Figure 1: Base molecule 2-Cyclohexa-1, 5-diphenyl-4-phenyl-[2, 3’] bithiazolyl-4’-one
|
|||||
Compounds |
S. aureus |
B. substills |
E. coli |
C. albicans |
A. niger |
3a |
+ |
+++ |
+ |
++ |
++ |
3b |
++ |
++ |
+++ |
+++ |
++ |
3c |
+ |
++ |
+++ |
++ |
++ |
3d |
_ |
+++ |
+ |
+++ |
+++ |
3e |
+++ |
++ |
++ |
+++ |
++ |
3f |
++ |
+++ |
_ |
++ |
++ |
3g |
+++ |
_ |
+ |
_ |
+++ |
3h |
++ |
+ |
+++ |
++ |
_ |
3i |
_ |
+++ |
+ |
+++ |
+++ |
3j |
_ |
+++ |
+ |
+++ |
+++ |
3k |
+++ |
++ |
++ |
+++ |
++ |
3l |
++ |
+++ |
_ |
++ |
++ |
3m |
+++ |
_ |
+ |
_ |
+++ |
3n |
++ |
+ |
+++ |
++ |
_ |
3o |
_ |
+++ |
+ |
+++ |
+++ |
SM (streptomycin) and G F (Griseofulvin). The inhibition diameter in
Mm (-) < 6, (+) 7-9, (++) 10-15, (+++) 16-22, (++++) 23-28
Table 1: Antibacterial and Antifungal activities of compounds 3a-o
|
|||||||||
Comp |
R* |
Mol. Formula |
Mol. Wt |
M.Pt (C0) |
RF Value |
% Yield |
Analysis found |
||
3a |
H |
C18H 14 O2 N 2S |
322 |
165 |
0.91 |
83 |
67.08 |
4.34 |
8.69 |
3b |
2-OH |
C17H16 O2N 2S |
338 |
172 |
0.72 |
79 |
63.90 |
4.14 |
7.62 |
3c |
3-OH |
C17H16 O2N 2S |
338 |
181 |
0.75 |
75 |
63.90 |
4.14 |
7.62 |
3d |
4-OH |
C17H16 O2N 2S |
338 |
188 |
0.82 |
58 |
63.90 |
4.14 |
7.62 |
3e |
2-NO2 |
C18H 13O4N3S |
367 |
191 |
0.77 |
54 |
58.85 |
3.54 |
11.4 |
3f
|
3-NO2 |
C18H 13O4N3S |
367 |
191 |
0.77 |
54 |
58.85 |
3.54 |
11.4 |
3g |
4-NO2 |
C18H 13O4N3S |
367 |
191 |
0.77 |
54 |
58.85 |
3.54 |
11.4 |
3h |
2-CL |
C18H13O2N2SCI |
356 |
161 |
0.75 |
56 |
60.67 |
3.65 |
7.86 |
3i |
4-CL |
C18H13O2N2SCI |
356 |
161 |
0.75 |
56 |
60.67 |
3.65 |
7.86 |
3j |
3-OCH3 |
C19H16O3N2S |
352 |
144 |
0.66 |
66 |
64.77 |
4.54 |
7.9 |
3k |
4-OCH3 |
C19H16O3N2S |
352 |
144 |
0.66 |
66 |
64.77 |
4.54 |
7.9 |
3l |
3-(OCH3)3 |
C21H20O3N2S |
380 |
138 |
0.73 |
68 |
66.31 |
5.26 |
7.36 |
3m |
-N(CH3)2 |
C20H19O2N3S |
365 |
172 |
0.77 |
62 |
65.75 |
5.20 |
11.5 |
3n |
2-Br |
C18H13O2N2SBr |
391 |
163 |
0.73 |
59 |
55.24 |
3.32 |
7.16 |
3o |
4-Br |
C18H13O2N2SBr |
391 |
163 |
0.73 |
59 |
55.24 |
3.32 |
7.16 |
Table 2: Characterization data of newly synthesized 2-[4 oxo-2-substituted-aryl Thiazolidinyl] substituted phenyl thiazole 3(a-o)
|
|||
compounds |
IR(KBr) |
H1NMR (300MHz DMSO) |
C13NMR (300MHz, DMSO-d6) |
3a |
2945 (C-H Aromatic stretch) 1791.8, 1713, 1641, 1520, 779 (C-S) |
9.53 (S1H NH) |
14.2,13.1,13.6,23.0,37.9,38.2, |
3b |
2945 (C-H Aromatic stretch),3275(OH of phenyl ring) 1639 & 1655 cyclic carbonyl ring,690 (C-S-C linkage of thiazolidinone ring),1152 (c-o str)3209 (N-H Stretch) 1791.8,1713,1641,1520,779(C-S); |
