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Online First                                                                                                                       Indian J Pharm Drug Studies | 1 

Original Article 

Synthesis, evaluation of antimicrobial activity, and DFT analysis of 1-(4,5-

diphenyl-1H-imidazol-2-yl)naphthalen-2-ol 

Pruthviraj K1, Chethan BS2, Lohith TN3, Chandrakumar R4, Dineshbabu NS4, Mohan Kumar4, Shivaraja 

G4, Sunil K1 

From, 1Department of Chemistry, Sri Siddhartha Institute of Technology, SSAHE, Tumakuru, 2Department of Basic Science (Physics), 

Amruta Institute of Engineering and Management Sciences, Bidadi, Bengaluru, 3Department of Studies in Physics, Manasagangothri, 

University of Mysore, Mysuru, Karnataka, 4Department of Studies and Research in Organic Chemistry, Tumkur University, Tumakuru. 

ABSTRACT 

In the present work, we report synthesis of 1-(4,5-diphenyl-1H-imidazol-2-yl)naphthalen-2-ol an asymmetric catalytic block, flurophore 

and pharmacologically potent triaryl imidazole derivative having naphthalene ring via solvent free eco-friendly method using Debus-

Radiszewski condensation reaction of benzil with 2-hydroxy napthaldehyde in presence of molecular iodine as the catalyst and 

ammonium acetate as the source of nitrogen this method offered the compound in good yield compared to conventional method. The 

structure of the compound was established based on FTIR, multi nuclear NMR (1H &13C) spectral data and mass spectrometry. 

Pharmacological potency was evaluated through in-vitro antimicrobial activity against four different bacterial strains (Gram-ve bacteria 

K aerogenes, E coli, P desmolyticm, Gram+ve bacteria S Aureus) and two strains of fungi (A flavus and C albicans) exhibiting potent 

Zone of inhibition of 500μg/50μl and 10μg/50μl respectively in comparison with the standard drugs, followed by in silico ADME 

evaluation obeying the Lipinski’s rule, molecular docking studies with the binding energy of -8.3 kcal/mo and -8.8 kcal/mol against 

docked antifungal and antibacterial protein respectively established the good agreement with the in-vitro result. Density functional 

theory (DFT), electro static potential diagram (ESP) and other computational techniques were utilized to analyze the physicochemical 

parameters like energy gap, ionization energy, and electron affinity successfully. 

Key words: 1-(4,5-diphenyl-1H-imidazol-2-yl)naphthalen-2-ol, In-vitro antimicrobial activity,  In silico ADME, Molecular docking 

studies, DFT analysis. 

eterocyclic scaffolds having widespread 

pharmacyological activities have attracted great 

attention among Imidazole-based heterocyclic 

scaffolds play a vital role in natural and synthetic 

organic chemistry, have been well exploited for many medicinal 

scaffolds exhibiting anti-HIV [1-3], anticancer [4-6], 

anticonvulsant [7-9], antifungal [10-12] antibacterial [13-15], 

and anti-tubercular agent [15-17]. This core also has been utilized 

in other diverse pharmaceutical applications, stands out as a 

flexible substance with a wide range of uses, including 

biomedical technology and sophisticated materials. Because of 

its special blend of electron transport, photo stability [18], 

fluorescence [19], and catalytic qualities [20], it is an important 

component of scientific research and technological advancement. 

MATERIALS AND METHODS 

Access this article online 

Received – 25th Apr 2024 

Initial Review – 17th May  2024 

Accepted – 02nd Jun 2024  

  

Quick Response Code 

The organic solvents and chemicals were purchased from SD fine 

and Sigma Aldrich, standard commercial sources used without 

further purification.1H and 13CNMR spectra were recorded on 

ECX500 Jeol 400 MHz high resolution multinuclear FT NMR 

Spectrometer with LN2 cooled probe using deuterated solvent 

(DMSO-d6), chemical shifts were expressed in parts per million 

(ppm) and Tetramethylsilane (TMS) as an internal standard. The 

Mass spectrum was recorded using waters micromass LCT mass 

detector. 

