Chiral AuI- and AuIII-Isothiourea Complexes: Synthesis, Characterization and Application

被引:13
作者
Gasperini, Danila [1 ]
Greenhalgh, Mark D. [1 ]
Imad, Rehan [2 ]
Siddiqui, Shezaib [2 ]
Malik, Anum [2 ]
Arshad, Fizza [2 ]
Choudhary, Muhammad Iqbal [2 ,3 ]
Al-Majid, Abdullah M. [4 ,5 ]
Cordes, David B. [1 ]
Slawin, Alexandra M. Z. [1 ]
Nolan, Steven P. [4 ,5 ,6 ]
Smith, Andrew D. [1 ]
机构
[1] Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland
[2] Univ Karachi, HEJ Res Inst Chem, Int Ctr Chem & Biol Sci, Karachi 75270, Pakistan
[3] King Abdulaziz Univ, Dept Biochem, Fac Sci, Jeddah 21412, Saudi Arabia
[4] King Saud Univ, Dept Chem, POB 2455, Riyadh 11451, Saudi Arabia
[5] King Saud Univ, Ctr Sustainable Chem, POB 2455, Riyadh 11451, Saudi Arabia
[6] Univ Ghent, Dept Chem, Coll Sci, Krijgslaan 281, B-9000 Ghent, Belgium
关键词
bioinorganic chemistry; coordination chemistry; gold; homogeneous catalysis; N ligands; N-HETEROCYCLIC CARBENE; ENANTIOSELECTIVE ALPHA-ALLYLATION; ACETIC-ACID ESTERS; ENAMINE CATALYSIS; PYRIDINE ADDUCTS; GOLD CATALYSIS; STRUCTURAL-CHARACTERIZATION; COOPERATIVE CATALYSIS; SYNERGISTIC CATALYSIS; PROPARGYLIC ALCOHOLS;
D O I
10.1002/chem.201804653
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
During an investigation into the potential union of Lewis basic isothiourea organocatalysis and gold catalysis, the formation of gold-isothiourea complexes was observed. These novel gold complexes were formed in high yield and were found to be air- and moisture stable. A series of neutral and cationic chiral gold(I) and gold(III) complexes bearing enantiopure isothiourea ligands was therefore synthesized and fully characterized. The steric and electronic properties of the isothiourea ligands was assessed through calculation of their percent buried volume and the synthesis and analysis of novel iridium(I)-isothiourea carbonyl complexes. The novel gold(I)- and gold(III)-isothiourea complexes have been applied in preliminary catalytic and biological studies, and display promising preliminary levels of catalytic activity and potency towards cancerous cell lines and clinically relevant enzymes.
引用
收藏
页码:1064 / 1075
页数:12
相关论文
共 129 条
[1]   PYRIDINE ADDUCTS OF THE GOLD HALIDES .1. SYNTHESIS AND STRUCTURE OF [HPY][AUCL4], AUCL3.PY, [AUCL2(PY)2]CL.H2O, AND [AUCL2(PY)2][AUCL2] [J].
ADAMS, HN ;
STRAHLE, J .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1982, 485 (02) :65-80
[2]   PYRIDINE ADDUCTS OF THE GOLD HALIDES .2. SYNTHESIS, PROPERTIES, AND CRYSTAL-STRUCTURE OF AUCL.NC5H5 AND AUI.NC5H5 [J].
ADAMS, HN ;
HILLER, W ;
STRAHLE, J .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1982, 485 (02) :81-91
[3]   Combinations of Aminocatalysts and Metal Catalysts: A Powerful Cooperative Approach in Selective Organic Synthesis [J].
Afewerki, Samson ;
Cordova, Armando .
CHEMICAL REVIEWS, 2016, 116 (22) :13512-13570
[4]   Gold-NHC complexes as potent bioactive compounds [J].
Al-Majid, Abdullah M. ;
Yousuf, Sammer ;
Choudhary, M. Iqbal ;
Nahra, Fady ;
Nolan, Steven P. .
CHEMISTRYSELECT, 2016, 1 (01) :76-80
[5]  
[Anonymous], 2013, ANGEW CHEM
[6]  
[Anonymous], 2004, ANGEW CHEM, DOI DOI 10.1002/ANGE.200460232
[7]   Gold(I) operational in synergistic catalysis for the intermolecular α-addition reaction of aldehydes across allenamides [J].
Ballesteros, Alberto ;
Moran-Poladura, Pablo ;
Gonzalez, Jose M. .
CHEMICAL COMMUNICATIONS, 2016, 52 (14) :2905-2908
[8]  
Belot S., 2009, Angew. Chem., V121, P9085
[9]   Enantioselective One-Pot Organocatalytic Michael Addition/Gold-Catalyzed Tandem Acetalization/Cyclization [J].
Belot, Sebastien ;
Vogt, Kim A. ;
Besnard, Celine ;
Krause, Norbert ;
Alexakis, Alexandre .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (47) :8923-8926
[10]   Gold(III) Complexes for Antitumor Applications: An Overview [J].
Bertrand, Benoit ;
Williams, Morwen R. M. ;
Bochmann, Manfred .
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (46) :11840-11851