J. Chil. Chem. Soc., 57, Nº 4 (2012)
Compound 3i IR (KBr, cm-1): 3432(N-H stretching of indole), 3237(N-H
stretching of hydrazinecarbothioamide moiety), 1700(C=O str), 1156(C=S str);
1HNMR(400MHz, DMSO-d6): δ 6.93 (d,1H,C4H proton), 7.53(d, 1H C6H
proton),7.78(d, 1HC7Hofindole), 7.22-7.90(m, 4H, Ar-H), 12.20(br, 1H, -NH-
Ar), 11.12 (s,1H, NH of indole ),11.18 (s,1H,NH of hydrazinecarbothioamide
moiety) ppm. Anal. Calcd for C15H10N4OSBr2: C, 39.64; H, 2.20; N, 12.33
Found: C, 39.50; H, 2.15; N, 12.30 %; MS: [M]+ at m/z 454.
6.61-7.42, (m, 3H, Ar-H), 4.8 (s, 2H, NH2), 12.01 (s, 1H,NNHCS), 8.7 (s, 1H,
cyclic CONH). Anal. Calcd for C H7BrN4OS: C, 36.14, H, 2.36, N, 18.73,
Found: C, 36.35, H, 2.37, N, 18.75.9
Compound 4h. IR (KBr, cm-1): 3468 (NHstr, ArNH2), 3334 (NH str,
CONH), 1080 (C=Sstr), 1677 (C=N), 885 (Ar-Br), 745 (Ar-Cl). 1HNMR
(DMSO) δ ppm: 7.01-8.06, (m, 7H, Ar-H), 5.28 (s, 2H, NH2), 12.21 (s, 1H,
NNHCS). Anal. Calcd. for C15H10BrN4OSCl: C, 43.98, H, 2.46, N, 13.68,
Found: C, 43.79, H, 2.47, N, 13.65.
Compound 3j IR (KBr, cm-1): 3432(N-H stretching of indole), 3237(N-H
stretching of hydrazinecarbothioamide moiety), 1700(C=O str), 1156(C=S str);
1HNMR (400MHz, DMSO-d6): δ2.28 (s, 3H, CH3), 6.78(d, 1H,C H proton),
7.05(t, 1H C H proton), 7.28(d, 1H C6H proton), 7.66 (d, 1H C7H4of indole),
7.54-7.72 (m5, 4H, Ar-H), 12.28 (br, 1H, -NH-Ar), 11.12 (s, 1H, NH of indole),
11.15 (s, 1H,NH of hydrazinecarbothioamide moiety) ppm; Anal. Calcd for
C16H14N4OS: C, 61.00; H, 4.50; N, 18.06; Found: C, 61.20; H, 4.55; N, 18.10
%; MS: [M]+ at m/z 310.
Compound 5a. IR (KBr, cm-1): 3430 (NHstr of indole), 3233 (NHstr of
thiosemicarbazone moiety), 1668 (C=Ostr), 1135 (C=Sstr). 1HNMR (DMSO)
δ ppm: 12.49(s, 2H, NH2 of thiosemicarbazone moiety), 11.03 (s, 1H NH str of
thiosemicarbazone moiety), 6.80-7.80 (m, 4H, Ar-H), 3.44 (br s, 2H, N-CH2-N
proton), 2.48 (m, 4H), 1.8 (s, 4H). Anal. Calcd. for C14H17N5O2S: C, 52.65, H,
5.37, N, 21.93, Found: C, 52.85, H, 5.38, N, 21.95.
Compound 3k IR (KBr, cm-1): 3432(N-H stretching of indole), 3237(N-H
stretching of hydrazinecarbothioamide moiety), 1700(C=O str), 1156(C=S str);
1HNMR (400MHz, DMSO-d ): δ2.28 (s, 3H, CH3), 6.87(d,1H,C4H proton),
7.28(d, 1H C6H proton),7.866 (d, 1H C7H of indole), 7.54-7.72 (m, 4H, Ar-
H), 12.28 (br, 1H, -NH-Ar), 11.12 (s,1H, NH of indole ),11.15 (s,1H,NH of
hydrazinecarbothioamide moiety) ppm; Anal. Calcd for C16H13N4OSCl: C,
55.73; H, 3.77; N, 16.25 Found: C, 55.60; H, 3.72; N, 16.28 %; MS: [M]+ at
m/z 344.5.
