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Design and Synthesis of Arylthiophene-2-Carbaldehydes via Suzuki-Miyaura Reactions and Their Biological Evaluation
Department of Chemistry, Government College University, Faisalabad 38000, Pakistan
Department of Agricultural, Food and Nutritional Science, University of Alberta, Edmonton, AB T6G2P5, Canada
Department of Chemistry, Islamia University of Bahawalpur, Bahawalpur 63000, Pakistan
Institute of Advanced Technology, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia
* Authors to whom correspondence should be addressed.
Received: 30 September 2013; in revised form: 13 November 2013 / Accepted: 14 November 2013 / Published: 27 November 2013
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.
Keywords: thiophene; Pd (0) catalyzed Suzuki coupling; antibacterial; heamolytic; antiurease; antioxidant; activities
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Ali, S.; Rasool, N.; Ullah, A.; Nasim, F.-U.-H.; Yaqoob, A.; Zubair, M.; Rashid, U.; Riaz, M. Design and Synthesis of Arylthiophene-2-Carbaldehydes via Suzuki-Miyaura Reactions and Their Biological Evaluation. Molecules 2013, 18, 14711-14725.
Ali S, Rasool N, Ullah A, Nasim F-U-H, Yaqoob A, Zubair M, Rashid U, Riaz M. Design and Synthesis of Arylthiophene-2-Carbaldehydes via Suzuki-Miyaura Reactions and Their Biological Evaluation. Molecules. 2013; 18(12):14711-14725.
Ali, Shaukat; Rasool, Nasir; Ullah, Aman; Nasim, Faiz-ul-Hassan; Yaqoob, Asma; Zubair, Muhammad; Rashid, Umer; Riaz, Muhammad. 2013. "Design and Synthesis of Arylthiophene-2-Carbaldehydes via Suzuki-Miyaura Reactions and Their Biological Evaluation." Molecules 18, no. 12: 14711-14725.