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
Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan.
Department of Chemistry, SBA School of Science & Engineering, Lahore University of Management Sciences, Sector U, DHA, Lahore Cantt. 54792, Pakistan.
Molecules. 2015 Mar 23;20(3):5202-14. doi: 10.3390/molecules20035202.
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.
本研究报道了通过钯催化的铃木交叉偶联反应，以中等到良好的产率合成了各种基于5-芳基-2-溴-3-己基噻吩的新衍生物。这种偶联方法涉及2,5-二溴-3-己基噻吩与几种芳基硼酸的反应，以便在可控和最佳反应条件下合成相应的噻吩衍生物。发现芳基硼酸上存在的不同取代基（CH3、OCH3、Cl、F等）对新产品的整体性能有显著的电子效应。对合成的噻吩分子进行了溶血、生物膜抑制和抗血栓溶解活性研究，几乎所有产品都显示出潜在的良好性能。特别是化合物2-溴-5-(3-氯-4-氟苯基)-3-己基噻吩在所有新合成的衍生物中表现出最高的溶血和生物膜抑制活性值。此外，化合物2-溴-3-己基-5-(4-碘苯基)噻吩也显示出高抗血栓溶解活性，表明这些新合成化合物具有潜在的药用价值。
