ACCEPTED MANUSCRIPT
R4
R6
N
R5
R4
R4
N
NO2
F
R6
N
R5
b
a
R5
R6
N
N
N
H
+
Cl
N
HN
N
N
Cl
Cl
R2
52a-p
5
1a-n
5
5
5
5
5
5
5
5
5
5
5
5
5
5
1a, R =Cl, R =2-(isopropylsulfonyl)phenyl, R =H
52a, R2=OMe, R4=Cl, R5=2-(isopropylsulfonyl)phenyl, R6=H
52b, R2=OMe, R4=H, R5=2-(isopropylsulfonyl)phenyl, R6=H
52c, R2=OMe, R4=CH3, R5=2-(isopropylsulfonyl)phenyl, R6=H
4
5
6
1b, R =H, R =2-(isopropylsulfonyl)phenyl, R =H
4
5
6
1c, R =CH , R =2-(isopropylsulfonyl)phenyl, R =H
4
3
5
6
5
2d, R =H,R =Cl, R =2-(isopropylsulfonyl)phenyl, R =H
1d, R =Cl, R =3-(trifluoromethyl)phenyl, R =H
2
4
5
6
4
5
6
1e, R =Cl, R =3-chloro-4-fluorophenyll, R =H
52e, R2=OCH(CH3)2, R4=CH3, R5=2-(isopropylsulfonyl)phenyl, R6=H
52f, R2=OMe, R4=Cl, R5=3-(trifluoromethyl)phenyl, R6=H
52g, R2=OMe, R4=Cl, R5=3-chloro-4-fluorophenyll, R6=H
4
5
6
1f, R =Cl, R =2,6-difluorophenyl, R =H
4
5
6
1g, R =Cl, R =thiophen-2-ylmethyl, R =H
4
5
6
5
2h, R =OMe, R =Cl, R =2,6-difluorophenyl, R =H
1h, R =Cl, R =cyclopropyl, R =H
2 4 5 6
4
5
6
1i, R =Cl, R =2-pivalamidophenyl, R =H
52i, R2=OMe, R4=Cl, R5=thiophen-2-ylmethyl, R6=H
52j, R2=OMe, R4=Cl, R5=cyclopropyl, R6=H
4
5
6
1j, R =Cl, R =3-(trifluoromethyl)phenyl, R =CH
4
5
6
3
1k, R =Cl, R =2-(N,N-dimethylsulfamoyl)phenyl, R =H 52k, R2=OMe, R4=Cl, R5=2-pivalamidophenyl, R6=H
4
5
6
5
2l, R =OMe, R =Cl, R =3-(trifluoromethyl)phenyl, R =CH
1l, R =Cl, R =2-(dimethylphosphoryl, R =H
2 4 5 6 3
4
5
6
1m, R =Cl, R =2-(methylcarbamoyl, R =H
52m, R2=OMe, R4=Cl, R5=2-(N,N-dimethylsulfamoyl)phenyl, R6=H
52n, R2=OMe, R4=Cl, R5=2-(dimethylphosphoryl, R6=H
4
5
6
1n, R =Cl, R =2-cyanophenyl, R =H
4
5
6
52o, R =OMe, R =Cl, R =2-(methylcarbamoyl, R =H
2 4 5 6
5
2p, R =OMe, R =Cl, R =2-cyanophenyl, R =H
2
4
5
6
R4
R4
R4
O
R6
R6
R6
N
R5
N
NO2
N
R5
N
NH2
e
N
R5
N
NH
c
d
N
N
N
HN
R3
HN
R3
HN
R3
R2
3a-i'
R2
R2
54a-i'
15-49
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
3a-54a,15; R =OCH , R =4-(4-methylpiperazin-1-yl)piperidin-1-yl, R =Cl, R =2-(isopropylsulfonyl)phenyl, R =H;
2
3
3
4
5
6
3b-54b,16; R =OCH , R =4-(methylsulfonyl)piperazin-1-yl, R =Cl, R =2-(isopropylsulfonyl)phenyl, R =H;
2
3
3
4
5
6
3c-54c,17; R =OCH , R =4-methylpiperazin-1-yl, R =Cl, R =2-(isopropylsulfonyl)phenyl, R =H;
2
3
3
4
5
6
3d-54d,18; R =OCH , R =4-methyl-1,4-diazepan-1-yl, R =Cl, R =2-(isopropylsulfonyl)phenyl, R =H;
2
3
3
4
5
6
3e-54e,19; R =OCH , R =4-isopropylpiperazin-1-yl, R =Cl, R =2-(isopropylsulfonyl)phenyl, R =H;
2
3
3
4
5
6
3f-54f, 20; R =OCH , R =4-(2-methoxyethyl)piperazin-1-yl, R =Cl, R =2-(isopropylsulfonyl)phenyl, R =H;
2
3
3
4
5
6
3g-54g, 21; R =OCH , R =4-cyclohexylpiperazin-1-yl, R =Cl, R =2-(isopropylsulfonyl)phenyl, R =H;
2
3
3
4
5
6
3h-54h, 22; R =OCH , R =4-morpholino, R =Cl, R =2-(isopropylsulfonyl)phenyl, R =H;
2
3
3
4
5
6
