Design, synthesis, molecular docking and antimicrobial evaluation of some tosyl carbamate derivatives

Article abstract of DOI:10.14233/ajchem.2020.22440

A series of tosyl carbamates have been synthesized and screened for their antibacterial and antifungal activities. All the synthesized compounds were characterized by spectral techniques (IR, ¹H, ¹³C NMR and mass) and elemental analysis. in silico Molecular docking method was performed to study their antimicrobial activity against the target protein 1T9U. Compound 27 showed good antibacterial activity against Gram-positive and Gram-negative bacterial strains and compound 19 showed good antifungal activity. Molecular docking results revealed that the compound 19 exhibits minimum CDOCKER energy. Tosyl carbamate derivatives having good antimicrobial activities compared to that standard and all the synthesized compounds exhibits moderate CDOCKER scores.

Full text of DOI:10.14233/ajchem.2020.22440

Asian Journal of Chemistry; Vol. 32, No. 4 (2020), 783-788
A
SIAN
J
OURNAL OF HEMISTRY
C
https://doi.org/10.14233/ajchem.2020.22440
Design, Synthesis, Molecular Docking and Antimicrobial
Evaluation of Some Tosyl Carbamate Derivatives
*
PANNEERSELVAM KALAIVANI, JAYARAMAN ARIKRISHNAN and MANNUTHUSAMY GOPALAKRISHNAN
Department of Chemistry, Annamalai University, Annamalai Nagar, Chidambaram-608002, India
*Corresponding author: E-mail: mgkrishnan61@gmail.com; kalaivanichem9@gmail.com
Received: 11 September 2019;
Accepted: 31 October 2019;
Published online: 25 February 2020;
AJC-19792
A series of tosyl carbamates have been synthesized and screened for their antibacterial and antifungal activities. All the synthesized
compounds were characterized by spectral techniques (IR, 1H, 13C NMR and mass) and elemental analysis. in silico Molecular docking
method was performed to study their antimicrobial activity against the target protein 1T9U. Compound 27 showed good antibacterial
activity against Gram-positive and Gram-negative bacterial strains and compound 19 showed good antifungal activity. Molecular docking
results revealed that the compound 19 exhibits minimum CDOCKER energy. Tosyl carbamate derivatives having good antimicrobial
activities compared to that standard and all the synthesized compounds exhibits moderate CDOCKER scores.
Keywords: Tosyl carbamates, Molecular docking, Protein 1T9U, CDOCKER energy.
been employed as demandable pharmaceuticals in the kinds
of drugs and pro drugs. They represent an important class of
compounds displaying various exciting properties [16]. The
importance of the present findings, chemistry provides an effi-
cient and practical approach to synthesize carbamates, which
play very crucial and also ubiquitous roles in pharmaceutical
drugs [17-22], agrochemicals [23] (pesticides, herbicides,
insecticides, fungicides, etc.) as intermediates in organic syn-
thesis [24] and material terrains [25]. Compounds containing
sulfonyl groups were studied recognition because of their
organic significance, chemical applications and a number of
aryl sulfonamide derivatives are a common place substructure
magnificence found in a huge number of active pharmaceutical
ingredients (APIs) [26]. The sulfonyl carbamate functional
group is an easily accessible carboxylic acid bioisostere and
traditionally brought inside the N-acylation of sulfonamides
with carbonic acid derivatives such as chloroformate or anhy-
dride [27]. Sulfonyl carbamates are also used as nitrogen
nucleophiles in Mitsonobu reaction [28] as shielding groups
for alcohols [29] and as dehydrating agents [30]. Sulfonamide
based medicines are antimicrobial agents, still widely used
for the treatment of numerous bacterial, protozoal and fungal
infections [31] and the first effective chemotherapeutic agents
to be available in safe therapeutic dosage ranges [32]. The
INTRODUCTION
Carbamate molecules play a vital role in modern drug
discovery and medicinal chemistry. Structurally, carbamate
functionality is related to amide ester hybrid functions and, in
standard displays good chemical and proteolytic stabilities.
