Synthesis and Biological evaluation of some newer Pyrazole Derivatives

 

Ajay Sharma*, Gyanendra Kumar Sharma, Himansu Chopra

Rajiv Academy for Pharmacy, Mathura-281001.

*Corresponding Author E-mail: Ajaysharma199740@gmail.com

 

ABSTRACT:

Pyrazoline is a 5-membered heterocyclic moiety has two adjoining nitrogen iotas and three carbon particles inside the ring. Pyrazoline subordinate are related wide scope of pharmacological and restorative exercises, for example, antibacterial, antifungal, pain relieving, calming, hostile to parasitic, against malarial, against oxidant. The ongoing work of exploration is fundamentally engaged at the revelation and improvement of a progression of 1,3,5-trisubstituted pyrazoline. A progression of new 1-phenyl-3-(4-nitrophenyl)- 5-(subbed phenyl) pyrazoline subordinates (2a-2j) were blended by the response of subbed acetophenone and subbed benzaldehyde within the sight of fluid sodium hydroxide arrangement by Claisen Schmidt buildup system. The subbed chalcone were integrated which is additionally dense with phenyl hydrazine in ethanol and results in the definition of conclusive subordinates of pyrazoline (2a-2j). The response blend was observed by TLC and the last mixes were refined by recrystallization from wanted dissolvable. All the structures of blended mixes were affirmed by FTIR, 1H NMR, mass unearthly information and essential investigation. All the recently combined mixes (2a-2j) were assessed for antibacterial and antifungal movement. Mixes 2f, 2i and 2h showed powerful inhibitory impact against on strains of both bacterial and parasitic species.

 

KEYWORDS: Pyrazoline, Antibacterial, Antifungal, Chalcone, Substituted benzaldehyde.

 

 


INTRODUCTION:

Pyrazoline is a five-membered heterocyclic compound with atomic recipe C3H6N2. Pyrazole contains two nitrogen molecules which are available at contiguous situations in regard to one another1. Among these two nitrogen particles, one has fundamental character and the different gets nonpartisan conduct in nature2. Pyrazoline is rich of pi-electrons and the fragrant conduct in pyrazoline shows up from the nearness of solitary sets present on the NH nitrogen3.

 

Pyrazole core are available in a few driving medications, for example, Viagra, celebrex and so on pyrazoles is a raised plateform for a few examination programmes in agro compound just as pharmaceutical field4.

 

Pyrazoline additionally containing two nitrogen particles however there is just single or one endocyclic bond5. Pyrazoline subsidiary are related wide scope of pharmacological and restorative exercises, for example, antibacterial, antifungal, pain relieving, calming, against parasitic, hostile to malarial6. Overview of some audit writing clarified that the pyrazoline subsidiaries have cerebro defensive impact and CNS depressant action7. We have integrated a progression of 1-phenyl-3-(4-nitrophenyl)- 5-(subbed phenyl) pyrazoline subordinates (2a-2j) by utilizing subbed chalcone subsidiaries (1a-1j). All the recently combined subsidiaries were assessed for antibacterial and antifungal exercises separately8. The antibacterial action was tried against Gram negative and Gram-positive microscopic organisms' on Nutrient agar media plates by paper circle dissemination strategy. Then again, the Antifungal action was completed against types of parasites strains on Nutrient agar media by circle dispersion strategy9.

 

MATERIAL AND METHOD:

All synthetics utilized in the union were of engineered grade and were provided by CDH Delhi, Qualigens Fine Labs Mumbai, S d fine chem. Ltd. Mumbai, Loba synthetic concoctions ltd. Dissolving purpose of the orchestrated mixes was finished by open cylinder slender strategy. Cleaning of the mixes was checked by TLC by utilizing Chloroform: Methanol (1:1). Spots were seen under iodine chamber. IR spectra 1H NMR-spectra were recorded in DMSO or CDCl3 utilizing TMS as the interior norm. (Compound move in ppm) and mass spectra were recorded on water OPLCTQDMS in positive mode10.

