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Open AccessArticle

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.
Molecules 2013, 18(12), 14711-14725; https://doi.org/10.3390/molecules181214711
Received: 30 September 2013 / Revised: 13 November 2013 / Accepted: 14 November 2013 / Published: 27 November 2013
(This article belongs to the Section Medicinal Chemistry)
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. View Full-Text
Keywords: thiophene; Pd (0) catalyzed Suzuki coupling; antibacterial; heamolytic; antiurease; antioxidant; activities 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.

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