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Greener Approach of Synthesis of Azo Derivatives and Bis- Pyrazole

Derivatives Along With Antimicrobial Screening

Article in World Journal of Pharmaceutical Research · April 2018

DOI: 10.20959/wjpr20187-11613

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 World Journal of Pharmaceutical Research
Chaudhari et al. SJIF Impact
World Journal of Pharmaceutical Factor 8.074
Research
Volume 7, Issue 7, 1640-1656. Research Article ISSN 2277– 7105

GREENER APPROACH OF SYNTHESIS OF AZO DERIVATIVES AND

BIS- PYRAZOLE DERIVATIVES ALONG WITH ANTIMICROBIAL
SCREENING

Prashant P. Chaudhari1* and Shankarsing S. Rajput2

1
Department of Engineering Science, Dr. D Y Patil School of Engineering, Dr. D Y Patil
Knowledge City, Charoli (Bk), Lohegaon, Pune (412105) Maharashtra, India.
2
Department of Chemistry, SVS’s Dadasaheb Rawal College, Dondaicha (425408),
Maharashtra, India.

ABSTRACT
Article Received on
19 February 2018, A clean, efficient and solvent free method for the synthesis of Azo
Revised on 11 March 2018, compounds was carried out with the help of PbO nanoparticles. They
Accepted on 01 April 2018,
DOI: 10.20959/wjpr20187-11613
have been synthesized by the reaction between 1-(N-methylpyridin-2-
yl)pyrrolidine/ piperidine -2,5/6-dione and propionaldehyde at room
temperature with the help of green chemistry. PbO nanoparticles
*Corresponding Author
employed as an efficient catalytic tool due to efficient, renewable and
Prashant P. Chaudhari
Department of Engineering eco-friendly heterogeneous characteristics. The bis pyrazoles are
Science, Dr. D Y Patil synthesized by a simple eco-friendly microwave instigated solvent free
School of Engineering, Dr. synthesis. It was carried out by the reaction of corresponding bis-
D Y Patil Knowledge City,
chalcones : 3,4/5-bis((E)-2-chlorobenzylidene)-1-(N-methylpyridin-2-
Charoli (Bk), Lohegaon,
yl)pyrrolidine/ piperidine -2,5/6-dione with hydrazine hydrate in
Pune (412105)
Maharashtra, India. presence of neutral Alumina. This method furnished various
advantages, such as straight forward work-up procedure,
environmentally benevolent, neutral condition and high yield. All the derivatives were
characterized and interpreted for antimicrobial activities.

KEYWORDS: Green Chemistry, clean, Solvent free, pyrrolidine-2,5-dione, piperidine-2,6-

dione, propionaldehyde, hydrazine hydrate.

INTRODUCTION
It is recognized that multi-functionalized benzopyrans and their derivatives are a very
important class compounds. They have been broadly applicable as medicine intermediates

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Chaudhari et al. World Journal of Pharmaceutical Research

because their synergetic pharmacological and biological properties, such as anticoagulant,

antibacterial, anticancer, spasmolytic, diuretic, hypnotic and insecticide.[1-7] Generally,
substituted pyrazole and their derivatives are synthesized in organic solvents[8-10] which can
be used as important pharmaceuticals and agricultural chemicals. Additionally, multi-
substitution benzopyrans can contribute a structural unit for a group of natural products [11-13]
and some of them along with their derivatives were signed up as photo-active materials.[14]

In recent years Pyrazoles are established as important class of heterocyclic community and
have attractive achievements in both in organic synthesis and medicinal chemistry.[15-20]
Pyrazoles are a very propitious synthetic intermediate which is source of an important
pharmacophore exist in a variety of biologically active and potential therapeutic
commixtures.[21-23] These admixtures have been mostly used in sententious antibacterial[24-28],
antipyretic[29-32], antidepressant[33], antiviral[34], antitumor[35-38], anti-inflammatory.[39-41] In
addition various pyrazoles have been considered as the extracting and chelating reagents for
different metal ions[42,43] and few of the pyrazolone derivatives are used in several marketable
drugs for myocardial and brain ischemia.[44,45] Now a days research is focused on eco-
friendly, solvent free efficient greener synthesis. In line of this few catalyst are invented for
the synthesis of pyrazoles like heteropolyacids[46, 47], acetic acid or piperidine[48], Na+-MMT-
[pmim]HSO4[49], cesium fluoride (CsF)[50], 3-aminopropylated silica gel[51], 1,3,5-
tris(hydrogensulfato) benzene (THSB)[52], sodium dodecyl sulfate (SDS)[53], ZnAl2O4
nanoparticles[54], silica-bonded S-sulfonic acid (SBSSA)[55], LiOH·H2O[56], [Cu(3,4-
tmtppa)](MeSO4)4[57] ceric ammonium nitrate (CAN), benzyltriethylammonium chloride[58]
and so on. However, it is well-known that several of the methods reported above faces
challenges like strong basic or acidic conditions, difficulty in handling and separation of
catalyst, use of costly catalysts long reaction time and huge solvent consumption. These
transactions include possibility of side reactions which restrict their usage in practical
applications. Wherefore, it is very important to ponder and develop novel eco-friendly
efficient and scalable synthetic routes which are able to construct pyrazolone derivatives in
high yields.

