880
Archana et al. / European Journal of Medicinal Chemistry 37 (2002) 873Á882
/
Table 4
Spectral data of compounds (1aÁ
/
1b), (2aÁ
/
2b), (3aÁ
/
3b), (4aÁ
/
4l) and (5aÁ5l)
/
Compound 1H-NMR (CDCl3) d (ppm)
IR (KBr) (cmꢀ1
)
1a
1b
9.60 (ss, 1H, NHCH2), 7.90Á
4.10 (q, 2H, Jꢂ7 Hz, COOCH2CH3), 2.30 (s, 3H, CH3), 1.20 (t, 3H, Jꢂ7 aromatic ring)
Hz, COOCH2CH3)
/
7.25 (m, 4H, ArÃH), 4.38 (d, 2H, NHCH2), 3250 (NH), 2840 (CH2), 1740 (CÄO of ester), 1550 (CÄC of
9.61 (ss, 1H, NHCH2), 7.80Á7.40 (m, 3H, ArÃH), 4.28 (d, 2H, NHCH2), 3300 (NH), 2835 (CH2), 1740 (CÄO of ester), 1560 (CÄC of
/
4.12 (q, 2H, Jꢂ7 Hz, COOCH2CH3), 2.23 (s, 3H, CH3), 1.27 (t, 3H, Jꢂ7 aromatic ring)
Hz, COOCH2CH3)
2a
2b
3a
3b
4a
4b
4c
4d
4e
9.40 (brs, 1H, NHCH2), 8.65 (m, 4H, NHNHCSÃNH2), 8.15Á
/
7.10 (m, 3400 (NH, NH2), 2853 (CH2), 1710 (CÄO of amides), 1130
4H, ArÃH), 4.40 (d, 2H, NHCH2), 2.30 (s, 3H, CH3)
(ÈCÄS)
9.48 (brs, 1H, NHCH2), 8.50 (m, 4H, NHNHCSÃNH2), 7.80Á
/
7.20 (m, 3380 (NH, NH2), 2845 (CH2), 1738 (CÄO of amides), 1135
(ÈCÄS)
3H, ArÃH), 4.45 (d, 2H, NHCH2), 2.25 (s, 3H, CH3)
9.50 (brs, 1H, NHCH2), 8.60 (s, 2H, NH2), 8.10Á
/
7.10 (m, 4H, ArÃH), 3420 (NH, NH2), 2845 (CH2), 1720 (CÄO of quinazolon
4.20 (d, 2H, NHCH2), 2.20 (s, 3H, CH3)
ring), 1610 (CÄN), 680 (CÃSÃC)
9.46 (brs, 1H, NHCH2), 8.45 (s, 2H, NH2), 7.60Á
4.50 (d, 2H, NHCH2), 2.30 (s, 3H, CH3)
/
7.20 (m, 3H, ArÃH), 3400 (NH, NH2), 2863 (CH2), 1750 (CÄO of quinazolon
ring), 1635 (CÄN), 690 (CÃSÃC)
3410 (NH), 2915 (CH2), 1720 (CÄO of quinazolon ring),
1620 (CÄN), 688 (CÃSÃC)
9.45 (brs, 1H, NHCH2), 8.45 (s, 1H, NÄCH ÃAr), 8.00Á
ArÃH), 4.22 (d, 2H, NHCH2), 2.26 (s, 3H, CH3)
9.45 (brs, 1H, NHCH2), 8.40 (s, 1H, NÄCH ÃAr), 8.20Á
/
7.10 (m, 9H,
/7.00 (m, 8H,
3400 (NH), 2910 (CH2), 1700 (CÄO of quinazolon ring),
ArÃH), 4.25 (d, 2H, NHCH2), 3.40 (s, 3H, ArÃOCH3), 2.40 (s, 3H, CH3) 1620 (CÄN), 683 (CÃSÃC)
9.42 (brs, 1H, NHCH2), 8.45 (s, 1H, NÄCH ÃAr), 8.20Á7.10 (m, 8H, 3400 (NH), 2912 (CH2), 1712 (CÄO of quinazolon ring),