 

Scheme of work:

 

1-phenyl-3-(4-nitrophenyl)-5-(substituted phenyl) pyrazoline (2a-2j)

 

Table 1: Substitution of Derivatives (2a-2j)

Compounds

R

1.

2-Chloro

2.

3-chloro

3.

2-nitro

4.

3-nitro

5.

4-nitro

6.

2-hydroxy

7.

3,4,5-trimethoxy

8.

4-methoxy

9.

4-fluoro

10.

4-dimethylamino

 

General procedure for Synthesis of 1-(4-Nitrophenyl)-3-(substitutedphenyl) prop-2-en-1-one (1a-1j):-

A blend of p-Nitroacetophenone (0.02mol) and fragrant subbed Benzaldehyde (0.02mol) was broken down in ethanol (40ml) and the arrangement was warmed to the bubbling. To this arrangement 20ml (40% NaOH) was included with consistent blending for 8 hour at room temperature to make the arrangement soluble. The strong mass was gotten which was kept for the time being and fermented by 10% HCl washed with NaHCO3 followed by water and recrystallized with ethanol11.

 

Step:-2 Synthesis of 1-phenyl-3-(4-nitrophenyl)-5-(substituted phenyl) pyrazoline derivatives (2a-2j

 

 
):-

A blend of substituted chalcone (0.05mol) react with phenyl hydrazine (0.05mol) in the presence of acetic acid (20ml) was refluxed for 3 hour. At that point filled ice cooled water. The hasten was isolated by filtration, washed liberated from corrosive to offered pyrazoline moiety and afterward dried and recrystallized from ethanol. The completion of reaction was monitored by TLC12.

 

5-(2-chlorophenyl)-4,5-dihydro-3-(4-nitrophenyl)-1-phenyl-1H-pyrazole (2a):

Yield 55%, Rf value- 0.64 m.p. 193℃ ; FTIR (KBr) νmaxcm-1: 3028.47 (Ar C-H, str.), 1674.31 (C=C, str.), 1528.12 (C=N, str.), 1322.18 (C-N, str.), 770.59 (C-Cl, str.), 1617.14 (C-C, str.), 1508 (Ar-NO2, str.); 1H NMR (DMSO-d6): δ 1.017-1.134 (d, 2H, C-H of aromatic pyrazoline), 4.026-4.209 (t, 1H, aromatic pyrazoline C-H), 6.126-6.892 (m, 9H, Ar-H), 7.912-8.091 (dd, 4H, Ar-H); Anal Calcd. For C21H16ClN3O2: C, 66.76; H, 4.27; N, 11.12. Found: C, 66.74; H, 4.29; N, 11.13%.

 

5-(3-Chlorophenyl)-4,5-Dihydro-3-(4-nitrophenyl)-1-phenyl-1H-pyrazole (2b):

Yield 51%, Rf value- 0.62 m.p. 193℃ ; FTIR (KBr) νmaxcm-1: 3073.86 (Ar C-H, str.), 1648.26 (C=C, str.), 1530.28 (C=N, str.), 1305.43 (C-N, str.), 768.95 (C-Cl, str.), 982.36 (C-C, str.), 1325.38 (Ar-NO2, str.); 1H NMR (DMSO-d6): δ 1.512-1.662 (d, 2H, C-H of aromatic pyrazoline), 4.132-4.398 (t, 1H, aromatic pyrazoline C-H), 6.235-7.012 (m, 9H, Ar-H), 7.801-8.001 (dd, 4H, Ar-H); Anal Calcd for C21H16ClN3O2: C, 66.76; H, 4.27; N, 11.12 Found: C, 66.74; H, 4.28; N, 11.14%.

