Novel water-soluble phosphatriazenes: versatile ligands for Suzuki–Miyaura, Sonogashira and Heck reactions of nucleosides

Bhilare, Shatrughn; Gayakhe, Vijay; Ardhapure, Ajaykumar V.; Sanghvi, Yogesh S.; Schulzke, Carola; Borozdina, Yulia; Kapdi, Anant R.

doi:10.1039/c6ra19039a

Cited by 40 publications

(51 citation statements)

References 65 publications

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“…By fine tuning the electronics and functional groups on these ligands, one can develop a range of complexes for a wide variety of applications including catalysis and anti‐tumour activity . In literature, although water‐soluble phosphines such as triphenylphosphine‐3,3′,3′′‐trisulfonic acid trisodium salt (TPPTS), 1,3,5‐triaza‐7‐phosphaadamantane (PTA) and its variant PTABS (butane sulfonate salt of PTA) as well as their subsequent palladium complexes have found applications as efficient catalysts for carrying out reactions in aqueous media, their possible applications as anti‐canceragents have not been explored. One of the reasons for this could be the lower stability of phosphine‐based complexes in water, over extended time periods.…”

Section: Resultsmentioning

confidence: 99%

New Water‐Soluble N‐Heterocyclic Carbene‐Palladium Complexes as Promising Anti‐Tumor Agents: Investigating DNA and Protein Interactions

et al. 2018

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This investigation focuses on the synthesis and characterization of three new, water-soluble palladium complexes, with potential to overcome the drawbacks of platinum-based anti-cancer drugs. The complexes contain small N-heterocyclic carbene (NHC) ligands, having groups that impart water solubility. The anti-cancer effects of these complexes were evaluated in two different cancer cell lines, namely,HeLa, a cervical cancer cell line and A549,adenocarcinoma human alveolar basal epithelial cell line. Cytotoxicity of the complexes was compared with cisplatin, an established platinum-based anti-cancer moiety, using the MTT assay (MTT is 3-(4,5-dimethylthiazol-2-yl)-2,5diphenyltetrazolium bromide). Aqueous solutions of the synthesized complexes demonstrated significant cytotoxicity in both the cell lines. The synthesized metal complexes resulted in a stronger, cytotoxic effect in A549 cells (lung cancer cells), as compared to cisplatin. Furthermore, interaction of these palladium compounds with DNA was studied using gel electrophoresis and spectrometry methods. The result suggested that the complexes interacted with DNA via intercalation. Interaction with BSA (Bovine Serum Albumin) was investigated using UV-Vis spectroscopy suggesting positive interaction of palladium complex with BSA proteins. Furthermore, fluorescence studies revealed quenching of protein fluorescence thus, indicating dynamic quenching mechanism with the number of association sites being calculated as~1.

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Section: Resultsmentioning

confidence: 99%

New Water‐Soluble N‐Heterocyclic Carbene‐Palladium Complexes as Promising Anti‐Tumor Agents: Investigating DNA and Protein Interactions

et al. 2018

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“…All the chemicals and solvents were obtained from commercial sources. PTAPS and PTABS ligands were prepared by using a reported procedure …”

Section: Methodsmentioning

confidence: 99%

Pd/PTABS: Catalyst for Efficient C−H (Hetero)Arylation of 1,3,4‐Oxadiazoles Using Bromo(Hetero)Arenes

2019

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A highly efficient catalytic protocol for the CÀ H (hetero)arylation of 1,3,4-oxadiazoles using low catalyst loading of Pd/PTABS system with bromo(hetero)arenes has been disclosed. The developed reaction conditions enable the synthesis of a library of differently (hetero)arylated oxadiazoles along with a commercially available fluorescent organic scintillation material, butyl-PBD as well as antitubercular agent PHOXPY. The combination of CÀ H arylation of oxadiazoles with Sonogashira reaction (steroidal substructures bearing alkynes), Heck alkenylation or Suzuki-Miyaura coupling in a one-pot tandem procedure was also made possible with an intent for new drug discovery possibilities.

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“…Our research group has over the years developed more efficient palladium-based catalytic systems involving caged phosphine ligands such as triazaphosphaadamantane (PTA) and its derivatives (PTABS and PTAPS). 30 These ligand systems either as complexes of palladium (e.g., PTA complexes such as [Pd(Sacc) 2 (PTA) 2 ] Cat 2 or [Pd(Mal) 2 (PTA) 2 ] Cat 3 shown in Figure 1) [31][32][33] or in situ activation with a palladium precursor [PTABS with Pd(OAc) 2 ] 34 have been effective in catalyzing the modification of nucleosides (Suzuki-Miyaura, Heck alkenylation, Sonogashira coupling, aminocarbonylation) 30,35 as well as the functionalization of chloroheteroarenes (amination, etherification, and thioetherification). [36][37][38] In 2015, utilization of [Pd(Sacc) 2 (PTA) 2 ] catalytic system in catalyzing the Heck alkenylation at 1.0 mol% concentration for 5′-O-DMTr-5-iodo-2′-deoxyuridine failed…”

Section: Figure 1 Catalytic Systems Used For Cross-coupling Reactionsmentioning

confidence: 99%

“…The original protocol for the synthesis of PTABS involved the reaction of PTA (1.0 equiv) with 1,4-butanesultone in acetone as a solvent at 60 °C for 24 hours. 30 The setup for the protocol is illustrated in Scheme 6. The synthesis of PTABS was found to be reproducible on gram-scale (Table 3).…”

Section: Psp Synthesismentioning

confidence: 99%

Scale-Up of a Heck Alkenylation Reaction: Application to the Synthesis of an Amino-Modifier Nucleoside ‘Ruth Linker’

et al. 2020

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Ruth linker is a C5 pyrimidine modified nucleoside analogue widely utilized for the incorporation of a primary amine in a synthetic oligonucleotide. The increasing demand for non-radioactive labeling, detection of biomolecules, and assembly of COVID-19 test kits has triggered a need for scale-up of Ruth linker. Herein, an efficient protocol involving a palladium-catalyzed Heck alkenylation is described. The synthesis has been optimized with a goal of low catalyst concentration, column-free isolation, high product purity, reproducibility, and shorter reaction time. The scalability and utility of the process have been demonstrated successfully on a 100 g scale (starting material). Additionally, for scale-up of the Heck alkenylation protocol, 7-phospha-1,3,5-triaza-adamantanebutane sulfonate (PTABS) as the coordinating caged phosphine ligand was also synthesized on a multigram scale after careful optimization of the conditions.

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Novel water-soluble phosphatriazenes: versatile ligands for Suzuki–Miyaura, Sonogashira and Heck reactions of nucleosides

Abstract: Two new water-soluble phosphatriazene as versatile ligands for catalyzing Suzuki–Miyaura reactions of purines and pyrimidines in neat water with the possibility of recycling. Copper-free Sonogashira and Heck reaction were also made possible.

Cited by 40 publications

References 65 publications

New Water‐Soluble N‐Heterocyclic Carbene‐Palladium Complexes as Promising Anti‐Tumor Agents: Investigating DNA and Protein Interactions

New Water‐Soluble N‐Heterocyclic Carbene‐Palladium Complexes as Promising Anti‐Tumor Agents: Investigating DNA and Protein Interactions

Pd/PTABS: Catalyst for Efficient C−H (Hetero)Arylation of 1,3,4‐Oxadiazoles Using Bromo(Hetero)Arenes

Scale-Up of a Heck Alkenylation Reaction: Application to the Synthesis of an Amino-Modifier Nucleoside ‘Ruth Linker’

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