Organic carbamates serve a crucial characteristic as optimum
protecting groups for amines and amino acids in organic synth-
esis and peptide chemistry [1]. Carbamates are traditionally
prepared from chloroformates or isocyanates through emerging
phosgene or its substitutes as starting materials [2]. The reaction
of alcohols with isocyanates giving carbamates (urethanes) and
its utility to polyfunctional alcohols and isocyanates is the basis
of the polyurethane industry [3]. Several attempts were made
to replace the classical synthesis, which involves the direct
reaction of alcohols with phosgene or its derivative isocyanates
with new methodologies employing less toxic and dangerous
reagents [4]. Carbamates are beneficial in biologically active
compounds. There are some drugs in the markets containing
carbamate functional group [5]. For example, a large number
of molecules with carbamate motifs had been found to possess
various bioactive potentials and have been developed into
marketed drugs that treat arrhythmias [6], seizures [7], asthma
[8-11] and AIDS [12-15]. Organic carbamates have regularly
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784 Kalaivani et al.
Asian J. Chem.
O
applications of sulfonyl carbamate moiety has greatly extended
from their primary function as potent antibacterial [33], anti-
microbial [34], antitumor [35], hypoglycemic [36], antithyroid
[37], anticarbonic anhydrase [38], anti-inflammatory [39], lipid
regulating [40], diuretic [41], COX-inhibitors, dihydropteroate
synthetase (DHPS), a key enzyme involved in folate synthesis,
anti-impotence drugs [42] and also have been used as azo dyes
for achieving improved light stability, water solubility, and
fixation to fiber properties [43]. Recently, several reports have
indicated that carbamate linkage present in between the active
pharmacophores of various structurally diverse molecules
increases mani-fold biological activities of semi-synthetic,
natural/synthetic molecules [44].
R2
R1
O
H
C
R2
R1
R3
R2
+
C2H5OH
H
O
Warm,15 Min
N
H
CH3
O
+
NH4
-O
2
+
1-9
NaBH4 CH3OH
O
S
HN
OH
R2
O
O
S N C O
R3
R1
O
O
R2
O
R3
R1
DCM, 6hrs Reflux
EXPERIMENTAL
N
H
N
H
All the chemicals were purchased from Avra chemicals.
Melting points of synthesized compounds were determined in
open capillaries and are uncorrected. IR spectra were recorded
in Agilent Cary 650 IR Spectrophotometer using the ATR
method. 1H spectra (400 MHz) and 13C spectra (100 MHz) were
recorded on BRUKERAVANCE III NMR spectrometer in DMSO
with tetramethylsilane the internal standard and the chemical
shifts were reported in parts per million scales. Mass spectra
were studied using API 3000 series mass spectrometer. The
purity of the compounds was checked by TLC on silica gel
and spots were developed using ultraviolet light and iodine
chamber.
3,5-Dialkyl-2,6-diarylpiperidin-4-ones (1-9) compounds
were synthesized by a condensation reaction of appropriate
aldehydes, ketones and ammonium acetate in 2:1:1 ratio [45].
Synthesis of 4-hydroxy-3,5-dialkyl-2,6-diarylpiperidine
(10-18): Sodium borohydride (0.1 mmol) was added slowly
to a solution of appropriate 3,5-dialkyl-2,6-diarylpiperidin-4-
ones (0.01mol) in methanol and the mixture was stirred at
room temperature until the reaction completes. The reaction
mixture was poured into crushed ice and the solid obtained
was filtered and dried.
General synthesis of 3,5-dialkyl-2,6-diaryl piperidine-
4-yltosyl carbamate (19-27):A stirred solution of 4-hydroxy-
3,5-dialkyl-2,6-diaryl-piperidine (0.01mol), p-toluene sulfonyl
isocyanate (0.01mol) and triethylamine in dichloromethane
were refluxed for 4-6 h and the reaction was monitored by TLC.
