Design and synthesis of arylthiophene-2-carbaldehydes via suzuki-miyaura reactions and their biological evaluation

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-Formylthiophene- 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-fluorophenyl) thiophene-2-carbaldehyde (2i) exhibited a superior haemolytic action and an outstanding urease inhibition, showing an IC50 value of 27.1 μg/mL. © 2013 by the authors; licensee MDPI, Basel, Switzerland.