Polyethylene glycol-bonded triethylammoniuml-prolinate: a new biodegradable amino-acid-based ionic liquid for the one-pot synthesis of bis(pyrazolyl)methanes as DNA binding agents

Polyethylene glycol-bonded triethylammoniuml-prolinate ([PEG-TEA]LP) was prepared as a new, highly efficient, reusable and biodegradable amino-acid-based ionic liquid catalyst using cheap and easily accessible starting materials. The [PEG-TEA]LP chemical structure was characterizedviaFT-IR and(1)H-N...

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Published inNew journal of chemistry Vol. 44; no. 39; pp. 16995 - 17012
Main Authors Kordnezhadian, Reza, Shekouhy, Mohsen, Karimian, Somaye, Tavaf, Zohreh, Malek-Hosseini, Saeed, Shahsavani, Mohammad Bagher, Amirghofran, Zahra, Yousefi, Reza, Khalafi-Nezhad, Ali
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.10.2020
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
CYTOTOXIC ACTIVITIES
ROOM-TEMPERATURE
ANTICANCER ACTIVITY
PSEUDO-5-COMPONENT SYNTHESIS
SOLVENTS
COMPLEXES
EFFICIENT SYNTHESIS
SULFURIC-ACID
4,4'-(ARYLMETHYLENE)BIS(3-METHYL-1H-PYRAZOL-5-OL) DERIVATIVES
RECYCLABLE CATALYST
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Summary:Polyethylene glycol-bonded triethylammoniuml-prolinate ([PEG-TEA]LP) was prepared as a new, highly efficient, reusable and biodegradable amino-acid-based ionic liquid catalyst using cheap and easily accessible starting materials. The [PEG-TEA]LP chemical structure was characterizedviaFT-IR and(1)H-NMR. [PEG-TEA]LP biodegradability was also assessed based on the ability ofEscherichia colibacteria to make use of this ionic liquid as a nutrient. In continuation, [PEG-TEA]LP was successfully applied as a catalyst for the one-pot pseudo-five-component synthesis of bis(pyrazolyl)methanes. High synthesized product diversity was obtained with good to excellent yields and short reaction times. Also, some bis-products of bis(pyrazolyl)methanes as more complex products were prepared to show the generality and practical efficiency of the presented strategy. The cytotoxicity of the synthesized bis(pyrazolyl)methanes against the K562 cancerous cell line was also checked and, in some cases, they were more cytotoxic than cisplatin. The DNA binding ability of the synthesized compounds was also studiedviaa UV-visible spectroscopic method, and the obtained results proved their interaction with DNA minor grooves.
ISSN:1144-0546
1369-9261
DOI:10.1039/d0nj02682d