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Efficient Double Suzuki Cross-Coupling Reactions of 2,5-Dibromo-3-hexylthiophene: Anti-Tumor, Haemolytic, Anti-Thrombolytic and Biofilm Inhibition Studies

Ikram HM 1 , Rasool N 2 , Zubair M 3 , Khan KM 4 , Abbas Chotana G 5 , Akhtar MN 6 Show all authors , Abu N 7 , Alitheen NB 8 , Elgorban AM 9 , Rana UA 10

Affiliations 

  • 1 Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan. chemistue@gmail.com
  • 2 Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan. nasirrasool@gcuf.edu.pk
  • 3 Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan. nr_308@hotmail.com
  • 4 International Center for Chemical and Biological Sciences, HEJ Research Institute of Chemistry, University of Karachi, Karachi 75270, Pakistan. Khalid.khan@iccs.edu
  • 5 Department of Chemistry, SBA School of Science & Engineering, Lahore University of Management Sciences, Sector U, DHA, Lahore Cantt. 54792, Pakistan. ghayoor.abbas@lums.edu.pk
  • 6 Faculty of Industrial Sciences & Technology, University Malaysia Pahang, Lebuhraya Tun Razak 26300, Kuantan Pahang, Malaysia. nadeemupm@gmail.com
  • 7 Faculty of Biotechnology and Biomolecular Sciences, University Putra Malaysia, Serdang, Selangor Darul Ehsan 43400, Malaysia. nadyaboo@gmail.com
  • 8 Faculty of Biotechnology and Biomolecular Sciences, University Putra Malaysia, Serdang, Selangor Darul Ehsan 43400, Malaysia. noorjahan@upm.edu.my
  • 9 Botany and Microbiology Department, College of Science, King Saud University, Riyadh 11451, Saudi Arabia. elgorban@yahoo.com
  • 10 Sustainable Energy Technologies (SET) Center, College of Engineering, King Saud University, Riyadh 11421, Saudi Arabia. urana@ksu.edu.sa
Molecules, 2016 Jul 27;21(8).
PMID: 27472312 DOI: 10.3390/molecules21080977

Abstract

The present study describes several novel 2,5-biaryl-3-hexylthiophene derivatives (3a-i) synthesized via a Pd(0)-catalyzed Suzuki cross-coupling reaction in moderate to good yields. The novel compounds were also analyzed for their anti-thrombolytic, haemolytic, and biofilm inhibition activities. In addition, the anti-tumor activity was also evaluated in vitro for newly-synthesized compounds, where 3-hexyl-2,5-bis(4-(methylthio)phenyl)thiophene exhibited the best anti-tumor activity against 4T1 cells with IC50 value of 16 μM. Moreover, 2,5-bis(4-methylphenyl)-3-hexylthiophene showed the highest activity against MCF-7 cells with an IC50 value of 26.2 μM. On the other hand, the compound 2,5-bis(4-chloropheny)-3-hexylthiophene exhibited excellent biofilm inhibition activity. Furthermore, the compound 2,5-bis(3-chloro-4-fluorophenyl)-3-hexylthiophene also exhibited better anti-thrombolytic and hemolytic activity results as compared to the other newly-synthesized compounds.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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