Selective C-arylation of 2,5-dibromo-3-hexylthiophene via Suzuki cross coupling reaction and their pharmacological aspects

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...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2015-03, Vol.20 (3), p.5202-5214
Main Authors: Ikram, Hafiz Mansoor, Rasool, Nasir, Ahmad, Gulraiz, Chotana, Ghayoor Abbas, Musharraf, Syed Ghulam, Zubair, Muhammad, Rana, Usman Ali, Zia-Ul-Haq, Muhammad, Jaafar, Hawa Ze
Format: Article
Language:English
Subjects:
2,5-dibromo-3-hexylthiophene
Acids
anti-thrombolytic assay
biofilm inhibition
Biofilms
Biofilms - drug effects
Blood Cells - drug effects
Carbon
Carbon - chemistry
Catalysis
Chemistry
Electronic mail systems
Fibrinolytic Agents - chemical synthesis
Fibrinolytic Agents - chemistry
Fibrinolytic Agents - pharmacology
hemolysis assay
Hemolytic Agents - chemical synthesis
Hemolytic Agents - chemistry
Hemolytic Agents - pharmacology
Humans
Molecular Structure
Palladium
Palladium - chemistry
Solvents
Thiophenes - chemical synthesis
Thiophenes - chemistry
Thiophenes - pharmacology
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules20035202