The document summarizes a project presentation on the synthesis, characterization, and biological evaluation of novel carbazole derivatives. It provides background on carbazole and the aim to synthesize derivatives by attaching an oxadiazole group to the carbazole nucleus. It then details the synthesis of 22 novel derivatives and summarizes their physical properties, spectral data, and biological activity evaluation. The overall goal is to develop new pharmacologically active drugs with properties like anticancer or antimicrobial activity.

1. Project Presentation
On
“Synthesis, Characterization and Biological
Evaluation of Some Newer Carbazole Derivatives”
Roll no. 006006657009
Divyanshu Sharma
CO-SUPERVISOR
Mr. Nitin Kumar
Assistant professor
Dept. of Pharmaceutical Chemistry
Rajiv Academy for Pharmacy,
Mathura (U.P.) – 281001
SUPERVISOR
Prof. (Dr.) Devender Pathak
Director, Professor and Head,
Dept. of Pharmaceutical Chemistry
Rajiv Academy for Pharmacy,
Mathura (U.P.) - 281001

2. Introduction:
Carbazole is an aromatic heterocyclic
organic compound. It has a tricyclic
structure, consisting of two six-
membered benzene ring fused on
either side of a five-membered
nitrogen-containing ring (Pyrrole).
General Properties
IUPAC name 9H-carbazole
Molecular
formula
C12H9N
Molar mass 167.206 g/mole
Density 1.301g/cm3
Melting point 246.3°C
Boiling point 354.69°C
Appearance Off-white
crystalline powder

3. Aim & Objective:
 Carbazole derivatives have documented consistent advances in the design
of novel anticancer, antimicrobial, neuroleptic and anticonvulsant agents.
Furthermore, various congeners of oxadiazole, thiadiazole, azetidinone and
thiazolidinone have also been reported to exhibit potential anticancer,
antimicrobial and anticonvulsant activity.
 In view of broad biological activity of carbazole derivatives, we planned to
synthesize new carbazole derivatives by incorporating new pharmacophore
such as oxadiazole at the 9th position of carbazole nucleus with the hope to
get better pharmacologically active drugs.

4. N
H
Carbazole
N
CH2COOC2H5
Ethyl 2-(9H-carbazol-9-yl)acetate
Cl -CH2COOC2H5
H2N
N
H
O
NH2
N N
O
N
NH2
5-((9H-Carbazol-9-yl)methyl)-1,3,4-oxadiazol-2-amine
HN NH
N N
O
N
N
H
N NH
R
CH
5-((9H-Carbazol-9yl)methyl)-N-((substituted phenyl)
(piperazin-1-yl)methyl)-1,3,4-oxadiazol-2-amine
R
CHO
N
H2C C
HN
O
N
H
C
O
NH2
1-(2-(9H-Carbazol-9-yl)acetyl)semicarbazide
H2SO4
p-nitro,
p-hydroxy,
p-chloro,
3,4,5-Trimethoxy,
p-(dimethyl)amino,
o-nitro,
m-hydroxy,
m-nitro,
o-hydroxy,
m-chloro,
o-chloro,
m-methoxy,
p-methoxy,
p-fluoro,
H
Here R is:Scheme of Work
(19)
(20)
(21)
(22 a-o)

5. Physical Properties of Synthesized Compounds:
Compd.
code
R Mol.
Formula
Mol. Weight
(g/mole)
Rf *
Value
%
Yield
m.p.
range(oC)
22a p-nitro C26H25N7O3 483.52 0.73 82.55 236-237
22b p-hydroxy C26H26N6O2 454.52 0.62 79.69 208-209
22c 3,4,5-trimethoxy C29H34N6O4 528.6 0.69 61.5 184-185
22d p-chloro C26H25ClN6O 472.97 0.75 73.22 221-222
22e p-dimethyl amino C28H31N7O 481.59 0.59 53.78 202-203
22f o-nitro C26H25N7O3 483.52 0.65 63.96 225-226
22g m-hydroxy C26H26N6O2 454.52 0.56 72.71 213-214
22h m-nitro C26H25N7O3 483.52 0.71 69.98 229-230
22i o-hydroxy C26H26N6O2 454.52 0.60 59.33 218-219
22j m-chloro C26H25ClN6O 472.97 0.67 67.07 231-232
22k o-chloro C26H25ClN6O 472.97 0.66 56.45 237-238
22l m-methoxy C27H28N6O2 468.55 0.77 52.54 192-193
22m p-methoxy C27H28N6O2 468.55 0.79 58.75 189-190
22n p-fluoro C26H25FN6O 456.51 0.54 55.0 234-235
22o Benzaldehyde C26H26N6O 438.52 0.63 51.23 176-177
*Solvent system: Benzene:Chloroform:Methanol (4:3:2)

