JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
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4.1.20. 1-(4-(3-Nitrophenyl)thiazol-2-yl)-2-(1-(pyridin-3-yl)ethylide- benzodioxole), 169.1 (C¼N, thiazole). Anal. Calcd for C17H12N4O4S:
C, 55.43; H, 3.28; N, 15.21. Found: C, 55.22; H, 3.04; N, 15.39.
ne)hydrazine (20)
Characterisation data were in agreement with those reported in
the literature30.
4.1.26. 1-(1-(Benzofuran-2-yl)ethylidene)-2-(4-(3-nitrophenyl)thia-
zol-2-yl)hydrazine (26)
Pink powder, mp 228–230 ꢂC, 81% yield; 1H NMR (400 MHz,
DMSO-d6): d 2.37 (s, 3H, CH3), 7.25–7.29 (m, 1H, Ar), 7.31(s, 1H,
C5H-thiazole), 7.34–7.37 (m, 1H, Ar), 7.61–7.63 (m, 4H, Ar)
8.14–8.16 (m, 1H, Ar), 8.32–8.34 (m, 1H, Ar), 8.73 (s, 1H, Ar), 11.61
(bs, 1H, NH, D2O exch.). 13C NMR (101 MHz, DMSO-d6): d 14.3
(CH3), 106.6 (Ar-C5, thiazole), 107.7 (Ar, benzofuran), 111.7 (Ar,
benzofuran), 120.5 (Ar), 122.0 (Ar, benzofuran), 122.5 (Ar), 123.8
(Ar, benzofuran), 125.9 (Ar, benzofuran), 128.6 (Ar, benzofuran),
130.7 (Ar), 132.0 (Ar), 136.7 (Ar), 139.1 (C¼N), 148.6 (Ar-NO2), 148.8
(Ar-C4, thiazole), 154.0 (Ar, benzofuran), 155.0 (Ar, benzofuran),
169.9 (C¼N, thiazole). Anal. Calcd for C19H14N4O3S: C, 60.31; H,
3.73; N, 14.81. Found: C, 60.07; H, 3.97; N, 15.00.
4.1.21. 1-(4-(3-Nitrophenyl)thiazol-2-yl)-2-(1-(pyridin-4-yl)ethylide-
ne)hydrazine (21)
Characterisation data were in agreement with those reported in
the literature30.
4.1.22. 1-(4-(3-Nitrophenyl)thiazol-2-yl)-2-(1-(pyrazin-2-yl)ethylide-
ne)hydrazine (22)
Yellow powder, mp 243–245 ꢂC, 85% yield; 1H NMR (400 MHz,
DMSO-d6): d 2.41 (s, 1H, CH3), 7.71–7.75 (m, 1H, Ar), 7.77 (s, 1H,
C5H-thiazole), 8.16–8.18 (m, 1H, Ar), 8.33–8.35 (m, 1H, Ar),
8.59–8.60 (m, 1H, Ar), 8.63–8.64 (m, 1H, Ar), 8.74–8.75 (m, 1H, Ar),
9.22–9.23 (m, 1H, Ar), 11.82 (bs, 1H, NH, D2O exch.). Anal. Calcd
for C15H12N6O2S: C, 52.93; H, 3.55; N, 24.69. Found: C, 53.20; H,
3.74; N, 24.84.
