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Preparation, characterization, crystal structure and bioactivity determination of ferrocenyl–thiazoleacylhydrazones
Author(s) -
Zhang Jie
Publication year - 2008
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1338
Subject(s) - chemistry , hydrogen bond , thiazole , crystal structure , ring (chemistry) , crystallography , molecule , hydrazide , hydrate , semicarbazone , carbohydrazide , carboxylate , stereochemistry , medicinal chemistry , organic chemistry
Abstract 4‐Methylthiazole‐5‐carbohydrazide was synthesized by heating 85% hydrazine hydrate and methyl 4‐methylthiazole‐5‐carboxylate in ethanol. Ferrocenyl–thiazoleacyl hydrazones were synthesized by condensing hydrazide with formylferrocene or acetylferrocene in the presence of a few drops of ice acetic acid. The structures of the synthetical compounds were confirmed using elemental analysis, IR and 1 H‐NMR. In addition, the structure of ( E )‐ N ′‐ferrocenylidene‐4‐methylthiazole‐5‐carbohydrazide was confirmed by single crystal X‐ray diffraction analyse. The compound crystallized in the tetragonal space group, P4(2)/ n with cell dimensions a = 21.041(3) Å, b = 21.041(3) Å, c = 7.1212(14) Å, β = 90.00° , V = 3152.6(9) Å 3 , D calc = 1.488 g cm −3 , Z = 8, µ = 1.093 mm −1 and F (000) = 1456, and its structure was refined to R 1 = 0.0423 and wR 2 = 0.0871 for 2906 observed reflections ( I > 2σ( I )). It showed the substituted cyclopentadiene ring to be approximately coplanar with the thiazole ring but a small twist between its two ring systems. In the crystal structure, molecules were linked by intermolecular hydrogen bonds NH···O bonds into closed eight‐membered loops and centrosymmetric dimers. The ferrocenyl–thiazoleacylhydrazone compounds were tested for their anti‐Human Immunodeficiency Virus Type 1 Reverse Transcriptase, anti‐Human Lung Cancer A549 cells and antibacterial bioactivities. It was found that they showed significant activity against Staphylococcus aureus, Esherichia coli and Pseudomonas aeruginosa with minimum inhibitory concentration values in the range of 25.0–100.0 µg/ml. Copyright © 2007 John Wiley & Sons, Ltd.