Studies and synthesis of substituted 4-biphenyl acetamide derivatives

Article abstract of DOI:10.14233/ajchem.2019.21579

A new series of substituted 4-biphenylamides have been synthesized by condensation of 4-biphenyl acetic acid with different primary amines (aromatic and aliphatic). 4-Biphenyl acetic acid was first treated with thionyl chloride in dry benzene to prepare substituted 4-biphenyl acetyl chloride, which is then treated with different aliphatic or aromatic amines to synthesize various substituted 4-biphenyl acid-amide derivatives. The structure of newly synthesized compounds has been established by analytical and spectral methods. These synthesized compounds have shown antifungal properties against Fusarium udum and Curvularia lunata.

Full text of DOI:10.14233/ajchem.2019.21579

Asian Journal of Chemistry; Vol. 31, No. 3 (2019), 510-514
A
SIAN
J
OURNAL OF HEMISTRY
C
https://doi.org/10.14233/ajchem.2019.21579
Studies and Synthesis of Substituted 4-Biphenyl Acetamide Derivatives
ANJU KHULLAR
Department of Chemistry, General Shivdev Singh Diwan Gurbachan Singh Khalsa College, Patiala-147001, India
Corresponding author: E-mail: anjukhullar9@gmail.com
Received: 13 July 2018;
Accepted: 22 August 2018;
Published online: 31 January 2019;
AJC-19236
A new series of substituted 4-biphenylamides have been synthesized by condensation of 4-biphenyl acetic acid with different primary
amines (aromatic and aliphatic). 4-Biphenyl acetic acid was first treated with thionyl chloride in dry benzene to prepare substituted
4-biphenyl acetyl chloride, which is then treated with different aliphatic or aromatic amines to synthesize various substituted 4-biphenyl
acid-amide derivatives. The structure of newly synthesized compounds has been established by analytical and spectral methods. These
synthesized compounds have shown antifungal properties against Fusarium udum and Curvularia lunata.
Keywords: Synthesis, 4-Biphenyl acetic acid, Substituted 4-biphenyl acid amides, Antifungal properties.
and also used in the treatment of adjuvant-arthritis [2].
Biphenyl-3-acetamide, 2-amino-thiazole shows antitumour
activity also used in the treatment of cancer, alzeimer’s disease,
viral infection, auto-immune disease or neurodegenerative
disorder [13]. 2-Biphenyl-acetic acid and 2-biphenyl acetamide
used as agrochemical antifungal agent [14-18]. Biphenyl con-
taining compounds possesses anti-psychotic and anxiolytic
activity [19]. Some of the biphenyl hydrazide-hydrazone are
known to exhibit good antimicrobial activity [20,21]. Some
of the compounds having biphenyl moiety possess valuable
medicinal properties like antihypertensive and calcium channel
blockers [22,23]. Tetrazole are well known to possess antimi-
crobial properties [24]. Polychlorinated biphenyls (PCBs)
are proved to cause reproductive, endocrine and neurological
disorders, thyroid dysfunction, cognitive and motor deficits.
Prenatal exposures are known to cause increased susceptibility
to infectious diseases in early childhood [25]. PCB’s influenced
plants diffuse oxygen in soil promoting the growth of aerobic
microbes. Soil aeration is also improved by formation of air
channels when roots die and decay and by direct root oxygen
release [26]. Molecules containing biaryl moieties are relatively
common within natural products. For their preparation, nature
has developed an ample array of biosynthetic strategies [27].
A number of these biaryl natural products belong to the bioge-
netic class of lignans [28]. During previous years, we have
been investigated a range of analogs of natural products [29].