 

4,5-dihydro-5-(2-nitrophenyl)-3-(4-nitrophenyl)-1-phenyl-1H-pyrazole (2c):

Yield 51%, Rf value- 0.56 m.p. 193℃ ; FTIR (KBr) νmaxcm-1: 3058.34 (Ar C-H, str.), 1630.32 (C=C, str.), 1550.81 (C=N, str.), 1317.14 (C-N, str.), 1623.36 (C-C, str.), 1373.15 (Ar-NO2, str.); 1H NMR (DMSO-d6): δ 1.653-1.812 (d, 2H, C-H of aromatic pyrazoline), 3.879-4.011 (t, 1H, aromatic pyrazoline C-H), 6.612-7.398 (m, 13H, Ar-H); Anal Calcd for C21H16N4O4: C, 64.94; H, 4.15; N, 14.43 Found: C, 64.92; H, 4.16; N, 14.43%.

 

4,5-dihydro-5-(3-nitrophenyl)-3-(4-nitrophenyl)-1-phenyl-1H-pyrazole (2d):

Yield 65%, Rf value- 0.57 m.p. 191℃ ; FTIR (KBr) νmaxcm-1: 3036.47 (Ar C-H, str.), 1648.23 (C=C, str.), 1536.64 (C=N, str.), 1223.65 (C-N, str.), 1617.55 (C-C, str.), 1436.58 (Ar-NO2, str.); 1H NMR (DMSO-d6): δ 1.698-1.818 (d, 2H, C-H of aromatic pyrazoline), 3.851-4.097 (t, 1H, aromatic pyrazoline C-H), 7.242-8.246 (m, 13H, Ar-H); Anal Calcd for C21H16N4O4: C, 64.94; H, 4.15; N,14.43 Found: C, 64.93; H, 4.12; N, 14.41%

 

4,5-dihydro-3,5-bis-(4-nitrophenyl)-1-phenyl-1H-pyrazole (2e):

Yield 65%, Rf value- 0.55 m.p. 191℃ ; FTIR (KBr) νmaxcm-1: 3041.21 (Ar C-H, str.), 1642.52 (C=C, str.), 1538.42 (C=N, str.), 1248.51 (C-N, str.), 1619.25 (C-C, str.), 1398.38 (Ar-NO2, str.); 1H NMR (DMSO-d6): δ 1.931-2.101 (d, 2H, C-H of aromatic pyrazoline), 3.856-4.001 (t, 1H, aromatic pyrazoline C-H), 7.233-8.012 (m, 13H, Ar-H); Anal Calcd for C21H16N4O4: C, 64.94; H, 4.15; N,14.43% Found: C, 64.91; H, 4.15; N, 14.41%

 

2-(4,5-dihydro-3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-5-yl)phenol (2f):

Yield 65%, Rf value- 0.59 m.p. 191℃ ; FTIR (KBr) νmaxcm-1: 3076.96 (Ar C-H, str.), 1649.59 (C=C, str.), 1610.03 (C=N, str.), 1305.48 (C-N, str.), 975.13 (C-C, str.), 1394.39 (Ar-NO2, str.), 3293.76 (C-OH, str.); 1H NMR (DMSO-d6): δ 2.178-2.363 (d, 2H, C-H of aromatic pyrazoline), 4.131-4.399 (t, 1H, aromatic pyrazoline C-H), 7.135-7.912 (m, 13H, Ar-H), 9.891 (s, 1H, OH); Anal Calcd for C21H17N3O3: C, 70.18; H, 4.77; N, 11.69 Found: C, 70.20; H, 4.74; N, 11.68%

 

4,5-dihydro-5-(3,4,5-trimethoxyphenyl)-3-(4-nitrophenyl)-1-phenyl-1H-pyrazole (2g):

