Efficient double Suzuki cross-coupling reactions of 2,5-dibromo-3-hexylthiophene

Anti-Tumor, haemolytic, anti-thrombolytic and biofilm inhibition studies

Hafiz Mansoor Ikram, Nasir Rasool, Muhammad Zubair, Khalid Mohammed Khan, Ghayoor Abbas Chotana, Muhammad Nadeem Akhtar, Nadiah Abu, Noorjahan Banu Alitheen, Abdallah Mohamed Elgorban, Usman Ali Rana

Research output: Contribution to journalArticle

6 Citations (Scopus)

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.

Original languageEnglish
Article number977
JournalMolecules
Volume21
Issue number8
DOIs
Publication statusPublished - 1 Aug 2016
Externally publishedYes

Fingerprint

biofilms
cross coupling
Cross Reactions
Biofilms
Inhibitory Concentration 50
Tumors
tumors
Thiophenes
MCF-7 Cells
Neoplasms
Derivatives
thiophenes
cells
In Vitro Techniques

Keywords

  • 2,5-biaryl-3-hexylthiophene derivatives
  • Anti-thrombolytic
  • Anti-tumor
  • Biofilm inhibition
  • Haemolysis
  • Suzuki cross-coupling reaction

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Efficient double Suzuki cross-coupling reactions of 2,5-dibromo-3-hexylthiophene : Anti-Tumor, haemolytic, anti-thrombolytic and biofilm inhibition studies. / Ikram, Hafiz Mansoor; Rasool, Nasir; Zubair, Muhammad; Khan, Khalid Mohammed; Chotana, Ghayoor Abbas; Akhtar, Muhammad Nadeem; Abu, Nadiah; Alitheen, Noorjahan Banu; Elgorban, Abdallah Mohamed; Rana, Usman Ali.

In: Molecules, Vol. 21, No. 8, 977, 01.08.2016.

Research output: Contribution to journalArticle

Ikram, Hafiz Mansoor ; Rasool, Nasir ; Zubair, Muhammad ; Khan, Khalid Mohammed ; Chotana, Ghayoor Abbas ; Akhtar, Muhammad Nadeem ; Abu, Nadiah ; Alitheen, Noorjahan Banu ; Elgorban, Abdallah Mohamed ; Rana, Usman Ali. / Efficient double Suzuki cross-coupling reactions of 2,5-dibromo-3-hexylthiophene : Anti-Tumor, haemolytic, anti-thrombolytic and biofilm inhibition studies. In: Molecules. 2016 ; Vol. 21, No. 8.
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