The current trends of research are focused on the applications of the solid support Al2O3 and
silica gel SiO2. They have pulled out much attention as not only they could be used as a
catalyst for many organic transactions which providing high yields but also cheaper and non-

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Chaudhari et al. World Journal of Pharmaceutical Research

toxic. Also, It is found that Al2O3 and SiO2 have greatly simplified the workup in a solvent-
free procedures.[59,60]

EXPERIMENTAL
MATERIAL METHODS
Melting points were recorded in open glass capillaries and were uncorrected. The chemical
structures of the obtained compounds were confirmed by spectral analyses. IR spectra in KBr
pallets were obtained on Simadzu and ATR Brucker alpha FT-IR spectrophotometer. 1H
NMR spectra were obtained on and 500.13 MHz by Brucker spectrophotometer. The
chemical shifts were reported as parts per million (ppm) with (CH3)4Si (TMS) as an internal
standard. Signal multiplicities are represented by: s (singlet), d (doublet), t (triplet), m
(multiplet). The purity of compound was checked by thin layer chromatography which was
performed by using pre-coated silica gel aluminium plates with mixture of diethyl ether and
ethyl acetate 7:3 proportion. Anti-microbial and Anti-fungal activities were carried out by
Agar diffusion assay (Disk diffusion method, Disk size 6 mm). PbO nanoparticle were
synthesized by taking a mixture of 10 ml of 0.1N sodium hydroxide and 0.025 mole citric
acid in distilled water was added to methanolic solution of 0.02 mole lead nitrate. The
reaction mixture was continuously stirred with the help of magnetic stirrer for 2 hours at
room temperature. The white polycrystalline product was obtained which is filtered, washed
with distilled water and dried at110ºC for 2 hours. The dried solid product was calcinized at
500 ºC for 2 hours. During this process, the PbO nanoparticle which has white colour earlier
turned to pale yellow colour. All the compounds (7a-f and 10a-f) were synthesized from the
corresponding Succinic and Glutaric Anhydride derivatives and commercially purchased
propionaldehyde, neutral alumina (Al2O3) and ethanol.

General Procedure of synthesis

Preparation of Azo derivatives: 2,7-diamino-9-(N-methylpyridin-2-yl)-4,5-dipropyl-5,9-
dihydro-4H-dipyrano[2,3-b:3',2'-d]pyrrole-3,6-dicarbonitrile (7a-c): A mixture of 0.01 mole
N-phenyl pyrrolidine-2,5-dione, 0.02 mole propionaldehyde, 0.02 mole malononitrile and
100 mg PbO nanoparticles were ground at a room temperature with a mortar and pestle. The
reaction was monitored by thin layer chromatography (TLC). After completion of reaction,
the product was washed with distilled water. The novel developed compounds were dried and
recrystallized from ethanol to afford pure compounds with high yield (Scheme – I).

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Preparation of Azo (Dipyrano): 2,8-diamino-10-(N-methylpyridin-2-yl)-4,6-dipropyl-

6,10-dihydro-4H,5H-dipyrano[2,3-b:3',2'-e]pyridine-3,7-dicarbonitrile (7d-f)
A mixture of 0.01 mole N-phenyl piperidine-2,6-dione, 0.02 mole propionaldehyde, 0.02
mole malononitrile and 100 mg PbO nanoparticles were ground at a room temperature with a
mortar and pestle. The reaction was monitored by thin layer chromatography (TLC). After
completion of reaction, the product was washed with distilled water. The novel developed
compounds were dried and recrystallized from ethanol to afford pure compounds with high
yield (Scheme – II).

