Molecules 2013, 18(12), 14711-14725; doi:10.3390/molecules181214711
Article

Design and Synthesis of Arylthiophene-2-Carbaldehydes via Suzuki-Miyaura Reactions and Their Biological Evaluation

1 Department of Chemistry, Government College University, Faisalabad 38000, Pakistan 2 Department of Agricultural, Food and Nutritional Science, University of Alberta, Edmonton, AB T6G2P5, Canada 3 Department of Chemistry, Islamia University of Bahawalpur, Bahawalpur 63000, Pakistan 4 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
(This article belongs to the Section Medicinal Chemistry)
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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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MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.

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