448 Letters in Drug Design & Discovery, 2019, Vol. 16, No. 4
Bhat et al.
(59.78) H (5.02) N (13.94) S (10.64) %; found C (59.55) H
(5.03) N (13.98) S (10.60)% [22].
2.1.1.7.
N-cyclohexyl-2-[(2-hydroxy-3-methoxyphenyl)
methylidene]hydrazine-1-carbothioamide (7)
IR KBr (cm−1): 3348 (OH str.), 3200 (NH str.), 1550
2.1.1.3. 2-[(2-Hydroxy-3-methoxyphenyl)methylidene]-N-
phenylhydrazine-1-carbothioamide (3)
1
(C=N str.), 1263 (NCSN str.), 1121 (C=S str.); H NMR
(DMSO‒d6, 500 MHz) δ: 1.12‒2.0 (10 H, m, cyclohexyl),
4.20 (1H, s, cyclohexyl), 6.70‒7.50 (3H, m, Ar‒H), 7.92
(1H, s, =CH), 8.41 (1H, s, =NNH, D2O exchg.), 11.38 (1H,
s, NHC=S, D2O exchg.); 13C NMR (DMSO‒d6, 125 MHz) δ:
25.3 (2CH2), 25.5 (CH2), 32.2 (2CH2), 53.0 (CH), 56.2
(OCH3), 113.1, 118.4, 119.4, 121.0, 139.7, 146.4, 148.3,
175.9 (C=S); MS (ESI) m/z: 307.40 [M]+; Analysis for
C15H21N3O2S: C (58.61) H (6.89) N (13.67) S (10.43) %;
found C (58.40) H (6.90) N (13.69) S (10.44)%.
IR KBr (cm−1): 3300 (OH str.), 3200 (NH str.), 1546
1
(C=N str.), 1206 (NCSN str.), 1150 (C=S str.); H NMR
(DMSO‒d6, 500 MHz) δ: 3.85 (3H, s, OCH3), 6.82-7.59 (8H,
m, Ar‒H), 8.07 (1H, s, =C-H), 9.55 (1H, =NNH, D2O
exchg.), 9.99 (s,1H, NHC=S, D2O exchg.); 13C NMR
(DMSO‒d6, 125 MHz) δ: 56.2 (OCH3), 113.1, 118.5, 119.3,
121.1, 139.8, 146.3, 148.2, 178.0 (C=S); MS (ESI) m/z:
301.14 [M]+; Analysis for C15H15N3O2S: C (59.78) H (5.02)
N (13.94) S (10.64) %; found C (59.58) H (5.01) N (13.98)%
[23].
2.1.1.8.
N-cyclohexyl-2-[1-(4-hydroxy-3-methoxyphenyl)
ethylidene]hydrazine-1-carbothioamide (8)
2.1.1.4. 2-[1-(4-Hydroxy-3-methoxyphenyl)ethylidene]-N-
phenylhydrazine-1-carbothioamide (4)
IR KBr (cm−1): 3335 (OH str.), 2936 (NH str.), 1550
1
IR KBr (cm−1): 3332 (OH str.), 3000 (NH str.), 1508
(C=N str.), 1201 (NCSN str.), 1117 (C=S str.); H NMR
1
(DMSO‒d6, 500 MHz) δ: 1.35-1.91 (10 H, m, cyclohexyl),
2.27 (3H, s, CH3), 4.20 (1H, s, cyclohexyl), 6.80‒7.42 (3H,
m, Ar‒H), 7.94 (1H, s, =CH), 7.80 (1H, s, =NNH, D2O
exchg.), 10.09 (1H, s, NHC=S, D2O exchg.); 13C NMR
(DMSO‒d6, 125 MHz) δ: 14.6 (CH3), 18.9 (CH2), 25.0
(CH2), 25.5 (CH2), 32.1 (CH2), 32.2 (CH2), 52.6 (CH), 56.5
(OCH3), 110.5, 115.5, 120.5, 129.3, 147.8, 148.7, 148.8,
176.9 (C=S); MS (ESI) m/z: 321.68 [M]+; Analysis for
C16H23N3O2S: C (59.78) H (7.21) N (13.7) S (9.98) %; found
C (59.55) H (7.24) N (13.74) S (9.95) %.
(C=N str.), 1313 (NCSN str.), 1150 (C=S str.); H NMR
(DMSO‒d6, 500 MHz) δ: 2.35 (3H, s, CH3), 3.85 (3H, s, -
OCH3), 6.80‒7.63 (8H, m, Ar‒H), 9.42 (1H, s, =NNH, D2O
exchg.), 9.98 (1H, s, NHC=S, D2O exchg.), 10.48 (1H, s, -
OH, D2O exchg.); 13C NMR (DMSO‒d6, 125 MHz) δ: 14.9
(CH3), 56.3 (OCH3), 111.2, 115.4, 121.0, 124.1, 125.6,
125.9, 128.5, 129.1, 139.6, 147.8, 148.9, 150.2, 176.9 (C=S);
MS (ESI) m/z: 312.14 [M-3]+; Analysis for C16H17N3O2S: C
(60.93) H (5.43) N (13.32) S (10.17) %; found C (60.70) H
(5.45) N (13.37) S (10.20)%.
2.1.1.5.