6. COMPOUND CODE IR (KBr) (cm-1) NMR (DMSO)  ppm
22a 3415.71 (N-H, str.), 3049.25 (Aromatic C-H,
str.), 2927.74 {Aliphatic C-H (Asymmetric),
str.}, 2846.74 {Aliphatic C-H (Symmetric),
str.}, 1674.96 (C=N, str.), 1606.59 (Aromatic
C=C, str.), 1533.30 (Asymmetric N-O, str.),
1340.43 (C-N (Tertiary), str.), 1291.23
(Symmetric N-O, str.), 1112.28 (C-O-C, str. in
oxadiazole ring), 837.05 (C-H, p-disubstituted
benzene (def.)).
1.898 (s, 1H, NH, D2O exchangeable),
2.481-2.513 (t, 4H, CH2), 2.652-2.702
(t, 4H, CH2), 3.976 (s, 1H, NH, D2O
exchangeable), 4.984 (s, 1H, CH),
5.165 (s, 2H, CH2), 7.094-7.112 (d, 2H,
Ar–H), 7.234-7.295 (t, 3H, Ar–H),
7.438-7.483 (t, 3H, Ar–H), 7.681-7.735
(d, 2H, Ar–H), 8.059-8.072 (d, 2H, Ar–
H).
MS (ESI) m/z [% rel. abundance]: 483.24 (100) [M]+
Fragments: 437.21 (29.9), 361.18 (22.2), 263.09 (16.6), 248.08
(38.0), 180.08 (14.4), 166.06 (13.3), 115.03 (6.0).
Elemental analysis:
Calcd for C26H25N7O3: C, 64.58; H, 5.21; N, 20.28.
Found: C, 64.57; H, 5.19; N, 20.25 %.
Spectral Studies:
22b 3642.77 (Phenolic O-H, str.), 3414.82 (N-H,
str.), 3046.18 (Aromatic C-H, str.), 2921.96
{Aliphatic C-H (Asymmetric), str.}, 2856.38
{Aliphatic C-H (Symmetric), str.}, 1670.24
(C=N, str.), 1600.81 (Aromatic C=C, str.),
1335.51 (C-N (Tertiary), str.), 1155.38 (C-O-
C, str. in oxadiazole ring), 844.76 (C-H, p-
disubstituted benzene (def.)).
1.978 (s, 1H, NH, D2O exchangeable),
2.425-2.483 (t, 4H, CH2), 2.672-2.713 (t,
4H, CH2), 4.092 (s, 1H, NH, D2O
exchangeable), 4.917 (s, 1H, OH, D2O
exchangeable), 5.155 (s, 1H, CH), 5.294
(s, 2H, CH2), 6.723-6.754 (d, 2H, Ar–H),
6.926-6.979 (t, 3H, Ar–H), 7.113-7.177 (t,
3H, Ar–H), 7.369-7.383 (d, 2H, Ar–H),
7.535-7.585 (d, 2H, Ar–H).
MS (ESI) m/z [% rel. abundance]: 454.21 (100) [M]+
Fragments: 437.36 (27.8), 361.25 (21.7), 263.17 (17.1), 248.01
(40.3), 180.05 (13.8), 166.10 (14.1), 115.85 (4.2).
Elemental analysis:
Calcd for C26H26N6O2: C, 68.70; H, 5.77; N, 18.49.
Found: C, 68.66; H, 5.75; N, 18.46 %.
UV max(DMSO):
356 nm
UV max(DMSO):
353 nm

7. COMPOUND CODE IR (KBr) (cm-1) NMR (DMSO)  ppm
22c 3413.27 (N-H, str.), 3047.09 (Aromatic C-H,
str.), 2908.45 {Aliphatic C-H (Asymmetric),
str.}, 2812.02 {Aliphatic C-H (Symmetric),
str.}, 1661.31 (C=N, str.), 1601.42 (Aromatic
C=C, str.), 1323.08 (C-N (Tertiary), str.),
1236.29 (Asymmetric C-O-C str. of aryl alkyl
ether), 1166.85 (C-O-C, str. in oxadiazole ring),
1068.49 (Symmetric C-O-C str. of aryl alkyl
ether).
1.962 (s, 1H, NH, D2O exchangeable),
2.413-2.463 (t, 4H, CH2), 2.667-2.703
(t, 4H, CH2), 3.734 (s, 9H, (OCH3)3),
4.135 (s, 1H, NH, D2O exchangeable),
4.993 (s, 1H, CH), 5.187 (s, 2H, CH2),
6.014-6.083 (d, 2H, Ar–H), 6.014-
6.083 (d, 2H, Ar–H), 6.959-6.972 (d,
2H, Ar–H), 7.181-7.215 (t, 3H, Ar–H),
7.434-7.489 (t, 3H, Ar–H).
MS (ESI) m/z [% rel. abundance]: 528.25 (100) [M]+
Fragments: 513.22 (34.2), 497.23 (30.6), 361.32 (24.3), 263.29
(15.9), 248.36 (36.6), 180.11 (15.8), 166.01 (13.1), 115.43 (3.9).
Elemental analysis:
Calcd for C29H32N6O4: C, 65.89; H, 6.10; N, 15.90.
Found: C, 65.86; H, 6.07; N, 15.88 %.
22d 3417.03 (N-H, str.), 3053.18 (Aromatic C-H,
str.), 2920.14 {Aliphatic C-H (Asymmetric),
str.}, 2854.45 {Aliphatic C-H (Symmetric),
str.}, 1660.09 (C=N, str.), 1601.23 (Aromatic
C=C, str.), 1330.8 (C-N (Tertiary), str.),
1147.57 (C-O-C, str. in oxadiazole ring),
1063.56 (Aromatic C-Cl, str.), 852.48 (C-H, p-
disubstituted benzene (def.)).
2.012 (s, 1H, NH, D2O exchangeable),
2.436-2.470 (t, 4H, CH2), 2.614-2.652 (t,
4H, CH2), 4.123 (s, 1H, NH, D2O
exchangeable), 4.955 (s, 1H, CH), 5.094
(s, 2H, CH2), 7.062-7.099 (d, 2H, Ar–H),
7.187-7.232 (t, 3H, Ar–H), 7.296-7.359
(t, 3H, Ar–H), 7.412-7.438 (d, 2H, Ar–
H), 7.675-7.692 (d, 2H, Ar–H).
MS (ESI) m/z [% rel. abundance]: 472.18 (100) [M]+, 473.18
(28.5) [M+1]+, 474.17 (32.2) [M+2]+
Fragments: 437.12 (26.2), 361.22 (23.5), 263.18 (18.4), 248.17
(38.0), 180.33 (14.2), 166.23 (12.8), 115.33 (5.2).
Elemental analysis:
Calcd for C26H25ClN6O: C, 66.03; H, 5.33; N, 17.77.
Found: C, 66.01; H, 5.32; N, 17.74 %.
UV max(DMSO):
360 nm
UV max(DMSO):
338 nm