Then the mixture was extracted with chloroform and washed
with water. The chloroform layer was dried over anhydrous
sodium sulfate and distilled off under vacuum. Purifications
with silica gel column chromatography with petroleum ether:
ethyl acetate mixture yielded the product (Scheme-I).
10-18
19-27
R1 = -CH3, - C2H5, n-C3H7, iso-C3H7,
n-C4H9, n-C5H11, n-C6H13
R2 = -H, -CH3; R3= -H, -CH3
Scheme-I: Synthesis of 3,5-dialkyl-2,6-diaryl piperidine-4-yl tosyl
carbamate
59.39, 21.3, 14.47. Elemental analysis for C26H28N2O4S (%):
C, 67.22; H, 6.07; N, 6.03; O, 13.78; S, 6.90.
3,3-Dimethyl-2,6-diphenylpiperidine-4-yltosyl carba-
mate (20): White solid, m.p.: 172-174 ºC,Yield: 72.5 %, m.w.:
478. FT-IR (KBr, νmax, cm-1): 3488 (amide-NH), 3345 (pip-
NH), 3058 (Ar C-H), 2976 (aliph. C-H), 1646 (C=O), 1351,
1144 (SO2). 1H NMR (400 MHz, DMSO-d6): (δ, ppm) 7.1-7.7
(m, 14H), 5.03 (s, NH), 3.8 (d, 1H), 2.5 (s, 3H), 2.3 (s, 1H),
1.9 (s, 2H), 0.47 (dd, 6H). 13C NMR (100 MHz, DMSO-d6) δ
ppm: 157.36, 142, 140, 126.08- 129.77, 65.79, 62.25, 38.39,
21.3, 14.23. Elemental analysis for C27H30N2O4S (%): C, 67.76;
H, 6.32; N, 5.85; O, 13.37; S, 6.70.
3,5-Dimethyl-2,6-diphenylpiperidine-4-yltosyl carba-
mate (21): White solid, m.p.: 172-176 ºC. Yield: 72 %, m.w.:
478. FT-IR (KBr, νmax, cm-1): 3491 (amide-NH), 3347 (pip-
NH), 3062 (Ar C-H), 2976 (aliph. C-H), 1647 (C=O), 1351,
1142 (SO2). 1H NMR (400 MHz, DMSO-d6): (δ, ppm) 7.3-7.6
(m, 14H), 5.01 (s, NH), 2.5 (s, 3H), 2.3 (s, 1H), 0.47 (dd, 6H).
13C NMR (100 MHz, DMSO-d6) δ ppm: 157, 141, 140, 126.08-
129.77, 65.79, 62.25, 38.39, 21.3, 14.23. Elemental analysis
for C27H30N2O4S (%): C, 67.76; H, 6.32; N, 5.85; O, 13.37; S,
6.70.
3-Ethyl-2,6-diphenylpiperidin-4-yltosyl carbamate
(22): White solid, m.p.: 168-170 ºC. Yield: 77.09 %, m.w.:
478. FT-IR (KBr, νmax, cm-1): 3567 (amide-NH), 3472 (pip-
NH), 3041 (Ar C-H), 2963 (aliph. C-H), 1637 (C=O), 1354,
1146 (SO2). 1H NMR (400 MHz, DMSO-d6): (δ, ppm) 7.5-7.2
(m, 14H), 4.8 (s, NH), 4.3 (dd, 2H), 4.2 (d,2H), 4.0 (d, 1H),
2.5 (s, 3H), 2.0 (s, NH), 1.9, 1.2, 0.8-0.9. 13C NMR (100 MHz,
DMSO-d6) δ ppm: 157, 126-129, 63.32, 62.35, 58.99, 56.08,
21.3, 19.5, 11. Elemental analysis for C27H30N2O4S (%): C,
67.76; H, 6.32; N, 5.85; O, 13.37; S, 6.70.
