Volume 7, Issue 38 e202203386
Research Article

Schiff Bases Derived from 2-Amino-6-methylbenzothiazole, 2-Amino-5-chloropyridine and 4-Chlorobenzaldehyde: Structure, Computational Studies and Evaluation of Biological Activity

Muhammad Hanif

Muhammad Hanif

Department of Chemistry, University of Malakand, 18800 Chakdara, Lower Dir Khyber Pakhtunkhwa, Pakistan

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Dr. Naveen Kosar

Dr. Naveen Kosar

Department of Chemistry, University of Management and Technology (UMT), C11, Johar Town, Lahore, Pakistan

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Prof. Dr. Tariq Mahmood

Prof. Dr. Tariq Mahmood

Department of Chemistry, College of Science, University of Bahrain, Main, campus, 32038 Sakhir, Kingdom of Bahrain.

Department of Chemistry, COMSATS University Islamabad, Abbottabad Campus, Abbottabad, 22060 Pakistan

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Dr. Mian Muhammad

Dr. Mian Muhammad

Department of Chemistry, University of Malakand, 18800 Chakdara, Lower Dir Khyber Pakhtunkhwa, Pakistan

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Dr. Farhat Ullah

Dr. Farhat Ullah

Department of Pharmacy, University of Malakand, 18800 Chakdara, Lower Dir Khyber Pakhtunkhwa, Pakistan

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Prof. Dr. Muhammad Nawaz Tahir

Prof. Dr. Muhammad Nawaz Tahir

Department of Physics, University of Sargodha, Sargodha, ounjab, Pakistan.

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Dr. Alany Ingrid Ribeiro

Dr. Alany Ingrid Ribeiro

Laboratorio de Produtos Naturais Departmento de Quimica, universidade Federal de sao, Carlos, UFSCar, Brazil

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Prof. Dr. Ezzat Khan

Corresponding Author

Prof. Dr. Ezzat Khan

Department of Chemistry, University of Malakand, 18800 Chakdara, Lower Dir Khyber Pakhtunkhwa, Pakistan

Department of Chemistry, College of Science, University of Bahrain, Main, campus, 32038 Sakhir, Kingdom of Bahrain.

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First published: 10 October 2022
Citations: 3

Graphical Abstract

Molecular structure of (E)-N-(4-chlorobenzylidene)-6-methylbenzo[d]thiazol-2-amine, (E)-N-(4-chlorobenzylidene)-5-chloropyridin-2-amine was determined in solution and solid states. Both the Schiff bases 1 and 2 crystallize as monoclinic system with identical space group P21/c. They were treated with Cu and Ag salts to obtain corresponding coordination complexes. Compounds were tested for their fluorescence, antibacterial, antioxidant and enzyme inhibition properties.

Abstract

Molecular structure of (E)-N-(4-chlorobenzylidene)-6-methylbenzo[d]thiazol-2-amine, (E)-N-(4-chlorobenzylidene)-5-chloropyridin-2-amine was determined in solution and solid states by various techniques such as UV/Vis, FT-IR, NMR spectroscopy, HRMS and X-ray diffraction. Both the Schiff base compounds crystallize as monoclinic system with identical space group P21/c. Supramolecular interactions observed in X-ray structure are validated via density functional theory (DFT) calculations. Further, the reactivities of both compounds (ligands) are analysed with the help of frontier molecular orbitals (FMOs) analysis. They were treated with Cu and Ag salts to obtain corresponding coordination complexes. Both the ligands contain three possible coordination sites namely, endocyclic nitrogen, sulfur and the imine nitrogen. Among these nucleophilic centres, imine nitrogen is more basic and readily coordinates with Cu and Ag metals. The compounds were tested for their fluorescence properties and all the compounds were found to be fluorescence active. The Schiff base ligands and their complexes were also tested for preliminary biological activities such as antibacterial, antioxidant and enzyme inhibition. Molecular docking studies were implemented to compare and validate the enzyme inhibition potentials of ligands. Moderate activities were observed for all compounds. The activities of ligands enhanced by complexation with Cu(II) and Ag(I) metals ions.

Conflict of interest

There is no conflict of interest to be declared.

Data Availability Statement

The data that support the findings of this study are available in the supplementary material of this article.