Platinum complexes of terpyridine: Synthesis, structure and reactivity

Cummings, Scott D.

doi:10.1016/j.ccr.2008.04.013

Cited by 115 publications

(20 citation statements)

References 167 publications

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“…In order to be more economic, the coupling reaction was performed with 8a at lower catalyst loads. As the catalyst load was decreased from 1 to 0.1 mol %, substrate conversion barely decreased (Table 1, entries [18][19][20]. A noticeable decline in conversion was only observed when the catalyst load was dropped to 0.05 mol % (Table 1, entries 21).…”

Section: Resultsmentioning

confidence: 99%

New symmetrical N^N^N palladium(II) pincer complexes: synthesis, characterization and catalytic evaluation in the Suzuki-Miyaura cross-coupling reaction

Yafele¹,

Mabasa²,

Vatsha³

et al. 2020

Arkivoc

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Owing to their activity, versatility and ease of synthesis, N^N^N complexes with a central pyridine unit are of significance in organic synthesis. However, these complexes are relatively uncommon in comparison to their benzene analogues. In addition, neutral complexes of this pincer type ligand that consists of a pyridine core are rare. In view of this, a series of cationic palladium(II) N^N^N pincer complexes derived from neutral ligands that are based on a rigid pyridine backbone were synthesized, characterized and then evaluated as precatalysts in the Suzuki-Miyaura cross coupling reaction. At a catalyst loading of 0.1 mol%, the complexes were found to be effective pre-catalysts in the cross-coupling reactions under aqueous conditions. The scope, structure-activity relationships and limitations of these complexes are discussed.

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Section: Resultsmentioning

confidence: 99%

New symmetrical N^N^N palladium(II) pincer complexes: synthesis, characterization and catalytic evaluation in the Suzuki-Miyaura cross-coupling reaction

Yafele¹,

Mabasa²,

Vatsha³

et al. 2020

Arkivoc

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“…Two derived terpyridine ligands (T1/T2) (Shi et al, 2006) and two 4-anilinoquinazoline ligands (L1/L2) were prepared following the literature methods (Du et al, 2015) with minor modification. Then T1 or T2 were reacted with Pt II precursors such as K 2 PtCl 4 or Pt(DMSO) 2 Cl 2 to give rise to the intermediates P1 and P2 (Cummings, 2009b). After the treatment of AgNO 3 to remove the chloride, final complexes 1-4 were received by the reaction of these as-prepared intermediates in methanol solution, with L1 or L2 at ambient temperature, as shown in Scheme 1.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Platinum(II) Terpyridine Anticancer Complexes Possessing Multiple Mode of DNA Interaction and EGFR Inhibiting Activity

Zhao

et al. 2020

Front. Chem.

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Platinum(II) terpyridine complexes has attracted increasing attention as they have displayed great potential as antitumor agents due to their high intercalation affinity with nucleic acids. Epidermal growth factor receptor (EGFR) is often overexpressed in various tumor cells, leading to uncontrolled growth of tumor, and is regarded as an important target for developing novel antitumor drugs. Herein, we report four platinum(II) terpyridine complexes bearing EGFR inhibiting 4-anilinoquinazoline derivatives as potent multi-targeting antiproliferation agents against a series of cancer cells. EGFR inhibition assay revealed that these complexes are highly potent EGFR inhibitors. But competitive DNA binding assay and docking simulations also suggested that these complexes exhibited multiple modes of DNA interaction, especially great affinity toward DNA minor groove. Finally, cellular uptake and distribution measurements by inductively coupled plasma mass spectrometry (ICP-MS) and time-of-flight secondary ion mass spectrometry (ToF-SIMS) demonstrated that both nucleus DNA and membrane proteins are important targets for their anticancer mechanisms. The complexes herein can therefore be regarded as promising multi-targeting anticancer agents.

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“…1,3,4-Thiadiazole derivatives attracted great attention from biochemists due to their various bioactivities including antibacterial (Zhong et al, 2017), antifungal (Chen, Li & Han, 2000), insecticidal (Luo & Yang, 2007), antiviral (Chen et al, 2010), herbicidal (Cummings, 2009), anticancer (Casey et al, 2004), anti-tubercular (Foroumadi, Kiani & Soltani, 2003), antiparasitic (Coura & De Castro, 2002), antidepressant (Siddiqui et al, 2011), antioxidant (Khan et al, 2010) and anti-inflammatory (Kumar et al, 2008) activities. Among the above biological activities, the remarkable antimicrobial activity of 1,3,4-thiadiazole derivatives were well reported during the past decades.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and antimicrobial activities of novel 1,3,5-thiadiazine-2-thione derivatives containing a 1,3,4-thiadiazole group

Yan

et al. 2019

PeerJ

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A series of novel 1,3,5-thiadiazine-2-thione derivatives containing a 1,3,4-thiadiazole group was designed and synthesized. The structures of all the compounds were well characterized using 1H NMR, 13C NMR and high-resolution mass spectrometer, and further confirmed by the X-ray diffraction analysis of 8d. The antimicrobial activities of all the target compounds against Xanthomonas oryzae pv. oryzicola, X. oryzae pv. oryzae, Rhizoctonia solani and Fusarium graminearum were evaluated. The in vitro antimicrobial bioassays indicated that some title compounds exhibited noteworthy antimicrobial effects against the above strains. Notably, the compound N-(5-(ethylthio)-1,3,4-thiadiazol-2-yl)-2-(5-methyl-6-thioxo-1,3,5-thiadiazinan-3-yl)acetamide (8a) displayed obvious antibacterial effects against X. oryzae pv. oryzicola and X. oryzae pv. oryzae at 100 μg/mL with the inhibition rates of 30% and 56%, respectively, which was better than the commercial bactericide thiodiazole-copper. In addition, the anti-R. solani EC50 value of 8a was 33.70 μg/mL, which was more effective than that of the commercial fungicide hymexazol (67.10 μg/mL). It was found that the substitutes in the 1,3,5-thiadiazine-2-thione and the 1,3,4-thiadiazole rings played a vital role in the antimicrobial activities of the title compounds. More active title compounds against phytopathogenic microorganisms might be obtained via further structural modification.

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Platinum complexes of terpyridine: Synthesis, structure and reactivity

Cited by 115 publications

References 167 publications

New symmetrical N^N^N palladium(II) pincer complexes: synthesis, characterization and catalytic evaluation in the Suzuki-Miyaura cross-coupling reaction

New symmetrical N^N^N palladium(II) pincer complexes: synthesis, characterization and catalytic evaluation in the Suzuki-Miyaura cross-coupling reaction

Platinum(II) Terpyridine Anticancer Complexes Possessing Multiple Mode of DNA Interaction and EGFR Inhibiting Activity

Design, synthesis and antimicrobial activities of novel 1,3,5-thiadiazine-2-thione derivatives containing a 1,3,4-thiadiazole group

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