Spectral data
3-Methyl-2,6-diphenylpiperidin-4-yltosyl carbamate
(19): White solid, m.p.: 174-178 ºC. Yield: 82.90 %, m.w.:
464. FT-IR (KBr, νmax, cm-1): 3469 (amide-NH), 3311 (pip-
NH), 3058 (Ar C-H), 2975 (aliph.ph. C-H), 1666 (C=O), 1378,
1142 (SO2). 1H NMR (400 MHz, DMSO-d6): (δ, ppm) 7.2-7.7
(m, 14H), 4.7 (s, NH), 4.0 (d, 2H), 3.8 (d, 1H), 3.2 (d, 1H), 2.5
(s, 3H), 1.9 (s, 1H), 1.4 (m, 1H), 0.6 (d, 3H). 13C NMR (100
MHz, DMSO-d6) δ ppm: 170.92, 142.40, 141.79, 140.66,
129.78, 128.82, 128.57, 127.75, 126.07, 72.38, 66.1, 60.27,
2,6-Diphenyl-3-propylpiperidin-4-yltosyl carbamate
(23): White solid, m.p.: 174-176 ºC.Yield: 68.3 % m.w.: 492.

Vol. 32, No. 4 (2020)
Design, Synthesis and Antimicrobial Evaluation of Some Tosyl Carbamate Derivatives 785
FT-IR (KBr, νmax, cm-1): 3428 (-NH), 3036 (Ar C-H), 2956 (aliph.
the best binding compounds depends on a variety of scoring
functions, such as CDOCKER energy and CDOCKER inter-
action and hydrogen bond interaction. The best binding poses
are selected as the lowest binding energy and least energy
difference between cdocker interaction energy and cdocker
energy of interacting compounds with targeted protein.
For the present investigation, X-ray crystal structure of
AcrB (PDB ID: 1T9U) were downloaded from the protein data
bank (PDB) based on the good resolution of 3.5 Å. AcrB is a
major multidrug exporter in Escherichia coli [48]. The retrieved
3D crystal structure ofAcrB (1T9U) was prepared and energy
minimized to stabilize the structure was followed by CHARMm
force field to avoid steric overlap and to relax the conformation
[49].
The compounds were drawn in Chem Draw 12.0. Three-
dimensional structure of the compounds was obtained by the
Chem Draw 3D Ultra 12.0 software. The designed ligands
were saved as mol format and examined as to generate the best
pose was determined the binding interactions. The co-factors,
unwanted water molecules and chains are removed.
1
C-H), 1637 (C=O), 1354,1144 (SO2). H NMR (400 MHz,
DMSO-d6): (δ, ppm) 7.2-7.7 (m, 14H), 5.01 (NH), 4.3 (dd,
2H), 3.9 (d, 1H), 2.5 (s, 3H), 2.3 (s, H), 2.08 (s, NH), 1.97 (d,
2H), 0.5-0.8 (m, 7H). 13C NMR (100 MHz, DMSO-d6): (δ,
ppm) 156.27 (CO), 142.3, 141.8, 140.3, 129.7, 128.9, 126.6,
62.44, 56.10, 46.13, 41.80, 21.3, 29.43, 14.2. Elemental
analysis for C28H32N2O4S (%): C, 68.27; H, 6.55; N, 5.69; O,
12.99; S, 6.51.
3-Isopropyl-2,6-diphenylpiperidin-4-yltosyl carbamate
(24): White solid, m.p.: 174-178 ºC. Yield: 74.76 %, m.w.:
464. FT-IR (KBr, νmax, cm-1): 3421 (amide NH), 3210 (pip-
1
NH), 2953 (aliph. C-H), 1633 (C=O), 1325, 1151 (SO2). H
NMR (400 MHz, DMSO-d6): (δ, ppm) 7.2-7.6 (m, 14H), 4.7
(s, 1H), 4.3 (dd, 2H), 2.5 (s, 3H), 2.3 (s, 1H), 2.1 (s, NH), 1.92
(d, 2H), 1.2 (m, 1H), 0.7 (d, 6H). 13C NMR (100 MHz, DMSO-
d6): (δ, ppm): 159.86, 141.99, 137.77, 129.78, 129.02, 128.89,
128.36, 127.23, 126.85, 126.08, 63.06, 61.10, 58.72, 56.10,
21.3, 20.9, 17.67. Elemental analysis for C28H32N2O4S (%): C,
68.27; H, 6.55; N, 5.69; O, 12.99; S, 6.51.
