N-Arylation of Protected and Unprotected 5-Bromo-2-aminobenzimidazole as Organic Material: Non-Linear Optical (NLO) Properties and Structural Feature Determination through Computational Approach

Mumtaz, Mubeen; Rasool, Nasır; Ahmad, Gulraız; Kosar, Naveen; Rashid, Umer

doi:10.3390/molecules26226920

Cited by 9 publications

(5 citation statements)

References 49 publications

(62 reference statements)

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“…α ο and β ο are highest in the case of compounds 1 and 19 indicating good NLO properties and can be used as an optical material as well as sensory material for optics. As polarizability actually shows the division of electronic charge and density in the chemical system, α ο value is greater for compounds having strong electron donating and withdrawing groups on opposite terminals [ 51 ]. Others have moderate values.…”

Section: Resultsmentioning

confidence: 99%

Investigation of Novel Benzoxazole-Oxadiazole Derivatives as Effective Anti-Alzheimer’s Agents: In Vitro and In Silico Approaches

et al. 2023

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Alzheimer’s disease (AD) is a progressive neurological illness that is distinguished clinically by cognitive and memory decline and adversely affects the people of old age. The treatments for this disease gained much attention and have prompted increased interest among researchers in this field. As a springboard to explore new anti-Alzheimer’s chemical prototypes, the present study was carried out for the synthesis of benzoxazole-oxadiazole analogues as effective Alzheimer’s inhibitors. In this research work, we have focused our efforts to synthesize a series of benzoxazole-oxadiazole (1–19) and evaluating their anti-Alzheimer properties. In addition, the precise structures of synthesized derivatives were confirmed with the help of various spectroscopic techniques including 1H-NMR, 13C-NMR and HREI-MS. To find the anti-Alzheimer potentials of the synthesized compounds (1–19), in vitro acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), inhibitory activities were performed using Donepezil as the reference standard. From structure-activity (SAR) analysis, it was confirmed that any variation found in inhibitory activities of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes were due to different substitution patterns of substituent(s) at the variable position of both acetophenone aryl and oxadiazole aryl rings. The results of the anti-Alzheimer assay were very encouraging and showed moderate to good inhibitory potentials with IC50 values ranging from 5.80 ± 2.18 to 40.80 ± 5.90 µM (against AChE) and 7.20 ± 2.30 to 42.60 ± 6.10 µM (against BuChE) as compared to standard Donepezil drug (IC50 = 33.65 ± 3.50 µM (for AChE) and 35.80 ± 4.60 µM (for BuChE), respectively. Specifically, analogues 2, 15 and 16 were identified to be significantly active, even found to be more potent than standard inhibitors with IC50 values of 6.40 ± 1.10, 5.80 ± 2.18 and 6.90 ± 1.20 (against AChE) and 7.50 ± 1.20, 7.20 ± 2.30 and 7.60 ± 2.10 (against BuChE). The results obtained were compared to standard drugs. These findings reveal that benzoxazole-oxadiazole analogues act as AChE and BuChE inhibitors to develop novel therapeutics for treating Alzheimer’s disease and can act as lead molecules in drug discovery as potential anti-Alzheimer agents.

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Section: Resultsmentioning

confidence: 99%

Investigation of Novel Benzoxazole-Oxadiazole Derivatives as Effective Anti-Alzheimer’s Agents: In Vitro and In Silico Approaches

et al. 2023

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“…The column chromatography using n-hexane and ethyl acetate in a 40:60 ratio was run to purify the product. Finally, the production of 3d was confirmed by the structure elucidation via 1 H NMR, 13 C NMR, IR, and elemental analysis [40][41][42].…”

Section: General Methods For the Coupling Of 6-bromoquinolin-4-ol Wit...mentioning

confidence: 95%

Facile Synthesis of Functionalized Phenoxy Quinolines: Antibacterial Activities against ESBL Producing Escherichia coli and MRSA, Docking Studies, and Structural Features Determination through Computational Approach

