Structural and biological investigation of ferrocene-substituted 3-methylidene-1,3-dihydro-2H-indol-2-ones

Spencer, John; Mendham, Andrew P.; Kotha, Arun K.; Richardson, Simon C. W.; Hillard, Elizabeth A.; Jaouen, Gérard; Male, Louise; Hursthouse, Michael B.

doi:10.1039/b816249b

Cited by 58 publications

(60 citation statements)

References 25 publications

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“…This offers the potential for synthesizing oxindoles with extended molecular architectures and biological properties (Spencer et al, 2009) and will be of continuing invaluable assistance to theoretical calculations (Kausar et al, 2009). …”

Section: Figurementioning

confidence: 99%

Seven 3-methylidene-1H-indol-2(3H)-ones related to the multiple-receptor tyrosine kinase inhibitor sunitinib

et al. 2010

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The solid‐state structures of a series of seven substituted 3‐methylidene‐1H‐indol‐2(3H)‐one derivatives have been determined by single‐crystal X‐ray diffraction and are compared in detail. Six of the structures {(3Z)‐3‐(1H‐pyrrol‐2‐ylmethylidene)‐1H‐indol‐2(3H)‐one, C13H10N2O, (2a); (3Z)‐3‐(2‐thienylmethylidene)‐1H‐indol‐2(3H)‐one, C13H9NOS, (2b); (3E)‐3‐(2‐furylmethylidene)‐1H‐indol‐2(3H)‐one monohydrate, C13H9NO2·H2O, (3a); 3‐(1‐methylethylidene)‐1H‐indol‐2(3H)‐one, C11H11NO, (4a); 3‐cyclohexylidene‐1H‐indol‐2(3H)‐one, C14H15NO, (4c); and spiro[1,3‐dioxane‐2,3′‐indolin]‐2′‐one, C11H11NO3, (5)} display, as expected, intermolecular hydrogen bonding (N—H...O=C) between the 1H‐indol‐2(3H)‐one units. However, methyl 3‐(1‐methylethylidene)‐2‐oxo‐2,3‐dihydro‐1H‐indole‐1‐carboxylate, C13H13NO3, (4b), a carbamate analogue of (4a) lacking an N—H bond, displays no intermolecular hydrogen bonding. The structure of (4a) contains three molecules in the asymmetric unit, while (4b) and (4c) both contain two independent molecules.

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Section: Figurementioning

confidence: 99%

Seven 3-methylidene-1H-indol-2(3H)-ones related to the multiple-receptor tyrosine kinase inhibitor sunitinib

et al. 2010

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“…Palladacycles 3a-d is cytotoxic and inhibits cathepsin B with IC 50 values in the low µM range [52][53][54]. This study are aiming to address some complexes can be used as biological probes for proteins and biomolecules, e.g.…”

Section: Resultsmentioning

confidence: 99%

“…However, complexes of palladacycles 4a-d and 5a-d displays good in vitro activity, with an IC 50 of 4.3 µM. Having established 5a-d as a "hit" from this primary screen, we have evaluated it in other immortal cell lines namely B16 (Murine Melanoma) and Vero (African Green Monkey Kidney Epithelia) [52][53][54]. Preliminary data show 3a-d to have submicromolar activity (Figures 1-3).…”

Section: Reaction With Bulky 1-naphthyl Isocyanate and Isothiocyanatementioning

confidence: 99%

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Synthesis of Novel Palladacycles Inhibitors of the Cathepsin B Activity and Antitumoral Agents

Elgazwy

Shehata²,

Zaki³

et al. 2013

Med chem (Los Angeles)

