Antitubercular Activity of Quinoxalines
CH-N), 3.9 (1H, s, C-NH) and 2.3 (3H, s, (Ar-CH3) p.p.m.; 13C (DMSO-
d6) d: 164.11, 165.52, 134.73 and 63.16 p.p.m.; FAB-MS (m ⁄ z): 505
(M+, 5%), 506 (M+ + 1, 4%), 504 (M+ ) 1, 7%), 428 (17%), 325
(27%), 235 (36%), 191 (37%), 132 (34%), 106 (100%) and 77(33%).
Anal. Calcd for C30H24ClN5O: C, 71.21%; H, 4.78%; N, 13.84%.
Found: C, 71.20%; H, 4.75%; N, 13.81%.
and 765 (Azetidinone, C-Cl); 1H NMR (DMSO-d6, 300 MHz) d: 5.8
(1H, s, CH-Cl of Azetidinone), 5.2 (1H, s, CH-N), 4.0 (1H, d, J = 1 .8,
C-NH), 4.9 (1H, s, Ar-OH) and 3.7 (3H, s, OCH3) p.p.m.; 13C (DMSO-
d6) d: 143.7, 150.2, 143.43, 63.79 and 56.21 p.p.m.; FAB-MS (m ⁄ z):
537 (M+, 4%), 538 (M+ +1, 4%), 536 (M+ ) 1, 3%), 431 (8%), 311
(6%), 221 (17%), 123 (30%), 80 (100%) and 90 (32%). Anal. Calcd
for C30H24ClN5O3: C, 66.97%; H, 4.53%; N, 13.00%. Found: C,
66.97%; H, 4.53%; N, 13.00%.
3-Choro-4-(4-(dimethylamino)phenyl)-1-(2-((E)-
((E)-3(phenylimino)-3,4-dihydroquinoxalin-2-(1H)-
ylidene)amino)phenyl)azetidin-2-one (2t)
2-(2-Hydroxyphenyl)-3-(2-((Z)-((E)-3-
Yield 11.48%; m.p. 190–192 ꢀC; IR (tmax, ⁄ cm, KBr): 3348 (N-
H),2967(C-H), 1437(C-N), 1753 (Azetidinone, C=O), 1655 (C=N), 1290
(N-(CH3)2) and 765 (Azetidinone, C-Cl); 1H NMR (DMSO-d6,
300 MHz) d: 5.3 (1H, s, CH-Cl of Azetidinone), 5.2 (1H, dd,
J = 1.7,8.34, CH-N), 4.0 (1H, s, C-NH) and 2.9 (6H, s, N-(CH3)2)
p.p.m.; 13C (DMSO-d6) d: 164.22, 162.34, 147.64, 135.56 and
40.3 p.p.m.; FAB-MS (m ⁄ z): 534 (M+, 9%), 535 (M + 1, 7%), 533
(M+ ) 1, 7%), 313 (16%), 222 (18%), 180 (28%), 132 (25%), 106
(100%), 103 (23%) and 77(42%). Anal. Calcd for C31H27ClN6O: C,
69.59%; H, 5.06%; N, 15.70%. Found: C, 69.55%; H, 5.06%; N,
15.70%.
(phenylimino)-3,4-dihydroquinoxalin-2-(1H)-
ylidene)amino)phenyl)thiazolidin-4-one (3n)
Yield 82%; m.p. 250–252 ꢀC; IR (tmax, ⁄ cm, KBr): 3367 (Ar-OH),
1
2993 (C-H), 1660 (C=O), 1451 (C=N) and 613 (C-S); H NMR (DMSO-
d6, 300 MHz) d: 4.5 (2H, s, NH), 3.5 (2H, s, CH2), 6.0 (1H, s, CH)
and 7.5(Ar-OH) p.p.m.; 13C (DMSO-d6) d: 162.02, 143.45,131.4, 119
and 110.6 p.p.m.; FAB-MS (m ⁄ z): 505 (M+ 6%), 506 (M+ + 1 3%),
504 (M+ ) 1 5%), 465(19%), 441 (18%), 367 (26%), 192 (25%), 132
(27%) and 91 (100%). Anal. Calcd for C29H23N5O2S: C, 68.89%; H,
4.59%; N, 13.85%. Found: C, 68.86%; H, 4.56%; N, 13.88%.
2-(4-Hydroxyphenyl)-3-(2-((Z)-((E)-3-
3-Choro-4-(3-nitrophenyl)-1-(2-((E)-((E)-
(phenylimino)-3,4-dihydroquinoxalin-2-(1H)-
ylidene)amino)phenyl)thiazolidin-4-one (3o)
3(phenylimino)-3,4-dihydroquinoxalin-2-(1H)-
ylidene)amino)phenyl)azetidin-2-one (2u)
Yield 45.03%; m.p. 212–214 ꢀC; IR (tmax, ⁄ cm, KBr):3347 (N-H),
1748 (Azetidinone, C=O), 1658 (C=N), 1557 (C-NO2) and 764 (Azetidi-
none, C-Cl); 1H NMR (DMSO-d6, 300 MHz) d: 5.7 (1H, d, J = 5.8,
CH-Cl of Azetidinone), 5.2 (1H, s, CH-N) and 3.8 (1H, s, C-NH)
p.p.m.; 13C (DMSO-d6) d: 163.01, 162.06, 162.06, 148.23, 135.31
and 62.74 p.p.m.; FAB-MS (m ⁄ z): 536 (M+, 7%), 537 (M+ + 1, 6%),
535 (M+ ) 1, 4%), 430 (8%), 310 (16%), 289 (12%), 225 (14%), 221
(18%), 144 (48%), 85(31%), 80 (100%) and 48(47%). Anal. Calcd for
C29H21ClN6O3: C, 64.87%; H, 3.94%; N, 15.65%. Found: C, 64.84%;
H, 3.91%; N, 14.51%.