N-cyclohexyl-2-[(4-hydroxy-3-methoxyphenyl)
2.1.1.9. 2-[(4-Hydroxy-3-methoxyphenyl)methylidene]-N-
(prop-2-en-1-yl)hydrazine-1-carbothioamide (9)
methylidene]hydrazine-1-carbothioamide (5)
IR KBr (cm−1): 3335 (OH str.), 2928 (NH str.), 1510
(C=N str.), 1281 (NCSN str.), 1117 (C=S str.); H NMR
IR KBr (cm−1): 3318 (OH str.), 3200 (NH str.), 1550
1
1
(C=N str.), 1278 (NCSN str.), 1121 (C=S str.); H NMR
(DMSO‒d6, 500 MHz) δ: 1.12‒1.91 (10 H, m, cyclohexyl),
4.20 (1H, s, cyclohexyl), 6.80‒7.32 (3H, m, Ar‒H), 7.80
(1H, s, =CH), 7.97 (1H, s, =NNH, D2O exchg.), 11.28 (1H,
s, NHC=S, D2O exchg.); 13C NMR (DMSO‒d6, 125 MHz) δ:
21.5 (CH2), 25.3 (CH2), 25.5 (CH2), 32.3 (2CH2), 52.9 (CH),
56.2 (OCH3), 110.9, 115.9, 122.0, 125.8, 143.2, 148.3,
149.2, 175.7 (C=S); MS (ESI) m/z: 308.38 [M+1]+; Analysis
for C15H21N3O2S: C (58.61) H (6.89) N (13.67) S (10.43) %;
found C (58.38) H (6.87) N (13.72) S (10.40)%.
(DMSO‒d6, 500 MHz) δ: 3.80 (3H, s, -OCH3), 4.22 (2H, d,
CH2), 5.10 (2H, m, =CH2), 5.88 (1H, m, =CH), 6.77‒7.37
(3H, m, Ar‒H), 7.95 (1H, s, =CH), 8.52 (1H, s, =NNH, D2O
exchg.), 11.35 (1H, s, NHC=S, D2O exchg.); 13C NMR
(DMSO‒d6, 125 MHz) δ: 21.6 (CH2), 46.1 (=CH2), 56.3
(OCH3), 110.5, 115.8, 112.4, 125.9, 135.6, 143.3, 148.4,
149.2, 177.2 (C=S); MS (ESI) m/z: 264.14 [M-1]+; Analysis
for C12H15N3O2S: C (54.32) H (5.70) N (15.84) S (12.08) %;
found C (54.11) H (5.71) N (15.90) S (12.05)%.
2.1.1.6.
N-cyclohexyl-2-[(3-hydroxy-4-methoxyphenyl)
2.1.1.10. 2-[(3-Hydroxy-4-methoxyphenyl)methylidene]-N-
(prop-2-en-1-yl)hydrazine-1-carbothioamide (10)
methylidene]hydrazine-1-carbothioamide (6)
IR KBr (cm−1): 3304 (OH str.), 3001 (NH str.), 1548
(C=N str.), 1280 (NCSN str.), 1125 (C=S str.); H NMR
IR KBr (cm−1): 3149 (OH str.), 2929 (NH str.), 1542
1
1
(C=N str.), 1272 (NCSN str.), 1121 (C=S str.); H NMR
(DMSO‒d6, 500 MHz) δ: 1.12‒1.91 (10 H, m, cyclohexyl),
4.20 (1H, s, cyclohexyl), 6.93‒7.29 (3H, m, Ar‒H), 7.86
(1H, s, =CH), 7.93 (1H, s, =NNH, D2O exchg.), 9.17 (1H, s,
NHC=S, D2O exchg.), 11.25 (1H, s, -OH, D2O exchg.); 13C
NMR (DMSO‒d6, 125 MHz) δ: 21.5 (CH2), 25.3 (CH2), 25.5
(CH2), 32.3 (2CH2), 52.8 (CH), 56.0 (OCH3), 112.0, 113.2,
120.9, 127.3, 143.1, 147.1, 150.0, 175.7 (C=S); MS (ESI)
m/z: 306.14 [M-1]+; Analysis for C15H21N3O2S: C (58.61) H
(6.89) N (13.67) S (10.43) %; found C (58.39) H (6.88) N
(13.70) S (10.41)%.
(DMSO‒d6, 500 MHz) δ: 3.80 (3H, s, -OCH3), 4.22 (2H, d,
CH2), 5.10 (2H, m, =CH2), 5.89 (1H, m, =CH), 6.77‒7.37
(3H, m, Ar‒H), 7.95 (1H, s, =CH), 8.52 (1H, s, =NNH, D2O
exchg.), 11.35 (1H, s, NHC=S, D2O exchg.); 13C NMR
(DMSO‒d6, 125 MHz) δ: 22.7 (CH2), 46.1 (=CH2), 56.0
(OCH3), 112.0, 113.4, 115.9, 120.8, 127.5, 135.6, 143.0,
147.1, 150.1, 177.3 (C=S); MS (ESI) m/z: 265.13 [M]+;
Analysis for C12H15N3O2S: C (54.32) H (5.70) N (15.84) S
(12.08) %; found C (54.50) H (5.69) N (15.87) S (12.07)%.