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The reaction of 2-bromo-3,4,5-trimethoxybenzaldehyde 1 with Pd(dba) 2 ; dba=dibenzylideneacetone) in the presence of a stoichiometric amount of nitrogen donor ligands, such as N,N,N',, 2,2'-bipyridine (bpy) 4,4'-dimethyl-2,2'-bipyridine (dmbpy) and an 1,10-phenanthroline (Phen), should be added to with equimolar ratio in degassed acetone under nitrogen to give mononuclear σ-aryl palladium (II) complexes cis-[2-Pd{C 6 H(CHO)-6-(OMe) 3 -3,4,5}BrL 2 ] 3a-d, where L 2 =TMEDA (3a); L 2 =bpy (3b); L 2 =dmbpy (3c); L 2 =Phen (3d) in good yields 48-65%. The reaction of the synthesized five-membered C,N-palladacycle cis-[2-Pd{C 6 H(CHO)-6-(OMe) 3 -3,4,5} BrL 2 ] 3a-d, where L 2 =TMEDA (3a); L=bpy (3b); L 2 =dmbpy (3c); L 2 =Phen (3d), with an1-naphthylisocyanates (C 10 H 7 -NCO) and an 1-naphthylisothiocyanates (C 10 H 7 -NCS), leads to the formation of novel palladacycle 4a-d and 5a-d, which was characterized in solution by 1 H NMR spectroscopy. The solid products were characterized by satisfactory elemental analysis and spectra studies. All the resulting complexes 3a-d, 4a-d and 5a-d were tested in vitro against a number of cell lines. For example, it inhibited K562 leukaemia cells with an IC 50 value in the range of (3.00 -4.3) µM (1 h exposure) and displayed cathepsin B inhibitory action with an IC 50 value in the range of (0.045-0.055 µM). .

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“…[34] Several other ferrocene conjugates have been seen to show anticancer activity. [35,36] Our use of the ferrocenyl moiety to design anticancer agents is based on its excellent stability in biological fluids, its redox activity and lipophilicity. [33] Although ferrocene is nontoxic, its activation leads to the generation of species that can damage cancer cells.…”

Section: Introductionmentioning

confidence: 99%

Ferrocene‐Conjugated Oxidovanadium(IV) Complexes as Potent Near‐IR Light Photocytotoxic Agents

et al. 2011

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Ferrocene‐conjugated oxidovanadium(IV) complexes [VO(Fc‐tpy)(B)](ClO4)2 (1–4) and [VO(Ph‐tpy)(dppz)](ClO4)2 (5) as a control [Fc = (η5‐C5H4)FeII(η5‐C5H5), Fc‐tpy = 4′‐ferrocenyl‐2,2′:6′,2″‐terpyridine, Ph‐tpy = 4′‐phenyl‐2,2′:6′,2″‐terpyridine, B = heterocyclic base: 2,2′‐bipyridine (bpy in 1), 1,10‐phenanthroline (phen in 2), dipyridoquinoxaline (dpq in 3), dipyridophenazine (dppz in 4)] were prepared and their DNA binding, DNA photocleavage activity and photocytotoxicity studied. The crystal structure of [VO(Fc‐tpy)(bpy)](PF6)2·3Me2CO shows a vanadyl group in six‐coordinate VIVON5 coordination geometry, in which Fc‐tpy and bpy display tridentate meridional and bidentate N‐donor axial–equatorial binding modes, respectively. The one‐electron paramagnetic complexes exhibit a charge‐transfer band near 590 nm in DMF. The VIV/VIII redox couple in 1–4 appears near –0.7 V, whereas the Fc moiety shows a response near 0.6 V vs. SCE in DMF/0.1 M TBAP. The complexes are good binders to calf thymus DNA with Kb values of 104–106 M–1. DNA melting and viscometric data suggest groove and/or partial intercalative DNA binding of the complexes. Complexes 3–5 display DNA photocleavage activity in near‐IR light of 785 nm. Complex 4 shows significant photocytotoxicity in visible light (400–700 nm) in HeLa cells with low dark toxicity.

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Structural and biological investigation of ferrocene-substituted 3-methylidene-1,3-dihydro-2H-indol-2-ones

Cited by 58 publications

References 25 publications

Seven 3-methylidene-1H-indol-2(3H)-ones related to the multiple-receptor tyrosine kinase inhibitor sunitinib

Seven 3-methylidene-1H-indol-2(3H)-ones related to the multiple-receptor tyrosine kinase inhibitor sunitinib

Synthesis of Novel Palladacycles Inhibitors of the Cathepsin B Activity and Antitumoral Agents

Ferrocene‐Conjugated Oxidovanadium(IV) Complexes as Potent Near‐IR Light Photocytotoxic Agents

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