INTRODUCTION
Biphenyls are the polynuclear aromatic hydrocarbons
(PAHs) having more than one aromatic nucleus. Biphenyl
acetic acid itself and its derivatives have been found to be
effective against many therapeutic diseases. Literature findings
have also been shown its various therapeutic uses, such as: anti-
inflammatory agent [1], as analgesic [2], antipyretic [3], anti-
arthritis [4], antirheumatoid [5], antihypertensive [2] and a
binder to human blood plasma-prealbumen, etc. 4-Biphenyl
acetic acid itself has been reported to possess many effective
pharmacological activities, such as anti-inflammatory, anal-
gesic, antibacterial [6] and topical steroidal anti-inflammatory
activity [7]. The ointment containing 4-biphenyl acetic acid
work very effectively as anti-inflammatory as well as analgesic
agents [8]. 4-Biphenyl acetic acid cyclodextrin inclusion comp-
ounds are reported to show effective mono-nuclearro-genic
anti-inflammatory properties and its phenyl alkanamide
derivatives have shown agro horticultural and bactericidal
activity [9]. Substituted biphenyls can also be used as anti-
allergic drugs [10]. Biphenyl compounds have stronger analgesic
activity along with antiallergic and anti-inflammatory activity
[7]. Substituted biphenyl-4-acetamides have therapeutic use
in the treatment of cancer [11] and is also used as an antitumor
agent [12]. Felbinac (an active metabolite of 4-biphenyl acetic
acid) patch shows anti-inflammatory and analgesic activities
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Vol. 31, No. 3 (2019)
Studies and Synthesis of Substituted 4-Biphenyl Acetamide Derivatives 511
These products and many derivatives thereof, both of natural
and synthetic origin, have been reported to to antioxidant, anti-
inflammatory, antitumor, antidiabetic, antimicrobial, antineuro-
degenerative, antidepressant, pain control, gastrointestinal,
cardiovascular and liver protective properties among others
[30,31]. Until 1971, 61 % of PCBs were used in closed electrical
systems, 13 % were used in nominally closed systems and 26
% were used in openend applications. After 1971, almost 100
% of all PCBs produced were used in closed electrical systems
[32]. In present work, we describe the synthesis of the first
representatives of previously unknown imidazoles, benzimida-
zoles containing a 4-biphenyl group at position 2 and different
substituents at nitrogen atom. The presence of not one but two
“privileged” fragments in the molecules of these compounds,
namely, imidazoles, benzimidazoles and biphenyl should
promote multitarget action. We also collected and analyzed
the data on the activity of the synthesized biphenyl compounds
with respect to a number of biological targets important for
the therapy of diabetes mellitus and its vascular complications
[33-36]. In view of these observations and in continuation of
our research work on biologically active biphenyl derivatives,
it is proposed to synthesize substituted biphenyl acid-amide
derivatives by the condensation of 4-biphenyl acetic acid
precursor first with thionyl chloride (to make its acid chloride)
and then with different primary amines (aliphatic or aromatic).
The obtained white or coloured crystalline solid was filtered
through Whattman filter paper (No. 42) and washed the preci-
pitation with n-hexane about 3-4 times to remove the impurities,
dried and weighed (Scheme-I).
Characterization data
Phenyl-4-biphenyl N-acetamide (2): Pale yellow crysta-
lline solid; m.f. C20H17NO, m.p.: 195-97 °C; yield: 875 mg
(64 %); TLC: Rf 0.44 (25 % EtOAc:hexane); Elemental
analysis calcd. (found) (%): C: 81.11 (81.11), H: 6.16 (6.92),
N: 6.14 (6.17); O: 6.60 (6.17); 1H NMR (DMSO-d6) δ: 6.14-
8.51 (18H-C6H5), 4.66 (1H-NH), 4.31 (2H-alicyclic-CH2); IR
(cm–1): 1519, 1650, 3232, 1219, 317.
4-Biphenyl acetamide (3): White crystalline solid; m.p.:
190-92 ºC; m.f. C14H13NO, yield: 1.210 g (84 %);TLC: Rf 0.4337
(20 % EtOAc:hexane); Elemental analysis calcd. (found) (%):
C: 79.31 (79.62), H: 6.91 (6.16), N: 6.58 (6.63), O: 8.51 (8.58);
1H NMR (DMSO-d6) δ: 6.10-8.18 (9H-C6H5), 4.99 (2H-NH2),
4.36 (2H-alicyclic CH2); IR (cm–1): 1518, 1652, 3243, 1217, 316.
p-Methylphenyl-4-biphenyl N-acetamide (4): Yellow
crystalline solid; ; m.f. C21H19NO, m.p.: 199-200 °C; Yield:
1.140 g (80.0 %); TLC: Rf 0.3139 (20 % EtOAc:hexane); Elem-
ental analysis calcd. (found) (%): C: 83.16 (83.72), H: 4.63
(4.31), N: 6.10 (4.65); O: 6.60 (6.31); 1H NMR (DMSO-d6) δ:
6.14-8.36 (13H-C6H5), 4.02 (1H-NH), 4.10 (2H-alicyclic-CH2),
4.33 (3H-alicyclic-CH3). IR (cm–1): 1517, 1639, 3352, 1215, 318.