Yield 69%; m.p. 238–240 ꢀC; IR (tmax
, ⁄ cm, KBr): 3349(N-H),
1
2885(C-H), 1614 (C=O), 1505(C=N) and 663 (C-S); H NMR (DMSO-
d6, 300 MHz) d: 4.3 (2H, s, NH), 3.7 (2H, s, CH2), 6.1 (1H, s, CH)
and 7.7 (Ar-OH) p.p.m.; 13C (DMSO-d6) d: 163.03, 156.4, 112.6,
133.4, 119. p.p.m.; FAB-MS (m ⁄ z): 505 (M+, 9%), 506 (M+ +1, 5%),
504 (M+ ) 1, 7%), 412(16%), 312 (15%), 221(18%), 192 (15%), 132
(13%) and 91 (100%). Anal. Calcd for C29H23N5O2S: C, 68.89%; H,
4.59%; N, 13.85%. Found: C, 68.87; H, 4.57; N, 13.88.
2-(2-Methoxyphenyl)-3-(2-((Z)-((E)-3-
(phenylimino)-3,4-dihydroquinoxalin-2-(1H)-
ylidene)amino)phenyl)thiazolidin-4-one (3p)
3-Choro-4-(furan-3-yl)-1-(2-((E)-((E)-
Yield 74%; m.p. 244–246 ꢀC; IR (tmax, ⁄ cm, KBr): 3365(N-H),
3(phenylimino)-3,4-dihydroquinoxalin-2-(1H)-
ylidene)amino)phenyl)azetidin-2-one (2v)
Yield 61.75%; m.p. 258–262 ꢀC; IR (tmax, ⁄ cm, KBr): 3349 (N-H),
2991(C-H), 1758 (Azetidinone, C=O), 1665 (C=N), and 765 (Azetidinone,
2992(C-H), 1613 (C=O), 1518(C=N), 1278(Ar-OCH3) and 720(C-S); 1H
NMR (DMSO-d6, 300 MHz) d: 4.2 (2H, s, NH), 3.4 (2H, s, CH2), 5.4
(1H, s, CH) and 4.8 (1H, s, OCH3) p.p.m.; 13C (DMSO-d6) d: 163.87,
150.6, 133.4, 130.3 and 119 p.p.m.; FAB-MS (m ⁄ z): 519(M+, 3%),
520 (M++ 1, 5%), 518 (M+ ) 1, 7%), 412 (31%) 288 (22%),130
(100%) 91 (36%) and 106 (29%). Anal. Calcd for C30H25N5O2S: C,
69.34%; H, 4.85%; N, 13.48%. Found: C, 69.31%; H, 4.77%; N,
13.35%.
1
C-Cl); H NMR (DMSO-d6, 300 MHz) d: 5.7 (1H, dd, J = 1.53, 8.23,
CH-Cl of Azetidinone), 5.1 (1H, d, J = 3.8, CH-N) and 4.0 (1H, s, C-NH)
p.p.m.; 13C (DMSO-d6) d: 162.04, 142.01, 129.26 and 62.87 p.p.m.;
FAB-MS (m ⁄ z): 481 (M+, 5%), 482 (M+ + 1, 5%), 480 (M+ ) 1, 3%),
414 (12%), 311 (7%), 221 (17%), 185 (23%), 170 (10%), 106 (100%)
and 91(39%). Anal. Calcd for C27H20ClN5O2: C, 67.29%; H, 4.18%; N,
14.53%. Found: C, 67.30%; H, 4.15%; N, 14.51%.
2-(4-Chlorophenyl)-3-(2-((Z)-((E)-3-(phenylimino)-
3,4-dihydroquinoxalin-2-(1H)-
ylidene)amino)phenyl)thiazolidin-4-one (3q)
Yield 71%; m.p. 251–253 ꢀC; IR (tmax, ⁄ cm, KBr):3369 (N-H), 2993
(C-H), 1613 (C=O), 1459 (C=N) and 612 (C-S); 1H NMR (DMSO-d6,
300 MHz) d: 4.3 (2H, s, NH), 3.4 (2H, s, CH2) and 5.8 (1H, s, CH)
p.p.m.; 13C (DMSO-d6) d: 164.32, 133.4, 131.56, 130.3 and
119 p.p.m.; FAB-MS (m ⁄ z): 523 (M+, 8%), 524 (M+ + 1, 5%), 522
3-Choro-4-(4-hydroxy-3-methoxyphenyl)-1-(2-
((E)-((E)-3(phenylimino)-3,4-dihydroquinoxalin-2-
(1H)-ylidene)amino)phenyl)azetidin-2-one (2w)
Yield 47.68%; m.p. 182–186 ꢀC; IR (tmax, ⁄ cm, KBr): 3389 (Ar-OH),
3348 (N-H), 1743 (Azetidinone, C=O), 1665 (C=N), 1229 (Ar-OCH3)
Chem Biol Drug Des 2011; 78: 988–998
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