/
ArÃH), 4.28 (d, 2H, NHCH2), 3.37 (s, 3H, ArÃOCH3), 2.36 (s, 3H, CH3) 1624 (CÄN), 682 (CÃSÃC)
9.43 (brs, 1H, NHCH2), 9.30 (s, 1H, ArÃOH), 8.46 (s, 1H, NÄCH ÃAr), 3380 (NH), 2913 (CH2), 1720 (CÄO of quinazolon ring),
8.40Á
/
7.15 (m, 8H, ArÃH), 4.25 (d, 2H, NHCH2), 2.32 (s, 3H, CH3)
1619 (CÄN), 686 (CÃSÃC)
3395 (NH), 2916 (CH2), 1718 (CÄO of quinazolon ring),
1617 (CÄN), 685 (CÃSÃC)
9.46 (brs, 1H, NHCH2), 8.43 (s, 1H, NÄCH ÃAr), 8.35Á
/7.20 (m, 8H,
ArÃH), 4.22 (d, 2H, NHCH2), 2.30 (s, 3H, CH3), 1.45 (s, 6H, ArÃN
(CH3)2)
4f
9.40 (brs, 1H, NHCH2), 9.25 (s, 1H, ArÃOH), 8.42 (s, 1H, NÄCH ÃAr), 3380 (NH), 2920 (CH2), 1720 (CÄO of quinazolon ring),
8.20Á7.00 (m, 7H, ArÃH), 4.20 (d, 2H, NHCH2), 3.38 (s, 3H, ArÃOCH3), 1615 (CÄN), 682 (CÃSÃC)
2.36 (s, 3H, CH3)
/
4g
4h
4I
4j
9.56 (brs, 1H, NHCH2), 8.40 (s, 1H, NÄCH ÃAr), 8.30Á
/
7.10 (m, 8H,
3400 (NH), 2910 (CH2), 1750 (CÄO of quinazolon ring),
1580 (CÄN), 680 (CÃSÃC)
3420 (NH), 2912 (CH2), 1740 (CÄO of quinazolon ring),
ArÃH), 4.18 (d, 2H, NHCH2), 2.30 (s, 3H, CH3)
9.53 (brs, 1H, NHCH2), 8.32 (s, 1H, NÄCH ÃAr), 8.35Á
/
7.15 (m, 7H,
ArÃH), 4.15 (d, 2H, NHCH2), 3.39 (s, 3H, ArÃOCH3), 2.35 (s, 3H, CH3) 1560 (CÄN), 682 (CÃSÃC)
9.60 (brs, 1H, NHCH2), 8.35 (s, 1H, NÄCH ÃAr), 8.30Á7.10 (m, 7H, 3420 (NH), 2914 (CH2), 1742 (CÄO of quinazolon ring),
/
ArÃH), 4.12 (d, 2H, NHCH2), 3.45 (s, 3H, ArÃOCH3), 2.36 (s, 3H, CH3) 1565 (CÄN), 682 (CÃSÃC)
9.55 (brs, 1H, NHCH2), 9.10 (s, 1H, ArÃOH), 8.30 (s, 1H, NÄCH ÃAr), 3410 (NH), 2920 (CH2), 1750 (CÄO of quinazolon ring),
7.45Á
/
7.20 (m, 7H, ArÃH), 4.15 (d, 2H, NHCH2), 2.30 (s, 3H, CH3)
1572 (CÄN), 690 (CÃSÃC)
3430 (NH), 2915 (CH2), 1758 (CÄO of quinazolon ring),
1560 (CÄN), 688 (CÃSÃC)
4k
9.58 (brs, 1H, NHCH2), 8.25 (s, 1H, NÄCH ÃAr), 7.45Á
/
7.15 (m, 7H,
ArÃH), 4.20 (d, 2H, NHCH2), 2.28 (s, 3H, CH3), 1.25 (s, 6H, ArÃN
(CH3)2)
4l