8. COMPOUND CODE IR (KBr) (cm-1) NMR (DMSO)  ppm
22e 3412.71 (N-H, str.), 3040.64 (Aromatic C-H,
str.), 2919.41 {Aliphatic C-H (Asymmetric),
str.}, 2851.23 {Aliphatic C-H (Symmetric),
str.}, 1666.38 (C=N, str.), 1598.88 (Aromatic
C=C, str.), 1323.28 (C-N (Tertiary), str.),
1159.82 (C-O-C, str. in oxadiazole ring), 817.76
(C-H, p-disubstituted benzene (def.)).
1.901 (s, 1H, NH, D2O exchangeable),
2.291-2.353 (t, 4H, CH2), 2.552-2.602
(t, 4H, CH2), 2.852 (s, 6H, N(CH3)2),
4.010 (s, 1H, NH, D2O exchangeable),
4.894 (s, 1H, CH), 5.085 (s, 2H, CH2),
6.449-6.462 (d, 2H, Ar–H), 6.649-6.719
(t, 3H, Ar–H), 6.894-6.917 (t, 3H, Ar–
H), 7.013-7.038 (d, 2H, Ar–H), 7.362-
7.389 (d, 2H, Ar–H).
MS (ESI) m/z [% rel. abundance]: 481.25 (100) [M]+, 482.05
(33.4) [M+1]+
Fragments: 466.23 (30.6), 437.20 (28.7), 361.14 (22.6), 263.22
(16.3), 248.13 (40.3), 180.23 (15.2), 166.05 (13.8), 115.28 (6.6).
Elemental analysis:
Calcd for C28H31N7O: C, 69.83; H, 6.49; N, 20.36.
Found: C, 69.81; H, 6.46; N, 20.32 %.
22f 3417.63 (N-H, str.), 3055.03 (Aromatic C-H,
str.), 2923.88 {Aliphatic C-H (Asymmetric),
str.}, 2855.45 {Aliphatic C-H (Symmetric), str.},
1659.95 (C=N, str.), 1610.4 (Aromatic C=C,
str.), 1525.59 (Asymmetric N-O, str.), 1343.58
(C-N (Tertiary), str.), 1296.52 (Symmetric N-O,
str.), 1153.35 (C-O-C, str. in oxadiazole ring),
740.61 (C-H, o-disubstituted benzene (def.)).
2.088 (s, 1H, NH, D2O exchangeable),
2.346-2.392 (t, 4H, CH2), 2.634-2.682
(t, 4H, CH2), 4.063 (s, 1H, NH, D2O
exchangeable), 4.843 (s, 1H, CH),
5.035 (s, 2H, CH2), 7.013-7.046 (d, 2H,
Ar–H), 7.328-7.374 (t, 3H, Ar–H),
7.642-7.695 (t, 3H, Ar–H), 7.751-7.787
(d, 2H, Ar–H), 7.992-8.013 (d, 2H, Ar–
H).
MS (ESI) m/z [% rel. abundance]: 483.78 (100) [M]+, 484.81
(27.1) [M+1]+
Fragments: 437.21 (30.6), 361.26 (22.3), 263.01 (18.3), 248.02
(39.1), 180.14 (14.3), 166.26 (13.6), 115.13 (4.6).
Elemental analysis:
Calcd for C26H25N7O3: C, 64.58; H, 5.21; N, 20.28.
Found: C, 64.54; H, 5.20; N, 20.27 %.
UV max(DMSO):
351 nm
UV max(DMSO):
352 nm