2.24,4.23,3.56 6.8-7.8 (M.8H Aromatic proton) 3.5 (s,2H,CH2 Thiazolidine ring) |
14.1,13.0,13.62,23.1,37.9,38. 137.1,160.2,162.1. |
3c |
2945 (C-H Aromatic stretch) 3272(OH of phenyl ring) 1637 & 1653 cyclic carbonyl ring,693(C-S-C linkage of thiazolidinone ring),1151 (c-o str)3208 (N-H Stretch) 1791.8,1713,1641,1520,779 (C-S); |
2.24,4.21,3.54 6.8-7.8(M.8H Aromatic proton)3.4(s,2H,CH2 Thiazolidine ring |
14.2,13.1,13.2,23.0,37.8,38.1, 34.2,39.4,40.1, 58.5,76.5,7.3,111.3,159.2,126.1, 137.32,160.2,162.2. |
3d |
2945 (C-H Aromatic stretch) 3274(OH of phenyl ring) 1638 & 1650 cyclic carbonyl ring,691(C-S-C linkage of thiazolidinone ring),1150 (c-o str) 3207(N-H Stretch) 1791.8,1713,1641,1520,779(C-S) |
2.25,4.20,3.52 6.8-7.8(M.8H Aromatic proton)3.3(s,2H,CH2 Thiazolidine ring) |
14.2,13.1,13.6,23.0,37.9,38.2, 34.5,39.4,40.0,58.5,76.8,7.3,111.8, 159.1,126.2,137.3,160.2,162.1. |
3e |
2945 (C-H Aromatic stretch)1791.8, 1713, 1641, 1520, 779(C-S) |
2.22,4.20,3.51 6.8-7.8(M.8H Aromatic proton)3.3(s, 2H,CH2 Thiazolidine ring) |
14.2, 13.1, 13.2, 23.1, 37.9, 38.1, 34.2, 39.4, 40.0, 58.1, 76.8, 7.3, 111.2, 159.0, 126.1, 137.3, 160.1, 162.1. |
3f |
2945 (C-H Aromatic stretch)1791.8, 1713, 1641, 1520, 779 (C-S) |
2.20,4.21,3.54m, 6.8-7.8(M.8H Aromatic proton) 3.3( s, 2H, CH2 Thiazolidine ring) |
14.1, 13.2, 13.0, 23.0, 37.9, 38.1, 34.5, 39.2, 40.0, 58.2, 76.8, 7.3, 111.2, 159.1, 126.2, 137.3, 160.2, 162.1. |
3g |
2942 (C-H Aromatic stretch) 1791.8, 1713, 1641, 1520, 779 (C-S) |
2.24,4.23,3.56 6.8-7.8 (M.8H Aromatic proton)3.4 (s,2H,CH2 Thiazolidine ring) |
14.0,13.1,13.6,23.1,37.9,38.0, 34.5, 39.4, 40.0, 58.2,76.2,7.3,111.3,159.1,126.1, 137.2,160.2,162.1. |
3h |
2944 (C-H Aromatic stretch) 1791.8,1713,1641,1520,779(C-S); 1689(C= O) of thiazolidinone ring |
2.24, 4.23, 3.56 6.5-7.8 (M.8H Aromatic proton) 3.3 ( s, 2H, CH2 Thiazolidine ring) |
14.0,13.213.6,23.0,37.9,38.2, 34.2,39.1,40.0,58.51,76.2,7.,111.3, 159.1,126.2,137.3,160.2,162.1. |
3i |
2941 (C-H Aromatic stretch) 1791.8, 1713, 1641, 1520, 779 (C-S); |
2.24, 4.23, 3.56, 6.7-7.8 (M.8H Aromatic proton) 3.3 (s, 2H, CH2 Thiazolidine ring) |
14.2,13.1, 13.5, 23.1, 37.9, 38. 2, 34.5, 39.4, 40.1,58.5,76.8,7.3,111.8,159.1, 126.2,137.3,160.2,162.1. |
3j |
2945 (C-H Aromatic stretch),3275(OH of phenyl ring) 1639 & 1655 cyclic carbonyl ring,690 (C-S-C linkage of thiazolidinone ring),1152 (c-o str)3209 (N-H Stretch) 1791.8,1713,1641,1520,779(C-S); |
2.24,4.23,3.56 6.8-7.8 (M.8H Aromatic proton) 3.5 (s,2H,CH2 Thiazolidine ring) |
14.1,13.0,13.62,23.1,37.9,38.0, 34.1,39.2,40.1,58.3,72.3,7.3,111.5, 159.1,126.0,137.1,160.2,162.1. |
3k |