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Physicochemical and analytical data for compounds 7a-f

2,7-diamino-9-(5-methylpyridin-2-yl)-4,5-dipropyl-5,9-dihydro-4H-dipyrano[2,3-b:3',2'-
d]pyrrole-3,6-dicarbonitrile (7a)
Yellow Orange Solid, Yield (82.14%), M. P. 268-70ºC, M.F. C24H26O2N6 M.W.430.50,
Composition: C (66.29%) H (6.35%) N (19.28%); IR (KBr): C≡N:2137.50; -N-H: 3334.46;
aromatic ring: 683.60; -CH3: 3214.75; C-N (Aliphatic): 1154.36; C-N (Aromatic): 1222.63; -
C-C- Stretch in a ring(2-Peaks): 1637.43, 1539.22; -CH3 bend: 1492.79, 1384.71 cm-1. 1H
NMR (500.13 MHz, DMSO, δ ppm): 0.90 (d, 6H), 1.22 (t, 4H, Methylene), 1.51 (t,4H,
Methylene), 2.12 (s,2H, methine),6.86 (s, 4H,-NH2), 7.30-8.49 (m, 3H, aromatic), 2.37 (s,
3H, CH3-pyridine).

2,7-diamino-9-(4-methylpyridin-2-yl)-4,5-dipropyl-5,9-dihydro-4H-dipyrano[2,3-b:3',2'-
d]pyrrole-3,6-dicarbonitrile (7b)
Yellow Orange Solid, Yield (78.15%), M. P. 312-14ºC, M.F. C24H26O2N6 M.W.430.50,
Composition: C (66.39%) H (6.26%) N (19.41%); IR (KBr): C≡N:2141.96; -N-H: 3330.28;
aromatic ring: 683.41; -CH3: 2921.49; C-N (Aliphatic): 1048.07; C-N (Aromatic): 1222.07; -
C-C- Stretch in a ring(2-Peaks): 1620.98, 1539.73; -CH3 bend: 1492.99, 1383.42 cm-1. 1H
NMR (500.13 MHz, DMSO, δ ppm): 0.94 (d, 6H), 1.24 (t,4H, Methylene), 1.52 (t,4H,
Methylene), 2.12 (s,2H, methine),6.80 (s, 4H,-NH2), 7.34-8.54 (m, 3H, aromatic), 2.37 (s,
3H, CH3-pyridine).

2,7-diamino-9-(6-methylpyridin-2-yl)-4,5-dipropyl-5,9-dihydro-4H-dipyrano[2,3-b:3',2'-
d]pyrrole-3,6-dicarbonitrile (7c)
Yellow Orange Solid, Yield (78.72%), M. P. 188-90ºC, M.F. C24H26O2N6 M.W.430.50,
Composition: C (66.62%) H (6.19%) N (19.37%); IR (KBr): C≡N: 2164.50; -N-H: 3337.62;
aromatic ring: 687.72; -CH3: 2968.39; C-N (Aliphatic): 1058.76; C-N (Aromatic): 1228.01 -
C-C- Stretch in a ring(2-Peaks): 1646.36, 1495.52; -CH3 bend: 1457.24, 1384.24 cm-1. 1H
NMR (500.13 MHz, DMSO, δ ppm): 0.90 (d, 6H), 1.27 (t,4H, Methylene), 1.54 (t,4H,
Methylene), 2.12 (s,2H, methine),6.91 (s, 4H,-NH2), 7.04-7.79 (m, 3H, aromatic), 2.64 (s,
3H, CH3-pyridine).

2,8-diamino-10-(5-methylpyridin-2-yl)-4,6-dipropyl-6,10-dihydro-4H,5H-dipyrano[2,3-
b:3',2'-e]pyridine-3,7-dicarbonitrile (7d)
Yellow Orange Color Solid, Yield (78.49%), M. P. 184-86ºC, M.F. C25H28O2N6 M.W.444.52,
Composition: C (67.02%) H (6.89%) N (18.26%); IR (KBr): C≡N:2135.17; -N-H: 3332.09;

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aromatic ring: 684.53; -CH2: 3001.18; -CH3: 2927.33; C-N (Aliphatic): 1153.27; C-N
(Aromatic): 1298.31; -C-C- Stretch in a ring(2-Peaks): 1730.05, 1532.34; -CH3 bend:
1451.66; -CH2 bend: 1380.28 cm-1. 1H NMR (500.13 MHz, DMSO, δ ppm): 0.89 (d, 6H),
1.17 (t,4H, Methylene), 2.44 (t,4H, Methylene), 2.56 (s,2H, methine), 3.53 (s, 2H, -CH2),
6.56 (s, 4H,-NH2), 7.19-7.75 (m, 3H, aromatic), 2.51 (s, 3H, CH3-pyridine).

