Next Article in Journal
iso-Petromyroxols: Novel Dihydroxylated Tetrahydrofuran Enantiomers from Sea Lamprey (Petromyzon marinus)
Previous Article in Journal
Syntheses of Nickel (II) Complexes from Novel Semicarbazone Ligands with Chloroformylarylhydrazine, Benzimidazole and Salicylaldehyde Moieties
Article Menu

Export Article

Open AccessArticle
Molecules 2015, 20(3), 5202-5214; doi:10.3390/molecules20035202

Selective C-Arylation of 2,5-Dibromo-3-hexylthiophene via Suzuki Cross Coupling Reaction and Their Pharmacological Aspects

1
Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan
2
Department of Chemistry, SBA School of Science & Engineering, Lahore University of Management Sciences, Sector U, DHA, Lahore Cantt. 54792, Pakistan
3
International Center for Chemical and Biological Sciences, HEJ Research Institute of Chemistry, University of Karachi, Karachi 75270, Pakistan
4
Sustainable Energy Technologies (SET) center, College of Engineering, PO-Box 800, King Saud University, Riyadh 11421, Saudi Arabia
5
The Patent Office, Karachi 74200, Pakistan
6
Department of Crop Science, Faculty of Agriculture, University Putra Malaysia, Serdang 43400, Selangor, Malaysia
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 4 December 2014 / Revised: 6 February 2015 / Accepted: 16 February 2015 / Published: 23 March 2015
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [865 KB, uploaded 25 March 2015]   |  

Abstract

The present study reports the synthesis of various new derivatives based on 5-aryl-2-bromo-3-hexylthiophene with moderate-to-good yields via a palladium-catalyzed Suzuki cross-coupling reaction. This coupling method involved the reaction of 2,5-dibromo-3-hexylthiophene with several arylboronic acids in order to synthesize corresponding thiophene derivatives under controlled and optimal reaction conditions. The different substituents (CH3, OCH3, Cl, F etc.) present on arylboronic acids are found to have significant electronic effects on the overall properties of new products. The synthesized thiophene molecules were studied for their haemolytic, biofilm inhibition and anti-thrombolytic activities, and almost all products showed potentially good properties. The compound 2-bromo-5-(3-chloro-4-fluorophenyl)-3-hexylthiophenein particular exhibited the highest values for haemolytic and bio-film inhibition activities among all newly synthesized derivatives. In addition, the compound 2-bromo-3-hexyl-5-(4-iodophenyl)thiophene also showed high anti-thrombolytic activity, suggesting the potential medicinal applications of these newly synthesized compounds. View Full-Text
Keywords: Palladium(0); 2,5-dibromo-3-hexylthiophene; biofilm inhibition; hemolysis assay; anti-thrombolytic assay Palladium(0); 2,5-dibromo-3-hexylthiophene; biofilm inhibition; hemolysis assay; anti-thrombolytic assay
Figures

Figure 1

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. (CC BY 4.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Ikram, H.M.; Rasool, N.; Ahmad, G.; Chotana, G.A.; Musharraf, S.G.; Zubair, M.; Rana, U.A.; Zia-Ul-Haq, M.; Jaafar, H.Z. Selective C-Arylation of 2,5-Dibromo-3-hexylthiophene via Suzuki Cross Coupling Reaction and Their Pharmacological Aspects. Molecules 2015, 20, 5202-5214.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top