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

Molecules

Shaukat Ali⁴  Nasir Rasool⁴  Aman Ullah¹  Faiz-ul-Hassan Nasim³  Asma Yaqoob³  Muhammad Zubair⁴  Umer Rashid² 

[1] Department of Agricultural, Food and Nutritional Science, University of Alberta, Edmonton, AB T6G2P5, Canada;Institute of Advanced Technology, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia; E-Mail:;Department of Chemistry, Islamia University of Bahawalpur, Bahawalpur 63000, Pakistan; E-Mails:;Department of Chemistry, Government College University, Faisalabad 38000, Pakistan;E-Mails:

关键词: thiophene;    Pd (0) catalyzed Suzuki coupling;    antibacterial;    heamolytic;    antiurease;    antioxidant;    activities;   

DOI  :  10.3390/molecules181214711

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2013 by the authors; licensee MDPI, Basel, Switzerland.