9. COMPOUND CODE IR (KBr) (cm-1) NMR (DMSO)  ppm
22g 3671.18 (Phenolic O-H, str.), 3416.77 (N-H,
str.), 3051.18 (Aromatic C-H, str.), 2925.61
{Aliphatic C-H (Asymmetric), str.}, 2860.24
{Aliphatic C-H (Symmetric), str.}, 1689.53
(C=N, str.), 1603.48 (Aromatic C=C, str.),
1330.79 (C-N (Tertiary), str.), 1157.59 (C-O-
C, str. in oxadiazole ring), 738.69 (C-H, m-
disubstituted benzene (def.)).
2.018 (s, 1H, NH, D2O exchangeable),
2.357-2.403 (t, 4H, CH2), 2.662-2.704 (t,
4H, CH2), 4.027 (s, 1H, NH, D2O
exchangeable), 4.925 (s, 1H, OH, D2O
exchangeable), 5.146 (s, 1H, CH), 5.287
(s, 2H, CH2), 6.419-6.432 (d, 2H, Ar–
H), 6.549-6.599 (t, 3H, Ar–H), 6.834-
6.907 (t, 3H, Ar–H), 7.053-7.078 (d, 2H,
Ar–H), 7.352-7.384 (d, 2H, Ar–H).
MS (ESI) m/z [% rel. abundance]: 454.63 (100) [M]+, 455.8 (30.1)
[M+1]+
Fragments: 437.31 (31.2), 361.19 (20.4), 263.24 (14.2), 248.09
(35.8), 180.27 (19.2), 166.02 (12.6), 115.15 (7.1).
Elemental analysis:
Calcd for C26H26N6O2: C, 68.70; H, 5.77; N, 18.49.
Found: C, 68.69; H, 5.76; N, 18.48 %.
22h 3415.86 (N-H, str.), 3053.11 (Aromatic C-H,
str.), 2925.81 {Aliphatic C-H (Asymmetric),
str.}, 2858.31 {Aliphatic C-H (Symmetric),
str.}, 1672.34 (C=N, str.), 1602.74 (Aromatic
C=C, str.), 1518.28 (Asymmetric N-O, str.),
1348.11 (C-N (Tertiary), str.), 1302.36
(Symmetric N-O, str.), 1157.21 (C-O-C, str. in
oxadiazole ring), 676.97 (C-H, m-disubstituted
benzene (def.)).
1.972 (s, 1H, NH, D2O exchangeable),
2.317-2.384 (t, 4H, CH2), 2.632-2.682 (t,
4H, CH2), 4.085 (s, 1H, NH, D2O
exchangeable), 4.944 (s, 1H, CH), 5.196
(s, 2H, CH2), 7.124-7.146 (d, 2H, Ar–
H), 7.324-7.392 (t, 3H, Ar–H), 7.538-
7.586 (t, 3H, Ar–H), 7.653-7.678 (d, 2H,
Ar–H), 8.082-8.104 (d, 2H, Ar–H).
MS (ESI) m/z [% rel. abundance]: 483.59 (100) [M]+, 484.35
(29.8) [M+1]+
Fragments: 437.18 (27.4), 361.07 (21.6), 263.06 (18.3), 248.09
(38.3), 180.12 (13.4), 166.05 (12.2), 115.68 (6.8).
Elemental analysis:
Calcd for C26H25N7O3: C, 64.58; H, 5.21; N, 20.28.
Found: C, 64.55; H, 5.17; N, 20.24 %.
UV max(DMSO):
346 nm
UV max(DMSO):
350 nm

10. COMPOUND CODE IR (KBr) (cm-1) NMR (DMSO)  ppm
22i 3691.61 (Phenolic O-H, str.), 3415.69 (N-H,
str.), 3053.23 (Aromatic C-H, str.), 2924.87
{Aliphatic C-H (Asymmetric), str.}, 2853.42
{Aliphatic C-H (Symmetric), str.}, 1668.31
(C=N, str.), 1606.69 (Aromatic C=C, str.),
1333.54 (C-N (Tertiary), str.), 1149.5 (C-O-C,
str. in oxadiazole ring), 740.61 (C-H, o-
disubstituted benzene (def.)).
2.013 (s, 1H, NH, D2O exchangeable),
2.437-2.489 (t, 4H, CH2), 2.654-2.693 (t,
4H, CH2), 4.022 (s, 1H, NH, D2O
exchangeable), 4.997 (s, 1H, OH, D2O
exchangeable), 5.109 (s, 1H, CH), 5.298
(s, 2H, CH2), 6.629-6.653 (d, 2H, Ar–H),
6.846-6.889 (t, 3H, Ar–H), 7.013-7.097
(t, 3H, Ar–H), 7.173-7.206 (d, 2H, Ar–
H), 7.487-7.515 (d, 2H, Ar–H).
MS (ESI) m/z [% rel. abundance]: 454.02 (100) [M]+, 455.25
(26.0) [M+1]+
Fragments: 437.31 (25.3), 361.23 (21.5), 263.12 (16.1), 248.06
(41.3), 180.31 (13.2), 166.08 (11.4), 115.06 (3.5).
Elemental analysis:
Calcd for C26H26N6O2: C, 68.70; H, 5.77; N, 18.49.
Found: C, 68.68; H, 5.74; N, 18.47 %.
22j 3415.58 (N-H, str.), 3050.70 (Aromatic C-H,
str.), 2912.81 {Aliphatic C-H (Asymmetric),
str.}, 2827.45 {Aliphatic C-H (Symmetric),
str.}, 1649.41 (C=N, str.), 1581.5 (Aromatic
C=C, str.), 1307.65 (C-N (Tertiary), str.),
1151.42 (C-O-C, str. in oxadiazole ring),
1080.06 (Aromatic C-Cl, str.), 661.54 (C-H, m-
disubstituted benzene (def.)).
2.102 (s, 1H, NH, D2O exchangeable),
2.327-2.376 (t, 4H, CH2), 2.562-2.604 (t,
4H, CH2), 4.076 (s, 1H, NH, D2O
exchangeable), 4.955 (s, 1H, CH), 5.011
(s, 2H, CH2), 6.953-6.989 (d, 2H, Ar–
H), 7.057-7.092 (t, 3H, Ar–H), 7.135-
7.184 (t, 3H, Ar–H), 7.247-7.268 (d, 2H,
Ar–H), 7.395-7.413 (d, 2H, Ar–H).
MS (ESI) m/z [% rel. abundance]: 472.91 (100) [M]+, 473.22
(29.6) [M+1]+, 474.06 (32.6) [M+2]+
Fragments: 437.16 (26.9), 361.29 (23.0), 263.13 (16.5), 248.23
(38.6), 180.38 (14.9), 166.20 (13.1), 115.13 (7.2).
Elemental analysis:
Calcd for C26H25ClN6O: C, 66.03; H, 5.33; N, 17.77.
Found: C, 65.99; H, 5.31; N, 17.75 %.
UV max(DMSO):
348 nm
UV max(DMSO):
333 nm

