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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
, 1,* , 2,* , 3
, 3
, 1
, 4
 and 1
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 / Revised: 13 November 2013 / Accepted: 14 November 2013 / Published: 27 November 2013
(This article belongs to the Section Medicinal Chemistry)
Download PDF [351 KB, 18 June 2014; original version 18 June 2014]

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 thiophene; Pd (0) catalyzed Suzuki coupling; antibacterial; heamolytic; antiurease; antioxidant; activities
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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