α-Naphthyl-4-biphenyl N-acetamide (5): Purple crysta-
lline solid; ; m.f. C24H19NO, m.p.: 188-190 °C;Yield: 610 mg
(45 %); TLC: Rf 0.418 (25 % EtOAc:hexane); Elemental analy-
sis calcd. (found) (%): C: 85.60 (87.45), H: 5.27 (5.63), N: 4.61
(4.10), O: 4.80 (4.74); 1H NMR (DMSO-d6) δ: 6.17-8.48 (16H-
C6H5), 4.04 (1H-NH), 4.35 (2H-alicyclic-CH2); IR (cm-1):
1515, 1658, 3232, 1234, 316.
Phenylthioamide-4-biphenyl N-acetamide (6): Light
purple crystalline solid; m.p.: 172-173 °C; m.f. C21H18N2OS,
Yield: 390 mg (30 %); TLC: Rf 0.45 (20 % EtOAc:hexane);
Elemental analysis calcd. (found) (%): C: 72.62 (72.83), H:5.32
(5.20), N: 8.30 (8.09), O: 3.35 (3.62), S: 9.23 (9.24); 1H NMR
(DMSO-d6) δ: 6.13-8.41 (14H-C6H5), 4.03 (2H-NH), 4.34 (2H-
alicyclic-CH2); IR (cm–1): 1516, 1652, 3349, 1215, 319.
p-Nitrophenyl-4-biphenyl N-acetamide (7): Pale yellow
crystalline solid; m.p.: 170-172 °C; m.f. C20H18N2O3, Yield:
0.78 g (88.64 %); TLC: Rf 0.559 (50 % chloroform:benzene);
Elemental analysis calcd. (found) (%): C: 72.92 (72.28), H:4.43
(4.42), N: 9.61 (9.43), O: 13.01 (14.45); 1H NMR (DMSO-d6)
δ: 6.18-8.54 (17H-C6H5), 4.03 (1H-NH), 4.32 (4H-alicyclic-
CH2); IR (cm–1): 1518, 1675, 3310, 1216, 316.
EXPERIMENTAL
Synthesis of N-substituted 4-biphenyl acid amide from
4-biphenyl acetic acid: 4-Biphenyl acetic acid (1 g) dissolved
in dry benzene (25 mL), added thionyl chloride (1 mL) drop-
wise along with constant stirring in a round bottom flask of
50 mL. then refluxed the reaction mixture for 2.5 h on water
bath at 78-80 °C. The recovered benzene and thionyl chloride
from reaction mixture through distillation traces of solvent
through vacuum pump. 4-Biphenyl acetyl chloride (1) obtained
as a viscous-oil (1.085 g, 100 % yield). It was used to form
amides in next step without further purification by condensed
it with different suitable primary amines (aromatic as well as
aliphatic) to form different types of substituted acid amides.
Synthesis of N-substituted 4-biphenyl acid amides (2-16)
from compound 1: Dissolved aliphatic or aromatic primary
amine in calculated amount of pyridine or 4 N NaOH (25 mL)
and added this mixture in to round bottom flask containing
compound 1. Dry benzene was added slowly drop wise at room
temperature under constant stirring. The TLC of reaction-
mixture showed that the reaction becomes complete, stirring
continue up to the completion of the reaction and then work
up the reaction mixture with suitable solvent after approximate
20 h. Reaction mixture was taken in separatory funnel along
with distilled water. Compound dissolved in the solvent,
washed the solvent with water about 3-4 times to remove the
basic nature of the solvent layer. The solvent layer becomes
neutral, solvent layer was taken in conical flask and added
MgSO4 (to absorb the moisture of solvent layer), waited for
5-10 min. Filtered the solution in round bottom flask and
recovered the solvent from reaction mixture by distillation and
traces of solvent with the help of vacuum pump. Concentrated
residue was treated with n-hexane to complete the precipitation.
