Synthesis, characterization, biological determination and catalytic evaluation of ruthenium(ii) complexes bearing benzimidazole-based NHC ligands in transfer hydrogenation catalysis

被引:23
作者
Slimani, Ichraf [1 ]
Chakchouk-Mtibaa, A. [2 ]
Mansour, L. [3 ]
Mellouli, L. [2 ]
Ozdemir, I [4 ]
Gurbuzd, Nevin [4 ]
Hamdi, Naceur [1 ]
机构
[1] Univ Carthage, Higher Inst Environm Sci & Technol, Res Lab Environm Sci & Technol LR16ES09, Hammam Lif, Tunisia
[2] Ctr Biotechnol Sfax, Lab Microorganisms & Biomol, Rd Sidi Mansour,Km 6 BP 1117, Sfax 3018, Tunisia
[3] King Saud Univ, Coll Sci, Zool Dept, POB 2455, Riyadh 11451, Saudi Arabia
[4] Inonu Univ, Fac Sci & Art, Dept Chem, Malatya, Turkey
关键词
HETEROCYCLIC CARBENE COMPLEXES; ASYMMETRIC TRANSFER HYDROGENATION; METAL-COMPLEXES; STRUCTURAL-CHARACTERIZATION; OLEFIN METATHESIS; ARYL CHLORIDES; SYSTEM; KETONES; ACTIVATION; CISPLATIN;
D O I
10.1039/d0nj00311e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new series of ruthenium(ii) N-heterocyclic carbene complexes has been synthesized via transmetalation. These complexes are easily handled in very good yields via synthesis of silver-NHC complexes and subsequent reaction with [RuCl2(p-cymene)](2) in dichloromethane (DCM) under argon atmosphere. The new ruthenium(ii)-NHC complexes were applied to transfer hydrogenation of ketone derivatives using 2-propanol as a hydrogen source and KOH as a co-catalyst. The results show that the corresponding alcohols could be obtained in good yield with high catalyst activity (up to 76%) under mild conditions. All new compounds were characterized by spectroscopic and analytical methods. The antibacterial activities of the corresponding ruthenium(ii)-NHC complexes 4a-i were tested against positive and negative bacteria using the agar dilution procedure and their IC50 values have been determined. A cytotoxicity study of the ruthenium(ii)-NHC complexes 4 was performed against the two human cancer cell lines MDA-MB-231 and MCF-7. In addition, the scavenging activity of the synthesized complexes for the DPPH radical was also determined.
引用
收藏
页码:5309 / 5323
页数:15
相关论文
共 93 条
[1]   Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis [J].
Altenhoff, G ;
Goddard, R ;
Lehmann, CW ;
Glorius, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15195-15201
[2]   Organometallic ruthenium-based antitumor compounds with novel modes of action [J].
Ang, Wee Han ;
Casini, Angela ;
Sava, Gianni ;
Dyson, Paul J. .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (05) :989-998
[3]   A STABLE CRYSTALLINE CARBENE [J].
ARDUENGO, AJ ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363
[4]   Transition metal hydrides as active intermediates in hydrogen transfer reactions [J].
Bäckvall, JE .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 652 (1-2) :105-111
[5]   Exploration of the medical periodic table: towards new targets [J].
Barry, Nicolas P. E. ;
Sadler, Peter J. .
CHEMICAL COMMUNICATIONS, 2013, 49 (45) :5106-5131
[6]  
BAUDE EA, 1954, J CHEM SOC, P3544
[7]  
Beligny S., 2004, N HETEROCYCLIC CARBE
[8]   Another silver complex of 1,3-dibenzylimidazol-2-ylidene: Solution and solid-state structures [J].
Berding, Joris ;
Kooijman, Huub ;
Spek, Anthony L. ;
Bouwman, Elisabeth .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (14) :2217-2221
[9]   Approaching tumour therapy beyond platinum drugs Status of the art and perspectives of ruthenium drug candidates [J].
Bergamo, A. ;
Gaiddon, C. ;
Schellens, J. H. M. ;
Beijnen, J. H. ;
Sava, G. .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2012, 106 (01) :90-99
[10]   An evaluation of the Noyori system "in reverse":: Thermodynamic and kinetic parameters of secondary alcohol transfer dehydrogenation catalyzed by [(η6-1-iPr-4-Me-C6H4)Ru(HN-CR′R"-CR′R"NTs)], R′ = H, Me; Ph, R" = H, Me [J].
Bierenstiel, Matthias ;
Dymarska, Magdalena ;
de Jong, Ebbing ;
Schlaf, Marcel .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2008, 290 (1-2) :1-14