EXPERIMENTAL  

Synthesis of (4,5-diphenyl-1H-imidazol-2-yl)naphthalen-2-ol 

[3]: A mixture of benzyl (1) 1mmol, 2-hydroxy-1-

naphthaldehyde (2) 1mmol, NH4OAC (1mmol), were heated in 

presence molecular iodine I2 (0.1 – 0.05mol) catalyst to70oC. The 

reaction progress was monitored by thin layer chromatography 

using n-hexane-Ethyl acetate (7:3) solvent system. After the 

completion of the reaction the mixture was poured aqueous  

___________________________________________________ 

Correspondence to: Sunil K, Department of Chemistry, Sri 

Siddartha Institute of Technology, SSAHE, Tumakuru. Email: 

sunilk999@gmail.com.  

H 

mailto:sunilk999@gmail.com


Pruthviraj et al.                 Synthesis and biopotency evaluation of 1-(4,5-diphenyl-1h-imidazol-2-yl)naphthalen-2-ol 

Online First                                                                                                                       Indian J Pharm Drug Studies | 2 

sodium thiosulphate (Na2S2O3) as the desired compound 

separated out with excess of iodine destroyed by the thiosulphate, 

the crude compound was recrystallized using hot ethanol to 

obtain a dark yellow solid. 

 

 
Scheme 1: Synthetic route for iodine assisted synthesis of 1-

(4,5-diphenyl-1H-imidazol-2-yl)naphthalen-2-ol (3). 

RESULTS 

Chemistry: 1-(4,5-diphenyl-1H-imidazol-2-yl)naphthalen-2-

ol(3) was synthesized as depicted (scheme-1) in the presence of 

I2 system. Further analytical characterization of the synthesized 

compound found to be IR (ATR): 3332cm-1(br) (Imidazole–

NH),2920cm-1 (intramolecular hydrogen bonded OH), 1613cm-1 

(aromatic, -C=C), 1503 cm-1 (Imidazole, –C=N), 1083 cm-1 (C-

O, alcohol stretching) 1H NMR (400MHz, DMSO-d6, δ, ppm): 

6.071(b, 1H, Ar-OH), 7.233-8.901 (m, 16H, ArH) 12.010 (s,1H, 

imidazole NH).13C NMR (100MHz,DMSO-d6, δ, ppm 

):117.889, 118.866, 119.834, 122.497, 123.829, 128.582, 

130.057, 130.153, 132.204, 133.190, 133.401, 134.350, 136.113, 

136.640, 154.634, 157.29. calcd m/z from MF (C25H18N2O) = 

362.1 found m/z = 363 (M+1). 

In-vitro Anitimicrobial Activity: 1-(4,5-diphenyl-1h-imidazol-

2-yl)naphthalen-2-ol (3) was assessed for their in 

vitro antibacterial activity against Gram-ve bacteria K.aerogenes, 

E.coli, P.desmolyticm, Gram+ve bacteria S.Aureus and the 

antifungal potency of these compounds was also tested against 

two fungal strains A.flavus and C.albicans using the using the 

agar well method. The antibacterial activity results of 1-(4,5-

diphenyl-1h-imidazol-2-yl)naphthalen-2-ol(3)revealed good 

antibacterial activity against tested bacterial strains group in 

comparison with the standard Ciprofloxacin (CPFX) as shown in 

Table 1. And from the antifungal results, it is evident that 

compound showed excellent inhibition effects against the tested 

fungal strains compared to Clotrimazole (CLT) may be due to the 

presence of electron-donating –OH group. The results of this 

antifungal activity were given in (Table 2). The measurements 

were made in triplicate for each compound and their average 

values are reported. 

