Abstract
The present study reports the synthesis of various new derivatives based on 5-aryl-2-bromo-3-hexylthiophene with moderate-to-good yields via a palladium-catalyzed Suzuki cross-coupling reaction. This coupling method involved the reaction of 2,5-dibromo-3-hexylthiophene with several arylboronic acids in order to synthesize corresponding thiophene derivatives under controlled and optimal reaction conditions. The different substituents (CH3, OCH3, Cl, F etc.) present on arylboronic acids are found to have significant electronic effects on the overall properties of new products. The synthesized thiophene molecules were studied for their haemolytic, biofilm inhibition and anti-thrombolytic activities, and almost all products showed potentially good properties. The compound 2-bromo-5-(3-chloro-4-fluorophenyl)-3-hexylthiophenein particular exhibited the highest values for haemolytic and bio-film inhibition activities among all newly synthesized derivatives. In addition, the compound 2-bromo-3-hexyl-5-(4-iodophenyl)thiophene also showed high anti-thrombolytic activity, suggesting the potential medicinal applications of these newly synthesized compounds.
Highlights
In the area of synthetic organic chemistry, Suzuki cross-coupling reactions have emerged as an efficient and remarkably effective method for carbon-carbon bond formation [1]
The present study reports the Suzuki-Miyaura cross-coupling reaction for the synthesis of a series of 5-aryl-2-bromo-3-hexylthiophene (2a–i)
TLC was used to examine the progress of reaction and purity of all new products, and their structure elucidation was confirmed by spectroscopic techniques
Summary
In the area of synthetic organic chemistry, Suzuki cross-coupling reactions have emerged as an efficient and remarkably effective method for carbon-carbon bond formation [1]. Substituted thiophene compounds are present in various natural and biologically active compounds [4]. Thiophene compounds have great applications in electrochromic devices [6], non-linear optics [7], azo dyes [4], energy storage devices [8], conductivity-based sensors, biodiagnostics, optoelectronics systems and superconductors [4]. In order to investigate an easy and facile scheme to make thiophene-based derivates, the aim of the present study was to synthesize different derivatives of
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