2945 (C-H Aromatic stretch) 3272(OH of phenyl ring) 1637 & 1653 cyclic carbonyl ring,693(C-S-C linkage of thiazolidinone ring),1151 (c-o str)3208 (N-H Stretch) 1791.8,1713,1641,1520,779(C-S) |
2.24,4.21,3.54 6.8-7.8(M.8H Aromatic proton)3.4(s,2H,CH2 Thiazolidine ring |
14.2,13.1,13.2,23.0,37.8,38.1,34.2, 39.4,40.1,58.5,76.5,7.3,111.3, 159.2,126.1,137.32,160.2,162.2. |
3l |
2945 (C-H Aromatic stretch) 3274(OH of phenyl ring) 1638 & 1650 cyclic carbonyl ring,691(C-S-C linkage of thiazolidinone ring),1150 (c-o str) 3207(N-H Stretch) 1791.8,1713,1641,1520,779(C-S) |
2.25,4.20,3.52 6.8-7.8(M.8H Aromatic proton)3.3(s,2H,CH2 Thiazolidine ring) |
14.2,13.1,13.6,23.0,37.9,38.2, 34.5,39.4,40.0,58.5, 76.8,7.3,111.8,159.1,126.2, 137.3,160.2,162.1
|
3m |
2945 (C-H Aromatic stretch)1791.8, 1713, 1641, 1520, 779(C-S) |
2.22,4.20,3.51 6.8-7.8(M.8H Aromatic proton)3.3(s, 2H,CH2 Thiazolidine ring) |
14.2, 13.1, 13.2, 23.1, 37.9, 38.1, 34.2, 39.4, 40.0, 58.1, 76.8, 7.3, 111.2, 159.0, 126.1, 137.3, 160.1, 162.1 |
3n |
2945 (C-H Aromatic stretch)1791.8, 1713, 1641, 1520, 779 (C-S) |
2.20,4.21,3.54m, 6.8-7.8(M.8H Aromatic proton) 3.3( s, 2H, CH2 Thiazolidine ring) |
14.1, 13.2, 13.0, 23.0, 37.9, 38.1, 34.5, 39.2, 40.0, 58.2, 76.8, 7.3, 111.2, 159.1, 126.2, 137.3, 160.2, 162.1 |
3o |
2942 (C-H Aromatic stretch) 1791.8, 1713, 1641, 1520, 779 (C-S) |
2.24,4.23,3.56 6.8-7.8 (M.8H Aromatic proton)3.4 (s,2H,CH2 Thiazolidine ring) |
14.0,13.1,13.6,23.1,37.9,38.0, 34.5, 39.4, 40.0, 58.2,76.2,7.3,111.3,159.1,126.1, 137.2,160.2,162.1 |
Table 3: IR, H1NMR & C13NMR of newly synthesized 3(a-o)
|
||||
|
Surface Dot 3-D structure |
Binding Energy |
H-bond distance |
Amino acids |
1* |
-11.6863 |
2.744652 |
955-DEF |
|
2 |
-10.7636 |
|
958- DEF |
|
3 |
-10.0056 |
2.452949 |
145 -ASP |
|
4 |
-10.0197 |
2.633822 |
83-LEU |
|
5 |
-10.0197 |
2.895364 |
145- ASP |
|
6 |
-10.3206 |
2.907496 |
125 -HIS |
|
7 |
-9.84859 |
2.555301, 2.892527, 2.900609A |
14 -THR |
|
8* |
-11.0653 |
2.980913A |
85-GLN,85-LEU |
|
9 |
|
|
|
|
10 |
-9.62396 |
2.59475, |
83-LEU |
|
11 |
-9.62396 |
2.59475, |
83-LEU |
|
12 |
-10.7636 |
--- |
|
|
13 |
-9.68543 |
---- |
|
|
14 |
-10.5341 |
2.840492 |
|
|
15 |
-10.475 |
1.064365 |
145- ASP |
Table 4: Lists obtained binding energies for all docked molecules
Figure 1: Base molecule 2-Cyclohexa-1, 5-diphenyl-4-phenyl-[2, 3’] bithiazolyl-4’-one
Figure 2: Natural Inhibitor 3-methoxy-4-{3-[4-(4-methylpiperazin-1-yl)-1H- benzimidazol-2-yl]-1H-indazol-6-yl} aniline of PDB ID 3EZR [9,10]
Figure 3: Substituted 2-Cyclohexa-1,5-dienyl-4-phenyl-[2,3] bithiazolyl-4-one
Scheme 1:
Tables at a glance
Figures at a glance