4.1.27. 1-(1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethylidene)-2-(4-
(3-nitrophenyl)thiazol-2-yl)hydrazine (27)
Orange powder, mp 242–244 ꢂC, 70% yield; 1H NMR (400 MHz,
DMSO-d6): d 2.28 (s, 3H, CH3), 4.28 (s, 4H, benzodioxine), 6.89–6.91
(m, 1H, Ar), 7.27–7.29 (m, 2H, Ar), 7.66 (s, 1H, C5H-thiazole),
7.70–7.74 (t, 1H, Ar), 8.15–8.17 (m, 1H, Ar), 8.31–8.33 (m, 1H, Ar),
8.73 (s, 1H, Ar), 11.28 (bs, 1H, NH, D2O exch.). 13C NMR (101 MHz,
DMSO-d6): d 14.5 (CH3), 64.5 (CH2), 64.7 (CH2), 107.2 (Ar-C5, thia-
zole), 114.9 (Ar, benzodioxine), 117.4 (Ar, benzodioxine), 119.5 (Ar,
benzodioxine), 120.4 (Ar), 122.4 (Ar), 130.7 (Ar), 131.6 (Ar, benzo-
dioxine), 132.0 (Ar), 136.7 (Ar), 143.6 (C¼N), 144.7 (Ar, benzodiox-
ine), 147.1 (Ar, benzodioxine), 148.5 (Ar-NO2), 148.7 (Ar-C4,
thiazole), 170.7 (C¼N, thiazole). Anal. Calcd for C19H16N4O4S: C,
57.57; H, 4.07; N, 14.13. Found: C, 57.80; H, 3.84; N, 58.02.
4.1.23. 1-((1H-Indol-3-yl)methylene)-2-(4-(3-nitrophenyl)thiazol-2-
yl)hydrazine (23)
Yellow powder, mp 253–255 ꢂC, 83% yield; 1H NMR (400 MHz,
DMSO-d6): d 7.20–7.25 (m, 2H, Ar), 7.45–7.47 (m, 1H, Ar), 7.62 (s,
1H, C5H-thiazole), 7.70–7.74 (m, 1H, Ar), 7.79–7.80 (m, 1H, Ar),
8.15–8.17 (m, 1H, Ar), 8.23–8.25 (m, 1H, Ar), 8.29–8.33 (m, 2H, Ar),
8.70 (s, 1H, ¼CH), 11.55 (bs, 1H, NH-indole, D2O exch.), 11.98 (bs,
1H, NH, D2O exch.). 13C NMR (101 MHz, DMSO-d6): d 106.0 (Ar-C5,
thiazole), 112.0 (Ar, indole), 112.4 (Ar, indole), 120.4 (Ar), 121.0 (Ar,
indole), 122.1 (Ar), 122.5 (Ar, indole), 123.1 (Ar, indole), 124.5 (Ar,
indole), 130.3 (Ar, indole), 130.7 (Ar), 132.1 (Ar), 136.6 (Ar), 137.6
(Ar, indole), 140.6 (C¼N), 148.0 (Ar-NO2), 148.7 (Ar-C4, thiazole),
168.7 (C¼N, thiazole). Anal. Calcd for C18H13N5O2S: C, 59.49; H,
3.61; N, 19.27. Found: C, 59.65; H, 3.39; N, 19.49.
4.1.28. 1-(Naphthalen-1-ylmethylene)-2-(4-(3-nitrophenyl)thiazol-2-
yl)hydrazine (28)
Orange powder, mp 212–214 ꢂC, 72% yield; 1H NMR (400 MHz,
DMSO-d6): d 7.59–7.63 (m, 2H, Ar), 7.67–7.75 (m, 3H, 2H Ar þ 1H
C5H-thiazole), 7.87–7.89 (d, J ¼ 8.0 Hz, 1H, Ar), 7.99–8.03 (t, 2H, Ar),
8.16–8.18 (m, 1H, Ar), 8.33–8.35 (d, J ¼ 8.0 Hz, 1H, Ar), 8.70–8.71
(m, 2H, 1H Ar þ 1H ¼ CH), 8.77–8.79 (d, J ¼ 8.0 Hz, 1H, Ar), 12.52
(bs, 1H, NH, D2O exch.). Anal. Calcd for C20H14N4O2S: C, 64.16; H,
3.77; N, 14.96. Found: C, 63.92; H, 3.90; N, 15.12.