3-Butyl-2,6-diphenylpiperidin-4-yltosyl carbamate
(25): White solid, m.p.: 208-212 ºC.Yield: 76.6 %, m.w.: 506.
FT-IR (KBr, νmax, cm-1): 3431 (-NH), 3036 (Ar C-H), 2955
(aliph. C-H), 1638 (C=O), 1353, 1144 (SO2). 1H NMR (400
MHz, DMSO-d6): (δ, ppm) 7.2-7.5 (m, 14H), 5.0 (NH), 4.3
(dd, 2H), 3.9 (d, 1H), 2.5 (s 3H), 2.3 (1H), 2.08 (d, 2H), 2.05
(s, 1H), 1.9, 0.8-1.0 (m, 9H). 13C NMR (100 MHz, DMSO-d6)
(δ, ppm): 157, 140.49, 126.72-129.09, 62.44, 56.18, 27.94,
26.72, 22.35, 21.31, 13.99. Elemental analysis for C29H34N2O4S
(%): C, 68.75; H, 6.76; N, 5.53; O, 12.63; S, 6.33.
in vitro Antimicrobial activity: The newly synthesized
compounds were assayed for in vitro antimicrobial activities
by filter paper disc diffusion method [50]. The bacterial species
(Gram-positive and Gram-negative) and fungal species were
incubated at 48 ºC for 24 h. The bacterial and fungal cultures
were grown in nutrient agar medium and subcultured for the
better growth and subcultured into the petri plates for the experi-
ments. The cultures were diluted with sterilized saline and the
compounds were diluted in DMSO for biological assays. The
bacterial and fungal cultures containing discs were placed on
the media and incubated at 48 ºC for 24 to 48 h for better obser-
vation. The sterile filter paper discs of 6 mm in diameter were
impregnated with a variety of test compounds and the results
were compared with the activity of standards ciprofloxacin
and amphotericin B. The results were measured and expressed
as a zone of inhibition in mm. In agar disc diffusion method,
test compounds were introduced into the discs and allowed to
dry at 48 ºC. The discs were positioned below the nutrient agar
petri plates previously seeded with a suspension of each bacterial
and fungal strain. The petri dishes were incubated for 24 h at
37 ºC and the diameter of zone of inhibition was observed and
measured.
3-Pentyl-2,6-diphenylpiperidin-4-yltosyl carbamate
(26): White solid, m.p.: 192-196ºC. Yield: 69 %, m.w.: 520.
FT-IR (KBr, νmax, cm-1): 3437 (-NH), 3039 (Ar C-H), 2951 (aliph.
1
C-H), 1637 (C=O), 1352, 1143 (SO2). H NMR (400 MHz,
DMSO-d6): (δ, ppm) 7.2-7.5 (m, 14H), 4.7 (NH), 4.3 (d, 2H),
4.03 (d, 1H), 2.5 (s, 3H), 2.3 (1H), 2.08 (d, 2H), 2.0 (NH), 1.9
(d, 2H), 0.5-1.08 (m, 11H). 13C NMR (100 MHz, DMSO-d6):
(δ, ppm): 157, 142, 141, 126.78-129.07, 62.43, 56.15, 41.79,
31.51, 27.07, 25.43, 22.1, 21.3, 14.2. Elemental analysis for
C30H36N2O4S (%): C, 69.20; H, 6.97; N, 5.38; O, 12.29; S,
6.16.
3-Hexyl-2,6-diphenylpiperidin-4-yltosyl carbamate
(27): White solid, m.p.: 188-190ºC. Yield: 70 %, m.w.: 534.
FT-IR (KBr, νmax, cm-1):3464 (-NH), 3064 (Ar C-H), 2929 (aliph.