et al. 2022

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The synthesis of new 6-Bromoquinolin-4-ol derivatives (3a–3h) by Chan–Lam coupling utilizing different types of solvents (protic, aprotic, and mixed solvents) and bases was studied in the present manuscript. Furthermore, their potential against ESBL producing Escherichia coli (ESBL E. coli) and methicillin-resistant Staphylococcusaureus (MRSA) were investigated. Commercially available 6-bromoquinolin-4-ol (3a) was reacted with different types of aryl boronic acids along with Cu(OAc)2 via Chan–Lam coupling methodology utilizing the protic and aprotic and mixed solvents. The molecules (3a–3h) exhibited very good yields with methanol, moderate yields with DMF, and low yields with ethanol solvents, while the mixed solvent CH3OH/H2O (8:1) gave more excellent results as compared to the other solvents. The in vitro antiseptic values against ESBL E. coli and MRSA were calculated at five different deliberations (10, 20, 30, 40, 50 mg/well) by agar well diffusion method. The molecule 3e depicted highest antibacterial activity while compounds 3b and 3d showed low antibacterial activity. Additionally, MIC and MBC standards were calculated against the established bacteria by broth dilution method. Furthermore, a molecular docking investigation of the derivatives (3a–3h) were performed. Compound (3e) was highly active and depicted the least binding energy of −5.4. Moreover, to investigate the essential structural and physical properties, the density functional theory (DFT) findings of the synthesized molecules were accomplished by using the basic set PBE0-D3BJ/def2-TZVP/SMD water level of the theory. The synthesized compounds showed an energy gap from 4.93 to 5.07 eV.

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“…Some organic compound exhibits a large NLO response, in many cases, the amplitude is several orders of magnitude larger than the wide range of known inorganic materials. [42,43] The phenyl rings in the compounds under investigation (5 a-5 i) serve as electron donors, while the amide ChemistrySelect group acts as an electron acceptor. The electron push-pull mechanism is effective when there are electron donor groups on the phenyl rings, and the hyperpolarizability (β) values are higher.…”

Section: Frontier Molecular Orbitals and Non-linear Opticsmentioning

confidence: 99%

“…Nonlinear optics (NLO) materials play an important role in the field of photonics, including data storage, sensor protector application and optical information processing etc. Some organic compound exhibits a large NLO response, in many cases, the amplitude is several orders of magnitude larger than the wide range of known inorganic materials [42,43] . The phenyl rings in the compounds under investigation ( 5 a–5 i ) serve as electron donors, while the amide group acts as an electron acceptor.…”

Section: Computational Studymentioning

confidence: 99%

Efficient Synthesis of 4‐Bromo‐N‐(1‐phenylethyl)benzamide, Arylation by Pd(0) Catalyst, Characterization and DFT Study

et al. 2022

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The (S)-4-bromo-N-(1-phenylethyl)benzamide (3) was synthesized in excellent yield (93 %) by the reaction of 4-bromobenzoic acid (1) and (S)-1-phenylethanamine (2) with the coupling reagent titanium tetrachloride (TiCl 4 ). Further, the Pd(0) catalyst was employed to form (S)-4-bromo-N-(1phenylethyl)benzamide analogues (5 a-i) by reacting various aryl boronic acids with 4-bromo-N-(1-phenylethyl)benzamide (3) in moderate to good yields (62-89 %). Furthermore, DFT studies were carried out to compute optimized geometries, frontier molecular orbitals, polarizability (α), hyperpolarizability (β), MESP, reactivity descriptors, and NMR spectra. The measured NMR values matched the experimental NMR values well. In this series (5 a-i), we predicted that the highest energy difference between the HOMO-LUMO of compound (5 a) has 4.98 eV, resulting in a more stable compound, and compound (5 g) has the lowest energy difference between the HOMO-LUMO 4.63 eV, resulting in the least stable compound. Compound (5h) has the highest hyperpolarizability (β) value, exhibits a better non-linear optical (NLO) behaviour compared as compare to other synthesized compounds in the series.

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N-Arylation of Protected and Unprotected 5-Bromo-2-aminobenzimidazole as Organic Material: Non-Linear Optical (NLO) Properties and Structural Feature Determination through Computational Approach

Cited by 9 publications

References 49 publications

Investigation of Novel Benzoxazole-Oxadiazole Derivatives as Effective Anti-Alzheimer’s Agents: In Vitro and In Silico Approaches

Investigation of Novel Benzoxazole-Oxadiazole Derivatives as Effective Anti-Alzheimer’s Agents: In Vitro and In Silico Approaches

Facile Synthesis of Functionalized Phenoxy Quinolines: Antibacterial Activities against ESBL Producing Escherichia coli and MRSA, Docking Studies, and Structural Features Determination through Computational Approach

Efficient Synthesis of 4‐Bromo‐N‐(1‐phenylethyl)benzamide, Arylation by Pd(0) Catalyst, Characterization and DFT Study

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