9.48 (brs, 1H, NHCH2), 9.25 (s, 1H, ArÃOH), 8.20 (s, 1H, NÄCH ÃAr), 3425 (NH), 2910 (CH2), 1760 (CÄO of quinazolon ring),
7.50Á7.10 (m, 6H, ArÃH), 4.22 (d, 2H, NHCH2), 3.40 (s, 3H, ArÃOCH3), 1568 (CÄN), 685 (CÃSÃC)
2.25 (s, 3H, CH3)
9.50 (brs, 1H, NHCH2), 8.30Á
/
5a
5b
5c
5d
5e
5f
/
7.15 (m, 9H, ArÃH), 6.14 (s, 1H, CH ÃAr), 3410 (NH), 2920 (CH2), 1745 (CÄO of b-thialactam
4.25 (d, 2H, NHCH2), 3.68 (s, 2H, CH2 of b-thialactam ring), 2.30 (s, 3H, moiety), 1718 (CÄO of quinazolon ring), 1632 (CÄN), 688
CH3)
(CÃSÃC)
9.40 (brs, 1H, NHCH2), 8.25Á
/
7.15 (m, 8H, ArÃH), 6.10 (s, 1H, CH ÃAr), 3400 (NH), 2900 (CH2), 1750 (CÄO of b-thialactam
4.20 (d, 2H, NHCH2), 3.65 (s, 2H, CH2 of b-thialactam ring), 3.60 (s, 3H, moiety), 1720 (CÄO of quinazolon ring), 1635 (CÄN), 690
ArÃOCH3), 2.39 (s, 3H, CH3)
9.45 (brs, 1H, NHCH2), 8.20Á
(CÃSÃC)
/
7.10 (m, 8H, ArÃH), 6.15 (s, 1H, CH ÃAr), 3400 (NH), 2910 (CH2), 1745 (CÄO of b-thialactam
4.25 (d, 2H, NHCH2), 3.62 (s, 2H, CH2 of b-thialactam ring), 3.40 (s, 3H, moiety), 1718 (CÄO of quinazolon ring), 1639 (CÄN), 689
ArÃOCH3), 2.32 (s, 3H, CH3)
9.55 (brs, 1H, NHCH2), 9.10 (s, 1H, ArÃOH), 8.10Á
6.20 (s, 1H, CH ÃAr), 4.30 (d, 2H, NHCH2), 3.60 (s, 2H, CH2 of b-
thialactam ring), 2.30 (s, 3H, CH3)
(CÃSÃC)
/
7.12 (m, 8H, ArÃH), 3420 (NH), 2918 (CH2), 1760 (CÄO of b-thialactam
moiety), 1720 (CÄO of quinazolon ring), 1645 (CÄN), 685
(CÃSÃC)
9.60 (brs, 1H, NHCH2), 8.10Á
/
7.00 (m, 8H, ArÃH), 6.10 (s, 1H, CH ÃAr), 3410 (NH), 2920 (CH2), 1750 (CÄO of b-thialactam
4.20 (d, 2H, NHCH2), 3.60 (s, 2H, CH2 of b-thialactam ring), 2.25 (s, 3H, moiety), 1725 (CÄO of quinazolon ring), 1640 (CÄN), 688
CH3), 1.55 (s, 6H, ArÃN (CH3)2)
9.50 (brs, 1H, NHCH2), 9.15 (s, 1H, ArÃOH), 8.20Á
(CÃSÃC)
/
7.00 (m, 7H, ArÃH), 3400 (NH), 2915 (CH2), 1740 (CÄO of b-thialactam
6.25 (s, 1H, CH ÃAr), 4.35 (d, 2H, NHCH2), 3.65 (s, 2H, CH2 of b-
thialactam ring), 3.45 (s, 3H, ArÃOCH3), 2.28 (s, 3H, CH3)
moiety), 1728 (CÄO of quinazolon ring), 1648 (CÄN), 682
(CÃSÃC)