11. COMPOUND CODE IR (KBr) (cm-1) NMR (DMSO)  ppm
22k 3428.21 (N-H, str.), 3056.09 (Aromatic C-H,
str.), 2941.42 {Aliphatic C-H (Asymmetric),
str.}, 2847.62 {Aliphatic C-H (Symmetric),
str.}, 1652.02 (C=N, str.), 1580.44 (Aromatic
C=C, str.), 1348.15 (C-N (Tertiary), str.),
1148.6 (C-O-C, str. in oxadiazole ring),
1056.92 (Aromatic C-Cl, str.), 756.04 (C-H,
o-disubstituted benzene (def.)).
1.995 (s, 1H, NH, D2O exchangeable),
2.366-2.412 (t, 4H, CH2), 2.587-2.619 (t,
4H, CH2), 4.067 (s, 1H, NH, D2O
exchangeable), 5.014 (s, 1H, CH), 5.208
(s, 2H, CH2), 7.001-7.024 (d, 2H, Ar–H),
7.106-7.137 (t, 3H, Ar–H), 7.226-7.273
(t, 3H, Ar–H), 7.322-7.348 (d, 2H, Ar–
H), 7.425-7.452 (d, 2H, Ar–H).
MS (ESI) m/z [% rel. abundance]: 472.59 (100) [M]+, 473.63 (28.0)
[M+1]+, 474.87 (32.2) [M+2]+
Fragments: 437.14 (30.6), 361.34 (22.5), 263.20 (16.9), 248.11 (41.1),
180.46 (18.6), 166.12 (14.1), 115.06 (5.7).
Elemental analysis:
Calcd for C26H25ClN6O: C, 66.03; H, 5.33; N, 17.77.
Found: C, 66.02; H, 5.30; N, 17.76 %.
22l 3415.30 (N-H, str.), 3060.82 (Aromatic C-H,
str.), 2931.6 {Aliphatic C-H (Asymmetric), str.),
2844.38 {Aliphatic C-H (Symmetric), str.},
1639.07 (C=N, str.), 1579.4 (Aromatic C=C,
str.), 1320.25 (C-N (Tertiary), str.), 1242.07
(Asymmetric C-O-C str. of aryl alkyl ether),
1124.42 (C-O-C, str. in oxadiazole ring),
1037.19 (Symmetric C-O-C str. of aryl alkyl
ether), 667.59 (C-H, m-disubstituted benzene
(def.)).
2.069 (s, 1H, NH, D2O exchangeable),
2.443-2.483 (t, 4H, CH2), 2.687-2.723
(t, 4H, CH2), 3.739 (s, 3H, OCH3),
4.068 (s, 1H, NH, D2O exchangeable),
4.953 (s, 1H, CH), 5.156 (s, 2H, CH2),
6.594-6.633 (t, 3H, Ar–H), 6.819-6.822
(d, 2H, Ar–H), 6.984-7.002 (d, 2H, Ar–
H), 7.076-7.092 (d, 2H, Ar–H), 7.275-
7.368 (t, 3H, Ar–H).
MS (ESI) m/z [% rel. abundance]: 468.23 (100) [M]+, 469.34 (29.1)
[M+1]+
Fragments: 453.20 (31.3), 437.48 (26.1), 361.10 (22.9), 263.25 (15.4),
248.29 (37.7), 180.14 (15.1), 166.19 (12.1), 115.11 (5.2).
Elemental analysis:
Calcd for C27H28N6O2: C, 69.21; H, 6.02; N, 17.94.
Found: C, 69.20; H, 6.00; N, 17.91 %.
UV max(DMSO):
330 nm
UV max(DMSO):
328 nm