Yield 56%, Rf value- 0.72 m.p. 220℃ ; FTIR (KBr) νmaxcm-1: 3066.21 (Ar C-H, str.), 1641.87 (C=C, str.), 1611.64 (C=N, str.), 1338.25 (C-N, str.), 1015.43 (C-C, str.), 1391.93 (Ar-NO2, str.), 1243.28 (C-O, str.), 2921.30 (Aliphatic C-H, str.); 1H NMR (DMSO-d6): δ 2.475-2.593 (d, 2H, C-H of aromatic pyrazoline), 3.532-3.793 (t, 1H, aromatic pyrazoline C-H), 6.905-7.812 (m, 9H, Ar-H), 6.291 (s, 1H, Ar-H), 5.219-5.742 (s, 9H, OCH3); Anal. Calcd for C24H23N3O5: C, 66.50; H, 5.35; N, 9.65 Found: C, 66.52; H, 5.32; N, 9.67%

 

4,5-dihydro-5-(4-methoxyphenyl)-3-(4-nitrophenyl)-1-phenyl-1H-pyrazole (2h):

Yield 56%, Rf value- 0.70 m.p. 220℃ ; FTIR (KBr) νmaxcm-1: 3085.17 (Ar C-H, str.), 1663.36 (C=C, str.), 1534.54 (C=N, str.), 1323.98 (C-N, str.), 1614.63 (C-C, str.), 1466.23 (Ar-NO2, str.), 1236.08 (C-O, str.), 2910.24 (Aliphatic C-H, str.); 1H NMR (DMSO-d6): δ 2.685-2.893 (d, 2H, C-H of aromatic pyrazoline), 4.421-4.693 (t, 1H, aromatic pyrazoline C-H), 5.246-6.246 (m, 9H, Ar-H), 3.501 (s, 3H, OCH3), 6.972-7.386 (dd, 4H, Ar-H); Anal. Calcd for C22H19N3O3: C, 70.76; H, 5.13; N, 11.25 Found: C, 70.74; H, 5.15; N, 11.24%

 

5-(4-fluorophenyl)-4,5-dihydro-3-(4-nitrophenyl)-1-phenyl-1H-pyrazole (2i):

Yield 65%, Rf value- 0.68 m.p. 191℃ ; FTIR (KBr) νmaxcm-1: 3058.83 (Ar C-H, str.), 1621.26 (C=C, str.), 1609.55 (C=N, str.), 1329.95 (C-N, str.), 1038.58 (C-C, str.), 1379.38 (Ar-NO2, str.), 813.57 (C-F, str.); 1H NMR (DMSO-d6): δ 3.235-3.393 (d, 2H, C-H of aromatic pyrazoline), 4.629-4.823 (t, 1H, aromatic pyrazoline C-H), 5.496-6.546 (m, 5H, Ar-H), 7.289-7.991 (dd, 4H, Ar-H), 8.151-8.491 (dd, 4H, Ar-H); Calcd for C21H16N3O2: C, 69.80; H, 4.46; N, 11.63 Found: C, 69.78; H, 4.48; N, 11.60%

 

4-(4,5-dihydro-3-(4-nitrophenyl)-1-phenyl-1H-pyrazole-5-yl)-N,N-dimethylbenzene (2j):

Yield 65%, Rf value- 0.77 m.p. 191℃ ; FTIR (KBr) νmaxcm-1: 2974.12 (Ar C-H, str.), 1637.59 (C=C, str.), 1603.59 (C=N, str.), 1326.09 (C-N, str.), 1108.81 (C-C, str.), 1328.85 (Ar-NO2, str.), 2953.87 (Aliphatic C-H, str.); 1H NMR (DMSO-d6): δ 2.981-3.113 (d, 2H, C-H of aromatic pyrazoline), 4.571-4.793 (t, 1H, aromatic pyrazoline C-H), 9.112-9.998 (m, 5H, Ar-H), 6.321-6.413 (dd, 4H, Ar-H), 7.521-7.613 (dd, 4H, Ar-H), 5.140-5.290 (s, 6H, Ar-N(CH3)2); Anal. Calcd for C23H22N4O2: C, 71.48; H, 5.74; N, 14.50 Found: C, 71.46; H, 5.72; N, 14.52%

 

Antibacterial activity:

The antibacterial activity of as of late fused auxiliaries of pyrazole was evaluated by paper plate dispersion strategy using supplement agar medium against following microorganism: S. aureus, B. subtilis, (Gram positive) and E. coli (Gram negative).