Compound 5b. IR (KBr, cm-1): 3432 (NHstr of indole), 3234 (NHstr
of thiosemicarbazone moiety), 1672 (C=Ostr), 1133 (C=Sstr), 735 (Ar-
1
Cl). HNMR (DMSO) δ ppm: 12.52-11.29 (s, 2H NH of thiosemicarbazone
moiety), 6.40-7.27 (m, 8H, Ar-H), 4.03 (br s, 2H, N-CH2-N proton), 2.24 (m,
4H), 1.50 (s, 4H). Anal. Calcd. for C H20ClN5O2S: C, 55.87, H, 4.69, N, 16.29,
Found: C, 55.68, H, 4.68, N, 16.27. 20
Compound 5c. IR (KBr, cm-1): 3434 (NHstr of indole), 3237 (NHstr
of thiosemicarbazone moiety), 1662 (C=Ostr), 1127 (C=Sstr), 855 (Ar-
Br). HNMR (DMSO) δ ppm: 12.42-11.19 (s, 2H NH of thiosemicarbazone
moiety), 6.30-7.37 (m, 8H, Ar-H), 4.05 (br s, 2H, N-CH2-N proton), 2.14 (m,
4H), 1.70 (s, 4H). Anal. Calcd. for C H20BrN5O2S: C, 50.64, H, 4.25, N, 14.76,
Found: C, 50.84, H, 4.26, N, 14.78. 20
Compound 3l IR (KBr, cm-1): 3432(N-H stretching of indole), 3237(N-H
stretching of hydrazinecarbothioamide moiety), 1700(C=O str), 1156(C=S str);
1HNMR (400MHz, DMSO-d6): δ2.28 (s, 3H, CH3), 6.93(d, 1H,C4H proton),
7.51(d, 1H C H proton), 7.78 (d, 1H C7H of indole), 7.54-7.72 (m, 4H, Ar-
H), 12.28 (br6, 1H, -NH-Ar), 11.12 (s, 1H, NH of indole), 11.15 (s, 1H,NH
of hydrazinecarbothioamide moiety) ppm ; Anal. Calcd for C16H13N4OSBr: C,
49.35; H, 3.34; N, 14.39 Found: C, 49.40; H, 3.37; N, 14.34 %; MS: [M]+ at
m/z 389.
1
Compound 5d. IR (KBr, cm-1): 3435 (NHstr of indole), 3236 (NHstr
of thiosemicarbazone moiety), 1672 (C=Ostr), 1137 (C=Sstr), 725-732 (Ar-
1
Cl). HNMR (DMSO) δ ppm: 12.32-11.09 (s, 2H NH of thiosemicarbazone
moiety), 6.50-7.88 (m, 7H, Ar-H), 4.02 (br s, 2H, N-CH2-N proton), 2.24 (m,
4H), 1.57 (s, 4H). Anal. Calcd. for C H19Cl2N5OS: C, 53.58, H, 4.27, N, 15.62,
Found: C, 53.78, H, 4.28, N, 15.64. 20
Compound 4a. IR (KBr, cm-1): 3452 (NHstr, ArNH2), 3320(NHstr,
CONH), 1060 (C=Sstr), 1650 (C=N). 1HNMR (DMSO) δ ppm: 6.76-7.53 (m,
4H, Ar-H), 4.8 (s, 2H, NH2), 7.01 (s, 1H, cyclic NNHCS), 8.5 (s, 1H, cyclic
CONH). Anal. Calcd. for C9H8N4OS: C, 49.08, H, 3.66, N, 25.44, Found: C,
49.25, H, 3.67, N, 25.47.
Compound 5e. IR (KBr, cm-1): 3433 (NHstr of indole), 3234 (NHstr of
thiosemicarbazone moiety), 1674 (C=Ostr), 1135 (C=Sstr), 742 (Ar-Cl), 885
(Ar-Br). 1HNMR (DMSO) δ ppm: 12.52-11.29 (s, 2H NHof thiosemicarbazone
moiety), 7.01-7.70 (m, 7H, Ar-H), 4.04 (br s, 2H, N-CH2-N proton), 2.25 (m,
4H), 1.59 (s, 4H). Anal. Calcd. for C H BrClN5OS: C, 48.74, H, 3.89, N,
14.21, Found: C, 48.94, H, 3.88, N, 14.2203.19
Compound 4b. IR (KBr, cm-1): 3450 (NH str, ArNH2), 3316 (NH str,
CONH), 1062 (C=S str), 1647 (C=N),735 (Ar-Cl). 1HNMR (DMSO) δ ppm:
6.66-7.73 (m, 8H, Ar-H), 5.2 (s, 2H, NH2), 12.14 (s, 1H, NNHCS). Anal.
Calcd. for C15H11ClN4OS: C, 54.46, H, 3.35, N, 16.94, Found: C, 54.27, H,
3.34, N, 16.96.
Compound 5f. IR (KBr, cm-1): 3431(NH str of indole), 3233 (NHstr
of thiosemicarbazone moiety), 1666 (C=Ostr), 1131 (C=Sstr), 732 (Ar-Cl).