2,8-diamino-10-(4-methylpyridin-2-yl)-4,6-dipropyl-6,10-dihydro-4H,5H-dipyrano[2,3-
b:3',2'-e]pyridine-3,7-dicarbonitrile (7e)
Yellow Orange Color Solid, Yield (72.41%), M. P. 166-68ºC, M.F. C25H28O2N6 M.W.444.52,
Composition: C (67.19%) H (6.93%) N (18.06%); IR (KBr): C≡N:2140.5; -N-H: 3331.19;
aromatic ring: 685.88; -CH2: 3003.54; -CH3: 2928.51; C-N (Aliphatic): 1050.34; C-N
(Aromatic): 1290.18; -C-C- Stretch in a ring(2-Peaks): 1740.22, 1531.94; -CH3 bend:
1453.53; -CH2 bend: 1379.36 cm-1. 1H NMR (500.13 MHz, DMSO, δ ppm): 0.91 (d, 6H),
1.20 (t,4H, Methylene), 2.39 (t,4H, Methylene), 2.35 (s,2H, methine), 3.53 (s, 2H, -CH2),
6.60 (s, 4H,-NH2), 7.22-7.35 (m, 3H, aromatic), 2.33 (s, 3H, CH3-pyridine).

2,8-diamino-10-(6-methylpyridin-2-yl)-4,6-dipropyl-6,10-dihydro-4H,5H-dipyrano[2,3-
b:3',2'-e]pyridine-3,7-dicarbonitrile (7f)
Pastel Orange Solid, Yield (78.22%), M. P. 240-42ºC, M.F. C25H28O2N6 M.W.444.52,
Composition: C (66.98%) H (6.11%) N (18.19%); IR (KBr): C≡N:2137.05; -N-H: 3327.75;
aromatic ring: 683.34; -CH2: 3002.44; -CH3: 2925.64; C-N (Aliphatic): 1156.90; C-N
(Aromatic): 1300.21; -C-C- Stretch in a ring(2-Peaks): 1744.42, 1496.28; -CH3 bend:
1452.13; -CH2 bend: 1388.53 cm-1. 1H NMR (500.13 MHz, DMSO, δ ppm): 0.94 (d, 6H),
1.15 (t,4H, Methylene), 2.40 (t,4H, Methylene), 2.64 (s,2H, methine), 3.59 (s, 2H, -CH2),
6.69 (s, 4H,-NH2), 7.25-7.64 (m, 3H, aromatic), 2.45 (s, 3H, CH3-pyridine).

General Procedure of Synthesis

Preparation of Pyrazole: 3,4-bis(2-chlorophenyl)-7-(N-methylpyridin-2-yl)-
3,3a,3b,4,5,7-hexahydro-2H-pyrrolo[2,3-c:5,4-c']dipyrazole (13a-c)
The bis-pyrazole (13a-c) derivatives were synthesized by the mixture of 0.01 mole of N-
phenyl pyrrolidine-2, 5-dione and 0.02 mole of aromatic aldehyde in 1 gm of neutral Al2O3
with the help of microwave irradiations. This mixture is maintained in microwave at 800W
power for 4-6 minutes in solvent free condition. The novel developed compounds were
recrystallized from ethanol (Scheme – III).

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Preparation of Pyrazole: 3,5-bis(2-chlorophenyl)-8-(N-methylpyridin-2-yl)-

2,3,3a,4,4a,5,6,8-octahydrodipyrazolo[3,4-b:4',3'-e]pyridine (13d-f)
The bis-pyrazole (13d-f) derivatives were synthesized by the mixture of 0.01 moles of N-
phenyl piperidine-2,6-dione and 0.02 mole of aromatic aldehyde in 1 gm of neutral Al2O3
with the help of microwave irradiations. This mixture is maintained in microwave at 800W
power for 5-8 minutes in solvent free condition. The novel developed compounds were
recrystallized from ethanol (Scheme – IV).

