ChemInform Abstract: Synthesis of Aminoanthraquinone Derivatives and Their in vitro Evaluation as Potential Anticancer Drugs

Katzhendler, Jehoshua; Gean, K.F.; Bar-Ad, Gidon; Tashma, Zeev; Ben-Shoshan, Raphael; Ringel, Israel; Bachrach, Uriel; Ramu, A

doi:10.1002/chin.198925133

Cited by 3 publications

(6 citation statements)

References 1 publication

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“…To further explore this phenomenon, we conjugated porphyrin 1 with the anthraquinone aminoderivative 8 [15] (Scheme 2) and proved the structure of conjugate 3 by 1 H NMR and HRMS.…”

Section: Resultsmentioning

confidence: 99%

Facile Synthesis of a Phototoxic Monofunctionalized Tetraarylporphyrin as Scaffold for Porphyrin-Quinone Conjugates

Sereda

Moorthy

Gamarra-Luques

et al. 2013

Synthetic Communications

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“…To further explore this phenomenon, we conjugated porphyrin 1 with the anthraquinone aminoderivative 8 [15] (Scheme 2) and proved the structure of conjugate 3 by 1 H NMR and HRMS.…”

Section: Resultsmentioning

confidence: 99%

Facile Synthesis of a Phototoxic Monofunctionalized Tetraarylporphyrin as Scaffold for Porphyrin-Quinone Conjugates

Sereda

Moorthy

Gamarra-Luques

et al. 2013

Synthetic Communications

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“…The synthesis of most of the ligands used in this study has been described recently. 29 We have prepared seven new ligands for this specific study and used the preparative routes outlined in Figure 2.29 Since all the ligands consist of an anthraquinone moiety bearing a side chain containing primary and/or secondary amines, purification of the ligands was effected by extraction into acidified aqueous solutions and their subsequent isolation as the hydrochloride salts.…”

Section: Resultsmentioning

confidence: 99%

“…The preparation and purification of 1C3, 1C4, 1C3C2, and 1C2C2 have already been detailed elsewhere. 29 We report the preparation of seven new anthraquinone derivatives used as ligands for the Pt complexes. All the ligands were characterized by NMR spectroscopy and mass spectrometry and their purity was verified by elemental analysis, melting point, and TLC.…”

Section: Methodsmentioning

confidence: 99%

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Preparation, characterization, and anticancer activity of a series of cis-PtCl2 complexes linked to anthraquinone intercalators

Gibson¹,

Gean²,

Ben-Shoshan³

et al. 1991

J. Med. Chem.

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A new series of complexes of the type cis-PtL2X2 [where L is a monodentate AQ-Y(CH2)nNH2 and L2 is a bidentate AQ-Y(CH2)nNH(CH2)2NH2; AQ = anthraquinone, X = Cl, I, Y = NH, O] in which anthraquinone intercalators are tethered to the cis-PtCl2 unit via an (aminoalkyl)amino, (oxyalkyl)amino, or polyethylene glycol (aminoethyl)amino linker chains was prepared and screened in vitro against P388 leukemia. In vivo toxicity studies were carried out on selected complexes. All complexes were characterized by means of elemental analysis, 195Pt NMR spectroscopy, and FTIR. The 1:1 Pt-intercalator complexes displayed much higher in vitro cytotoxic activities than the 1:2 Pt-intercalator complexes. The dichloride complexes were consistently more active than their diiodide counterparts. Among the 1:1 Pt-intercalator complexes those with the shorter linker chains (n = 2, 3) exhibited the highest cytotoxic activities. Three compounds, [[2-[[2-(anthraquinon-1- ylamino)ethyl]amino]ethyl]amine-N,N']dichloroplatinum(II), [[2-[[3-(anthraquinon-1-ylamino)propyl]amino]ethyl]amine- N,N']dichloroplatinum(II), and [[2-[[3-anthraquinon-1- yloxy)propyl]amino]ethyl]amine-N,N']dichloroplatinum(II), were as active in vitro as cisplatin (ED50 = 2-4 x 10(-7) M) while on a molar basis their acute in vivo toxicity was significantly lower than that of cisplatin. In vivo screening against P388 leukemia indicated that these complexes have activity comparable to cisplatin.

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“…The procedure is outlined in Scheme 2. Thus, 1C2OH and 2C3OH were prepared in a manner analogous to that described by Katzhendler et al 29 for the preparation of 1C3OH. The preparation of 1C3Br has been reported by Gibson et al 30 and the preparation of 1C2Br and 2C3Br by the same method was successful.…”

Section: Macrocycle/intercalator Synthesesmentioning

confidence: 99%

The preparation and characterisation of cyclam/anthraquinone macrocyle/intercalator complexes and their interactions with DNA

Ellis

Perkins²,

Turner

et al. 2003

Dalton Trans.

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ChemInform Abstract: Synthesis of Aminoanthraquinone Derivatives and Their in vitro Evaluation as Potential Anticancer Drugs

Cited by 3 publications

References 1 publication

Facile Synthesis of a Phototoxic Monofunctionalized Tetraarylporphyrin as Scaffold for Porphyrin-Quinone Conjugates

Facile Synthesis of a Phototoxic Monofunctionalized Tetraarylporphyrin as Scaffold for Porphyrin-Quinone Conjugates

Preparation, characterization, and anticancer activity of a series of cis-PtCl2 complexes linked to anthraquinone intercalators

The preparation and characterisation of cyclam/anthraquinone macrocyle/intercalator complexes and their interactions with DNA

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