Dynamic imine chemistry in metal–organic polyhedra

Vardhan, Harsh; Mehta, Akshay; Nath, Ipsita; Verpoort, Francis

doi:10.1039/c5ra10801b

Cited by 31 publications

(18 citation statements)

References 157 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Due to the potent physiochemical properties, half-sandwich ruthenium, iridium, and rhodium molecular clips are predominantly employed by various research groups in the synthesis of discrete architectures for a plethora of applications [33,34,35,36,37,38,39,40,41,42,43]. Moreover, the dynamic imine chemistry is also widely utilized for the preparation of platonic, Archimedean, stellated, and faceted solids [44]. In particular, sensing of mono-carboxylate or multi-carboxylate anions is of significant importance owing to their crucial role in chemical, biological, and environmental systems [45,46,47,48].…”

Section: Introductionmentioning

confidence: 99%

Investigation of the Anticancer Activity of Coordination-Driven Self-AssembledTwo-Dimensional Ruthenium Metalla-Rectangle

et al. 2019

View full text Add to dashboard Cite

Coordination-driven self-assembly is an effective synthetic tool for the construction of spatially and electronically tunable supramolecular coordination complexes (SCCs), which are useful in various applications. Herein, we report the synthesis of a two-dimensional discrete metalla-rectangle [(η6-p-cymene)4Ru4(C6H2O4)2(2)2](CF3SO3)4 (3) by the reaction of a dinuclear half-sandwich ruthenium (II) complex [Ru2(η6-p-cymene)2(C6H2O4)Cl2] (1) and bis-pyridyl amide linker (2) in the presence of AgO3SCF3. This cationic ruthenium metalla-rectangle (3) has been isolated as its triflate salt and characterized by analytical techniques including elemental analysis, Fourier-transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance spectroscopy (1H-NMR), carbon nuclear magnetic resonance spectroscopy (13C-NMR), 1H-1H correlation spectroscopy (COSY), 1H-1H nuclear Overhauser effect spectroscopy (NOESY), diffusion ordered spectroscopy (DOSY), and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS). Significantly, the 2D cationic ruthenium metalla-rectangle showed better anticancer activity towards three different cell lines (A549, Caki-1 and Lovo) as compared with the parent ruthenium complex (1) and the commercially used drug, cisplatin.

show abstract

Section: Introductionmentioning

confidence: 99%

Investigation of the Anticancer Activity of Coordination-Driven Self-AssembledTwo-Dimensional Ruthenium Metalla-Rectangle

et al. 2019

View full text Add to dashboard Cite

show abstract

“…The imine bond plays a notable role in supramolecular and dynamic covalent chemistry (DCC) as well as materials science. [1][2][3] By rendering classical covalent bonds reversible, the eld of DCC has been ourishing over the past decade. [4][5][6] Among the most explored dynamic covalent reactions (DCRs) imine formation and exchange have been widely used for the assembly of discrete structures, such as macrocycles, cages, and knots.…”

Section: Introductionmentioning

confidence: 99%

n → π* interactions as a versatile tool for controlling dynamic imine chemistry in both organic and aqueous media

Chen

Yun

et al. 2020

Chem. Sci.

View full text Add to dashboard Cite

show abstract

“…Schiff bases are important compounds in chemistry and biochemistry due to their flexibility (Mayans et al, 2018;Pramanik et al, 2018), easy preparation (Erxleben, 2018;ISSN 2053ISSN -2296 # 2020 International Union of Crystallography Ganguly et al, 2014), exceptional chelating ability (Malik et al, 2018;Vardhan et al, 2015) and to their broad spectrum of biological and pharmaceutical activities, such as antimicrobial (Anush et al, 2018;Unver & Bektas, 2018;Bharathi et al, 2018;Carreñ o et al, 2018), anti-inflammatory (Venkatesan et al, 2018;Farag et al, 2017;Bano et al, 2017;Khayyat et al, 2015) and anticancer properties (Unver & Bektas, 2018;Santhosh Kumar et al, 2018;Kalaiarasi et al, 2018;Ariyaeifar et al, 2018). Thus, the chemistry of Schiff bases has always been a promising field of research.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structures, antiproliferative activities and reverse docking studies of eight novel Schiff bases derived from benzil