Table 1: The antibacterial activity of the 1-(4,5-diphenyl-1h-imidazol-2-yl)naphthalen-2-ol (3)  

Sample Treatment 

Zone of Inhibition in mm 

Antibacterial activity 

K. aerogenes E. coli P. desmolyticm S. Aureus 

3 
250μg/50μl 10 ± 0.03** 10 ± 0.03** 12 ± 0.04** 13 ± 0.06** 

500μg/50μl 11 ± 0.05** 12 ± 0.00** 14 ± 0.05** 13 ± 0.11** 

CPFX 5μg/50μl 19 ± 0.5** 18 ± 0.5** 17 ± 0.5** 33 ± 1.0** 

DMSO - - - - - 

 

Table 2: The antifungal activity of the 1-(4,5-diphenyl-1h-

imidazol-2-yl)naphthalen-2-ol (3) 

Sample Treatment 

Zone of Inhibition in mm 

Antifungal activity 

C. albicans A. flavus 

3 
5μg/50μl 11 ± 0.33** 14 ± 1.0** 

10μg/50μl 25 ± 0.05** 28 ± 1.0** 

CLT 5μg/50μl 18 ± 0.03** 23 ± 0.33** 

DMSO  - - - 

CPFX: Ciprofloxacin, CLT: Clotrrimazole, NA: No activity, (±) 

Standard deviation values are the mean of three determinations, 

the ranges of which are <5% of the mean in all cases.  

In-silico ADME evaluation: The molecular properties and 

Lipinski rule of five for the compounds were determined by 

Swissadme online server [21]. Exploration of in-silico ADME 

properties of synthesized compounds in terms of molecular 

properties and toxicity profile are listed in (Table 3). Drug-

likeness is a quantitative parameter that measures a compound’s 

oral bioavailability. Abbot bioavailability score predicts the 

chance of a compound to have at least 10% oral bioavailability in 

rat or measurable Caco-2 cell line permeability experiment using 

a model for human intestinal absorption of drugs Drug-likeness 

scores were also calculated by considering (ALogP, TPSA, 

nAtoms, nON, nOH/NH, rotb& MW) based on Lipinski’s rule 

for the prediction of bioactivity score. The results of these 

prediction showed that the compound obeyed Lipinski’s rule. 

This semi-quantitative rule-based score defines the compounds 

into four probability score classes i.e. 11%, 17%, 55% and 85%. 

The acceptable probability score is 55% which indicates that it 

passed the rule of five. Further, synthetic accessibility was 

assessed to quantify the complexity of the molecular structure. 

The results showed that the score 3.00 revealed that the 

compounds does not have complex synthetic route [22]. 



Pruthviraj et al.                 Synthesis and biopotency evaluation of 1-(4,5-diphenyl-1h-imidazol-2-yl)naphthalen-2-ol 

Online First                                                                                                                       Indian J Pharm Drug Studies | 3 

Table 3: In-silico ADME properties 

Comp MW Alog P nHBA nHBD nRB TPSA (Å) nViolations 

3 

362.42 4.01 2 2 3 48.91 0 

Bioactivity Score Synthetic accessibility Skin Sensitization BBB Score 

0.55 (55%) 3.00 Nil 0.044 BBB+ 

nHBA: Hydrogen Bond Acceptor, nHBD: Hydrogen Bond Donor, MW: Molecular Weight, Alogp: Logarithm of partition b/w n-

octanol and water, nRB: No. rotatable bonds, TPSA: Topological Polar Surface Area. *MW < 500 Dalton, *Alog P < 5 *nHBA<5 

