PEG-mediated one-pot multicomponent reactions for the efficient synthesis of functionalized dihydropyridines and their functional group dependent DNA cleavage activity

Pal, Suman Kalyan; Singh, Vandana; Das, Prolay; Choudhury, Lokman H.

doi:10.1016/j.bioorg.2013.03.003

Cited by 47 publications

(22 citation statements)

References 58 publications

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“…The PO2 band at 1219 cm -1 shifted toward higher frequencies after zero time to 1250 cm -1 , and to 1252 cm -1 after 1 hour, returning to 1950 cm -1 after 48 hours. The band at 1086 cm -1 related to the phosphate symmetric stretching vibration exhibited minor absorption changes and shifted to a lower frequency at 1085 after 48 hours, higher frequency at 1088 after 1 hour, and with no shifting changes after zero time upon ct DNA complexation (Pal et al, 2013).…”

Section: Peg 400 and Po2 Bindingmentioning

confidence: 93%

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Spectroscopic Characterization of PEG-DNA Biocomplexes by FTIR

2014

J. App. Pharm. Sci.

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Understanding the mode involved in the binding of certain molecules to DNA is of prime importance, and PEG offers wide-ranging applications in biological, medical and pharmaceutical contexts. FTIR spectroscopy has been used to characterize how the formed biocomplexes bind or dissociate to/from each other between PEG400-ctDNA under different conditions. Characterization and investigation of the effect of incubation time on PEG400-ctDNA biocomplexes formation were studied through spectroscopic technique FTIR. The influence of time duration and incubation on intermolecular interaction was analysed at three different selected times (Zero, 1hr, and 48 hrs.) at 1:1 PEG400-ctDNA monomer to nucleotide ratio. The experiment was carried out at room temperature 22 ºC, with prior vortex stirrer of biocomplex for 10 min to improve homogeneity of sample. The results showed that the binding reaction of PEG400-ctDNA proceeds rapidly through DNA base pairs and phosphate DNA backbone, and complexation was reached after a maximum 1hr after mixing PEG400 and ctDNA at 1:1 ratio. FTIR spectroscopy results suggest that PEG400 binds with ctDNA by weak to moderate biocomplexes formation, with both hydrophilic and hydrophobic contact through DNA base pairs, with minor binding preference towards phosphate backbone of DNA helix. The mode of interaction most likely referred to an interaction through outside groove binding or electrostatic binding modes. FTIR highlighted the significant effect of incubation time on the stable biocomplexes of non-ionic PEG400 and ctDNA. Moreover, FTIR spectroscopy technique was rapid, showed good stability, and is a valuable tool for studying the biological properties of biocomplexes of PEG400 and ctDNA.

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Section: Peg 400 and Po2 Bindingmentioning

confidence: 93%

“…This technique has been widely employed in recent years to study and monitor in situ biological processes (Ami et al, 2005). In particular, FTIR spectroscopy enabled the characterization and identification of spectral markers of polyplexes of macromolecules (Pijanka et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic Characterization of PEG-DNA Biocomplexes by FTIR

2014

J. App. Pharm. Sci.

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“…Pal et al, described a synthesis of functionalized dihydropyridines via multicomponent reactions, at room temperature under catalyst free conditions in good yields. This methodology involved the reaction between different aromatic aldehydes, anilines, malononitrile derivatives, and dimethyl acetylenedicarboxylate (Scheme 130) [162].…”

Section: Reactions In Bio-based Solventsmentioning

confidence: 99%

“…Nagaraju et al (2015) Pal et al described a synthesis of functionalized dihydropyridines via multicomponent reactions, at room temperature under catalyst free conditions in good yields. This methodology involved the reaction between different aromatic aldehydes, anilines, malononitrile derivatives, and dimethyl acetylenedicarboxylate (Scheme 130)[162].Pal et al (2013) Paidepala et al reported the successful construction of several polyhydroquinolines by performing a four-component coupling of aldehydes, dimedone, ethylacetoacetate, and ammonium acetate using polyethylene glycol as solvent at room temperature for a short time (Scheme 131) [163]. Paidepala et al (2014) Pal et al (2013).…”

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confidence: 99%

Greener Synthesis of Nitrogen-Containing Heterocycles in Water, PEG, and Bio-Based Solvents

Campos

Berteina‐Raboin

2020

Catalysts

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The solvents used in chemistry are a fundamental element of the environmental performance of processes in corporate and academic laboratories. Their influence on costs, health safety, and nature cannot be neglected. Quantitatively, solvents are the most abundant constituents of chemical transformations; therefore, acting on solvents and replacing standard solvents with safer products can have a great ecological impact. However, not all green solvents are suitable for the wide scope of organic chemistry reactions. A second point to consider is that 50% of pharmaceutical drugs are nitrogen heterocycles compounds. It therefore appeared important to provide an overview of the more ecological methodologies for synthesizing this class of compounds. In this review, all publications since 2000 that describe green reactions leading to the formation of nitrogen heterocycles using safe solvents were considered. We chose water, PEG, and bio-based solvents for their negligible toxicity. The synthesis of five-, six-, and seven-membered aromatic nitrogen heterocycles using green reactions reported in the literature to date is described.

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“…One of the most generally used approaches for the synthesis of this class of compounds is three-component reactions of anilines, aromatic aldehydes and acetoacetates in the presence of L-proline/TFA, 19 bromodimethylsulfonium bromide (BDMS), 20 tetrabutylammonium tribromide (TBATB), 21 molecular iodine, 22 indium chloride (InCl 3 ), 23 zirconium oxy chloride (ZrOCl 2 ), 24 ceric ammonium nitrate (CAN) 25 and silica-supported boron trifluoride (BF 3 .SiO 2 ). 26 Four-component reactions of acetylenedicarboxylates, malononitrile, aldehydes and amines in the presence of polyethylene glycol (PEG), 27 L-proline/FeCl 3 28 and the base conditions, 29 is also reported to give tetrahydropyridines. The reaction of Meldrumʼs acid, acetoacetates, aromatic aldehydes and ammonium acetate by using Lawessonʼs reagent under microwave irradiation is also known to give tetrahydropyridines.…”

Section: Introductionmentioning

confidence: 99%

A one-pot synthesis of highly substituted tetrahydropyridines from N-benzylidenemethanamines, dialkyl acetylenedicarboxylates and benzylidenemalononitriles

Mehrabi¹,

Ahmad²

2016

Arkivoc

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A simple and efficient synthesis of highly substituted tetrahydropyridines has been developed using a one-pot, two step reactions. The synthesis of a series of N-benzylidenemethanamines from benzylamines and benzaldehydes in the presence of acetic acid, followed by cyclization with dialkyl acetylenedicarboxylates and benzylidenemalononitriles, gave the corresponding tetrahydropyridines in good yields.

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PEG-mediated one-pot multicomponent reactions for the efficient synthesis of functionalized dihydropyridines and their functional group dependent DNA cleavage activity

Cited by 47 publications

References 58 publications

Spectroscopic Characterization of PEG-DNA Biocomplexes by FTIR

Spectroscopic Characterization of PEG-DNA Biocomplexes by FTIR

Greener Synthesis of Nitrogen-Containing Heterocycles in Water, PEG, and Bio-Based Solvents

A one-pot synthesis of highly substituted tetrahydropyridines from N-benzylidenemethanamines, dialkyl acetylenedicarboxylates and benzylidenemalononitriles

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