12. COMPOUND CODE IR (KBr) (cm-1) NMR (DMSO)  ppm
22m 3416.42 (N-H, str.), 3053.11 (Aromatic C-H,
str.), 2935.08 {Aliphatic C-H (Asymmetric),
str.}, 2839.02 {Aliphatic C-H (Symmetric),
str.}, 1645.88 (C=N, str.), 1595.31 (Aromatic
C=C, str.), 1323.08 (C-N (Tertiary), str.),
1251.72 (Asymmetric C-O-C str. of aryl alkyl
ether), 1161.07 (C-O-C, str. in oxadiazole
ring), 1016.42 (Symmetric C-O-C str. of aryl
alkyl ether), 854.41 (C-H, p-disubstituted
benzene (def.)).
1.952 (s, 1H, NH, D2O exchangeable),
2.403-2.483 (t, 4H, CH2), 2.627-2.663 (t,
4H, CH2), 3.731 (s, 3H, OCH3), 4.085
(s, 1H, NH, D2O exchangeable), 4.899
(s, 1H, CH), 5.207 (s, 2H, CH2), 6.653-
6.698 (t, 3H, Ar–H), 6.883-6.902 (d, 2H,
Ar–H), 7.041-7.065 (d, 2H, Ar–H),
7.122-7.156 (d, 2H, Ar–H), 7.309-7.372
(t, 3H, Ar–H).
MS (ESI) m/z [% rel. abundance]: 468.72 (100) [M]+, 469.66 (28.7)
[M+1]+
Fragments: 453.38 (30.7), 437.31 (27.1), 361.15 (22.6), 263.11 (16.6),
248.04 (40.4), 180.18 (14.0), 166.20 (10.6), 115.08 (4.6).
Elemental analysis:
Calcd for C27H28N6O2: C, 69.21; H, 6.02; N, 17.94.
Found: C, 69.18; H, 6.01; N, 17.93 %.
22n 3417.63 (N-H, str.), 3051.18 (Aromatic C-H,
str.), 2933.01 {Aliphatic C-H (Asymmetric),
str.}, 2843.29 {Aliphatic C-H (Symmetric),
str.}, 1653.14 (C=N, str.), 1575.73 (Aromatic
C=C, str.), 1334.65 (C-N (Tertiary), str.),
1257.5 (Aromatic C-F, str.), 1151.42 (C-O-C,
str. in oxadiazole ring), 860.19 (C-H, p-
disubstituted benzene (def.)).
2.052 (s, 1H, NH, D2O exchangeable),
2.356-2.407 (t, 4H, CH2), 2.618-2.653 (t,
4H, CH2), 4.152 (s, 1H, NH, D2O
exchangeable), 4.895 (s, 1H, CH), 5.104
(s, 2H, CH2), 6.822-6.859 (d, 2H, Ar–H),
6.907-6.952 (t, 3H, Ar–H), 7.056-7.099
(t, 3H, Ar–H), 7.121-7.148 (d, 2H, Ar–
H), 7.325-7.352 (d, 2H, Ar–H).
MS (ESI) m/z [% rel. abundance]: 456.21 (100) [M]+, 457.35
(27.9) [M+1]+
Fragments: 437.04 (27.3), 361.06 (22.1), 263.19 (15.4), 248.16
(39.3), 180.02 (16.3), 166.09 (12.8), 115.18 (7.6).
Elemental analysis:
Calcd for C26H25FN6O: C, 68.40; H, 5.52; N, 18.41.
Found: C, 68.39; H, 5.49; N, 18.38 %.
UV max(DMSO):
330 nm
UV max(DMSO):
342 nm

13. COMPOUND CODE IR (KBr) (cm-1) NMR (DMSO)  ppm
22o 3410.65 (N-H, str.), 3045.22 (Aromatic C-H,
str.), 2931.6 {Aliphatic C-H (Asymmetric),
str.}, 2832.54 {Aliphatic C-H (Symmetric),
str.}, 1678.38 (C=N, str.), 1604.66 (Aromatic
C=C, str.), 1325.01 (C-N (Tertiary), str.),
1157.2 (C-O-C, str. in oxadiazole ring).
2.082 (s, 1H, NH, D2O exchangeable),
2.406-2.440 (t, 4H, CH2), 2.594-2.642 (t,
4H, CH2), 4.083 (s, 1H, NH, D2O
exchangeable), 5.017 (s, 1H, CH), 5.214
(s, 2H, CH2), 7.012-7.039 (d, 2H, Ar–H),
7.157-7.192 (t, 3H, Ar–H), 7.226-7.269
(t, 3H, Ar–H), 7.312-7.338 (d, 2H, Ar–
H), 7.402-7.428 (d, 2H, Ar–H).
MS (ESI) m/z [% rel. abundance]: 438.22 (100) [M]+, 439.42
(27.6) [M+1]+
Fragments: 361.40 (22.4), 263.01 (16.5), 248.10 (38.0), 180.05
(17.4), 166.06 (13.2), 115.71 (5.5).
Elemental analysis:
Calcd for C26H26N6O: C, 71.21; H, 5.98; N, 19.16.
Found: C, 71.19; H, 5.95; N, 19.15 %.
UV max (DMSO):
320 nm