RESULTS AND DISCUSSION
1
The parent compound, piperidine-4-one derivative was
synthesized by the Mannich reaction as shown in Scheme-I.
Then it was reduced to hydroxyalkyl piperidine derivatives
using sodium borohydride. The reduced compound was further
reacted with p-toluene sulfonyl isocyanate. The obtained product
was subjected to column chromatography using pet ether:ethyl
acetate (1:3) as an eluent and good yielded. The formation of
tosyl carbamates (19-27) was confirmed by recording their
FT-IR, 1H & 13C NMR and mass spectrometry.
In the FT-IR spectra of the synthesized compounds, 19-
27 contained absorption bands in the range of 3469-3311 cm-1
due to stretching vibrations of the NH group, 1666 cm-1 due to
the presence of CO stretching and at 1378 and 1142 cm-1 were
confirmed the presence of SO2 asymmetric and symmetric
C-H), 1678 (C=O), 1354, 1143 (SO2). H NMR (400 MHz,
DMSO-d6): (δ, ppm): 7.7-7.1 (m, 14H), 4.7 (s, NH), 3.9 (dd,
2H), 3.6 (d, 1H), 2.5 (s, 3H), 2.0 (s, NH), 1.0-1.1 (m, 13H).
13C NMR (100 MHz, DMSO-d6): (δ, ppm): 157, 142.34, 141.8,
124-129, 71.04, 64.70, 59.45, 31.4, 29.69, 27.7, 25.67, 22.43,
21.37, 14.36. Elemental analysis for C31H38N2O4S (%): C,
69.63; H, 7.16; N, 5.25; O, 11.97; S, 6.00.
Molecular docking studies: A molecular docking study
was performed using the Biovia discovery studio 2016 program
[46]. For the present investigation, the CDOCKER (CHARMm
based DOCKER) is grid-based molecular docking protocol
that operates on the CDOCKER algorithm utilizing CHARMm
force field and offers full flexibility to ligands including dihedral,
angles and bonds [47]. Docking was performed to investigate

786 Kalaivani et al.
Asian J. Chem.
stretching vibrations. In 1H NMR, compounds 19-27 (DMSO-
d6) revealed the following signals: a singlet equivalent to one
proton in the δ 5.0 and 2.0 ppm range assigned for the amide
NH and piperidone protons, a singlet equivalent to three protons
at δ 2.5 ppm assigned tosyl CH3 protons, a doublet at δ 0.45
ppm assigned of piperidone methyl protons, and a multiplet
at δ 7.39-7.66 ppm assigned for the aromatic protons, respec-
tively. In 13C NMR, compounds 19-27 show the chemical shift
values of carbon atoms appear δ 157 ppm due to carbonyl atom,
δ 126.08- 129.77 ppm due to aromatic carbons atoms, δ 65.7-
62.25 ppm due to piperidone ring carbon atoms and δ 14.23
ppm is due to piperidone ring attached methyl carbon atom,
respectively. Molecular and fragmented ion peaks in the mass
spectra have given further evidence for the structural elucidation
of the compounds.
Molecular docking studies:The comparative and automated
docking studies with the compounds onAcrB (PDB ID: 1T9U)
were performed with the CDOCKER algorithm in the docking
program over the Discovery studio. The better interacting comp-
ounds were decided based on the binding compatibility of the
compound. The strength of the protein-ligand interaction was
analyzed based on the docking score, the number of hydrogen
bonds and binding energy. The top-ranked compounds with
lowest docked binding affinities and high docking were selected
and summarized in Table-1. The conformation with the lowest
binding energy was considered as the most favourable docking
pose. From that result, synthesized compound 19 shows a good
cdocker energy (kcal/mol) and cdocker interaction energy
(kcal/mol). A two-dimensional structure of synthetic ligands
(19-27) is produced using discovery studio (v 16.1.0.15350)
(Fig. 1) in the two-dimensional structure, dotted lines represent
van derWaals interactions, hydrogen bonding and pi-alkyl inter-
actions. Docking of these compounds against theAcrB (1T9U)
structure of the active site residues is performed by the discovery
studio. Compound 21 shows interaction with the amino acid
residues. An interaction of docked structure 21 is shown in
Figs. 2 and 3. Out of nine docked compounds, 19, 22 and 24
compounds showed lowest cdocker energy with the amino acid
residues of the receptor molecule.
