Synthesis, Characterization, Crystal Structure and Biological Study of Carboxamides Obtained from 2-Aminothiazole Deriva
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ORIGINAL PAPER
Synthesis, Characterization, Crystal Structure and Biological Study of Carboxamides Obtained from 2‑Aminothiazole Derivatives Sachin S. Wazalwar1 · Anita R. Banpurkar1 · Franc Perdih2 Received: 24 January 2019 / Accepted: 18 July 2019 © Springer Science+Business Media, LLC, part of Springer Nature 2019
Abstract Two series of novel thiazolylcarboxamide derivatives were synthesized by the reaction of ethyl 2-amino-4-methylthiazole5-carboxylate or 1-(2-amino-4-methylthiazol-5-yl)ethan-1-one with four substituted carbonyl chlorides at 0 °C in excellent yield. All products were characterized by FTIR, 1H NMR spectroscopy and mass spectrometry. Crystal structures of four compounds were studied by X-ray analysis. All the synthesized compounds were screened against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Streptococcus pyogenes for antibacterial activity and against Candida albicans, Aspergillusniger and Aspergillus clavatus for antifungal activity. Graphic Abstract Present study describes the biological activity and crystal structure study of carboxamides obtained from 2-aminothaizol derivatives. Owing to the insolubility of these amides in single volatile solvent, crystals were grown in a mixture of solvents.
Keywords Thiazolylcarboxamides · Aminothiazole · Carbonyl chloride · Amidation · Antibacterial and antifungal activity · Single crystal X-ray study
Introduction The amides of 2-aminothiazoles are pharmaceutically very important from drug discovery point of view and are found in many important disease-intervening substances. For example, meloxicam is a selective cyclooxygenase-2 * Sachin S. Wazalwar [email protected] 1
Department of Applied Chemistry, Rajiv Gandhi College of Engineering, Research & Technology, Chandrapur, MS 442403, India
Faculty of Chemistry and Chemical Technology, University of Ljubljana, 1000 Ljubljana, Slovenia
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inhibitor from the group of non-steroidal anti-inflammatory drugs (NSAID) [1–4] and thiazotropsin A is binding to the minor groove of duplex DNA [5, 6]. Sulfur and nitrogen containing 1,3-thiazoles are very important class of heterocyclic compounds [7, 8]. They are well known for their biological activities [9–12]. Structures are shown in Scheme 1. Ethyl 2-amino-4-methylthiazole-5-carboxylate and its 2-substituted derivatives are building blocks in organic synthesis in making biologically and medicinally useful moieties [13, 14]. Also 1-(2-amino-4-methylthiazol-5-yl)ethan-1one is used as an intermediate for synthesis of 4-methyl5-formylthiazole, a key intermediate for cefditoren pivoxil [15–17]. Derivatives of ethyl 2-amino-4-methylthiazole5-carboxylate have been reported to have shown significant
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Scheme 1 Structures of drugs showing presence of 2-aminothiazole amide linkage
antileukemic activity on various human cells and exhibited a promising antineoplastic potential [13]. Amidation of 2-aminothiazol is of great interest to the researchers due to the weak nucleophilicity of the amino group. 2-benz
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