Bioactive 1,1′-unsymmetrical bi-functional ferrocenyl compounds using a novel solvent free one pot multicomponent reaction method

被引:13
作者
Barik, Tulasi [1 ]
Ghosh, Avishek [1 ]
Mishra, Abtar [2 ]
Dhiman, Rohan [2 ]
Sasamori, Takahiro [3 ]
Chatterjee, Saurav [1 ]
机构
[1] Natl Inst Technol Rourkela, Dept Chem, Rourkela 769008, Odisha, India
[2] Natl Inst Technol Rourkela, Dept Life Sci, Rourkela 769008, Odisha, India
[3] Nagoya City Univ, Grad Sch Nat Sci, Nagoya, Aichi 4678501, Japan
关键词
Solvent free; Anticancer; Ferrocenyl; Unsymmetrical; Rice husk ash; RAPID COLORIMETRIC ASSAY; KNOEVENAGEL CONDENSATION; SELECTIVE REDUCTION; DIPEPTIDE CHAINS; METAL-COMPLEXES; SERUM-ALBUMIN; THIOSEMICARBAZONES; ANTIBACTERIAL; ALDEHYDES; IRON;
D O I
10.1016/j.jorganchem.2019.121095
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A solvent free synthetic method using rice husk ash (RHA) as solid support has been designed for selective functionalization and preparation of novel 1,1'- unsymmetrically bi-functionalized ferrocenyl compounds. The selectively functionalized intermediate compound, Ferrocenyl-1-acetyl-1'-thiosemicarbazone, has been structurally characterized using single crystal X-ray diffraction technique which revealed distinct inter-molecular hydrogen bonding interactions across the thiosemicarbazone chains. Cytotoxic evaluation of five different unsymmetrically bi-functionalized thiosemicarbazone - hydrazone compounds showed potent activity against human leukemia (THP-1) cell line. The unsymmetrical ferrocenyl compounds also showed strong BSA and DNA binding interactions and reversible redox properties. (C) 2019 Elsevier B.V. All rights reserved.
引用
收藏
页数:11
相关论文
共 98 条
[41]   Deltoid versus Rhomboid: Controlling the Shape of Bis-ferrocene Macrocycles by the Bulkiness of the Substituents [J].
Hoffmann, Viktor ;
le Pleux, Loic ;
Haeussinger, Daniel ;
Unke, Oliver T. ;
Prescimone, Alessandro ;
Mayor, Marcel .
ORGANOMETALLICS, 2017, 36 (04) :858-866
[42]   Biimidazole containing cobalt(III) mixed ligand complexes: Crystal structure and photonuclease activity [J].
Indumathy, Ramasamy ;
Weyhermueller, Thomas ;
Nair, Balachandran Unni .
DALTON TRANSACTIONS, 2010, 39 (08) :2087-2097
[43]   The renaissance of polypharmacology in the development of anti-cancer therapeutics: Inhibition of the "Triad of Death" in cancer by Di-2-pyridylketone thiosemicarbazones [J].
Jansson, Patric J. ;
Kalinowski, Danuta S. ;
Lane, Darius J. R. ;
Kovacevic, Zaklina ;
Seebacher, Nicole A. ;
Fouani, Leyla ;
Sahni, Sumit ;
Merlot, Angelica M. ;
Richardson, Des R. .
PHARMACOLOGICAL RESEARCH, 2015, 100 :255-260
[44]   Impact of O → S Exchange in Ferrocenyl Amides on the Structure and Redox Chemistry [J].
Kienz, Torben ;
Foerster, Christoph ;
Heinze, Katja .
ORGANOMETALLICS, 2014, 33 (18) :4803-4812
[45]   New ferrocenyl-substituted heterocycles. Formation under Biginelli conditions, DFT modelling, and structure determination [J].
Kiss, K. ;
Csampai, A. ;
Sohar, P. .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2010, 695 (15-16) :1852-1857
[46]   BASE AND ACID CATALYSIS BY THE ALKALI-CONTAINING MCM-41 MESOPOROUS MOLECULAR-SIEVE [J].
KLOETSTRA, KR ;
VANBEKKUM, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (10) :1005-1006
[47]   Preparation of ferrocenyl mono- and dienone derivatives through aldol condensation of 1,1′-diacetylferrocene with aromatic aldehydes in dry conditions [J].
Liu, WY ;
Xu, QH ;
Chen, BH ;
Liang, YM ;
Ma, YX ;
Liu, WM .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 637 :782-785
[48]   DNA/protein interaction and cytotoxic activity of imidazole terpyridine derived Cu(II)/Zn(II) metal complexes [J].
Manikandamathavan, V. M. ;
Weyhermueller, T. ;
Parameswari, R. P. ;
Sathishkumar, M. ;
Subramanian, V. ;
Nair, Balachandran Unni .
DALTON TRANSACTIONS, 2014, 43 (34) :13018-13031
[49]   Donor/acceptor organotriiron(II) hydrazone chromophores:: structural, spectroscopic and electrochemical properties [J].
Manzur, C ;
Millán, L ;
Fuentealba, M ;
Mata, JA ;
Carrillo, D ;
Hamon, JR .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (05) :1265-1272
[50]   Syntheses, crystal structures and electrochemical studies of bi- and trimetallic conjugated ferrocene-based complexes [J].
Mata, JA ;
Peris, E .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2001, (24) :3634-3640