Interactions
van der Waals
Pi-Anion
Conventional hydrogen bond
Carbon hydrogen bond
Pi-Cation
Pi-Donor hydrogen bond
Pi-Sulfur
Pi-Alkyl
Fig 1. Two-dimensional diagram of compound 21 docked with 1T9U protein
Fig. 2. Structure of 1T9U protein in complex with compound 21
TABLE-1
DOCKING RESULTS OF THE DESIGNED
COMPOUNDS (19-27) TOWARDS 1T9U
-CDOCKER energy -CDOCKER interaction
S. No.
Entry
(kcal/mol)
23.87
26.37
26.79
24.17
26.45
24.17
27.90
27.03
30.70
energy (kcal/mol)
1
2
3
4
5
6
7
8
9
19
20
21
22
23
24
25
26
27
38.25
37.55
37.73
38.70
39.86
40.42
42.42
40.14
Fig. 3. Docking interactions of 1T9U protein with compound 21
47.38
coli, Pseudomonas aeruginosa and Proteus morganii) bacterial
strains and five fungal strains (Candida albicans, Candida
glabrata, Candida krusei, Candida tropicalls and Candida
parapsilosis) had been chosen to display the antimicrobial
activity. Ciprofloxacin and amphotericin B were used as the
standards in the antibacterial and antifungal activities, respec-
in vitro Antimicrobial activity: in vitro Antimicrobial
activity (antibacterial and antifungal activities) of synthesized
tosyl carbamate derivatives (19-27) were investigated using
the disc diffusion method. Two Gram-positive (Staphylococcus
aureus and Bacillus subtilis) and three Gram-negative (Escherichia

Vol. 32, No. 4 (2020)
Design, Synthesis and Antimicrobial Evaluation of Some Tosyl Carbamate Derivatives 787
TABLE-2
ANTIBACTERIAL AND ANTIFUNGAL ACTIVITIES OF SYNTHESIZED COMPOUNDS (19-27) BY DISC DIFFUSION METHOD
Zone of inhibition (mm)
Antibacterial activity
Antifungal activity
Compounds
S.
aureus
20
P.
B.
subtilis
E.
coli
P.
C.
albicans
C.
C.
C.
C.
morganii
glabrata parapsilosis
krusei
tropicalis
aeruginosa
09
10
08
12
11
20
21
15
17
18
–
18
12
16
22
13
15
16
07
20
23
–
13
17
13
06
17
15
19
09
19
21
–
19
11
14
22
10
19
20
15
20
26
–
21
18
09
14
17
11
08
09
16
–
10
14
19
09
13
20
16
17
16
–
23
19
24
19
08
22
23
13
20
–
20
17
18
13
09
19
20
09
21
–
17
09
16
14
10
23
16
08
18
–
19
20
21
22
23
24
25
26
27
16
19
15
20
18
17
14
20
Ciprofloxacin
Amphotericin B
25
–
22
18
26
20
19
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inhibition of compounds (19-27) against the bacterial strains
is given in Table-2. Compounds 19, 23 and 27 against S. aureus;
and compounds 22 and 27 against E. coli showed significantly
high antibacterial activity at a diameter zone of inhibition
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compounds 19, 20, 21 and 24 exhibited better antifungal activ-
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of the synthesized compounds were docked with target protein
1T9U were carried out and the results of such studies were
reported. in silico Studies revealed that synthesized compounds
19 and 21 have relatively lesser CDOCKER energy scores. The
synthesized compounds were tested in vitro antimicrobial
activity by disc diffusion method.All the compounds demons-
trated mild to the moderate zone of inhibition against the
standard drugs.
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