 

In the method for paper plate dispersion, the paper hover impregnated with blends separate in DMSO at center 25, 50 and 100g ml-1 were used. Hover impregnated with DMSO was used as dissolvable control for antibacterial development because of free dissolvability of test blends. The microorganism culture was spread over enhancement agar media in petri dishes, and a short time later the hover impregnated with the course of action was determined to the outside of the media inoculated with the bacterial strain13.

 

The plates were brought forth at 35℃ for 24 hrs for bacterial social orders. In the wake of incubating, the zones of restraint around the circle were viewed. The zones of hindrance show that the blends prevent improvement of microorganism. Each testing is done in triplicate.


 

Table 2: Antibacterial activities of synthesized compounds

Code of compound

Diameter of zone of inhibition (mm)[ mean S.D. (n=3)]

B.subtilis

E. coli

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

25 g ml-1

50 g ml-1

100 g ml-1

2a

3.220.31

5.190.52

10.210.42

3.280.39

3.200.40

13.180.42

3.250.45

3.280.53

10.230.32

2b

4.510.52

6.610.43

11.560.50

3.200.40

5.760.61

11.080.44

4.620.63

7.360.26

10.660.75

2c

6.290.40

7.230.52

11.50.45

4.590.84

8.760.83

10.280.45

4.560.26

10.760.86

11.790.80

2d

4.230.52

6.260.38

10.360.50

6.160.35

9.961.00

11.30.40

0.000.00

5.360.40

10.620.82

2e

4.720.42

8.560.40

12.420.39

7.430.60

13.761.00

11.40.42

5.060.40

7.520.40

12.600.82

2f

4.360.40

9.560.41

14.620.42

4.380.40

6.550.45

10.280.60

4.830.70

6.760.78

14.161.00

2g

4.840.41

10.480.30

17.360.50

3.340.82

4.630.84

15.680.60

4.100.40

6.940.60

11.441.00

2h

6.580.30

11.620.40

12.920.40

4.630.41

12.960.45

13.00.40

4.550.60

6.911.02

16.040.60

2i

6.830.30

12.080.31

19.350.40

6.150.60

8.920.82

14.40.80

6.381.04

8.550.63

13.420.60

2j

4.620.20

6.380.41

14.380.40

4.830.21

11.420.20

13.690.30

3.750.30

5.580.42

11.900.31

Ciprofloxacin

-

-

19.480.30

-

-

20.520.40

-

-

19.680.90

 


Ciprofloxacin at fixation 100 g ml-1 was used as standard medicine for antibacterial development. The recently integrated mixes 2g, 2i and 2j have greatest strength against B.subtilis. Mixes 2f and 2h displayed most extreme movement against S.aureus. Mixes 2g and 2i contain most extreme intensity against E.coli14.

 

Antifungal activity:

The as of late mixed blends were pursued for their antifungal activity using circle dispersion method on supplement agar media. The in vitro assessment was cultivated for all the coordinated blends for the connection of antifungal activity. The goings with strains were used: Aspergillus niger and Candida albicans.

 

A spore suspension in ordinary saline was set up from the lifestyle of the test living beings on sabouraud's stock media. Each Petri dish was orchestrated into 5 identical portions along the estimation to put one plate. Three plate of test were put on three sections alongside one hover with reference sedate Fluconazole and a plate impregnated with the dissolvable (DMF) as a negative control15. Test were attempted at 25, 50, 100 g/ml obsession in DMF. Fluconazole in the grouping of 50g/ml was used as standard drug for antifungal activity.