14. BIOLOGICAL EVALUATION
1. Antibacterial activity: Method: Disc diffusion method; Media- Nutrient Agar
Standard Drug: Ciprofloxacin
Code of
Compounds
Diameter of zone of inhibition in mm [mean  S.D. (n=3)]
B.subtilis S.aureus
25 g ml-1 50 g ml-1 100 g ml-1 25 g ml-1 50 g ml-1 100 g ml-1
22a 12.87 ± 0.19 16.24 ± 0.31 18.75 ± 0.28 13.68 ± 0.22 16.18 ± 0.35 19.25 ± 0.14
22b 10.26 ± 0.13 12.6 ± 0.18 13.45 ± 0.09 11.47 ± 0.40 14.69 ± 0.19 17.19 ± 0.27
22c 9.1 ± 0.41 10.19 ± 0.37 13.16 ± 0.25 10.62 ± 0.63 12.83 ± 0.34 14.59 ± 0.49
22d 11.71 ± 0.28 15.64 ± 0.14 17.62 ± 0.32 13.50 ± 0.09 16.28 ± 0.16 19.11 ± 0.24
22e 10.98 ± 0.37 14.1 ± 0.35 18.36 ± 0.19 11.64 ± 0.43 15.94 ± 0.11 18.87 ± 0.19
22f 11.91 ± 0.15 13.66 ± 0.28 17.89 ± 0.21 12.14 ± 0.37 14.82 ± 0.25 17.99 ± 0.13
22g 10.07 ± 0.33 11.31 ± 0.11 13.77 ± 0.16 11.1 ± 0.41 13.63 ± 0.23 16.2 ± 0.18
22h 12.56 ± 0.22 15.42 ± 0.14 18.1 ± 0.20 11.82 ± 0.39 15.22 ± 0.14 18.73 ± 0.31
22i 9.91 ± 0.10 10.86 ± 0.29 12.65 ± 0.41 9.9 ± 0.21 11.46 ± 0.16 14.81 ± 0.08
22j 10.84 ± 0.26 14.38 ± 0.30 16.32 ± 0.37 10.68 ± 0.15 13.74 ± 0.29 16.97 ± 0.20
22k 10.59 ± 0.17 13.53 ± 0.13 15.68 ± 0.26 10.05 ± 0.14 12.41 ± 0.35 15.49 ± 0.26
22l 8.87 ± 0.23 10.14 ± 0.42 12.19 ± 0.10 7.9 ± 0.22 8.89 ± 0.14 11.76 ± 0.46
22m 9.4 ± 0.36 9.95 ± 0.11 11.96 ± 0.46 8.48 ± 0.25 10.32 ± 0.13 12.67 ± 0.38
22n 13.94 ± 0.11 16.87 ± 0.24 19.21 ± 0.39 14.21 ± 0.06 16.52 ± 0.15 19.89 ± 0.27
22o 7.83 ± 0.27 8.23 ± 0.17 8.8 ± 0.11 9.43 ± 0.20 9.91 ± 0.31 11.16 ± 0.25
Ciprofloxacin - 15.51 ± 0.27 - 17.84 ± 0.65
a) Antibacterial activity of synthesized compounds for gram positive strains

15. Code of
Compounds
Diameter of zone of inhibition in mm [mean  S.D. (n=3)]
E. coli P. aeruginosa
25 g ml-1 50 g ml-1 100 g ml-1 25 g ml-1 50 g ml-1 100 g ml-1
22a 18.87 ± 0.19 22.09 ± 0.22 26.46 ± 0.14 19.89 ± 0.24 24.01 ± 0.15 27.25 ± 0.36
22b 16.91 ± 0.33 20.29 ± 0.14 23.65 ± 0.40 17.41 ± 0.12 19.54 ± 0.23 22.86 ± 0.29
22c 15.23 ± 0.24 17.16 ± 0.17 18.82 ± 0.61 15.28 ± 0.30 17.19 ± 0.21 19.53 ± 0.23
22d 19.04 ± 0.14 21.81 ± 0.19 26.01 ± 0.03 20.37 ± 0.46 24.16 ± 0.12 26.68 ± 0.31
22e 18.75 ± 0.17 22.31 ± 0.55 26.28 ± 0.32 18.99 ± 0.39 22.74 ± 0.31 25.83 ± 0.54
22f 17.72 ± 0.10 21.63 ± 0.25 24.93 ± 0.5 20.19 ± 0.26 23.05 ± 0.41 24.96 ± 0.18
22g 15.8 ± 0.56 19.45 ± 0.28 21.33 ± 0.35 16.29 ± 0.11 18.08 ± 0.16 20.89 ± 0.49
22h 18.35 ± 0.09 21.97 ± 0.26 25.83 ± 0.31 18.45 ± 0.22 22.49 ± 0.12 25.26 ± 0.27
22i 16.18 ± 0.17 18.65 ± 0.15 20.51 ± 0.54 17.01 ± 0.18 19.16 ± 0.44 21.2 ± 0.39
22j 17.19 ± 0.09 20.84 ± 0.12 25.79 ± 0.21 19.74 ± 0.33 23.71 ± 0.28 25.98 ± 0.14
22k 16.84 ± 0.22 21.04 ± 0.30 24.48 ± 0.14 17.88 ± 0.25 21.5 ± 0.32 23.63 ± 0.27
22l 14.15 ± 0.38 15.89 ± 0.18 17.72 ± 0.44 12.91 ± 0.46 15.63 ± 0.10 17.98 ± 0.32
22m 14.98 ± 0.20 16.77 ± 0.39 18.2 ± 0.18 15.11 ± 0.5 17.24 ± 0.21 20.16 ± 0.24
22n 19.26 ± 0.17 22.69 ± 0.11 26.87 ± 0.26 20.24 ± 0.30 23.67 ± 0.15 26.81 ± 0.17
22o 12.07 ± 0.32 14.55 ± 0.18 17.74 ± 0.61 14.17 ± 0.11 15.95 ± 0.27 18.27 ± 0.53
Ciprofloxacin - 22.2 ± 0.46 - - 26.50 ± 0.54 -
b) Antibacterial activity of synthesized compounds for gram negative strains

