J 6.4 Hz, CH ), 1.25 (m, 24H, 12CH ), 1.66 (m, 2H, CH β), 2.33
CH ), 2.33 (t, 2H, J 7.7 Hz, CH α), 2.48 (t, 1H), 3.9 (m, 1H),
2 2
3
2
2
(
2
t, 2H, J 7.3 Hz, CH α), 7.61 (dd, 2H, 2CH-aromatic), 8.67 (dd,
5.47 (m, 2H, CH -vinyl), 7.63 (d, 2H, 2CH-aromatic), 8.69 (s,
2
2
1
3
13
H, 2CH-aromatic), 9.42 (s, 1H, NH), 10.61 (s, 1H, NH).
C
2H, 2CH-aromatic), 9.25 (s, 1H, NH), 10.43 (s, 1H, NH).
C
NMR (75 MHz, CDCl ): δ (ppm) 14.1 (CH ), 22.7–34.2 (14CH ),
NMR (75 MHz, CDCl ): δ (ppm) 14.1 (CH ), 22.6–36.8 (13CH ),
3 3 2
3
3
2
1
20.9 (2CH-aromatic), 138.2 (C-aromatic), 150.5 (2CH-
71.64 (1C), 121.8 (2CH-aromatic), 125.4 (2CH-vinyl), 133 (C-
aromatic), 149.2 (2CH-aromatic), 162.5 (CO), 171.9 (CO).
aromatic), 162.6 (CO), 171.7 (CO).
4
.4.4. N'-octadecaisonicotinohydrazide (3b)
4.4.8. (6Z,9Z)-N'-octadeca-6,9-dienoylisonicotinohydrazide (3f)
-
1
-1
MW 403 g·mol . White solid. Yield: 0.3 g, 60%. Anal. calcd.
for C H O N : C, 70.59; H, 10,24; N, 10.41; found C, 70.59; H,
1
MW 399 g·mol . Yellow pasty solid. Yield: 0.45 g, 90%.
Anal. calcd. for C H O N : C, 72.14; H, 9.33; N, 10.52; found
2
4
41
2
3
24 37
2
3
1
6
-
0.37; N, 10.61. Mp 125–127 °C (Lit. 125–126 °C). IR (KBr): v
C, 69.19; H, 9.57; N, 9.32. Mp: 70–72 °C. IR (NaCl, film): v (cm
) 1465 (m), 1645 (F), 1695 (f), 2854 (f), 2927 (F), 3010 (f), 3217
(m). H NMR (300 MHz, CDCl ): δ (ppm) 0.81 (t, 3H, J 6.8 Hz,
-
1
1
(cm ) 1409 (m), 1550 (f), 1597 (F), 2848 (F), 2916 (F), 3014
1
1
(m), 3215 (F). H NMR (300 MHz, CDCl ): δ (ppm) 0.88 (t, 3H,
3
3
J 6.8 Hz, CH ), 1.25 (m, 28H, 14CH ), 1.69 (m, 2H, CH β), 2.34
CH ), 1.23 (m, 14H, 7CH ), 1.58 (m, 2H, CH β), 1.97 (m, 4H,
3
2
2
3
2
2
(
2
t, 2H, J 7.78 Hz, CH α), 7.62 (dd, 2H, 2CH-aromatic), 8.7 (dd,
H, 2CH-aromatic), 9.04 (s, 1H, NH). C NMR (75 MHz,
2CH -allyl), 2.25 (t, 2H, CH α), 2.69 (t, 2H, 2CH-bis-allyl), 5.28
2 2
2
1
3
(m, 4H, 2CH-vinyl), 7.56 (dd, 2H, 2CH-aromatic), 8.59 (dd, 2H,
1
3
CDCl ): δ (ppm) 13.9 (CH ), 22.5–34 (16 CH ), 121.3 (2CH-
2CH-aromatic), 9.21 (s, 1H, NH), 9.68 (s, 1H, NH). C NMR
3
3
2
aromatic), 139.5 (C-aromatic), 150 (2 CH-aromatic), 163.7 (CO),
(100 MHz, CDCl ): δ (ppm) 14 (CH ), 22.5–34.1 (12CH ), 121.1
3
3
2
1
72 (CO).
(2CH-aromatic), 127.9 (CH-vinyl), 128.1 (CH-vinyl), 129.9 (CH-
vinyl), 130.2 (CH-vinyl), 138.6 (C-aromatic), 150.4 (2CH-
aromatic), 162.8 (CO), 171.5 (CO).
4
.4.5. (Z)-N'-octadeca-9-enoylisonicotinohydrazide (3c)
-
1
MW 401 g·mol . Yellow pasty solid. Yield: 0.44 g, 88%.
Anal. calcd. for C H O N : C, 71.78; H, 9.79; N, 10.46; found
C, 71.71; H, 9.74; N, 9.88. Mp: 86–88 °C (Lit. 80–81 °C). IR
2
4
39
2
3
4.4.9. (9Z,12Z,15Z)-N'-octadeca-9,12,15-
trienoylisonicotinohydrazide (3g)
1
7
-
1
-1
(NaCl, film): v (cm ) 1463 (m), 1645 (F), 1695 (f), 2854 (f),
MW 397 g·mol . Yellow pasty solid. Yield: 0.35 g, 71%.