1HNMR (DMSO) δ ppm: 12.09(s, 2H, NH2 of thiosemicarbazone moiety),
11.08 (s, 1H NHstr of thiosemicarbazone moiety), 6.20-7.03 (m, 3H, Ar-H),
3.64 (br s, 2H, N-CH2-N proton), 2.58 (m, 4H), 1.9 (s, 4H). Anal. Calcd. for
C14H16ClN5OS: C, 49.77, H, 4.77, N, 20.73, Found: C, 49.98, H, 4.76, N, 20.75.
Compound 4c. IR (KBr, cm-1): 3455 (NH str, ArNH2), 3318 (NH str,
CONH), 1068 (C=S str), 1654(C=N), 825 (Ar-Br). 1HNMR (DMSO) δ ppm:
6.70-7.68 (m, 8H, Ar-H), 5.4 (s, 2H, NH2), 12.01(s, 1H, NNHCS). Anal. Calcd.
for C15H11N4OSBr: C, 49.01, H, 2.95, N, 14.93, Found: C, 49.19, H, 2.96, N,
14.96.
Compound 6a. IR (KBr, cm-1): 3350 (NHstr of indole), 1590-1654 (C=N),
1131 (C=Sstr). 1HNMR (DMSO) δ ppm: 6.60-7.53 (m, 4H, Ar-H), 4.4 (s, 2H
NH of indole), 7.90 (s, 1H, NNHCS). Anal. Calcd. for C9H6N4S: C, 53.45, H,
2.29, N, 27.70, Found: C, 53.66, H, 2.28, N, 27.72.
Compound 4d. IR (KBr, cm-1) 3450 (NH str, ArNH2), 3310 (NH str,
CONH), 1080 (C=S str), 1667 (C=N), 730 (Ar-Cl). 1HNMR (DMSO) δ ppm:
6.76-7.53 (m, 3H, Ar-H), 4.8 (s, 2H, NH2), 7.01 (s, 1H, cyclic NNHCS), 8.5
(s, 1H, CONH). Anal. Calcd. for C9H7N4ClN4OS: C, 42.44, H, 2.77, N, 22.00,
Found: C, 42.64, H, 2.78, N, 22.03.
Compound 6b. IR (KBr, cm-1): 3352 (NHstr of indole), 1580-1653 (C=N),
1132 (C=Sstr). 1HNMR (DMSO) δ ppm: 6.66-7.58 (m, 3H, Ar-H), 4.6 (s, 2H
NH of indole), 7.11 (s, 1H, NNHCS). Anal. Calcd. for C9H5ClN4S: C, 45.67, H,
2.13, N, 23.67, Found: C, 45.87, H, 2.14, N, 23.69.
Compound 4e. IR (KBr, cm-1): 3453 (NH str, ArNH2), 3322 (NH str,
1
CONH), 1082 (C=S str), 1666 (C=N), 715 -730 (Ar-Cl). HNMR (DMSO) δ
ppm: 6.22-7.68, (m, 7H, Ar-H), 5.8 (s, 2H, NH2), 12.11(s, 1H, NHCS). Anal.
Calcd. for C15H10Cl2N4OS: C, 49.33, H, 2.76, N, 15.34, Found: C, 49.52, H,
2.75, N, 15.36.
Compound 6c. IR (KBr, cm-1): 3355 (NHstr of indole), 1592-1664 (C=N),
1134 (C=Sstr). 1HNMR (DMSO) δ ppm: 6.70-7.83 (m, 3H, Ar-H), 4.7 (s, 2H
NH of indole), 7.70 (s, 1H, NNHCS). Anal. Calcd. for C9H5BrN4S: C, 38.45,
H, 1.79, N, 19.93, Found: C, 38.67, H, 1.77, N, 19.96.
Compound 4f. IR (KBr, cm-1): 3460 (NHstr, ArNH2), 3323 (NH str,
CONH), 1072 (C=Sstr), 1676 (C=N), 725 (Ar-Cl) 855 (Ar-Br). 1HNMR
(DMSO) δ ppm: 7.01-8.02, (m, 7H, Ar-H), 5.8 (s, 2H, NH2), 12.11(s, 1H,
NNHCS). Anal. Calcd. for C15H10ClN4OSBr: C, 43.98, H, 2.46, N, 13.68,
Found: C, 43.77, H, 2.47, N, 13.66.
Antimicrobial activity
Antibacterial activity. Synthesized compounds (3a-l) were screened
for their antibacterial activity against Gram-positive bacteria Bacillus cereus
(MTCC 0430) and Gram-negative bacteria Enterobacter aerogenes (MTCC
2824) and compounds (4b, 4d, 4g, 4h, 5a, 5b, 5d, 5f, 6a, 6b) against
Escherichia coli, Staphylococcus aureus, and K. pneumoniae by the Agar Well
Compound 4g. IR (KBr, cm-1): 3464 (NHstr, ArNH2), 3324 (NH str,
1
CONH), 1070 (C=Sstr), 1673(C=N), 875 (Ar-Br). HNMR (DMSO) δ ppm:
1352