*nHBD< 5, *nRB< 10, * TPSA b/w 40-130

Molecular Docking Studies & Computational analysis: The 

molecule structures were generated based on spectral data multi 

nuclear NMR (1H & 13C) and Mass Spectrometry. These structures 

were drawn in Marvin JS software and they were cleaned & 

orientation to 3D. All these molecule structures were prepared in 

Auto Dock 4.2 software and exported into PDB file format. The 

crystal structure of anti-fungal protein target - candida albicans n-

myristoyltransferase (PDB ID: 1IYL), and anti-bacterial protein 

target – C (30) carotenoid dehydrosqualene synthase from 

staphylococcus aureus (PDB ID: 3ACX), were retrieved from 

Protein Data Bank. These protein structures prepared by removing 

the water molecules and small molecules in the complex.The 

molecular docking was performed in Auto Dock Vina 1.1.2 software 

to evaluate the binding affinity of the synthesized molecules with the 

protein targets. The Kollman charge was added to the protein residues 

and Lamarckian genetic algorithm was incorporated as scoring 

function. The grid box size for each protein was set significantly to 

cover the active site residues were standard drug bound. The default 

values were taken for all other parameters. Based on docking the top 

10 poses will be generated and ranked based on binding 

energy.Docking Results are listed in (Table 4) and 2D binding 

pattern / poses of compound is shown in (Figure 1, 2) extracted using 

Schrodinger visualizer, it’s found to be 1-(4,5-diphenyl-1H-imidazol-

2-yl)naphthalen-2-ol (3) is nearly as potent as other standard drugs 

with a minute difference in binding score [23-25]. 

 

Table 4: Binding / Docking Energy 

Comp 

Code 

PDB ID Role Binding Score 

(Kcal/mol) 

No of  

Interactions 

Interactive residues 

3 
1IYL 

Anti-fungal protein 

target 

-8.3 21 

Leu 415, Glu 109, Val 108, Tyr 107, Gly 212, Thr 211, Phe 

176, Phe 117, Thr 119, Val 449, Leu 450, Leu 451, Leu 357, 

Tyr 335, Tyr 225, Tyr 354, Leu 394, Gln 226, Hid 227, Cys 

393, Asn 392. 

CLT -9.4 - 

3 
3ACX 

Anti-bacterial 

protein target 

-8.8 19 

PHE 22, LEU 164, GLN 165, TYR 248, ASN 168, ARG 171, 

ASP 172, GLU 175, ASP 176, ARG 265, TYR 129, TYR 183, 

HIS 18, TYR 41, CYS 44, VAL 137, ARG 45, ASP 48 

CPFX -9.6 - 
 

 
Figure 1: 2D docking poses / binding patterns with 3AC



Pruthviraj et al.                 Synthesis and biopotency evaluation of 1-(4,5-diphenyl-1h-imidazol-2-yl)naphthalen-2-ol 

Online First                                                                                                                       Indian J Pharm Drug Studies | 4 

 

 

Figure 2: 2D docking poses / binding patterns with 1IYL  

DFT Analysis: The theoretical calculations using density 

functional theory (DFT) have been utilized to study molecular 

properties like charge analysis, reduced density gradient (RDG) 

analysis, along with molecular electrostatic potential surface 

analysis gives a clear understanding of the structure of the 

molecule [26-27]. The molecular orbital energies and 

electrostatic potential of the molecule were calculated in the 

ground state using DFT. The reduced density gradient and global 

descriptors such as chemical potential, electronegativity, 

hardness, softness, and electrophilicity index were studied [28-29]. 

Theoretical calculations: The Becke’s three parameter hybrid 

functional (B3) for the exchange part and the Lee-Young-Parr 

(LYP) correlation function at 6-31G(d,p) is used to perform the 

density functional theory calculations using GAMESS-US 

software [30]. All DFT calculations were performed in the gas 

phase only. The required input for the gamess software was 

generated using Avogadro [31]. The same parameters were used 

for the optimization structure and to calculate electronic 

properties. The surface potential and RDG were generated using 

Multiwfn-3.8 [32], and visualized using Visual Molecular 

Dynamics (VMD) software [33]. 

Frontier molecular orbital (HOMO-LUMO) analysis and 

chemical reactivity indices: The frontier molecular orbitals 

(FMO) analysis is very helpful in understanding the nature of 

orbitals involved in chemical reactions. The FMO energy level of 

the compounds was computed using the DFT method at 

B3LYP/6-31G(d,p) level of theory in the gas phase. The surface 

of some important FMO’s along with MEPs and RDGIs shown 

in (Figure 3). The energy gap between the highest occupied 

molecular orbital (HOMO) and lowest unoccupied molecular 

orbital (LUMO) was calculated found to be 9.969ev indicating 

its stability, further promoting high temperature conditions or 

acidic media for the reactiveness. The chemical reactivity 

parameters like chemical hardness (η), electronegativity (χ), 

electronic chemical potential (μ), and electrophilicity index (ω) 