3i-54i, 23; R =OCH , R =piperidin-1-yl, R =Cl, R =2-(isopropylsulfonyl)phenyl, R =H;
2
3
3
4
5
6
3j-54j, 24; R =H, R =4-(4-methylpiperazin-1-yl)piperidin-1-yl, R =Cl, R =2-(isopropylsulfonyl)phenyl, R =H;
2
3
4
5
6
3k-54k, 25; R =OCH(CH ) , R =4-ethylpiperazin-1-yl, R =Cl, R =2-(isopropylsulfonyl)phenyl, R =H;
2
3 2
3
4
5
6
3l-54l, 26; R =OCH , R =4-(4-methylpiperazin-1-yl)piperidin-1-yl, R =CH , R =2-(isopropylsulfonyl)phenyl, R =H;
2
3
3
4
3
5
6
3m-54m, 27; R =OCH , R =4-ethylpiperazin-1-yl, R =CH , R =2-(isopropylsulfonyl)phenyl, R =H;
2
3
3
4
3
5
6
3n-54n, 28; R =OCH , R =4-ethylpiperazin-1-yl, R =H, R =2-(isopropylsulfonyl)phenyl, R =H;
2
3
3
4
5
6
3o-54o, 29; R =OCH , R =4-methylpiperazin-1-yl, R =Cl, R =3-(trifluoromethyl)phenyl, R =H;
2
3
3
4
5
6
3p-54p, 30; R =OCH , R =4-methylpiperazin-1-yl, R =Cl, R =3-chloro-4-fluorophenyl, R =H;
2
3
3
4
5
6
3q-54q, 31; R 2=OCH , R =4-methylpiperazin-1-yl, R =Cl, R =2,6-difluorophenyl, R =H;
3
3
4
5
6
3r-54r, 32; R =OCH , R =4-methylpiperazin-1-yl, R =Cl, R =thiophen-2-ylmethyl, R =H;
2
3
3
4
5
6
3s-54s, 33; R =OCH , R =4-methylpiperazin-1-yl, R =Cl, R =cyclopropyl, R =H;
2
3
3
4
5
6
3t-54t, 34; R =OCH , R =4-methylpiperazin-1-yl, R =Cl, R =2-pivalamidophenyl, R =H;
2
3
3
4
5
6
3u-54u, 35; R =OCH , R =4-methylpiperazin-1-yl, R =Cl, R =3-(trifluoromethyl)phenyl, R =CH ;
2
3
3
4
5
6
3
3v-54v, 36; R =OCH , R =4-methylpiperazin-1-yl, R =Cl, R =2-(N,N-dimethylsulfamoyl)phenyl, R =H;
2
3
3
4
5
6
3w-54w, 37; R =OCH , R =4-ethylpiperazin-1-yl, R =Cl, R =2-(dimethylphosphoryl, R =H;
2
3
3
4
5
6
3x-54x, 38; R =OCH , R =4-4-(dimethylamino)piperidin-1-yl, R =Cl, R =2-(dimethylphosphoryl, R =H;
2
3
3
4
5
6
3y-54y, 39; R =OCH , R =4-morpholino, R =Cl, R =2-(dimethylphosphoryl, R =H;
2
3
3
4
5
6
3z-54z, 40; R =OCH , R =4-(methylsulfonyl)piperazin-1-yl, R =Cl, R =2-(dimethylphosphoryl, R =H;
2
3
3
4
5
6
'
3a -54a', 41; R =OCH , R =1,4'-bipiperidin]-1'-yl, R =Cl, R =2-(dimethylphosphoryl, R =H;
2
3
3
4
5
6
3b'-54b', 42; R =OCH , R =4-methylpiperazin-1-yl, R =Cl, R =2-(methylcarbamoyl, R =H;
2
3
3
4
5
6
3c'-54c', 43; R =OCH , R =4-isopropylpiperazin-1-yl, R =Cl, R =2-(methylcarbamoyl, R =H;
2
3
3
4
5
6
'
3d -54d', 44; R =OCH , R =4-acetylpiperidin-1-yl, R =Cl, R =2-(methylcarbamoyl, R =H;
2
3
3
4
5
6
3e'-54e', 45; R =OCH , R =4-(1-methylpiperidin-4-yl)piperazin-1-yl, R =Cl, R =2-(methylcarbamoyl R =H;
2
3
3
4
5
6
3f'-54f', 46; R =OCH , R =4-ethylpiperazin-1-yl, R =Cl, R =2-cyanophenyl, R =H;
2
3
3
4
5
6
3g'-54g', 47; R =OCH , R =4-isopropylpiperazin-1-yl, R =Cl, R =2-cyanophenyl, R =H;
2
3
3
4
5
6
3h'-54h', 48; R =OCH , R =4-morpholino, R =Cl, R =2-cyanophenyl, R =H;
2
3
3
4
5
6
3i'-54i', 49; R =OCH , R =4-(4-methylpiperazin-1-yl)piperidin-1-yl, R =Cl, R =2-cyanophenyl, R =H;
2
3
3
4
5
6