Medicinal Chemistry

Atta-ur-Rahman  
Honorary Life Fellow
Kings College
University of Cambridge
Cambridge
UK
Email: mc@benthamscience.org

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Synthesis, In Vitro Biological Screening and Molecular Docking Studies of Novel Camphor-Based Thiazoles

Author(s): Krzysztof Z.  Laczkowski, Konrad Misiura, Anna Biernasiuk, Anna Malm, Agata Siwek, Tomasz Plech, Emilia Ciok-Pater, Krzysztof Skowron and Eugenia Gospodarek

Affiliation: Department of Chemical Technology and Pharmaceuticals, Faculty of Pharmacy, Collegium Medicum, Nicolaus Copernicus University, Jurasza 2, 85-089 Bydgoszcz, Poland.

Keywords: Antifungal drugs, gram-positive bacteria, molecular modelling, thiazoles, terpenes, thiosemicarbazones.

Graphical Abstract:


Abstract:

Synthesis, characterization and investigation of antibacterial and antifungal activities of twelve camphor based 2,4-disubstituted 1,3-thiazoles is presented. Their structures were determined using NMR, IR, FAB MS and HRMS analyses. Among the derivatives, 3i and 5 were found to exhibit antifungal and antibacterial activities comparable to that of fluconazole and ciprofloxacin against yeast belonging to Candida spp., MIC 0.12-0.98 μg/ml and Gram-positive bacteria including both pathogenic S. aureus and opportunistic S. epidermidis, MIC 0.98-7.81 μg/ml, B. subtilis and B. cereus, MIC 3.91-31.25 μg/ml, and M. luteus, MIC 0.98 μg/ml species, respectively. Molecular docking studies of all compounds into the active sites of microbial enzymes indicated a possible targets SAP and NMT, thiazoles 3a-j, 4, 5 showed more favourable affinity than the native ligand.

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Article Details

VOLUME: 10
ISSUE: 6
Page: [600 - 608]
Pages: 9
DOI: 10.2174/15734064113096660054