Erna Fitriana Alfanti
Erna Fitriana Alfanti
Erna Fitriana Alfanti
ABSTRACT
INTRODUCTION
Chalcones either natural or synthetic are known to exhibit various biological
activities. Chalcones were prepared by condensation of acetophenone with aromatic
aldehydes in presence of suitable condensing agent1,2. They undergo a variety of chemical
reactions that leads to many heterocyclic compounds3-6. Chalcones have been used as
intermediates for the preparation of compounds having therapeutic value7,8. Many reviews
reveal that chalcone derivatives exhibit diverse pharmacological activities, such as potential
Cytotoxic agents, antimicrobial agents, antiviral, anti-inflammatory, anesthetic, etc.9,10. In the
view of the varied biological and pharmacological applications, we have planned to
synthesize some heterocyclic derivatives of chalcone and test their antibacterial activity.
Whereas pyrazole is a class of organic compounds, which has many applications in different
field. One of the methods for the synthesis of such compound is from α, β-unsaturated
carbonyl by the cyclization with substituted hydrazines.
EXPERIMENTAL
Melting points of all synthesized compounds were determined in open capillary
METHODS
SPECTRAL INTERPRETATION
2-(4-Chloro-phenyl)-1-{2-[3-(4-hydroxy-phenyl)-5-thiophen-2-yl-4,5-dihydro-pyrazole-
1-carbonyl]-phenyl}-ethanone 5b
IR (cm-1): v (OH) 3384; v (CH) 2984; v (C=O) 1705; v (C=O) 1675; v (N-N=C) 1238.
1H NMR d (ppm): 2. 0 (d, 2H, CH2); 3.80 (s, 2H, CH2); 4.9 (t, 1H, CH); 5.2 (s, 1H, OH);
7.05- 8.3 (m, 15H, Ar-H);
13 C NMR d ppm: 38.25 (CH2); 42.23 (CH2); 40.32 (CH2); 122-149 (Ar-C); 156-158
(-C=N,); 168.4 (C=O); 196.4 (C=O); MS: 500.5 (M+)
2-(4-Chloro-phenyl)-1-[2-(5-thiophen-2-yl-3-p-tolyl-4,5-dihydro-pyrazole-1-carbonyl)-
phenyl]-ethanone 5c
IR (cm-1): v (CH) 2980; v (C=O) 1700; v (C=O) 1680; v (N-N=C) 1231.
1H NMR d (ppm): 1.9 (s, 3H, CH3); 2. 0 (d, 2H, CH2); 3.80 (s, 2H, CH2);4.9 (t, 1H, CH);
7.05- 8.3 (m, 15H, Ar-H);
13 C NMR d ppm: 22.25 (CH3); 37.28 (CH2); 43.21 (CH2); 40.32 (CH2); 123-148 (Ar-C);
156-158 (-C=N,); 168.8 (C=O); 195.5 (C=O); MS: 498.5 (M+)
2-(4-Chloro-phenyl)-1-{2-[3-(4-chloro-phenyl)-5-phenyl-4,5-dihydro-pyrazole-1-
carbonyl]-phenyl}-ethanone 6a:
IR (cm-1): v (CH) 2980; v (C=O) 1700; v (C=O) 1680; v (N-N=C) 1231.
1H NMR d (ppm): 2. 1 (d, 2H, CH2); 3.85 (s, 2H, CH2);4.8 (t, 1H, CH); 7.05- 7.6 (m, 15H,
Ar-H);
13 C NMR d ppm: 38.28 (CH2); 42.21 (CH2); 40.72 (CH2); 118-145 (Ar-C); 156-158
(-C=N,); 168.8 (C=O); 195.5 (C=O); MS: 512 (M+)
OH
NHNH2
O
1) SOCl2 / MDC stirr RT O
2) NH2NH2.H2O / CH3OH
Cl
(2) Cl
(1)
O
H
C CH
S R HC CH
O R
(3) (4)
R N N R
S N N
O
O
O
O
Cl
Cl (6)
(5)
5a 17 16 16 18 15 17 10
5b 15 14 17 18 16 12 11
5c 16 18 19 19 17 9 10
6a 17 16 18 17 19 10 9
6b 14 16 17 20 16 9 9
6c 16 17 16 20 18 11 10
6d 14 14 17 21 15 12 10
DMSO 0 0 0 0 0 0 0
Ampicilin® 24 20 19 22 24 14 14
E.coli. = Escherichia coli; P.putide = Pseudomonas Putide; B. subtilis = Bacillus Subtilis; S.
lactis = Sterptococcus lactis; A. niger = Aspergillus niger; P. Sp. = Penicillium Sp; C. albicans =
candida Albicans.
The sensitivity of microorganisms to the tested compounds is identified in the following manner*;
Highly Sensitive = Inhibition zone: 15-20 mm
Moderately Sensitive = Inhibition zone: 10-15 mm
Slightly Sensitive = Inhibition zone: 5-10 mm
Not Sensitive = Inhibition zone: 0 mm
* Each result represents the average of triplicate readings.
* N.B. Concentration selected was 100 µg/ml and DMSO was used as the solvent.
CONCLUSION
The synthesized pyrazolines 5a-c & 6a-d all are novel. Compounds with electron
releasing groups such as hydroxyl, methoxy and compounds having pharmacophores such as
chloro groups and all these groups are present in moiety exhibited good antimicrobial
activity. The synthesized compounds 5a-c & 6a-d showed convincing activity against Fungi,
ACKNOWLEDGEMENT
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