The petri plates inoculated with infectious social orders were agonized at 25℃ for 48 hrs. Antifungal activity was directed by evaluating the separation across of the limitation zone for triplicate sets. The separations across got for the test was differentiated and that made by the standard drug Fluconazole. the recently integrated mixes 2a, 2h and 2i indicated great antifungal movement for both parasitic strains when given at fixation 50g ml-1. Results were deciphered in distance across (mm) as far as zone of restraint16.

 

RESULT AND DISCUSSION:

another arrangement of 1-phenyl-3-(4-nitrophenyl)- 5-(subbed phenyl) pyrazoline were inferred by the response of subbed acetophenone and subbed benzaldehyde within the sight of fluid sodium hydroxide arrangement by Claisen Schmidt buildup component17. The subbed chalcone were combined which is additionally consolidated with phenyl hydrazine in ethanol and results in the plan of definite subordinates of pyrazoline (2a-2j). The response blend was checked by TLC which is performed on silica gel G plates and the last mixes were separated and cleaned by recrystallization from wanted dissolvable18.

 

Table 3: Antifungal activity of synthesized compound

Code of compound

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

2a

6.240.21

12.720.22

21.280.30

6.050.12

9.050.24

14.300.10

2b

4.510.10

10.400.14

16.500.31

2.720.10

9.660.35

11.400.50

2c

8.400.20

8.180.21

20.180.26

5.700.10

7.310.32

16.350.33

2d

5.660.90

10.320.10

18.780.15

5.720.05

10.120.20

19.390.21

2e

3.880.60

7.700.06

13.080.08

1.660.05

7.450.10

10.580.36

2f

3.500.20

9.110.12

10.520.35

4.780.15

11.700.12

15.490.32

2g

2.360.10

9.650.20

15.450.72

4.760.08

10.340.17

13.350.10

2h

11.480.11

13.200.40

25.810.70

8.200.20

11.661.08

21.860.80

2i

7.400.20

13.560.18

24.460.10

2.350.05

12.260.50

11.540.21

2j

5.360.10

9.450.42

15.450.18

3.200.38

10.340.15

16.150.30

Fluconazole

-

16.650.06

-

-

16.850.16

-

Control

-

-

-

-

-

-

 


The structures of recently integrated subordinates (2a, 2b, 2c, 2d, 2e, 2f, 2g, 2h, 2i, 2j) were tried and affirmed by FTIR, 1H NMR, and Mass otherworldly information. The FTIR spectra of recently orchestrated subordinates demonstrated the nearness of trademark ingestion band in the district 3100-3000 cm-1 for sweet-smelling C-H str., 1610-1520 cm-1 for C=N extending, and 1350-1220 cm-1 for C-N extending, 1680-1530 cm-1 for C=C extending, 1360-1310 cm-1 for C-N extending (tertiary str). 1H NMR spectra of integrated subsidiaries showed the trademark tops in the area 6.673-8.035ppm for sweet-smelling protons, 3.501 for OCH3 protons, 9.891ppm for OH protons. The outcomes affirmed that recently orchestrated mixes 2g, 2i and 2j have most extreme power against B.subtilis. Mixes 2f and 2h showed most extreme movement against S.aureus. Mixes 2g and 2i contain most extreme power against E.coli. Mixes 2a, 2h and 2j were seen as moderate strength against E.coli19. Mixes 2a, 2h and 2i showed greatest strength against C.ablicans. Subsidiaries 2f, 2h and 2i have great action against A. niger. In last of the outcome, the electron withdwaring, electron giving and electronegative gatherings on benzene ring increment the strength of mixes.

 

CONCLUSIONS:

The blend os 1,3,5-trisubstituted pyrazoline by the above strategy brought about excellent yields and affirmed by FTIR, 1H NMR, Mass unearthly information, essential investigation, organic examinations indicated that mixes displayed huge antibacterial and antifungal movement.

 

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Received on 29.07.2020 Modified on 18.12.2020

Accepted on 24.02.2021 RJPT All Right Reserved

Research J. Pharm. and Tech 2021; 14(12):6304-6308.

DOI: 10.52711/0974-360X.2021.01090