl3, 3.26 (dd, JXM = 11.0 Hz, JXA = 5.2 Hz, 1H, CH2
pyrazoline), 3.80–3.88 [m, 7H, (OCH3)2 & 1H of CH2
pyrazoline], 5.62 (dd, JAX = 5.2 Hz, JAM = 6.7 Hz, 1H, CH
pyrazoline), 6.81–7.79 (m, 17H, Ar-H); MS: m/z 462 (M+).
Anal. Calcd for C30H26N2O3: C, 77.92; H, 5.62; N, 6.06;
Found: C, 77.83; H, 5.67; N, 6.12.
Compound 3h: yield 78%, mp 152 ꢁC; IR (KBr, m cmꢀ1):
1639 (C@O), 1590 (C@N), 1249 (C–O–C); 1H NMR
(CDCl3, d): 3.22 (dd, JXM = 10.9 Hz, JXA = 4.8 Hz, 1H,
CH2 pyrazoline), 3.81–3.89 [m, 10H, (OCH3)3 & 1H of
CH2 pyrazoline], 5.50 (dd, JAX = 4.8 Hz, JAM = 6.8 Hz,
1H, CH pyrazoline), 6.79–7.83 (m, 16H, Ar-H); MS: m/z
492 (M+); Anal. Calcd for C31H28N2O4: C, 75.60; H, 5.69;
N, 5.69. Found: C, 75.51; H, 5.73; N, 5.62.
25. Winter, C. A.; Risley, E. A.; Nuss, G. W.. Proc. Soc. Exp.
Biol. Med. 1962, 111, 544.
26. Adeyemi, O. O.; Okpo, O. S.; Okpaka, O. J. Ethnophar-
macol. 2004, 90, 45.
27. Cioli, V.; Putzolu, S.; Rossi, V.; Barcellona, S. P.;
Corradino, C. Toxicol. Appl. Pharmacol. 1979, 50, 283.
28. Ohkawa, H.; Ohishi, N.; Yagi, K. Anal. Biochem. 1979, 95,
351.
29. Reitman, S.; Frankel, S. Am. J. Clin. Pathol. 1957, 28, 56.
30. King, E. J.; Armstrong, A. R. A. Can. Med. Assoc. J.
1934, 31, 376.
Compound 3d: yield 71%, mp 154 ꢁC; IR (KBr, m cmꢀ1):
1
1634 (C@O), 1587 (C@N); H NMR (CDCl3, d): 2.91 (s,
6H, (CH3)2), 3.21 (dd, JXM = 13.05 Hz, JXA = 4.3 Hz, 1H,
CH2 pyrazoline), 3.61 (dd, JMX = 13.05 Hz, JMA = 6.2 Hz,
1H, CH2 pyrazoline), 5.74 (dd, JAX = 4.3 Hz,
JAM = 6.2 Hz, 1H, CH pyrazoline), 7.03–8.08 (m, 18H,
Ar-H); MS: m/z 445 (M+); Anal. Calcd for C30H27N3O: C,
31. Practical Clinical Biochemistry; Varley, H., Ed., 1st ed.;
CBS Publishers and Distributors: New Delhi, 1988; p 236.
32. Manual of Histological Staining Methods of the Armed
Forces Institute of Pathology; Luna, L. G., Ed., 3rd ed.;
Mc-Graw-Hill: New York, 1968; p 567.