1
2
926 (F), 3012 (m), 3221 (F). H NMR (400 MHz, CDCl ): δ
Anal. calcd. for C H O N : C, 72.51; H, 8.87; N, 9.78; found C,
3
24 35
2
3
-
1
(ppm) 0.86 (t, 3H, J 7.09 Hz, CH ), 1.26 (m, 20H, 10CH ), 1.64
69.73; H, 8.73; N, 9.78.IR Mp: 69–71 °C. (NaCl, film): v (cm )
3
2
(
m, 2H, CH β), 1.98 (m, 4H, J 6.1 Hz, 2CH -allyl), 2.31 (t, 2H, J
1465 (m), 1643 (F), 1695 (f), 2854 (f), 2929 (F), 3014 (F), 3223
2
2
1
7
2
1
.4 Hz, CH α), 5.32 (m, 2H, J 4.4 Hz, 2CH-vinyl), 7.61 (d, 2H,
(m). H NMR (400 MHz, CDCl ): δ (ppm) 0.97 (t, 3H, J 7.5 Hz,
2
3
CH-aromatic), 8.65 (d, 2H, 2CH-aromatic), 9.37 (s, 1H, NH),
CH ), 1.3 (m, 10H, 5CH ), 1.64 (m, 2H, CH β), 2.07 (m, 4H,
3
2
2
1
3
0.3 (s, 1H, NH). C NMR (100 MHz, CDCl ): δ (ppm) 14.1
2CH -allyl), 2.32 (t, 2H, J 7.4 Hz, CH α), 2.80 (t, 4H, J 5.7 Hz,
2 2
3
(
1
1
CH ), 22.6–34 (14CH ), 121 (2 CH-aromatic), 129.6 (CH-vinyl),
30 (CH-vinyl), 138.4 (C-aromatic), 150.5 (2 CH-aromatic),
62.8 (CO), 171.6 (CO).
2CH -bis-allyl), 5.36 (m, 6H, 3CH -vinyl), 7.62 (dd, 2H, 2CH-
2 2
aromatic), 9.27 (s, 1H, NH), 10.33 (s, 1H, NH). C NMR (100
3
2
1
3
MHz, CDCl ): δ (ppm) 14.2 (CH ), 20.5–34.2 (12CH ), 121.1
3
3
2
(2CH-aromatic), 127.8 (CH-vinyl), 128.1 (CH-vinyl), 129.9 (CH-
4
.4.6. (E)-N'-octadeca-9-enoylisonicotinohydrazide (3d)
vinyl), 130 (CH-vinyl), 138.4 (C-aromatic), 150.24 (2CH-
aromatic), 162.8 (CO), 171.5 (CO).
-
1
MW 401 g·mol . White solid. Yield: 0.3 g, 60%. Anal. calcd.
for C H O N : C, 71.78; H, 9.79; N, 10.46; found C, 71.90; H,
9
1
2
4
39
2
3
-
1
.80; N, 9.88. Mp: 100–101 °C. IR (KBr): v (cm ) 1411 (m),
Acknowledgments
550 (f), 1598 (F), 2848 (f), 2920 (F), 3020 (f), 3165 (m). ¹H
NMR (400 MHz, CDCl ): δ (ppm) 0.86 (t, 3H, J 6.1 Hz, CH ),
The authors are thankful for financial support from the
Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
(CAPES), the Fundação de Apoio à Pesquisa do Estado do Rio
Grande do Sul (FAPERGS/PRONEM), and the Conselho
Nacional de Desenvolvimento Científico e Tecnológico (CNPq).
The authors would also like to acknowledge fellowships from
CAPES for M. O. Rodrigues and L. A. Piovesan.
3
3
1
4
.26 (m, 20H, 10 CH ), 1.65 (m, 2H, J 7.1 Hz, CH β), 1.94 (m,
2 2
H, 2CH -allyl), 2.3 (t, 2H, J 7.5 Hz, CH α), 5.36 (m, 2H, 2CH-
2
2
vinyl), 7.6 (d, 2H, J 4.8 Hz, J 0.8 Hz, 2CH-aromatic), 8.66 (d,
H, J 5.3 Hz, 2CH-aromatic), 9.1 (s, 1H, NH), 10.12 (s, 1H, NH).
³C NMR (100 MHz, CDCl ): δ (ppm) 14 (CH ), 22.6–34.2
2
¹
3
3
(
14CH ), 120.9 (2CH-aromatic); 130.1 (CH-vinyl), 130.5 (CH-
2
vinyl), 138.5 (C-aromatic), 150.6 (2CH-aromatic), 162.6 (CO),
1
71.2 (CO).
References and notes
1
.
World Health Organization (2010), The Global Plan to Stop TB
Lougheed, K. E. A.; Taylor, D. L.; Osborne, S. A.; Bryans, J. S.;
Buxton, R. S. Tuberculosis 2009, 89, 364.
4
.4.7. (R,Z)-N'-(12-hydroxyoctadec-9-enoyl)
2
isonicotinohydrazide (3e)
MW 417 g·mol . White solid. Yield: 0.15 g, 60%. Anal. calcd.
for C H O N : C, 69.03; H, 9.41; N, 10.06; found C, 61.08; H,
-
1
2
.
2
4
39
2
3
-
1
8
.42; N, 9.67. Mp: 68–70 °C. IR (KBr): v (cm ) 1411(m), 1550
3. Kochi, A.; Vareldzis, B.; Styblo, K. Res. Microbiol. 1993, 144,
04.
Vilchèze, C.; Lacobs Jr., W. R. Annu. Rev. Microbiol. 2007, 61,
5.
1
(f), 1598 (F), 2848 (f), 2920 (F), 3020 (f), 3165 (m). ¹H NMR
4
.
(300 MHz, CDCl ): δ (ppm) 0.90 (m, 3H, CH ), 1.28 (m, 16H, 8
3
3
3
CH ), 1.52 (m, 2H, CH β), 1.7 (m, 4H, 2CH ), 2.02 (m, 2H,
2
2
2