Synthesis, X-ray crystal structures and biomimetic and anticancer activities of novel copper(II)benzoate complexes incorporating 2-(4′-thiazolyl)benzimidazole (thiabendazole), 2-(2-pyridyl)benzimidazole and 1,10-phenanthroline as chelating nitrogen donor ligands

Devereux, Michael; Shea, Denis O; Kellett, Andrew; McCann, Malachy; Walsh, Maureen; Egan, Denise A.; Deegan, Carol; Kędziora, Kinga; Rosair, Georgina M.; Müller‐Bunz, Helge

doi:10.1016/j.jinorgbio.2007.02.002

Cited by 182 publications

(74 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[9,10] One phenanthroline derivative, phenanthroline-5,6-dione (phendione), displays significant anticancer activity, both with and without a coordinated metal. [11,12] Some specific phenanthroline-7-ones are already well known for their excellent cytotoxic properties. Delfourne et al have probed the effect of various substituents on different rings of these tetracyclic aromatic compounds.…”

Section: Introductionmentioning

confidence: 99%

Phenanthroline Derivatives with Improved Selectivity as DNA‐Targeting Anticancer or Antimicrobial Drugs

et al. 2008

View full text Add to dashboard Cite

Phenanthroline derivatives are of interest due to their potential activity against cancer, and viral, bacterial, and fungal infections. In a search for highly specific antitumor and antibacterial compounds, we report the activities of 1,10‐phenanthroline‐5,6‐dione (phendione or L1), dipyrido[3,2‐a:2′,3′‐c]phenazine (dppz or L2), and their corresponding platinum complexes ([PtL1Cl2] and [PtL2Cl2]), and provide the solid‐state 3D structure for [PtL1Cl2]. It is generally known that a toxic metal ion coordinated to an active organic moiety leads to a synergistic effect; however, we report herein that the platinum complexes [PtL1Cl2] and [PtL2Cl2] have weaker activities relative to those of the free ligands, especially against bacteria. Testing these agents against a variety of human cancer cell lines revealed that L1 and [PtL1Cl2] were at least as active as cisplatin against several of the cell lines (including a cisplatin‐resistant cell line). The absence of antibacterial activity of [PtL1Cl2] removes the detrimental effect of phenanthrolines toward intestinal flora, suggesting a highly promising new strategy for the development of anticancer drugs with reduced side effects.

show abstract

Section: Introductionmentioning

confidence: 99%

Phenanthroline Derivatives with Improved Selectivity as DNA‐Targeting Anticancer or Antimicrobial Drugs

et al. 2008

View full text Add to dashboard Cite

show abstract

“…Treatment of aromatic aldehyde 1, quinolin-6-amine 2 and cyclopentanone 3 in THF in the presence of 5 mol% iodine at reflux condition afforded the corresponding 10,11-dihydro-8-aryl-9H-cyclopenta[a] [4,7]phenanthroline 4 in good yields (Scheme 1). THF 5 trace 3 50 THF 5 72 4 reflux THF 5 82 5 reflux THF 1 68 6 reflux THF 10 82 7 reflux CHCl 3 5 74 8 reflux benzene 5 80 9 reflux CH 3 CN 5 78 10 80 DMF 5 65 a Reaction conditions: solvent (10 mL), 4-bromobenzaldehyde (0.370 g, 2 mmol), 2 mmol quinolin-6-amine (0.288 g, 2 mmol), cyclopentanone (0.176 g, 2.1 mmol ), b Isolated yields.…”

Section: Resultsmentioning

confidence: 99%

“…A series of 10,11-dihydro-8-aryl-9H-cyclopenta[a] [4,7]phenanthroline derivatives was prepared by a three-component reaction of aromatic aldehyde, quinolin-6-amine and cyclopentanone using iodine as catalyst. The structure of 4e is confirmed by X-ray diffraction analysis, and the crystal structure is discussed in detail.…”

Section: Introductionmentioning

confidence: 99%

“…The latter possess remarkable physiological and pharmacological activities. Their activities include anticancer (copper(II)), 4 antiinflammatory (copper(II)), 5 antitumor (Pt(II)), in 2003. However, this method suffered from the drawbacks of low yields (27-41%) and multistep reactions.…”

mentioning

confidence: 99%

“…In view of the importance of phenanthroline derivatives and as a continuation of our research devoted to the development of new methods for the preparation of heterocycles via multi-component reactions catalyzed by iodine, 10 herein we describe the synthesis of 8-aryl-9H-cyclopenta[a] [4,7]phenanthroline derivatives by a reaction of aromatic aldehyde, and quinolin-6-amine and cyclopentanone in THF catalyzed by iodine.…”

mentioning

confidence: 99%

See 2 more Smart Citations

An efficient synthesis of 8-aryl-9H-cyclopenta[a][4,7]phenanthroline derivatives catalyzed by iodine

Yin¹,

Zhang²,

Wang³

et al. 2011

Arkivoc

View full text Add to dashboard Cite

A series of 10,11-dihydro-8-aryl-9H-cyclopenta[a] [4,7]phenanthroline derivatives was prepared by a three-component reaction of aromatic aldehyde, quinolin-6-amine and cyclopentanone using iodine as catalyst. The structure of 4e is confirmed by X-ray diffraction analysis, and the crystal structure is discussed in detail. Compared to the previous method, this iodine-catalyzed procedure has the advantages of mild reaction conditions, good yields and operational simplicity.

show abstract

Copper Complexes as Anticancer Agents

Franco¹,

Porchia²,

Tisato³

et al. 2021

Encyclopedia of Inorganic and Bioinorganic Chemistry

View full text Add to dashboard Cite

Following the great impetus provided by the discovery of the anticancer activity of cisplatin [ cis ‐diamminedichloridoplatinum(II)] in the 1960s, extensive search for alternative metal‐based drugs with improved pharmacological properties has been attempted. Actually, the outstanding efficacy showed by clinically approved Pt(II) compounds is counterbalanced by severe toxic effects on normal tissues, and by the early appearance of drug resistance phenomena. Among non‐Pt compounds, copper complexes are considered promising alternatives to platinum drugs as antitumor agents. In particular, the discovery of significant alterations in cancer cell copper metabolism and the different responses to copper between normal and tumor cells have paved the way for the development of copper‐based anticancer drugs. This article aims to summarize the extant literature on the most well‐studied classes of anticancer copper complexes, with special emphasis on research performed in the last 10 years, most relevant to the elucidation of the involved mechanisms of action and/or reporting on in vivo efficacy evaluations.

show abstract

Synthesis, X-ray crystal structures and biomimetic and anticancer activities of novel copper(II)benzoate complexes incorporating 2-(4′-thiazolyl)benzimidazole (thiabendazole), 2-(2-pyridyl)benzimidazole and 1,10-phenanthroline as chelating nitrogen donor ligands

Cited by 182 publications

References 38 publications

Phenanthroline Derivatives with Improved Selectivity as DNA‐Targeting Anticancer or Antimicrobial Drugs

Phenanthroline Derivatives with Improved Selectivity as DNA‐Targeting Anticancer or Antimicrobial Drugs

An efficient synthesis of 8-aryl-9H-cyclopenta[a][4,7]phenanthroline derivatives catalyzed by iodine

Copper Complexes as Anticancer Agents

Contact Info

Product

Resources

About