4.1.24. 1-(1-(1H-Indol-3-yl)ethylidene)-2-(4-(3-nitrophenyl)thiazol-2-
yl)hydrazine (24)
Green powder, mp 209–211 ꢂC, 87% yield; 1H NMR (400 MHz,
DMSO-d6): d 2.36 (s, 3H, CH3), 7.25–7.28 (m, 2H, 1H C5H-thiazole þ
1H Ar), 7.43–7.47 (m, 1H, Ar), 7.63–7.90 (m, 3H, Ar), 8.12–8.21 (m,
1H, Ar), 8.31–8.50 (m, 2H, Ar), 8.78 (s, 1H, Ar), 11.08 (bs, 1H, NH-
indole, D2O exch.), 11.48 (bs, 1H, NH, D2O exch.). Anal. Calcd for
C19H15N5O2S: C, 60.46; H, 4.01; N, 18.56. Found: C, 60.70; H, 3.83;
N, 18.37.
4.1.29. 1-(1-(Naphthalen-1-yl)ethylidene)-2-(4-(3-nitrophenyl)thia-
zol-2-yl)hydrazine (29)
White powder, mp 226–228 ꢂC, 74% yield; 1H NMR (400 MHz,
DMSO-d6): d 2.33 (s, 3H, CH3), 7.54–7.59 (m, 4H, 3H Ar þ 1H C5H-
thiazole), 7.91–8.00 (m, 4H, Ar), 8.26–8.41 (m, 2H, Ar), 8.56–8.58
(m, 1H, Ar), 8.71–8.75 (m, 1H, Ar), 12.14 (bs, 1H, NH, D2O exch.).
Anal. Calcd for C21H16N4O2S: C, 64.93; H, 4.15; N, 14.42. Found: C,
65.10; H, 3.89; N, 14.21.
4.1.25.
1-(Benzo[d][1,3]dioxol-5-ylmethylene)-2-(4-(3-nitrophe-
nyl)thiazol-2-yl)hydrazine (25)
Yellow powder, mp 255–256 ꢂC, 84% yield; 1H NMR (400 MHz,
DMSO-d6): d 6.08 (s, 2H, OCH2O), 6.96–6.98 (m, 1H, Ar), 7.11–7.13
(m, 1H, Ar), 7.23 (s, 1H, Ar), 7.63 (s, 1H, C5H-thiazole), 7.68–7.72 (m,
1H, Ar), 7.96 (s, 1H, Ar), 8.13–8.15 (m, 1H, Ar), 8.28–8.30 (m, 1H,
Ar), 8.66 (s, 1H, ¼CH), 12.17 (bs, 1H, NH, D2O exch.). 13C NMR
(101 MHz, DMSO-d6): d 101.9 (OCH2O, benzodioxole), 105.1 (Ar,
benzodioxole), 106.7 (Ar-C5, thiazole), 109.0 (Ar, benzodioxole),
120.4 (Ar), 122.4 (Ar), 122.7 (Ar, benzodioxole), 129.2 (Ar, benzo-
dioxole), 130.7 (Ar), 132.0 (Ar), 136.7 (Ar), 142.0 (C¼N), 148.4 (Ar-
4.1.30. 1-(1-(Naphthalen-2-yl)ethylidene)-2-(4-(3-nitrophenyl)thia-
zol-2-yl)hydrazine (30)
Yellow powder, mp 152–154 ꢂC, 77% yield; 1H NMR (400 MHz,
DMSO-d6): d 2.36 (s, 3H, CH3), 7.53–7.55 (m, 2H, Ar), 7.70–7.72 (m,
2H, 1H Ar þ 1H C5H-thiazole), 7.90–7.94 (m, 2H, Ar), 7.96–7.98
NO2), 148.6 (Ar, benzodioxole), 148.7 (Ar-C4, thiazole), 149.0 (Ar, (m, 1H, Ar), 8.03–8.05 (m, 1H, Ar), 8.07–8.09 (m, 1H, Ar), 8.22–8.24