由醋酸钯催化剂生成的高效N-杂环卡宾钯（II）用于芳基硼酸与2-溴吡啶在惰性条件下的羰基化铃木偶联反应，生成不对称芳基吡啶酮：合成、表征及细胞毒性活性

Efficient N-heterocyclic carbene palladium(ii) generated from Pd(OAc) catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities.

作者信息

Touj Nedra, Al-Ayed Abdullah S, Sauthier Mathieu, Mansour Lamjed, Harrath Abdel Halim, Al-Tamimi Jamil, Özdemir Ismail, Yaşar Sedat, Hamdi Naceur

机构信息

Research Laboratory of Environmental Sciences and Technologies (LR16ES09), Higher Institute of Environmental Sciences and Technology, University of Carthage Hammam-Lif Tunisia

Chemistry Department, College of Science and Arts, Qassim University Al-Rass Kingdom of Saudi Arabia.

出版信息

RSC Adv. 2018 Dec 5;8(70):40000-40015. doi: 10.1039/c8ra08897g. eCollection 2018 Nov 28.

,-Substituted benzimidazole salts were successfully synthesized and characterized by H-NMR, C {H} NMR and IR techniques, which support the proposed structures. Catalysts generated were efficiently used for the carbonylative cross-coupling reaction of 2 bromopyridine with various boronic acids. The reaction was carried out in THF at 110 °C in the presence of KCO under inert conditions and yields unsymmetrical arylpyridine ketones. All ,-substituted benzimidazole salts 2a-i and 4a-i studied in this work were screened for their cytotoxic activities against human cancer cell lines such us MDA-MB-231, MCF-7 and T47D. The ,-substituted benzimidazoles 2e and 2f exhibited the most cytotoxic effect with promising cytotoxic activity with IC values of 4.45 μg mL against MDA-MB-231 and 4.85 μg mL against MCF7 respectively.

成功合成了α-取代苯并咪唑盐，并通过氢核磁共振（¹H-NMR）、碳-氢核磁共振（¹³C{¹H}NMR）和红外光谱（IR）技术对其进行了表征，这些技术支持所提出的结构。所生成的催化剂被有效地用于2-溴吡啶与各种硼酸的羰基化交叉偶联反应。该反应在四氢呋喃（THF）中，于110℃、碳酸钾（K₂CO₃）存在下，在惰性条件下进行，生成不对称芳基吡啶酮。对本研究中所研究的所有α-取代苯并咪唑盐2a-i和4a-i针对人癌细胞系（如MDA-MB-231、MCF-7和T47D）进行了细胞毒性活性筛选。α-取代苯并咪唑2e和2f表现出最强的细胞毒性作用，对MDA-MB-231的半数抑制浓度（IC）值为4.45μg/mL，对MCF-7的IC值为4.85μg/mL，具有良好的细胞毒性活性。