o-Toluene-4-biphenyl N-acetamide (8): Light brown
crystalline solid; m.p.: 163-165 °C; m.f. C21H19NO, Yield: 930
mg (70 %); TLC: Rf 0.418 (70 % EtOAc:hexane); Elemental
analysis calcd. (found) (%): C: 80.04 (81.72), H: 2.73 (2.31),
N: 7.37 (7.65), O: 9.21 (9.31); 1H NMR (DMSO-d6) δ: 6.11-
8.28 (13H-C6H5), 4.08 (1H-NH); 4.33 (2H-alicyclic-CH2) 4.38
(3H-alicyclic-CH3); IR (cm–1): 1518, 1688, 3230, 1212, 314.
2-Pyridine-4-biphenyl N-acetamide (9): Light brown
crystalline solid; m.p.: 208-210 °C; m.f. C19H16N2O,Yield: 260
mg (42 %); TLC: Rf 0.705 (5 % methanol:chloroform); Elem-
ental analysis calcd. (found) (%): C: 78.85 (78.16), H: 5.90 (5.55),
N: 9.23 (9.72), O: 5.29 (5.55); 1H NMR (DMSO-d6) δ: 6.11-

512 Khullar
Asian J. Chem.
CH2CONH
CH2CONH
CH2CONHCSNH
CH2CONH
CH2CONH
CH2CONH
N
CH3
(6)
(8)
(9)
(5)
Phenylthioamide-4-biphenyl
N-acetamide
o
-Toluene-4-biphenyl
N-acetamide
2-Pyridine-4-biphenyl
N-acetamide
α
-Naphthyl-4-biphenyl
N-acetamide
CH3
NO2
(7)
-Nitrophenyl-4-biphenyl
N-acetamide
(4)
p
p
-Methylphenyl-4-biphenyl
N-acetamide
H2N
CH3
N
N
H
2
CH2CONH
CH2CONH2
(3)
3
4-Biphenyl acetamide
l
C
H
-
CH2COCl
COOH
CH2CONH
(1)
4-Biphenyl-acetyl chloride
(10)
p
-Benzoic acid-4-biphenyl
N-acetamide
(2)
Phenyl-4-biphenyl N-acetamide
CH2CONHNH2·H2O
(11)
Amino-4-biphenyl
N-acetamide
CH2CONHCH2
(16)
Benzyl-4-biphenyl
N-acetamide
CH2CONH
CH2CONH
Cl
CH2CONH
COOH
CH2CONHOH·HCl
Br
(15)
(13)
ortho-Benzoic acid
4-biphenyl N-acetamide
(12)
(14)
para-Bromo-phenyl-
4-biphenyl N-acetamide
2-Chloro-4-biphenyl
N-acetamide
para-Hydroxy-4-biphenyl
N-acetamide chloride
Scheme-I

Vol. 31, No. 3 (2019)
Studies and Synthesis of Substituted 4-Biphenyl Acetamide Derivatives 513
8.39 (13H-C6H5), 4.02 (1H-NH), 4.52 (2H-NH2), 4.36 (2H
alicyclic -CH2); IR (cm–1): 1514, 1669, 3331, 1216, 315.
p-Benzoic acid-4-biphenyl N-acetamide (10): Cream
crystalline solid; m.p.: 243-245 °C; m.f. C21H17NO3,Yield: 220
mg (44 %); TLC: Rf 0.341 (20 % methanol:chloroform); Elem-
ental analysis calcd. (found) (%): C:72.86 (72.13), H: 6.40 (6.13),
N: 5.56 (5.22), O: 15.01 (15.50); 1H NMR (DMSO-d6) δ: 6.05-
8.31 (13H-C6H5), 4.02 (1H-NH); 4.35 (2H-alicyclic-CH2); IR
(cm–1): 1513, 1666, 3305, 1207, 133.