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Physicochemical and analytical data for compounds 13a-f

3,4-bis(2-chlorophenyl)-7-(5-methylpyridin-2-yl)-3,3a,3b,4,5,7-hexahydro-2H-pyrrolo[2,3-
c:5,4-c']dipyrazole (13a)
Green Brown Solid, Yield (71.33%), M. P. 136-38ºC, M.F. C24H20N6Cl2 M.W.463.36,
Composition: C (63.25%) H (3.81%) N (14.47%); IR (KBr): -C-Cl:645.06; -N-H: 3177.50;
>C=N: 1655.70; aromatic ring (2-Peaks): 3063.07, 824.28; -CH3: 3004.38; C-N (Aliphatic):
1209.99; C-N (Aromatic): 1274.57; -C-C- Stretch in a ring(2-Peaks): 1564.02, 1506.82; -CH3
bend: 1467.09, 1371.66 cm-1. 1H NMR (500.13 MHz, DMSO, δ ppm): 2.20 (t, 2H, Methine),
3.40 (d, 2H, Methine), 9.85 (s, 2H,-N-H), 6.64-7.88 (m, 11H, aromatic), 2.28 (s, 3H, CH3-
pyridine).

3,4-bis(2-chlorophenyl)-7-(4-methylpyridin-2-yl)-3,3a,3b,4,5,7-hexahydro-2H-pyrrolo[2,3-
c:5,4-c']dipyrazole (13b)
Faint Clay Brown Solid, Yield (76.24%), M. P. 194-96ºC, M.F. C24H20N6Cl2 M.W.463.36,
Composition: C (63.30%) H (3.37%) N (14.55%); IR (KBr): -C-Cl:644.71; -N-H: 3150.16;
>C=N: 1655.17; aromatic ring (2-Peaks): 3051.27, 825.15; -CH3: 3003.82; C-N (Aliphatic):
1211.31; C-N (Aromatic): 1271.43; -C-C- Stretch in a ring(2-Peaks): 1566.17, 1528.29; -CH3
bend: 1465.26, 1373.61 cm-1. 1H NMR (500.13 MHz, DMSO, δ ppm): 2.28 (t, 2H, Methine),
3.47 (d, 2H, Methine), 9.96 (s, 2H,-N-H), 6.57-7.95 (m, 11H, aromatic), 2.29 (s, 3H, CH3-
pyridine).

3,4-bis(2-chlorophenyl)-7-(6-methylpyridin-2-yl)-3,3a,3b,4,5,7-hexahydro-2H-pyrrolo[2,3-
c:5,4-c']dipyrazole (13c)
Saffron Yellow Solid, Yield (63.20%), M. P. 326-28ºC, M.F. C24H20N6Cl2 M.W.463.36,
Composition: C (63.61%) H (3.76%) N (14.39%); IR (KBr): -C-Cl:643.26; -N-H: 3165.52;
>C=N: 1664.68; aromatic ring (2-Peaks): 3048.18, 823.25; -CH3: 3001.55; C-N (Aliphatic):
1212.44; C-N (Aromatic): 1275.36; -C-C- Stretch in a ring(2-Peaks): 1532.77, 1572.25; -CH3
bend: 1461.12, 1372.45 cm-1. 1H NMR (500.13 MHz, DMSO, δ ppm): 2.17 (t, 2H, Methine),
3.08 (d, 2H, Methine), 9.95 (s, 2H,-N-H), 6.27-7.45 (m, 11H, aromatic), 2.36 (s, 3H, CH3-
pyridine).

3,5-bis(2-chlorophenyl)-8-(5-methylpyridin-2-yl)-2,3,3a,4,4a,5,6,8-
octahydrodipyrazolo[3,4-b:4',3'-e]pyridine (13d)
Honey Yellow Solid, Yield (77.38%), M. P. 332-34ºC, M.F. C25H22N6Cl2 M.W.477.38,
Composition: C (63.05%) H (4.91%) N (17.21%); IR (KBr): -C-Cl:643.64; -N-H: 3176.69;

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>C=N: 1654.66; aromatic ring (2-Peaks): 3002.00, 856.72; -CH3: 2856.80; -CH2: 2827.62; C-
N (Aliphatic): 1210.84; C-N (Aromatic): 1275.79; -C-C- Stretch in a ring(2-Peaks): 1594.73,
1563.93; -CH3 bend: 1436.03, 1365.69; -CH2 bend: 1466.81 cm-1. 1H NMR (500.13 MHz,
DMSO, δ ppm): 2.26 (m, 2H, methine), 3.79 (m, 2H, methine), 1.69 (m, 2H, methylene),
9.94 (s, 2H,-N-H), 6.51-7.83 (m, 11H, aromatic), 2.14 (s, 3H, CH3-pyridine).

