Abstract
One of the best ways to design new biocidal agents is synthesizing hybrid molecules by combining two or more bioactive moieties in a single molecular scaffold. So, new series of pyrroles bearing a thiazole moiety were synthesized using 1-methyl-1H-pyrrole-2-carbaldehyde thiosemicarbazones 1a-c. Cyclization of thiosemicarbazone derivatives 1a-c with ethyl chloroacetate, ethyl 2-chloropropanoate, chloroacetone and phenacyl bromide afforded the corresponding thiazolidin-4-ones 2a-c, 5-methylthiazolidin-4-ones 3a-c, 4-methyl-2,3-dihydrothiazoles 4a-c, and 4-phenyl-2,3-dihydrothiazoles 5a-c, respectively. The antimicrobial activity of the new thiazole derivatives was evaluated.
Highlights
One of the most serious future challenges to health care professionals is the emergence of multi-drug resistance pathogenic bacteria that rapidly develop resistance to currently used antibiotics
The starting 1-methyl-1H-pyrrole-2-carbaldehyde thiosemicarbazones 1a–c were synthesized through the condensation reaction between 1-methyl-1H-pyrrole-2-carbaldehyde and thiosemicarbazide derivatives in ethanol under reflux (Scheme 1). 1H NMR spectrum of 1b indicated doublet and singlet signals at δ 3.01 and 3.80 ppm for NH-CH3 and NCH3 protons, two signals at δ 7.88 and 11.14 ppm assignable for two NH protons, in addition to three multiplet signals at δ 6.08, 6.51 and 6.94 ppm for pyrrole protons with singlet signal at δ 8.04 ppm corresponding to CH=N proton
Thiosemicarbazones 1a–c were subjected to cycloalkylation with different halogenated compounds in the hope of obtaining biologically activity thiazoles
Summary
One of the most serious future challenges to health care professionals is the emergence of multi-drug resistance pathogenic bacteria that rapidly develop resistance to currently used antibiotics. Thiazole moiety frequently appears in the structure of many natural products as well as biologically active compounds. The starting 1-methyl-1H-pyrrole-2-carbaldehyde thiosemicarbazones 1a–c were synthesized through the condensation reaction between 1-methyl-1H-pyrrole-2-carbaldehyde and thiosemicarbazide derivatives in ethanol under reflux (Scheme 1).
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