were also calculated. The chemical hardness is given by 

η=(ELUMO-EHOMO)/2 is connected with the stability and reactivity 

of a chemical system [34]. The electronegativity is defined as the 

ability to attract electrons towards it and is given by the 

expression χ=-(EHOMO+ELUMO)/2 found to be -0.1967 which is 

helpful in transport of electrons which is further supported by 

presence of aromatic rings. The negative of the electronegativity 

of a molecule is determined by using an equation 

μ=(EHOMO+ELUMO)/2 is known as chemical potential. Parr has 

introduced the electrophilicity index (ω), is calculated using the 

electronic chemical potential and chemical hardness from the 

equation ω=μ2/2η. The calculated values of chemical reactivity 

parameters are listed in (Table 5). 

Table 5: The calculated values of chemical reactivity parameters 

EHOMO (eV) ELUMO (eV) Energy gap (Δ) 

(eV) 

Ionization energy (I) 

(eV) 

Electron affinity 

(A) (eV) 

-5.1814 4.788 9.969 5.1814 -4.788 

Electronegativity (χ) (eV) Chemical potential 

(μ) (eV) 

Global hardness (η) 

(eV) 

Global softness (s) (eV-1) 

-0.1967 0.1967 4.9847 0.200 

 

DISCUSSION 

The synthesized organic derivative via environmentally benign 

approach found to be potent biological agent exhibiting ZOI of 

10mm, 10mm, 11mm & 13mm against four different strain of 

bacteria’s K aerogenes E coli P desmolyticm S Aureus 

respectively and two different fungi strainst C albicans A.flavus 

CLT-1IYL 

3-1IYL 



Pruthviraj et al.                 Synthesis and biopotency evaluation of 1-(4,5-diphenyl-1h-imidazol-2-yl)naphthalen-2-ol 

Online First                                                                                                                       Indian J Pharm Drug Studies | 5 

found to be susceptible witth the ZOI of 11mm and 14mm 

respectively at 5μg/50μl concentraion in comprison with the 

statnadrd drug, the evaluation of preliminary ADME properties 

foud to be compound is obeying the Lipinski’s rule of five and 

in-vitro data are further supported with the in silico molecular 

docking analysis, obtained binding enegy values are supportig 

the in-vitro data. The DFT anaylsis established the molecular 

paramerters. 

CONCLUSION 

In this work, we have successfully prepared 1-(4,5-diphenyl-1H-

imidazol-2-yl) naphthalen-2-olimidazole (3) a versatile 

asymmetric building blockusing I2 as catalyst. In-vitro 

antimicrobial activity followed by computer aided drug 

designing involving ADMETox and molecular docking studies 

were performed to establish the pharmaceutical activity and the 

physiochemical parameters were calculated using DFT analysis. 

In this paper we discuss the synthesis of of 1-(4,5-diphenyl-1H-

imidazol-2-yl)naphthalen-2-ol (3) a versatile building block for 

assymetric catalyst was synthesized using modified method 

reported by the only available synthetic report, further the 

compound was evaluated for its pharmacological potency against 

bacterial and fungi strains. Additionally, computer aided drug 

discovery approaches like ADME, and molecular docking 

studies were carried out against 2 proteins. Results were 

compared against extensively used antibacterial,and antifungal 

standard drugs Ciprofloxacin (CPFX), Clotrimazole (CLT) 

respectively. Finally, the synthesized title compound was 

subjected to DFT analysis to establish physicochemical parameters. 

 

Figure 3: HOMO-LUMO energy gap of compound along 

with electrostatic potential diagram and RDG 

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How to cite this article: Pruthviraj K, Chethan BS, Lohith TN, 

Dineshbabu NS, Chandrakumar R, Mohan Kumar, Shivaraja 

G, Sunil K. Synthesis, evaluation of antimicrobial activity, and 

DFT analysis of 1-(4,5-diphenyl-1H-imidazol-2-yl) 

naphthalen-2-ol. Indian J Pharm Drug Studies. 2024; Online 

First. 

Funding: None;                   Conflicts of Interest: None Stated  

 

https://doi.org/10.1016/j.cdc.2020.100452