Amino-4-biphenyl N-acetamide (11): Pale yellow crysta-
lline solid; m.p.: 232-233 °C; m.f. C14H16N2O2,Yield: 490 mg
(92 %); TLC: Rf 0.474 (5 % methanol:chloroform); Elemental
analysis calcd. (found) (%): C:70.76 (70.85), H: 5.80 (5.55),
N: 10.80 (10.47), O: 12.90 (12.11); 1H NMR (DMSO-d6) δ:
6.02-8.05 (9H-C6H5), 4.05 (1H-NH); 4.37 (2H-alicyclic-CH2);
IR (cm–1): 1516, 1692, 3209, 1233, 312.
derivatives. 4-Biphenyl acetic acid was treated with thionyl
chloride in dry benzene on water bath for 2-3 h at 70-80 °C.
After 1 h, the colour of reaction mixture becomes change from
pale yellow to orange and then on completion of reaction, it
changes from orange to brown. This oily mass of 4-biphenyl
acetyl chloride is then treated with different types of aliphatic
and aromatic amines in pyridine or 4 N-NaOH to synthesis a
series of amides. These synthesized-4-biphenyl acid amides
were treated with n-hexane for crystallization. The synthesized
4-biphenyl amides have been studied for their antifungal
activity against Fusarium udum and Curvularia lunata. The
culture of each species was incubated at 12 3 °C and the
zone of the inhibition was measured after 120 h. Most of these
compounds were found to be active against these fungi.
ACKNOWLEDGEMENTS
2-Chloro-4-biphenyl N-acetamide (12):White crystalline
solid; m.p.: 136-38 °C; m.f. C20H16NOCl, Yield: 325 mg (92
%); TLC: Rf 0.392 (10 % EtOAc:hexane); Elemental analysis
calcd. (found) (%): C:76.76 (76.12), H: 5.20 (5.12), N: 4.49
(4.36), O: 4.16 (4.98), Cl: 10.09 (10.05); 1H NMR (DMSO-
d6) δ: 6.12-8.29 (13H-C6H5), 4.05 (1H-NH); 4.27 (2H-alicyclic-
CH2); IR (cm–1): 1524, 1692, 3248, 1223, 131.
The author thanks Chemistry and Botany Departments of
Narain College, Shikohabad, India for providing facilities.
Thanks are also due to Dr. Nidhi Rani Gupta and Dr. Heena Rekhi,
Chemistry Department, Khalsa College, Patiala, India for their
valuable support and suggestions.
CONFLICT OF INTEREST
ortho-Benzoic acid 4-biphenyl N-acetamide (13): Dirty
Yellow crystalline solid; m.p.: 162-163 °C; m.f. C21H17NO3,Yield:
225 mg (32 %); TLC: Rf 0.2809 (30 % EtOAc:hexane); Elem-
ental analysis calcd. (found) (%): C: 72.86 (72.13), H: 6.40
(6.13), N: 5.56 (5.22), O: 15.01 (15.50); 1H NMR (DMSO-d6)
δ: 6.17-8.28 (13H-C6H5), 4.01 (1H-NH); 4.34 (2H-alicyclic-
CH2) 11.2 (1H. CO-OH); IR (cm–1): 1509, 1663, 3451, 1233,
130.
para-Hydroxy-4-biphenyl N-acetamide chloride (14):
Mustered crystalline solid; m.p.: 178-180 ºC; m.f. C14H14NO3Cl,
Yield: 175 mg (35 %); TLC: Rf 0.648 (70 % EtOAc:hexane);
Elemental analysis calcd. (found) (%): C: 68.08 (63.87), H:
5.17 (5.32), N: 9.48 (9.32), O: 5.24 (5.16), Cl: 11.78 (13.30);
1H NMR (DMSO-d6) δ: 6.01-8.07 (11H-C6H5), 4.04 (1H-NH);
12.01 (1H-COOH), 4.32 (2H-alicyclic-CH2); IR (cm–1): 1512,
1617, 3199, 1219, 135.
The authors declare that there is no conflict of interests
regarding the publication of this article.
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RESULTS AND DISCUSSION
Commercially available 4-biphenyl acetic acid was used
for the preparation of substituted 4-biphenyl acid amide

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