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. Author manuscript; available in PMC: 2010 Oct 1.
Published in final edited form as: Eur J Med Chem. 2009 May 21;44(10):4169–4178. doi: 10.1016/j.ejmech.2009.05.009

Table 1. Preparation of Schiff Bases 2.

Entry Compound R1 R2 % Yield mp, °C C log Pa MIC, μg/mLb
1. 3 H 2-(OCH2C6H5)C6H4 90 185 4.57 0.06c
2. 4 (CH2)4CH3 C6H5 64 116-117 4.49 0.39
3. 5 H 4-BrC6H4 91 218-219 3.84 3.13
4. 6 H 2-ClC6H4 66 218-221 3.56 0.78
5. 7 H 3,4-F2C6H3 86 195-196 3.32 1.56
6. 8 H 4-IC6H4 92 243 4.30 0.20
7. 9 H 3-I-4,5-(OCH3)2C6H2 90 234 3.80 0.20
8. 10 H 3-I-4-OH-5-OCH3C6H2 87 221 3.76 0.39
9. 11 H 4-ClC6H5 94 215-216 3.56 0.20
10. 12 H 3,4-Cl2C6H3 88 241-244 4.08 0.20
11. 13 H 2,6-F2C6H3 100 239 3.32 0.10
12. 14 H 2,3-Cl2C6H3 98 227 4.08 0.78
13. 15 H 2,6-Cl2C6H3 97 semisolid 4.08 <6.25
14. 16 H 2-NO2C6H4 97 230 1.06 0.39
15. 17 H 4-Cl-3-NO2C6H3 100 231 1.58 0.39
16. 18 CH3 C6H5 92 169-170 2.68 <6.25
17. 19 H 4-CH3(CH2)5OC6H4 87 135-138 5.49 0.39
18. 20 H 3-NO2C6H4 85 225 1.06 0.125c
19. 21 H C6H5 98 197 3.04 0.05
20. 22 H 4-CH3(CH2)3OC6H4 91 148-149 4.00 0.10
21. 23 H t-CH=CHCH2CH3 54 161-164 2.24 0.05
22. 24 H t-CH=CHCH3 73 198-201 1.85 <6.25
23. 25 H t-CH=CHCH2CH2CH3 93 152-154 2.64 <6.25
24. 26 H t-CH=CH(CH2)3CH3 84 152-154 3.03 <6.25
25. 27 H C=CCH3CH2CH2CH=CH2 59 124-125 2.97 0.10
26. 28 H CH2CHCH3CH2CH2CH=C(CH3)2 29 78-80 3.58 0.20
27. 29 CH3 CH3 48 161-162 1.70 0.10
28. 30 CH2Ph CH2CO2CH2CH3 90 104 3.78 0.10
29. 31 R1R2 = CCH2CH(CH3)CH2C(CH3)2CH2 76 149-151 3.94 <0.025
30. 32 H CH=C(C6H5)2 86 223 4.43 0.10
31. 33 H t-CH=CH-4-OCH3C6H4 89 218 2.73 0.20
32. 34 H t-CH=CH-2-NO2C6H4 94 204 1.08 0.25c
33. 35 H C(n-C3H7)=CH(CH2)3CH3 84 121 4.10 0.50
34. 36 H C(i-C3H7)=CHCH2CH(CH3)2 99 129 3.97 0.06c
35. 37 H t-CH=CH-2-OCH3C6H4 92 206 2.81 0.10
36. 38 H t-CCH3=CHC6H5 90 200 3.34 0.50
37. 39 H CH=NNHCOC5H4N 90 >300 (d)d 1.58 0.10
38. 40 CH2CH2CH3 CH2CO2CH2CH3 98 89-90 2.96 0.39
39. 41 CH3 CH2CO2CH2CH3 85 99 1.93 0.20
40. 42 H 4-(CH=NNHCOC5H4N)C6H4 90 >300 (d)d 4.04 0.05
41. 43 CH2CH2C6H5 CO2CH2CH3 90 104 4.24 0.10
42. 44 H CH3(CH2)11CH2 73 89-91 5.73 0.20
43. 45 H CH3(CH2)10CH2 73 92-93 5.33 0.20
44. 46 R1R2 = C(CH2CH2)2CH2 81 167-168 2.85 0.03
a

Calculated using HyperChem Pro, Version 7.5. For INH, C log P is 0.49.

b

MIC90 against M. tuberculosis strain H37Rv, unless otherwise noted. MIC INH control 0.03-0.06 μg/mL.

c

MIC90 against M. tuberculosis strain Erdman. MIC INH control 0.03-0.06 μg/mL. MIC PAS control 0.03-0.06 μg/mL.

d

Decomposed without melting.