16. 2. Antifungal activity: Method: Disc diffusion method; Media: Nutrient agar
Standard drug: Fluconazole
Code of
Compounds
Diameter of zone of inhibition in mm [mean  S.D. (n=3)]
C. albicans A. niger
25 g ml-1 50 g ml-1 100 g ml-1 25 g ml-1 50 g ml-1 100 g ml-1
22a 12.68 ± 0.18 16.36 ± 0.38 18.53 ± 0.21 8.63 ± 0.18 11.1 ± 0.26 15.47 ± 0.20
22b 9.8 ± 0.09 13.11 ± 0.17 15.69 ± 0.4 7.54 ± 0.09 9.91 ± 0.16 12.46 ± 0.30
22c 8.27 ± 0.37 10.16 ± 0.46 11.92 ± 0.33 6.2 ± 0.36 8.19 ± 0.51 10.58 ± 0.37
22d 12.2 ± 0.24 16.13 ± 0.19 18.35 ± 0.27 8.29 ± 0.11 11.72 ± 0.29 15.66 ± 0.32
22e 13.21 ± 0.43 15.37 ± 0.26 17.66 ± 0.41 7.33 ± 0.33 10.59 ± 0.25 14.43 ± 0.12
22f 11.77 ± 0.34 14.9 ± 0.16 16.71 ± 0.30 8.84 ± 0.27 10.28 ± 0.18 13.8 ± 0.33
22g 8.91 ± 0.19 12.26 ± 0.35 14.35 ± 0.22 7.0 ± 0.53 9.57 ± 0.40 11.45 ± 0.24
22h 12.56 ± 0.28 15.10 ± 0.44 17.48 ± 0.25 8.01 ± 0.39 10.96 ± 0.10 14.86 ± 0.42
22i 10.88 ± 0.5 14.91 ± 0.20 16.86 ± 0.11 7.41 ± 0.14 10.38 ± 0.31 13.79 ± 0.22
22j 11.31 ± 0.29 15.62 ± 0.31 17.89 ± 0.39 7.86 ± 0.23 10.87 ± 0.43 14.73 ± 0.32
22k 10.85 ± 0.32 15.1 ± 0.19 16.89 ± 0.25 6.61 ± 0.30 10.4 ± 0.35 14.24 ± 0.28
22l 6.15 ± 0.40 8.9 ± 0.42 10.38 ± 0.36 5.38 ± 0.11 7.15 ± 0.26 8.63 ± 0.20
22m 7.48 ± 0.27 9.52 ± 0.10 11.66 ± 0.24 6.14 ± 0.41 8.39 ± 0.15 9.74 ± 0.30
22n 11.89 ± 0.5 15.97 ± 0.39 18.1 ± 0.12 7.91 ± 0.38 11.45 ± 0.47 15.18 ± 0.34
22o 5.95 ± 0.27 8.12 ± 0.28 10.16 ± 0.46 3.61 ± 0.35 5.83 ± 0.12 7.98 ± 0.41
Fluconazole - 16.91 ± 0.58 - 11.87 ± 0.32

17.  Graph showing antibacterial activity
of synthesized compounds (22a – 22o)
and ciprofloxacin as a standard drug
at 50g/ml concentration
 Graph showing antifungal activity
of synthesized compounds (22a-22o)
and fluconazole as a standard drug
at 50g/ml concentration

18. 3. Anticancer activity: In-vitro testing on MCF7 cell line done at Tata Memorial Centre
Method: Sulforhodamine B assay; Cell line: MCF7
Human Breast Cancer Cell Line MCF7
%Control Growth
Drug Concentrations (µg/ml)
Compound no. 10 20 40 80
22a 40.4 27.4 10.3 2.1
22b 58.5 45.3 38.2 30.8
22c 52.4 40.9 34.7 29.2
22d 43.7 19.1 10.0 2.8
22e 59.6 41.5 30.2 22.6
22f 53.4 38.7 27.2 13.3
22g 61.6 50.2 41.9 36.0
22h 51.9 33.7 28.5 16.4
22i 58.2 49.3 37.0 31.3
22j 55.8 38.5 27.6 18.1
22k 46.9 31.5 11.8 3.4
22l 50.6 37.3 29.7 20.2
22m 49.2 34.6 18.3 13.9
22n 35.4 11.3 8.4 1.2
22o 66.4 53.7 45.2 39.4
ADR (Std.) 0.3 -10.7 -33.6 -59.7

19. Results of anticancer activity in terms of GI50 values
Concentration (µg/ml)
GI50 (Calculated from graph): MCF7 Cell
Line
22a <10
22b 27.1
22c 24.6
22d <10
22e 19.3
22f 11.8
22g 31.0
22h 13.2
22i 28.5
22j 14.3
22k <10
22l 15.8
22m 11.2
22n <10
22o 35.0
ADR <10

20. CONCLUSION
 Carbazole derivatives were synthesized by conventional method.
Synthesized compounds were identified on the basis of physical
parameters (Solubility, melting point), chromatographic methods (TLC)
and spectroscopic methods (UV, IR, 1H NMR and Mass spectrometry).
 The results revealed that newly synthesized compounds 22n, 22a and 22d
were found to be potent against B. subtilis; 22n, 22d and 22a against S.
aureus; 22n and 22e against E. coli; 22d and 22a against P. aeruginosa
and antifungal activity 22a and 22d against C. albicans while 22d, 22n
and 22a were found to be potent against A. niger.
 The results indicated that the compound 22n have minimum G150 value
among all the tested compounds. Compound 22n was found to be most
potent with 35.4 % control growth and < 10 µg/ ml GI50 value.
Compounds 22a, 22d and 22k were also found to be potent with 40.4,
43.7 and 46.9 % control growth and < 10 µg/ ml GI50 value respectively.

21. Future Scope:
 A series of carbazole derivatives were synthesized and
screened for antibacterial, antifungal and anticancer
activities. Some of the derivatives showed promising
activities viz, 22n, 22a, 22d and 22k.
 These derivatives can further be evaluated for clinical
and toxicity studies.

22. Thanks…