3,5-bis(2-chlorophenyl)-8-(4-methylpyridin-2-yl)-2,3,3a,4,4a,5,6,8-
octahydrodipyrazolo[3,4-b:4',3'-e]pyridine (13e)
Clay Brown Solid, Yield (65.74%), M. P. 278-80ºC, M.F. C25H22N6Cl2 M.W.477.38,
Composition: C (62.09%) H (4.21%) N (17.18%); IR (KBr): -C-Cl:641.28; -N-H: 3210.31;
>C=N: 1655.41; aromatic ring (2-Peaks): 3001.98, 855.33; -CH3: 2879.28; -CH2: 2825.19; C-
N (Aliphatic): 1209.75; C-N (Aromatic): 1274.39; -C-C- Stretch in a ring(2-Peaks): 1580.29,
1565.74; -CH3 bend: 1434.28, 1365.47; -CH2 bend: 1463.08 cm-1. 1H NMR (500.13 MHz,
DMSO, δ ppm): 2.21 (m, 2H, methine), 3.77 (m, 2H, methine), 1.75 (m, 2H, methylene),
9.93 (s, 2H,-N-H), 6.49-7.86 (m, 11H, aromatic), 2.16 (s, 3H, CH3-pyridine).

3,5-bis(2-chlorophenyl)-8-(6-methylpyridin-2-yl)-2,3,3a,4,4a,5,6,8-
octahydrodipyrazolo[3,4-b:4',3'-e]pyridine (13f)
Deep Orange Solid, Yield (75.61%), M. P. 334-36ºC, M.F. C25H22N6Cl2 M.W.477.38,
Composition: C (62.18%) H (4.22%) N (17.01%); IR (KBr): -C-Cl:640.65; -N-H: 3202.88;
>C=N: 1657.50; aromatic ring (2-Peaks): 3004.91, 858.21; -CH3: 2949.15; -CH2: 2926.74; C-
N (Aliphatic): 1208.87; C-N (Aromatic): 1273.11; -C-C- Stretch in a ring(2-Peaks): 1587.44,
1568.37; -CH3 bend: 1435.39, 1373.13; -CH2 bend: 1463.94 cm-1. 1H NMR (500.13 MHz,
DMSO, δ ppm): 2.37 (m, 2H, methine), 3.86 (m, 2H, methine), 1.71 (m, 2H, methylene),
9.91 (s, 2H,-N-H), 6.32-7.62 (m, 11H, aromatic), 2.21 (s, 3H, CH3-pyridine).

RESULTS AND DISCUSSION

Chemistry
The series of Azo derivatives 7a-f were synthesized by the reaction of 1-(N-methylpyridin-2-
yl)pyrrolidine/ piperidine -2,5/6-dione, propionaldehyde and malononitrile with the help of
PbO nanoparticles. The formation of Azo derivatives was confirmed by IR, 13C NMR and 1H
NMR and elemental analysis. The series of bis-pyrazole derivatives 13a-f were synthesized
by the reaction of bis chalcones 3,4/5-bis((E)-2-chlorobenzylidene)-1-(N-methylpyridin-2-
yl)pyrrolidine/ piperidine -2,5/6-dione and hydrazine hydrate in presence of neutral Al2O3

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with the help of microwave irradiations. The formation of bis-pyrazoles was confirmed by
IR, 13C NMR and 1H NMR and elemental analysis.

Antimicrobial Activities
All the synthesized Azo derivatives 7a-f and bis-pyrazole derivatives 13a-f were screened for
their antibacterial activity against gram positive bacteria Staphylococcus aureus (NCIM
2079), Bacillus subtilis (NCIM 2250) and gram negative bacteria Escherichia coli (NCIM
2109), Pseudomonas aeruginosa (NCIM 2036) using DMSO solvent. All these novel
synthesized compounds were screened against Fungi (Yeast) Candida albicans (NCIM 3471)
and Aspergillus niger (NCIM 545). The bacterial cultures were purchased from NCIM:
National Collection of Industrial Microorganisms, National Chemical Laboratory (NCL),
Pune 411008 [India]. Some of the compound showed moderate to good activities against
gram positive bacteria S. aureus and synergetic activities against Fungi A. niger as shown in
the Table –I, II and Graph –I, II.

