Abstract
A series of various novel 4-arylthiophene-2-carbaldehyde compounds were synthesized in moderate to excellent yields via Suzuki-Miyaura cross-coupling with different arylboronic pinacol esters/acids. The synthesized products were screened for their antibacterial, haemolytic, antiurease, and nitric oxide (NO) scavenging capabilities and interestingly, almost all products turned out to have good activities. 3-(5-Formyl-thiophene-3-yl)-5-(trifloromethyl)benzonitrile (2d) revealed excellent antibacterial activity, showing an IC50 value of 29.7 µg/mL against Pseudomonas aeruginosa, compared to the standard drug streptomycin with an IC50 value 35.2 µg/mL and was also found to be the best NO scavenger, with an IC50 value of 45.6 µg/mL. Moreover, 4-(3-chloro-4-fluoro-phenyl)thiophene-2-carbaldehyde (2i) exhibited a superior haemolytic action and an outstanding urease inhibition, showing an IC50 value of 27.1 µg/mL.
Highlights
In the recent years, Suzuki-Miyaura reactions have become one of the most powerful tools to build carbon-carbon bonds between weakly basic heterocyclic compounds and various arylboronic acids/esters [1,2]
Suzuki-Miyaura reactions were successfully exploited to synthesize a series of 4-arylthiophene-2carbaldehyde 2a–j
The reaction progress and purity of all synthesized compounds were monitored by TLC and products were characterized and their structure confirmed by NMR, elemental analysis, mass spectroscopy and melting points
Summary
Suzuki-Miyaura reactions have become one of the most powerful tools to build carbon-carbon bonds between weakly basic heterocyclic compounds and various arylboronic acids/esters [1,2]. These reactions have been widely exploited in the synthesis of natural products [3,4], and the design of the pharmaceuticals [5]. Suzuki cross-coupling reactions have acquired great importance in the synthesis of substituted aromatic compounds because these reactions are among the major and essential routes for any synthetic organic chemist They are a well-established family of chemical reactions very useful for the synthesis of aryl-substituted thiophenes. To the best of our knowledge, the antibacterial, antiurease, heamolytic, and antioxidant activities of these compounds have not been reported in the literature so far
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