et al. 2020

View full text Add to dashboard Cite

Eight novel Schiff bases derived from benzil dihydrazone (BDH) or benzil monohydrazone (BMH) and four fused-ring carbonyl compounds (3-formylindole, FI; 3-acetylindole, AI; 3-formyl-1-methylindole, MFI; 1-formylnaphthalene, FN) were synthesized and characterized by elemental analysis, ESI–QTOF–MS, 1H and 13C NMR spectroscopy, as well as single-crystal X-ray diffraction. They are (1Z,2Z)-1,2-bis{(E)-[(1H-indol-3-yl)methylidene]hydrazinylidene}-1,2-diphenylethane (BDHFI), C32H24N6, (1Z,2Z)-1,2-bis{(E)-[1-(1H-indol-3-yl)ethylidene]hydrazinylidene}-1,2-diphenylethane (BDHAI), C34H28N6, (1Z,2Z)-1,2-bis{(E)-[(1-methyl-1H-indol-3-yl)methylidene]hydrazinylidene}-1,2-diphenylethane (BMHMFI) acetonitrile hemisolvate, C34H28N6·0.5CH3CN, (1Z,2Z)-1,2-bis{(E)-[(naphthalen-1-yl)methylidene]hydrazinylidene}-1,2-diphenylethane (BDHFN), C36H26N4, (Z)-2-{(E)-[(1H-indol-3-yl)methylidene]hydrazinylidene}-1,2-diphenylethanone (BMHFI), C23H17N3O, (Z)-2-{(E)-[1-(1H-indol-3-yl)ethylidene]hydrazinylidene}-1,2-diphenylethanone (BMHAI), C24H19N3O, (Z)-2-{(E)-[(1-methyl-1H-indol-3-yl)methylidene]hydrazinylidene}-1,2-diphenylethanone (BMHMFI), C24H19N3O, and (Z)-2-{(E)-[(naphthalen-1-yl)methylidene]hydrazinylidene}-1,2-diphenylethanone (BMHFN) C25H18N2O. Moreover, the in vitro cytotoxicity of the eight title compounds was evaluated against two tumour cell lines (A549 human lung cancer and 4T1 mouse breast cancer) and two normal cell lines (MRC-5 normal lung cells and NIH 3T3 fibroblasts) by MTT assay. The results indicate that four (BDHMFI, BDHFN, BMHMFI and BMHFN) are inactive and the other four (BDHFI, BDHAI, BMHFI and BMHAI) show severe toxicities against human A549 and mouse 4T1 cells, similar to the standard cisplatin. All the compounds exhibited weaker cytotoxicity against normal cells than cancer cells. The Swiss Target Prediction web server was applied for the prediction of protein targets. After analyzing the differences in frequency hits between these active and inactive Schiff bases, 18 probable targets were selected for reverse docking with the Surflex-dock function in SYBYL-X 2.0 software. Three target proteins, i.e. human ether-á-go-go-related (hERG) potassium channel, the inhibitor of apoptosis protein 3 and serine/threonine-protein kinase PIM1, were chosen as the targets. Finally, the ligand-based structure–activity relationships were analyzed based on the putative protein target (hERG) docking results, which will be used to design and synthesize novel hERG ion channel inhibitors.

show abstract

Dynamic imine chemistry in metal–organic polyhedra

Cited by 31 publications

References 157 publications

Investigation of the Anticancer Activity of Coordination-Driven Self-AssembledTwo-Dimensional Ruthenium Metalla-Rectangle

Investigation of the Anticancer Activity of Coordination-Driven Self-AssembledTwo-Dimensional Ruthenium Metalla-Rectangle

n → π* interactions as a versatile tool for controlling dynamic imine chemistry in both organic and aqueous media

Synthesis, crystal structures, antiproliferative activities and reverse docking studies of eight novel Schiff bases derived from benzil

Contact Info

Product

Resources

About