Table-I: Antimicrobial activities of Azo derivatives 7a-f.

E. coli P. aeruginosa S. aureus B. subtilis C. albicans A. niger
Sr. No. Sample
Mean±SD Mean ±SD Mean ±SD Mean ±SD Mean ±SD Mean ±SD
1 7a - - - - - - 7.66±0.20 - - - - - -
2 7b - - - - - - 8.96±0.09 - - - - - - - - -
3 7c - - - - - - 12.06±0.07 9.05±0.13 - - - 14.2±0.07
4 7d - - - - - - 13.09±0.02 13.19±0.06 - - - 16.2±0.01
5 7e - - - - - - 11.09±0.14 10.49±0.05 - - - 20±0.12
6 7f - - - - - - 7.86±0.11 8.40±0.06 - - - 19.2±0.11
Choram
24.09±0.10 14.39±0.07 23.92±0.17 28.43±0.29 NA NA
phenicol
Amphot
NA NA NA NA 15.21±0.15 11.8±0.08
ericin B

Graph-I: Antimicrobial activities of Azo derivatives 7a-f.

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 Chaudhari et al. World Journal of Pharmaceutical Research

Table-II: Antimicrobial activities of bis pyrazole derivatives 13a-f.

Sr. E. coli P. aeruginosa S. aureus B. subtilis C. albicans A. niger
Sample
No. Mean±SD Mean ±SD Mean ±SD Mean ±SD Mean ±SD Mean ±SD
1 13a 8.28±0.09 - - - - - - - - - - - - - - -
2 13b 10.01±0.18 - - - - - - - - - - - - - - -
3 13c 10.08±0.13 - - - - - - - - - - - - - - -
4 13d - - - - - - - - - - - - - - - - - -
5 13e 15.93±0.14 - - - 9.85±0.15 - - - - - - 9.11±0.04
6 13f 16.1±0.18 - - - 7.82±0.03 - - - - - - 10.3±0.16
Choram
24.09±0.10 14.39±0.07 23.92±0.17 28.43±0.29 NA NA
phenicol
Amphot
NA NA NA NA 15.21±0.15 11.8±0.08
ericin B

Graph-II: Antimicrobial activities of bis pyrazole derivatives 13a-f.

CONCLUSION
The greener path used catalyst PbO nanoparticle which is solvent-free and produced sensible
yield. 13e and 13f have showed ameliorate activities against S. aureus. Also, the series of
compounds 13a-c reveals excellent and congenial activities against A. niger strain.

ACKNOWLEDGMENT
I wish to express my profound gratitude to Hon’ble Dr Ajeenkya DY Patil, President of
Ajeenkya DY Patil University and Chairman of Ajeenkya DY Patil Group on promoting me
to contribute a quality work by allowing all facilities. I wish to express my insightful
gratitude to Hon’ble Mr. Jaykumar Rawal, Minister, Employment Guarantee Scheme and
Tourism Development, Government of Maharashtra. With deep sense of regards I express my
thanks to Dr Nilesh Vishanath, Director, DYPKC, Mr. Sushant Patil, Advisor, DYPKC. I am

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Chaudhari et al. World Journal of Pharmaceutical Research

equally grateful for I express my thanks to Dr. S. S. Sonavane, Director – TC, Prof. A. P.
Deshmukh, Dean Academics and Dr. S. M. Khairnar, Head, Dept. of Engineering Science,
Dr. D. Y. Patil School of Engineering, Pune. I would like to extend my appreciation to Dr.
Ravindra S. Dhivare, Assistant Professor, Sangola College, Sangola, Kadlas road, State
Highway 71, Sangola, 413307, Maharashatra, India for valuable advice and discussion during
research work. I express my sincere thanks to the Director, Central Instrumentation Facility,
Savitribai Phule Pune University, Pune. I am grateful to Ms. Snehal Dhokale, Mr. Datta
Ukale, Mr. Umesh Kasabe and Mr. Ritesh Walecha, Project Assistant of NMR and HRMS
spectroscopy in Savitribai Phule Pune University, Maharashtra.

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